<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019e46c4-307b-7db6-89cd-d8efc49dd268,g:f2b220a3-eea6-46fc-9e26-3740b00c7d04-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodStartLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/netLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/net-2009-12-16.xsd#netLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedNetLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedNetLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTerseLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodEndLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodEndLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTotalLabel"/>
  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
    <link:label id="lab_ecd_TradingArrByIndTable_terseLabel_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual</link:label>
    <link:label id="lab_ecd_TradingArrByIndTable_label_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrByIndTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TradingArrByIndTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrByIndTable" xlink:to="lab_ecd_TradingArrByIndTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TradingArrAxis_terseLabel_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangement:</link:label>
    <link:label id="lab_ecd_TradingArrAxis_label_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TradingArrAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrAxis" xlink:to="lab_ecd_TradingArrAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_019e46c4-3a42-787a-bf25-da624f23c4cd_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill_019e46c4-3ae3-71fb-952c-7dec8be9ddef_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets and goodwill acquired</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired and Goodwill</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired and Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:to="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_019e46c4-3a42-79bb-8f8a-12923e57fb3d_terseLabel_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:label id="lab_dei_Security12bTitle_label_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_Security12bTitle" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_Security12bTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_Security12bTitle" xlink:to="lab_dei_Security12bTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019e46c4-3a42-7ae4-9a6c-f4d537120a2b_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (losses) per share numerators, Total</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventMember_019e46c4-3ae4-7fd8-ab19-8e5148fe0679_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event</link:label>
    <link:label id="lab_us-gaap_SubsequentEventMember_label_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventMember" xlink:to="lab_us-gaap_SubsequentEventMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_019e46c4-3a42-7d5d-9e55-8be4f0349030_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in MediaAlpha</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsMember" xlink:to="lab_us-gaap_EquityMethodInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_019e46c4-3a42-7de0-9a3f-44cc96ae8171_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation, Amount</link:label>
    <link:label id="lab_ecd_AdjToCompAmt_label_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAmt" xlink:to="lab_ecd_AdjToCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PledgedStatusAxis_019e46c4-3a42-7dba-9d50-7b0f37765de3_terseLabel_en-US" xlink:label="lab_us-gaap_PledgedStatusAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged Status [Axis]</link:label>
    <link:label id="lab_us-gaap_PledgedStatusAxis_label_en-US" xlink:label="lab_us-gaap_PledgedStatusAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pledged Status [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PledgedStatusAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PledgedStatusAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PledgedStatusAxis" xlink:to="lab_us-gaap_PledgedStatusAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_019e46c4-3969-7a82-9eda-8895bc938824_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentAxis" xlink:to="lab_us-gaap_FinancialInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_WTMPartnersDebtMember_019edefb-1a39-7b90-84f0-09feb250bbf2_terseLabel_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Partners Debt</link:label>
    <link:label id="lab_wtm_WTMPartnersDebtMember_label_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">WTM Partners Debt [Member]</link:label>
    <link:label id="lab_wtm_WTMPartnersDebtMember_documentation_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">WTM Partners Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_WTMPartnersDebtMember" xlink:href="wtm-20260630.xsd#wtm_WTMPartnersDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_WTMPartnersDebtMember" xlink:to="lab_wtm_WTMPartnersDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingAbstract_019e46c4-3969-7890-9d64-cc4b4dc2051e_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingAbstract_label_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingAbstract" xlink:to="lab_us-gaap_SegmentReportingAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets_019fb80b-c1a9-7351-916d-aac54c3c2984_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock_019e46c4-3ae3-7d25-9d4e-6674a599ee9b_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of fair value measurements for investment securities by level</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_019e46c4-3ae3-7ca1-8671-3c59704d5370_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt covenant, loan to value percent</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Loan to Value Ratio, Maximum</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Loan to Value Ratio, Maximum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentCovenantLoanToValueRatioMaximum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:to="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_019e46c4-3ae3-743c-85c1-33cbbd9ade46_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in unearned insurance premiums</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherSignificantTransactionsTable_019e46c4-3ae3-76cc-a7ad-22c0c49d67f3_terseLabel_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Table]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsTable_label_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Table]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsTable_documentation_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsTable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the disclosure of other significant transactions.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherSignificantTransactionsTable" xlink:href="wtm-20260630.xsd#wtm_OtherSignificantTransactionsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherSignificantTransactionsTable" xlink:to="lab_wtm_OtherSignificantTransactionsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberOfInvestments_019e46c4-3a42-7b16-a1e7-8e28dec3f5b6_terseLabel_en-US" xlink:label="lab_wtm_NumberOfInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of investments</link:label>
    <link:label id="lab_wtm_NumberOfInvestments_label_en-US" xlink:label="lab_wtm_NumberOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Investments</link:label>
    <link:label id="lab_wtm_NumberOfInvestments_documentation_en-US" xlink:label="lab_wtm_NumberOfInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberOfInvestments" xlink:href="wtm-20260630.xsd#wtm_NumberOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NumberOfInvestments" xlink:to="lab_wtm_NumberOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived_019e46c4-3969-7f97-9c59-30ebf325465f_terseLabel_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incremental proceeds received</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived_label_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived_documentation_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:href="wtm-20260630.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:to="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_019f5952-d7ce-7aae-9092-24f3c46784a7_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract assets</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerAssetNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetNet" xlink:to="lab_us-gaap_ContractWithCustomerAssetNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition_019e46c4-3a42-7603-bd92-4722ecd8b850_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of restricted share awards</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Restricted Stock Unit, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentRiskAxis_019e46c4-3a42-7afb-94ff-f8c26d523c12_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentRiskAxis_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentRiskAxis" xlink:to="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_019e46c4-3969-7704-b62e-99481a5035fd_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance payable</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities_019e46c4-3969-7682-905f-5fdb276ed503_negatedTerseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liabilities Assumed, Other Liabilities</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liabilities Assumed, Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:to="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_019e46c4-3969-73dc-abc2-d25308589b72_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Investment in Debt and Equity Securities, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DeferredTaxLiabilityReversal_019e46c4-3a42-70fa-bc21-4834191719b0_terseLabel_en-US" xlink:label="lab_wtm_DeferredTaxLiabilityReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities</link:label>
    <link:label id="lab_wtm_DeferredTaxLiabilityReversal_label_en-US" xlink:label="lab_wtm_DeferredTaxLiabilityReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liability Reversal</link:label>
    <link:label id="lab_wtm_DeferredTaxLiabilityReversal_documentation_en-US" xlink:label="lab_wtm_DeferredTaxLiabilityReversal" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Tax Liability Reversal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DeferredTaxLiabilityReversal" xlink:href="wtm-20260630.xsd#wtm_DeferredTaxLiabilityReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DeferredTaxLiabilityReversal" xlink:to="lab_wtm_DeferredTaxLiabilityReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByMeasurementFrequencyAxis_019e46c4-3a42-7bb6-9b60-4e9fc70345d2_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementFrequencyAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByMeasurementFrequencyAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:to="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_019e46c4-3a42-7371-b305-3c34616157c2_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sale of Bamboo Group</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_019e46c4-3a42-7809-a614-630f5acf1f4f_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net cash proceeds</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Divestiture of Businesses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDivestitureOfBusinesses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:to="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_019e46c4-3969-7d4c-9127-1d0c276de542_terseLabel_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">U.S. Government and agency obligations</link:label>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_label_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">US Treasury and Government [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_USTreasuryAndGovernmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:to="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_019e46c4-3a42-7c9f-ba6e-9406cfe7ebe7_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_019e46c4-3a42-70b8-8c91-0cab42ad4738_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding (in shares)</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DevelopedTechnologyRightsMember_019e46c4-3a42-7a0e-a166-47ea6f41db57_terseLabel_en-US" xlink:label="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Developed technology</link:label>
    <link:label id="lab_us-gaap_DevelopedTechnologyRightsMember_label_en-US" xlink:label="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Developed Technology Rights [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DevelopedTechnologyRightsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DevelopedTechnologyRightsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DevelopedTechnologyRightsMember" xlink:to="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss_019e46c4-3a42-7623-8474-7c2455f02598_negatedTerseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Unrealized Loss</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:to="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock_019e46c4-3969-73da-a413-7ad987b224ad_terseLabel_en-US" xlink:label="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule investments in private equity funds subject to lock-up periods</link:label>
    <link:label id="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock_label_en-US" xlink:label="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity Lock-Up Period [Table Text Block]</link:label>
    <link:label id="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock_documentation_en-US" xlink:label="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tabular disclosure of expected lock up period of private equity investments.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_PrivateEquityLockUpPeriodTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:to="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_019e46c4-3ae3-7739-aebc-002987960da4_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage and asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_019e46c4-3ae3-77b6-9cfe-eb3dad99672a_verboseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total mortgage and asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NotesReceivableNominalFairValueDisclosure_019e46c4-3a42-75c9-8702-bca1012e7977_periodStartLabel_en-US" xlink:label="lab_wtm_NotesReceivableNominalFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning nominal value</link:label>
    <link:label id="lab_wtm_NotesReceivableNominalFairValueDisclosure_019e46c4-3a42-737d-8ca0-634af6cbbc29_periodEndLabel_en-US" xlink:label="lab_wtm_NotesReceivableNominalFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending nominal value</link:label>
    <link:label id="lab_wtm_NotesReceivableNominalFairValueDisclosure_label_en-US" xlink:label="lab_wtm_NotesReceivableNominalFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Receivable, Nominal Fair Value Disclosure</link:label>
    <link:label id="lab_wtm_NotesReceivableNominalFairValueDisclosure_documentation_en-US" xlink:label="lab_wtm_NotesReceivableNominalFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Notes Receivable, Nominal Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NotesReceivableNominalFairValueDisclosure" xlink:href="wtm-20260630.xsd#wtm_NotesReceivableNominalFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NotesReceivableNominalFairValueDisclosure" xlink:to="lab_wtm_NotesReceivableNominalFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems_019e46c4-3a42-7642-9461-df7c7227b104_terseLabel_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Line Items]</link:label>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_019e46c4-3a42-7ad9-901b-3c3357d366ff_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToMinorityShareholders_019e46c4-3ae3-7ae9-a607-efa9e4bdd79d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToMinorityShareholders" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Distributions to other noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_PaymentsToMinorityShareholders_label_en-US" xlink:label="lab_us-gaap_PaymentsToMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Noncontrolling Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToMinorityShareholders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToMinorityShareholders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToMinorityShareholders" xlink:to="lab_us-gaap_PaymentsToMinorityShareholders" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativePremiumPaid_019e46c4-3a42-74cd-8c8b-1ed071e3c486_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativePremiumPaid" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums paid</link:label>
    <link:label id="lab_us-gaap_DerivativePremiumPaid_label_en-US" xlink:label="lab_us-gaap_DerivativePremiumPaid" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativePremiumPaid" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativePremiumPaid"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativePremiumPaid" xlink:to="lab_us-gaap_DerivativePremiumPaid" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PercentageOfParValueOfPolicyReinsured_019e46c4-3a42-76b3-bf77-114a43bd3269_terseLabel_en-US" xlink:label="lab_wtm_PercentageOfParValueOfPolicyReinsured" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of par value of policy reinsured</link:label>
    <link:label id="lab_wtm_PercentageOfParValueOfPolicyReinsured_label_en-US" xlink:label="lab_wtm_PercentageOfParValueOfPolicyReinsured" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Percentage of Par Value of Policy Reinsured</link:label>
    <link:label id="lab_wtm_PercentageOfParValueOfPolicyReinsured_documentation_en-US" xlink:label="lab_wtm_PercentageOfParValueOfPolicyReinsured" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Percentage of par value of policy reinsured.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PercentageOfParValueOfPolicyReinsured" xlink:href="wtm-20260630.xsd#wtm_PercentageOfParValueOfPolicyReinsured"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PercentageOfParValueOfPolicyReinsured" xlink:to="lab_wtm_PercentageOfParValueOfPolicyReinsured" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_019fa1c1-bcd4-7b65-8940-7887c6380930_terseLabel_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of private debt instruments</link:label>
    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_label_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Private Debt Instruments</link:label>
    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_documentation_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Private Debt Instruments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberOfPrivateDebtInstruments" xlink:href="wtm-20260630.xsd#wtm_NumberOfPrivateDebtInstruments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NumberOfPrivateDebtInstruments" xlink:to="lab_wtm_NumberOfPrivateDebtInstruments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche2Member_019e46c4-3ae3-7e17-b7b0-2f0143eca0a1_terseLabel_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes Tranche 2</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche2Member_label_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 2 [Member]</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche2Member_documentation_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:href="wtm-20260630.xsd#wtm_Ark2021SubordinatedNotesTranche2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:to="lab_wtm_Ark2021SubordinatedNotesTranche2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis_019e46c4-3969-78df-9d8a-202283f6b556_terseLabel_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity interest percent of ownership basis</link:label>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis_label_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Members or Limited Partners, Ownership Interest, Look-through Basis</link:label>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis_documentation_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Members or Limited Partners, Ownership Interest, Look-through Basis</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:href="wtm-20260630.xsd#wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:to="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_019e46c4-3a42-7b91-a77e-d80e7d677f33_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, par value per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_ExchangeDomain_019e46c4-3ae3-7ebf-84d5-c536c2988c4a_terseLabel_en-US" xlink:label="lab_dei_ExchangeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exchange [Domain]</link:label>
    <link:label id="lab_dei_ExchangeDomain_label_en-US" xlink:label="lab_dei_ExchangeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Exchange [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_ExchangeDomain" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_ExchangeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_ExchangeDomain" xlink:to="lab_dei_ExchangeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_019e46c4-3a42-7df4-bfa9-e86d5c889111_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total other intangible assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_019e46c4-3a42-7148-90cc-66dd2f366903_periodStartLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets (excluding goodwill), beginning balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_019e46c4-3a42-73ce-9ffd-0d5945627bb2_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets (excluding goodwill), ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_019e46c4-3969-7e19-a309-72467d5176a5_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning of period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_019e46c4-3969-76a3-b34d-2b2e16b5f53b_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments_019e46c4-3ae3-7c84-b65d-e22f52135217_negatedLabel_en-US" xlink:label="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net change in short-term investments</link:label>
    <link:label id="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments_label_en-US" xlink:label="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Other Short-Term Investments</link:label>
    <link:label id="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments_documentation_en-US" xlink:label="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:href="wtm-20260630.xsd#wtm_PaymentsForProceedsFromOtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:to="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_019fd2db-c0da-7d98-ada4-3966bbbb54b8_terseLabel_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">General and administrative expenses</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_label_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Including Amortization of Other Intangible Assets</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_documentation_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Including Amortization of Other Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:href="wtm-20260630.xsd#wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:to="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCollateralAmount_019e46c4-3ae3-7840-8bea-0ac1bff116e7_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged collateral</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCollateralAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Collateral Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCollateralAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCollateralAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCollateralAmount" xlink:to="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_019e46c4-3a42-7c7d-91a2-e986fa2be95a_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark</link:label>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_019e46c4-3a42-72e6-bd5b-9bc7af501b96_verboseLabel_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ark</link:label>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_label_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Ark Insurance Holdings Limited [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Ark Insurance Holdings Limited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryArkInsuranceHoldingsLimitedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:to="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_019e46c4-3ae3-7439-a3ab-05472f2b4a89_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of reportable segments</link:label>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Reportable Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfReportableSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NumberOfReportableSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfReportableSegments" xlink:to="lab_us-gaap_NumberOfReportableSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CustomerRelationshipsMember_019e46c4-3969-7fc1-a9f2-0bac35b97720_terseLabel_en-US" xlink:label="lab_us-gaap_CustomerRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Customer relationships</link:label>
    <link:label id="lab_us-gaap_CustomerRelationshipsMember_label_en-US" xlink:label="lab_us-gaap_CustomerRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Customer Relationships [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CustomerRelationshipsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CustomerRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CustomerRelationshipsMember" xlink:to="lab_us-gaap_CustomerRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_019e46c4-3ae4-76dd-8334-1c079ba04cae_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTable" xlink:to="lab_us-gaap_ConcentrationRiskTable" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressCityOrTown_019e46c4-3a42-73ba-821e-14713693348e_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_019e46c4-3a42-760d-8d53-ff84ff8914a0_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New grants (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod_019e46c4-3969-7242-b76c-383a7fe2d78d_negatedLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Assumed forfeitures (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Forfeited in Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_019e46c4-3ae3-77fb-ba3b-ee2e0dd11947_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based compensation arrangement by share-based payment award</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RestrictedCashHeldForSale_019e46c4-3ae3-75bb-a5c8-c3d7a1d295ca_terseLabel_en-US" xlink:label="lab_wtm_RestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash, restricted cash held for sale</link:label>
    <link:label id="lab_wtm_RestrictedCashHeldForSale_label_en-US" xlink:label="lab_wtm_RestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash, Held For Sale</link:label>
    <link:label id="lab_wtm_RestrictedCashHeldForSale_documentation_en-US" xlink:label="lab_wtm_RestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Restricted Cash, Held For Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_RestrictedCashHeldForSale" xlink:href="wtm-20260630.xsd#wtm_RestrictedCashHeldForSale"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_RestrictedCashHeldForSale" xlink:to="lab_wtm_RestrictedCashHeldForSale" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_019e46c4-3a42-7437-a757-c53cac918030_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_019e46c4-3ae3-7c1c-bd44-bc34032e026e_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, net carrying value</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019e46c4-3a42-7a77-a4e5-83408372cd72_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE incurred relating to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments_019e46c4-3ae3-7e4b-adf8-90eed95f67d5_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted average portfolio period, excluding short-term investment</link:label>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments_label_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period, Excluding Short-Term Investments</link:label>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period, Excluding Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:to="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_WTMCreditFacilityMember_019e46c4-3ae3-706f-9501-810bfef58c13_terseLabel_en-US" xlink:label="lab_wtm_WTMCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Credit Facility</link:label>
    <link:label id="lab_wtm_WTMCreditFacilityMember_label_en-US" xlink:label="lab_wtm_WTMCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">WTM Credit Facility [Member]</link:label>
    <link:label id="lab_wtm_WTMCreditFacilityMember_documentation_en-US" xlink:label="lab_wtm_WTMCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">WTM Credit Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_WTMCreditFacilityMember" xlink:href="wtm-20260630.xsd#wtm_WTMCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_WTMCreditFacilityMember" xlink:to="lab_wtm_WTMCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember_019e46c4-3a42-7243-8906-9cd3384c4500_terseLabel_en-US" xlink:label="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Terminal Cash Flow Exit Multiple</link:label>
    <link:label id="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember_label_en-US" xlink:label="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Terminal Cash Flow Exit Multiple [Member]</link:label>
    <link:label id="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember_documentation_en-US" xlink:label="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Measurement Input, Terminal Cash Flow Exit Multiple</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:href="wtm-20260630.xsd#wtm_MeasurementInputTerminalCashFlowExitMultipleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:to="lab_wtm_MeasurementInputTerminalCashFlowExitMultipleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_019e46c4-3969-73d6-8399-ddd1455e9375_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnVsPeerGroupTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:to="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019e46c4-3969-7b9e-a23c-ee429397ba3c_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive income (loss), net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonRule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum_019e46c4-3ae3-71f3-a3a6-1e4caa68354f_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Solvency capital requirement</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Solvency Capital, Minimum</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Solvency Capital, Minimum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentCovenantSolvencyCapitalMinimum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:to="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum" xlink:type="arc" order="1"/>
    <link:label id="lab_country_US_019e46c4-3a42-7939-9934-6f24f859d01a_terseLabel_en-US" xlink:label="lab_country_US" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">United&#160;States</link:label>
    <link:label id="lab_country_US_label_en-US" xlink:label="lab_country_US" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED STATES</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_US" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_US"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_US" xlink:to="lab_country_US" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember_019e46c4-3a42-713d-a57a-e37b600d36b3_terseLabel_en-US" xlink:label="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLMC</link:label>
    <link:label id="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember_label_en-US" xlink:label="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal Home Loan Mortgage Corporation Certificates and Obligations (FHLMC) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:to="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NetInvestmentIncomeAdjusted_019fd340-5d51-76c7-8cea-5b21601c7d18_terseLabel_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_wtm_NetInvestmentIncomeAdjusted_label_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income, Adjusted</link:label>
    <link:label id="lab_wtm_NetInvestmentIncomeAdjusted_documentation_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Investment Income, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NetInvestmentIncomeAdjusted" xlink:href="wtm-20260630.xsd#wtm_NetInvestmentIncomeAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NetInvestmentIncomeAdjusted" xlink:to="lab_wtm_NetInvestmentIncomeAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_019e46c4-3a42-71a2-9c8b-db6ef87adb65_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeAxis" xlink:to="lab_us-gaap_SubsequentEventTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_019e46c4-3a42-7e75-962a-188f6fbff45d_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:to="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_019e46c4-3ae3-7119-ba53-576480441460_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Long-term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EffectsOfReinsuranceFootnotesAbstract_019e46c4-3ae3-7893-9232-6621261300e9_terseLabel_en-US" xlink:label="lab_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance Footnotes [Abstract]</link:label>
    <link:label id="lab_wtm_EffectsOfReinsuranceFootnotesAbstract_label_en-US" xlink:label="lab_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance Footnotes [Abstract]</link:label>
    <link:label id="lab_wtm_EffectsOfReinsuranceFootnotesAbstract_documentation_en-US" xlink:label="lab_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance Footnotes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:href="wtm-20260630.xsd#wtm_EffectsOfReinsuranceFootnotesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:to="lab_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_019e46c4-3ae3-7e8a-a29c-179693345969_netLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Commission and fee revenues</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_019e46c4-3ae3-724a-8062-b6a32d829210_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee revenues</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019e46c4-3ae3-7562-958f-7dc7e5bb772f_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_019e46c4-3a42-7529-88a3-9e1c30135477_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of financial information for segments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock_019e46c4-3ae3-7bbc-bca3-dea6a60192b3_terseLabel_en-US" xlink:label="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of performance share activity</link:label>
    <link:label id="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock_label_en-US" xlink:label="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Nonvested Performance Share Activity [Table Text Block]</link:label>
    <link:label id="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock_documentation_en-US" xlink:label="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tabular disclosure of the changes in nonvested performance shares outstanding and the amount accrued for performance shares.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:to="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_019e46c4-3a42-7a32-91a6-3a1613c6c754_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e46c4-3ae3-7b1e-ab9a-223a6882fc0d_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive income (loss), net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019e46c4-3a42-7509-abff-bd10083416d0_terseLabel_en-US" xlink:label="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total mortgage and asset-backed securities and collateralized loan obligations</link:label>
    <link:label id="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_label_en-US" xlink:label="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage and Asset-Backed Securities and Collateralized Loan Obligations [Member]</link:label>
    <link:label id="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_documentation_en-US" xlink:label="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage and Asset-Backed Securities and Collateralized Loan Obligations</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:href="wtm-20260630.xsd#wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:to="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesReceivableFairValueDisclosure_019e46c4-3a42-71da-bb35-37cc2e704336_verboseLabel_en-US" xlink:label="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">BAM Surplus Notes, at fair value</link:label>
    <link:label id="lab_us-gaap_NotesReceivableFairValueDisclosure_019e46c4-3a42-7895-af96-9edfb8657a91_terseLabel_en-US" xlink:label="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes receivable, fair value disclosure</link:label>
    <link:label id="lab_us-gaap_NotesReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Receivable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NotesReceivableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesReceivableFairValueDisclosure" xlink:to="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_019e46c4-3a42-754a-9d0e-27f74eb4f192_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Debt, Net of Issuance Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDebtNetOfIssuanceCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:to="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationDomain_019e46c4-3ae3-77f3-a96a-eb35298debdf_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskCollateralizationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskCollateralizationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskCollateralizationDomain" xlink:to="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GuaranteeObligationsLineItems_019e46c4-3ae3-70cd-870b-b340055c171a_terseLabel_en-US" xlink:label="lab_us-gaap_GuaranteeObligationsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Guarantor Obligations [Line Items]</link:label>
    <link:label id="lab_us-gaap_GuaranteeObligationsLineItems_label_en-US" xlink:label="lab_us-gaap_GuaranteeObligationsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantor Obligations [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GuaranteeObligationsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GuaranteeObligationsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GuaranteeObligationsLineItems" xlink:to="lab_us-gaap_GuaranteeObligationsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_019e46c4-3ae3-7ffa-bef3-2f6eb50bd56b_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:label id="lab_dei_DocumentPeriodEndDate_label_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentPeriodEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentPeriodEndDate" xlink:to="lab_dei_DocumentPeriodEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss_019e46c4-3a42-734e-b2bb-2422d731a919_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net&#160;Foreign Currency Gains (Losses)</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Net Foreign Currency Gain (Loss)</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Net Foreign Currency Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:to="lab_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedManagementMember_019e46c4-3a42-7dc8-921f-002959cfe303_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedManagementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished Management</link:label>
    <link:label id="lab_wtm_DistinguishedManagementMember_label_en-US" xlink:label="lab_wtm_DistinguishedManagementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Management [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedManagementMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedManagementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Management</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedManagementMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedManagementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedManagementMember" xlink:to="lab_wtm_DistinguishedManagementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_019e46c4-3969-7a8b-a221-1bb53c852632_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Face value</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicAbstract_019e46c4-3969-7c2d-934f-f3358ff10172_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Basic and diluted earnings per share (in dollars):</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicAbstract" xlink:to="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt_019e46c4-3a42-7da1-8c57-3d75a1bb4697_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Long-Term Debt, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage_019e46c4-3ae3-789a-a22b-1dda4c8cb75d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective yield (as a percent)</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Effective Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentInterestRateEffectivePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts_019e46c4-3a42-76f5-b9c0-15efd4e1bb67_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transaction costs</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Transaction Cost, Excluding Separately Recognized Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:to="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_019fd325-090e-7124-9958-661d7171f9f5_terseLabel_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE</link:label>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_label_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Adjusted</link:label>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_documentation_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:href="wtm-20260630.xsd#wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:to="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel12And3Member_019e46c4-3a42-7aa7-a3ab-dc2d9db202a7_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1, Level 2, and Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel12And3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1, Level 2, and Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel12And3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel12And3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel12And3Member" xlink:to="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMinorityShareholders_019e46c4-3969-75db-805e-9c2c00d301af_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contributions from other noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMinorityShareholders_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Noncontrolling Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMinorityShareholders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMinorityShareholders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMinorityShareholders" xlink:to="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember_019e46c4-3a42-7e6f-8b8d-d2d11e5fac2f_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished - Management Equity Incentives</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember_label_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Partners, Management Equity Incentives [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Partners, Management Equity Incentives</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:to="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_019e46c4-3ae3-79d0-ab53-928bf171f69d_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableMember" xlink:to="lab_us-gaap_ReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_019e46c4-3969-7208-a241-9d1dd218ba06_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in reinsurance payable</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Reinsurance Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_019e46c4-3ae3-7aff-a178-f7b8c810e4a2_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsDomain_019e46c4-3a42-7296-920a-df75a8335235_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:label id="lab_srt_ConsolidationItemsDomain_label_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsDomain" xlink:to="lab_srt_ConsolidationItemsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherDisposalGroupMember_019e46c4-3969-7c23-94da-ebbfae8099e8_terseLabel_en-US" xlink:label="lab_wtm_OtherDisposalGroupMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Disposal Group</link:label>
    <link:label id="lab_wtm_OtherDisposalGroupMember_label_en-US" xlink:label="lab_wtm_OtherDisposalGroupMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Disposal Group [Member]</link:label>
    <link:label id="lab_wtm_OtherDisposalGroupMember_documentation_en-US" xlink:label="lab_wtm_OtherDisposalGroupMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Disposal Group</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherDisposalGroupMember" xlink:href="wtm-20260630.xsd#wtm_OtherDisposalGroupMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherDisposalGroupMember" xlink:to="lab_wtm_OtherDisposalGroupMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic_019e46c4-3ae3-7757-a240-75631317cda3_totalLabel_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total undistributed net earnings (losses), net of restricted common share amounts</link:label>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic_label_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Undistributed Continuing Operation Earnings (Loss), Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UndistributedContinuingOperationEarningsLossBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:to="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_019e46c4-3ae3-75cd-a87d-70ea850a3058_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_019e46c4-3ae3-7492-a8d6-8931d1e34d7b_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Earnings (loss) per share attributable to White Mountains&#8217;s common shareholders:</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_019e46c4-3a42-7351-bec5-65667d785a83_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireSurplusNotes_019e46c4-3969-7aa1-805e-fa81ff7c3ba9_terseLabel_en-US" xlink:label="lab_wtm_PaymentsToAcquireSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase of surplus notes</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireSurplusNotes_label_en-US" xlink:label="lab_wtm_PaymentsToAcquireSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Surplus Notes</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireSurplusNotes_documentation_en-US" xlink:label="lab_wtm_PaymentsToAcquireSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments to Acquire Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsToAcquireSurplusNotes" xlink:href="wtm-20260630.xsd#wtm_PaymentsToAcquireSurplusNotes"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireSurplusNotes" xlink:to="lab_wtm_PaymentsToAcquireSurplusNotes" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets_019e46c4-3a42-7aa9-a6da-0cb387397305_totalLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net tangible assets acquired (liabilities assumed)</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired And Liabilities Assumed, Net Tangible Assets</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired And Liabilities Assumed, Net Tangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:to="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_019e46c4-3ae3-7c2f-bd1d-de996cfca5cd_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_019e46c4-3ae3-74ca-b650-a714d27b07b9_terseLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_019e46c4-3a42-770d-a960-c72d72d0e74c_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputDiscountRateMember_019e46c4-3ae4-7b4f-bb39-2e854c0c73ce_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discount Rate</link:label>
    <link:label id="lab_us-gaap_MeasurementInputDiscountRateMember_label_en-US" xlink:label="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Discount Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputDiscountRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputDiscountRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputDiscountRateMember" xlink:to="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne_019e46c4-3a42-7bc9-a27d-a56209b70630_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in one year or less</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:to="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract_019e46c4-3a42-70ce-81f2-ed9825c46d1c_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Goodwill and Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, after Accumulated Amortization [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019e46c4-3a42-7371-b18b-edd7e3836bf2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of assets acquired and liabilities assumed</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired and Liability Assumed [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureName_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureName_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureName" xlink:to="lab_ecd_CoSelectedMeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_019e46c4-3ae3-7ad3-9c8c-5fb1cba13b27_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate_019e46c4-3a42-7afc-a107-db66eed748b8_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed rate</link:label>
    <link:label id="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate_label_en-US" xlink:label="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Percentage Bearing Fixed Interest, Percentage Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtPercentageBearingFixedInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:to="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_019e46c4-3ae4-7aeb-bba6-cb521005e3a7_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New and existing contracts deployed</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long Term Investments, Increase (Decrease) in Participation Contracts</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long Term Investments, Increase (Decrease) in Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:to="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_019e46c4-3969-7e6b-9597-aa20035209ef_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskLineItems" xlink:to="lab_us-gaap_ConcentrationRiskLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution_019e46c4-3ae3-7261-b53a-3f8c60ad298f_terseLabel_en-US" xlink:label="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payments to acquire interest in subsidiaries and affiliates, additional contribution</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution_label_en-US" xlink:label="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Interest in Subsidiaries and Affiliates, Additional Contribution</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution_documentation_en-US" xlink:label="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Right to Sell Units, Payment Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:href="wtm-20260630.xsd#wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:to="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment_019e46c4-3ae3-7f8c-aa25-53cc1a4929ce_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Post-closing purchase price adjustment</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment_label_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Post-Closing Purchase Price Adjustment</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Post-Closing Purchase Price Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:to="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember_019e46c4-3ae4-7f44-b5a2-865ae145fedb_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Kudu</link:label>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember_label_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Kudu Investment Management, LLC [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Kudu Investment Management, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryKuduInvestmentManagementLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:to="lab_wtm_SubsidiaryKuduInvestmentManagementLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCost_019e46c4-3a42-70b0-aebc-e78db56ecffe_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCost_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityDomain_019e46c4-3a42-7f86-85fe-8c074fd46f0a_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityDomain" xlink:to="lab_us-gaap_CreditFacilityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019e46c4-3a42-77a4-a4b7-b4028da9dee6_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and loss adjustment expense reserves</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019e46c4-3a42-76ee-95f8-60aa13383e9b_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Gross beginning balance</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019e46c4-3a42-7bfb-b493-5074ced77cb8_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Gross ending balance</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019e46c4-3a42-7705-996a-d318edb62d23_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operations:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears_019e46c4-3a42-7ff2-a7d5-3476f111289e_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">5&#160;&#8211;&#160;10&#160;years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Five to Ten Years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Five to Ten Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareCashPaid_019e46c4-3969-7ba8-a4ad-55777c75ccae_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends paid per White Mountains&#8217;s common share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareCashPaid_label_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Dividends, Per Share, Cash Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockDividendsPerShareCashPaid"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:to="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote</link:label>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_label_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EquityValuationAssumptionDifferenceFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:to="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherAssetBackedSecuritiesMember_019e46c4-3a42-7790-99b7-6cc4add13538_terseLabel_en-US" xlink:label="lab_wtm_OtherAssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_wtm_OtherAssetBackedSecuritiesMember_label_en-US" xlink:label="lab_wtm_OtherAssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Asset-Backed Securities [Member]</link:label>
    <link:label id="lab_wtm_OtherAssetBackedSecuritiesMember_documentation_en-US" xlink:label="lab_wtm_OtherAssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Asset-Backed Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherAssetBackedSecuritiesMember" xlink:href="wtm-20260630.xsd#wtm_OtherAssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherAssetBackedSecuritiesMember" xlink:to="lab_wtm_OtherAssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain_019e46c4-3ae3-7755-b9bc-655b353e33dd_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain_label_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:to="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3_019e46c4-3969-7ee2-8ea6-14246b0ef1eb_negatedLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Transfers out</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Transfers out of Level 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_019e46c4-3ae3-7607-a261-91ea1eca3d06_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of pre-tax net investment income</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeTextBlock" xlink:to="lab_us-gaap_InvestmentIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxesAndTaxCredits_019e46c4-3969-7b30-bffa-e89889e1b4b0_verboseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxesAndTaxCredits" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Deferred income tax expense (benefit)</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxesAndTaxCredits_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxesAndTaxCredits" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Taxes and Tax Credits</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxesAndTaxCredits" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxesAndTaxCredits"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxesAndTaxCredits" xlink:to="lab_us-gaap_DeferredIncomeTaxesAndTaxCredits" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment_019e46c4-3a42-7705-a3b0-d0efd77141d9_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls and paydowns of fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Maturity, Repayment, and Call, Debt Security, Trading, Held-for-Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment" xlink:to="lab_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DividendsPayableCurrentAndNoncurrent_019e46c4-3ae4-732a-8db0-780d1432b2a8_terseLabel_en-US" xlink:label="lab_us-gaap_DividendsPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends payable</link:label>
    <link:label id="lab_us-gaap_DividendsPayableCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_DividendsPayableCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DividendsPayableCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DividendsPayableCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DividendsPayableCurrentAndNoncurrent" xlink:to="lab_us-gaap_DividendsPayableCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_019e46c4-3ae3-706e-8961-9f7225816db8_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Share-based Compensation Arrangements by Share-based Payment Award [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Share-Based Compensation Arrangements by Share-Based Payment Award [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:to="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract_019e46c4-3969-7f4f-a8eb-0700126b9fac_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Line Items]</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InsuranceLinkedSecuritiesFundsMember_019e46c4-3a42-76c7-89b9-8f659388f991_terseLabel_en-US" xlink:label="lab_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">ILS funds</link:label>
    <link:label id="lab_wtm_InsuranceLinkedSecuritiesFundsMember_label_en-US" xlink:label="lab_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance-Linked Securities Funds [Member]</link:label>
    <link:label id="lab_wtm_InsuranceLinkedSecuritiesFundsMember_documentation_en-US" xlink:label="lab_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Insurance-Linked Securities Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:href="wtm-20260630.xsd#wtm_InsuranceLinkedSecuritiesFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:to="lab_wtm_InsuranceLinkedSecuritiesFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_019e46c4-3ae3-73c1-88a9-9ebdd6907b98_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of fair value investments by level</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIntangibleAssetsMember_019e46c4-3a42-75c1-a5cc-2ecbbeca3788_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIntangibleAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_OtherIntangibleAssetsMember_label_en-US" xlink:label="lab_us-gaap_OtherIntangibleAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Intangible Assets [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIntangibleAssetsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIntangibleAssetsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIntangibleAssetsMember" xlink:to="lab_us-gaap_OtherIntangibleAssetsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet_019e46c4-3ae3-7d4a-9bf8-e019a251d5eb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net other operating activities</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Other Operating Assets and Liabilities, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod_019e46c4-3969-7bc9-825c-d88eaab2bcb9_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, period for interest rate increase</link:label>
    <link:label id="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod_label_en-US" xlink:label="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Increase In Interest Rate, Period</link:label>
    <link:label id="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Increase In Interest Rate, Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentIncreaseInInterestRatePeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:to="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt_019e46c4-3ae3-7e12-88af-28f13f24117d_verboseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Long-Term Debt</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:to="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined</link:label>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_label_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgPredtrmndFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgPredtrmndFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgPredtrmndFlag" xlink:to="lab_ecd_AwardTmgPredtrmndFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired_019e46c4-3ae3-798e-9692-9510c439df26_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling interest</link:label>
    <link:label id="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired_label_en-US" xlink:label="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Nonredeemable Noncontrolling Interest Acquired</link:label>
    <link:label id="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Nonredeemable Noncontrolling Interest Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:to="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_019e46c4-3a42-759e-866b-ec9924ba198a_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019e46c4-3ae3-7db9-8e95-a3066ab136d9_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Net loss and LAE reserves</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019e46c4-3ae3-7352-8cfe-094739e18c47_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net ending balance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_019e46c4-3ae3-7d8e-97eb-ce97accaca9a_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective tax rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnSaleOfInvestments_019e46c4-3a42-7cbd-80ab-7332ef4971a3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less: net realized and unrealized gains (losses) on investment securities sold during the period</link:label>
    <link:label id="lab_us-gaap_GainLossOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnSaleOfInvestments" xlink:to="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GrossPremiumsEarned_019e46c4-3969-7ab7-aef5-f478c87f603f_totalLabel_en-US" xlink:label="lab_wtm_GrossPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Gross earned premiums</link:label>
    <link:label id="lab_wtm_GrossPremiumsEarned_019e46c4-3969-73b7-a14c-9a1c74cfac6d_terseLabel_en-US" xlink:label="lab_wtm_GrossPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross earned premiums</link:label>
    <link:label id="lab_wtm_GrossPremiumsEarned_label_en-US" xlink:label="lab_wtm_GrossPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Premiums Earned</link:label>
    <link:label id="lab_wtm_GrossPremiumsEarned_documentation_en-US" xlink:label="lab_wtm_GrossPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GrossPremiumsEarned" xlink:href="wtm-20260630.xsd#wtm_GrossPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GrossPremiumsEarned" xlink:to="lab_wtm_GrossPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock_019e46c4-3a42-7e92-9886-77f61a33fc03_terseLabel_en-US" xlink:label="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of performance shares outstanding and accrued expense for performance shares awarded</link:label>
    <link:label id="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock_label_en-US" xlink:label="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Performance Shares Outstanding and Accrued Expense by Performance Cycle under Incentive Plan [Table Text Block]</link:label>
    <link:label id="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock_documentation_en-US" xlink:label="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tabular disclosure of performance shares outstanding and the amount accrued by performance cycle, under the entity's Incentive Plan.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:to="lab_wtm_ScheduleOfPerformanceSharesOutstandingAndAccruedExpenseByPerformanceCycleUnderIncentivePlanTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition_019e46c4-3ae3-7b17-a00a-cb82dff31c03_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recognition of equity-based compensation expense of subsidiaries</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment_019e46c4-3ae3-76e9-aa1d-2d4b7eca3933_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sales of fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale, Debt Security, Trading, and Equity Security, FV-NI, Held-for-Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:to="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateDebtInstrumentMember_019e46c4-3ae3-70cb-bdb9-52fee92a9837_terseLabel_en-US" xlink:label="lab_wtm_PrivateDebtInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private debt instruments</link:label>
    <link:label id="lab_wtm_PrivateDebtInstrumentMember_label_en-US" xlink:label="lab_wtm_PrivateDebtInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Debt Instrument [Member]</link:label>
    <link:label id="lab_wtm_PrivateDebtInstrumentMember_documentation_en-US" xlink:label="lab_wtm_PrivateDebtInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Private Debt Instrument [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateDebtInstrumentMember" xlink:href="wtm-20260630.xsd#wtm_PrivateDebtInstrumentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateDebtInstrumentMember" xlink:to="lab_wtm_PrivateDebtInstrumentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue_019e46c4-3ae3-7185-ad52-7eeca285a14f_negatedLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Repurchases and retirements of common shares</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased and Retired During Period, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedAndRetiredDuringPeriodValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:to="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAbstract_019e46c4-3ae3-7038-b330-32bcdf691c35_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impaired [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillImpairedAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAbstract" xlink:to="lab_us-gaap_GoodwillImpairedAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod_019e46c4-3a42-7580-9b81-4c52aa373276_negatedLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Shares paid or expired (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Shares Paid In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">The number of target performance shares that were paid out (including deposits into a deferred compensation plan) or that expired due to failure to meet performance criteria.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod1Member_019e46c4-3969-76de-a4a5-3ab5ba278dcc_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriod1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 1</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod1Member_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriod1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 1 [Member]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod1Member_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriod1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriod1Member" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriod1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriod1Member" xlink:to="lab_wtm_DebtCovenantPeriod1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_019e46c4-3969-73dc-a4bb-2baacd24c884_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019e46c4-3969-7561-93f9-4bbe75b5054d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019e46c4-3969-7131-b459-6870f91144a2_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_label_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:to="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_019e46c4-3ae3-722c-a699-28b4892c7393_terseLabel_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_label_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioUnspecifiedDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScenarioUnspecifiedDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioUnspecifiedDomain" xlink:to="lab_srt_ScenarioUnspecifiedDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherOperationsDebtMember_019e46c4-3a42-740d-afee-bff50b4d3ed7_terseLabel_en-US" xlink:label="lab_wtm_OtherOperationsDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Operations Debt</link:label>
    <link:label id="lab_wtm_OtherOperationsDebtMember_label_en-US" xlink:label="lab_wtm_OtherOperationsDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Operations - Debt [Member]</link:label>
    <link:label id="lab_wtm_OtherOperationsDebtMember_documentation_en-US" xlink:label="lab_wtm_OtherOperationsDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Operations - Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherOperationsDebtMember" xlink:href="wtm-20260630.xsd#wtm_OtherOperationsDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherOperationsDebtMember" xlink:to="lab_wtm_OtherOperationsDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_019e46c4-3969-7e44-932e-9e3cf79878c3_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:to="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock_019e46c4-3ae3-7c9b-919f-d2ae710c4dff_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of carrying values for other long-term investments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Investments Not Readily Marketable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:to="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019e46c4-3969-7210-85ac-17bad5b287f8_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE paid relating to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_019e46c4-3ae3-7544-9765-454da3be70ac_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net assets acquired</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired to Liability Assumed, Excess (Less), and Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock_019e46c4-3a42-77a2-a6e0-f423df5e293b_terseLabel_en-US" xlink:label="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of undistributed earnings</link:label>
    <link:label id="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock_label_en-US" xlink:label="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Undistributed Earnings [Table Text Block]</link:label>
    <link:label id="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock_documentation_en-US" xlink:label="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule of Undistributed Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_ScheduleOfUndistributedEarningsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:to="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_019e46c4-3ae4-7efd-93b0-3b3a3ab8e0a0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestLineItems_019e46c4-3969-75a9-acb9-73359ab6cefa_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Line Items]</link:label>
    <link:label id="lab_us-gaap_MinorityInterestLineItems_label_en-US" xlink:label="lab_us-gaap_MinorityInterestLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestLineItems" xlink:to="lab_us-gaap_MinorityInterestLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_019e46c4-3ae3-70a2-bcb2-82a0e79719c7_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock_019e46c4-3ae3-7239-b03f-e86af184df90_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Securities</link:label>
    <link:label id="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment in Debt and Equity Securities and Other Trading Assets [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:to="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsOfDividendsCommonStock_019e46c4-3ae3-7db1-ba37-241b0473853e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsOfDividendsCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Cash dividends paid to common shareholders</link:label>
    <link:label id="lab_us-gaap_PaymentsOfDividendsCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsOfDividendsCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments of Ordinary Dividends, Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDividendsCommonStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsOfDividendsCommonStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsOfDividendsCommonStock" xlink:to="lab_us-gaap_PaymentsOfDividendsCommonStock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrExpirationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expiration Date</link:label>
    <link:label id="lab_ecd_TrdArrExpirationDate_label_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Expiration Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrExpirationDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrExpirationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrExpirationDate" xlink:to="lab_ecd_TrdArrExpirationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SignificantTransactionsAbstract_019e46c4-3969-769b-8e92-3c07fda53cbe_terseLabel_en-US" xlink:label="lab_wtm_SignificantTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, pro forma information, pro forma revenue</link:label>
    <link:label id="lab_wtm_SignificantTransactionsAbstract_label_en-US" xlink:label="lab_wtm_SignificantTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Significant Transactions [Abstract]</link:label>
    <link:label id="lab_wtm_SignificantTransactionsAbstract_documentation_en-US" xlink:label="lab_wtm_SignificantTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Significant Transactions [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SignificantTransactionsAbstract" xlink:href="wtm-20260630.xsd#wtm_SignificantTransactionsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SignificantTransactionsAbstract" xlink:to="lab_wtm_SignificantTransactionsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock_019e46c4-3ae4-7770-aebe-f4a16eae3918_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of HG's future premium revenues</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Premium Received over Contract Period [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_019e46c4-3ae3-737f-98f8-fe5f8e49be78_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash balance</link:label>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_label_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:to="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_019e46c4-3a42-7aed-aff1-480a1eb5fc35_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_019e46c4-3a42-76ba-97ff-ed256349ed82_periodStartLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balances</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_019e46c4-3a42-7e43-b126-2e3725159b96_periodEndLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balances</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Including Portion Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_019e46c4-3969-799b-abef-7e20d0a6c9ca_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubordinatedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebtMember" xlink:to="lab_us-gaap_SubordinatedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems_019e46c4-3969-73b9-9cdd-666825a40cff_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operations [Line Items]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operations [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue_019e46c4-3ae3-798d-ba7e-bdcab80f3705_terseLabel_en-US" xlink:label="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition Date Fair Value</link:label>
    <link:label id="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue_label_en-US" xlink:label="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets (Excluding Goodwill), Acquisition Date, Fair Value</link:label>
    <link:label id="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue_documentation_en-US" xlink:label="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets (Excluding Goodwill), Acquisition Date, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:href="wtm-20260630.xsd#wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:to="lab_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsumerSectorMember_019e46c4-3ae3-75ca-8787-7dcbdc47c646_terseLabel_en-US" xlink:label="lab_us-gaap_ConsumerSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consumer</link:label>
    <link:label id="lab_us-gaap_ConsumerSectorMember_label_en-US" xlink:label="lab_us-gaap_ConsumerSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consumer Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsumerSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsumerSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConsumerSectorMember" xlink:to="lab_us-gaap_ConsumerSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtPnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:to="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeTable_019e46c4-3969-75f0-8db4-30230dbd68f5_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative [Table]</link:label>
    <link:label id="lab_us-gaap_DerivativeTable_label_en-US" xlink:label="lab_us-gaap_DerivativeTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeTable" xlink:to="lab_us-gaap_DerivativeTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OutriggerReMember_019e46c4-3a42-7b8d-943d-c147e9f58127_terseLabel_en-US" xlink:label="lab_wtm_OutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outrigger Re</link:label>
    <link:label id="lab_wtm_OutriggerReMember_label_en-US" xlink:label="lab_wtm_OutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outrigger Re [Member]</link:label>
    <link:label id="lab_wtm_OutriggerReMember_documentation_en-US" xlink:label="lab_wtm_OutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Outrigger Re</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OutriggerReMember" xlink:href="wtm-20260630.xsd#wtm_OutriggerReMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OutriggerReMember" xlink:to="lab_wtm_OutriggerReMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_019fc6df-5716-7be8-8bec-c6ba0b2ff1c2_negatedTerseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net contributions (distributions) and dilution from other noncontrolling interests</link:label>
    <link:label id="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_label_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Contribution and Dilution From Noncontrolling Interest During Period</link:label>
    <link:label id="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Contribution and Dilution From Noncontrolling Interest During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:href="wtm-20260630.xsd#wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:to="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_019e46c4-3969-7581-a0df-03b7923cd421_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LimitedPartnershipsMember_019e46c4-3969-7f3d-b5e0-71f3c2f38934_terseLabel_en-US" xlink:label="lab_wtm_LimitedPartnershipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Limited Partnerships</link:label>
    <link:label id="lab_wtm_LimitedPartnershipsMember_label_en-US" xlink:label="lab_wtm_LimitedPartnershipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Limited Partnerships [Member]</link:label>
    <link:label id="lab_wtm_LimitedPartnershipsMember_documentation_en-US" xlink:label="lab_wtm_LimitedPartnershipsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Limited Partnerships</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LimitedPartnershipsMember" xlink:href="wtm-20260630.xsd#wtm_LimitedPartnershipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LimitedPartnershipsMember" xlink:to="lab_wtm_LimitedPartnershipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable_019e46c4-3ae3-7edb-880b-0154992a13fa_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations [Table]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentDomain_019e46c4-3969-72b7-975d-f9e78b0dade5_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:label id="lab_us-gaap_SegmentDomain_label_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentDomain" xlink:to="lab_us-gaap_SegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember_019e46c4-3969-76a0-afc8-41493ca60099_terseLabel_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - Build America Mutual Assurance Company</link:label>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember_label_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - Build America Mutual Assurance Company [Member]</link:label>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember_documentation_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - Build America Mutual Assurance Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:href="wtm-20260630.xsd#wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:to="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_019e46c4-3a42-7dd3-b4af-309fae6f007e_terseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementScenarioAxis_019e46c4-3a42-7372-a511-0a9de2aa215f_terseLabel_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:label id="lab_srt_StatementScenarioAxis_label_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementScenarioAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StatementScenarioAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementScenarioAxis" xlink:to="lab_srt_StatementScenarioAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued_019e46c4-3ae3-789f-b1bb-b10271093883_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issued</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued_label_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount Issued</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued_documentation_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">The total fair value (on the date of issue) for restricted share awards issued during the period.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:href="wtm-20260630.xsd#wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:to="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupClassificationDomain_019e46c4-3ae3-7bf9-9226-171e3a75b628_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Domain]</link:label>
    <link:label id="lab_us-gaap_DisposalGroupClassificationDomain_label_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupClassificationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupClassificationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupClassificationDomain" xlink:to="lab_us-gaap_DisposalGroupClassificationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_019e46c4-3a42-71b0-81d1-6fab1153bd35_negatedLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Unamortized issuance cost</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentLoanToValuePercentage_019e46c4-3969-75d5-9041-45478b4e4612_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentLoanToValuePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt covenant, maximum loan to value percent</link:label>
    <link:label id="lab_wtm_DebtInstrumentLoanToValuePercentage_label_en-US" xlink:label="lab_wtm_DebtInstrumentLoanToValuePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Loan To Value, Percentage</link:label>
    <link:label id="lab_wtm_DebtInstrumentLoanToValuePercentage_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentLoanToValuePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Loan To Value, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentLoanToValuePercentage" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentLoanToValuePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentLoanToValuePercentage" xlink:to="lab_wtm_DebtInstrumentLoanToValuePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BishopStreetMember_019e46c4-3ae4-721c-822f-18553142d4d0_terseLabel_en-US" xlink:label="lab_wtm_BishopStreetMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bishop Street</link:label>
    <link:label id="lab_wtm_BishopStreetMember_label_en-US" xlink:label="lab_wtm_BishopStreetMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bishop Street [Member]</link:label>
    <link:label id="lab_wtm_BishopStreetMember_documentation_en-US" xlink:label="lab_wtm_BishopStreetMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bishop Street</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BishopStreetMember" xlink:href="wtm-20260630.xsd#wtm_BishopStreetMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BishopStreetMember" xlink:to="lab_wtm_BishopStreetMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoActuallyPaidCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoActuallyPaidCompAmt" xlink:to="lab_ecd_PeoActuallyPaidCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredOtherTaxExpenseBenefit_019e46c4-3a42-7dae-9750-16c4023438dc_verboseLabel_en-US" xlink:label="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net deferred tax benefit</link:label>
    <link:label id="lab_us-gaap_DeferredOtherTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Other Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredOtherTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:to="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredDebtMember_019e46c4-3ae4-7dde-9f23-1a2cda908730_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Debt</link:label>
    <link:label id="lab_us-gaap_SecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredDebtMember" xlink:to="lab_us-gaap_SecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes_019e46c4-3ae3-78f6-a565-d5cbcee8f990_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Surplus notes</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Surplus Notes</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance_019e46c4-3969-78c2-88dd-e633300bf176_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplement trust target</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Target Balance</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Target Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_019e46c4-3ae4-7858-b2b0-be63b7dce99a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stated margin</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_019e46c4-3a42-7a38-aaf2-fad74dc0084d_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DividendsCommonStockCash_019e46c4-3969-7a45-a10c-dd7bbc45211a_negatedLabel_en-US" xlink:label="lab_us-gaap_DividendsCommonStockCash" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Dividends declared on common shares</link:label>
    <link:label id="lab_us-gaap_DividendsCommonStockCash_label_en-US" xlink:label="lab_us-gaap_DividendsCommonStockCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends, Common Stock, Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DividendsCommonStockCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DividendsCommonStockCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DividendsCommonStockCash" xlink:to="lab_us-gaap_DividendsCommonStockCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquity_019e46c4-3969-7672-8a7f-39152a312987_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total White Mountains&#8217;s common shareholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_019e46c4-3969-754f-8be2-691b142e4eb4_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total White Mountains&#8217;s common shareholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityListingsExchangeAxis_019e46c4-3ae3-7984-a2d1-e87f5f03afc0_terseLabel_en-US" xlink:label="lab_dei_EntityListingsExchangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Listings, Exchange [Axis]</link:label>
    <link:label id="lab_dei_EntityListingsExchangeAxis_label_en-US" xlink:label="lab_dei_EntityListingsExchangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Listings, Exchange [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityListingsExchangeAxis" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityListingsExchangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityListingsExchangeAxis" xlink:to="lab_dei_EntityListingsExchangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember_019e46c4-3a42-75d8-8414-92fa04d21037_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group, Disposed of by Sale, Not Discontinued Operations</link:label>
    <link:label id="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember_label_en-US" xlink:label="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Disposed of by Sale, Not Discontinued Operations [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:to="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow_019e46c4-3969-7050-bc5c-342c8a689f08_terseLabel_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds held in escrow</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow_label_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received, Held In Escrow</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow_documentation_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received, Held In Escrow</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:href="wtm-20260630.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:to="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsAbstract_019e46c4-3969-797d-87e9-10348e1c7bcb_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested_019e46c4-3ae3-7359-9493-c50a411227ce_negatedTerseLabel_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Vested</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested_label_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount Vested</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested_documentation_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount Vested</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:href="wtm-20260630.xsd#wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:to="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum_019e46c4-3ae3-7de7-bafc-5b7355609204_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt service coverage ratio</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Debt Service Coverage Ratio, Minimum</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Debt Service Coverage Ratio, Minimum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:to="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetImpairment_019e46c4-3a42-79f6-9363-d068e4cee4fd_totalLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible asset impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetImpairment_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetImpairment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeCapInterestRate_019e46c4-3969-7c6c-b2a2-2b998416abd8_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeCapInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative, cap interest rate</link:label>
    <link:label id="lab_us-gaap_DerivativeCapInterestRate_label_en-US" xlink:label="lab_us-gaap_DerivativeCapInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Cap Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeCapInterestRate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeCapInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeCapInterestRate" xlink:to="lab_us-gaap_DerivativeCapInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillPurchaseAccountingAdjustments_019e46c4-3969-703c-a014-8258ce773ebd_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_us-gaap_GoodwillPurchaseAccountingAdjustments_label_en-US" xlink:label="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillPurchaseAccountingAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:to="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable_019e46c4-3969-7fab-a3eb-cdd44e9c0732_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Table]</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PerformanceSharesMember_019e46c4-3969-7619-b89e-0c4311a846e1_terseLabel_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Share</link:label>
    <link:label id="lab_us-gaap_PerformanceSharesMember_label_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Shares [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PerformanceSharesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PerformanceSharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PerformanceSharesMember" xlink:to="lab_us-gaap_PerformanceSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019e46c4-3ae3-7001-86c4-69186bffc2f8_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019e46c4-3ae3-75af-804c-485dc3856e3a_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net incurred loss and LAE</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019e46c4-3ae3-71bd-8ba8-2c7fc1bf618a_netLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ChangeInLongTermDebtRollForward_019e46c4-3ae3-7aee-9687-d7abb150f2c0_verboseLabel_en-US" xlink:label="lab_wtm_ChangeInLongTermDebtRollForward" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Kudu, Bamboo and Distinguished Credit Facility</link:label>
    <link:label id="lab_wtm_ChangeInLongTermDebtRollForward_label_en-US" xlink:label="lab_wtm_ChangeInLongTermDebtRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Change in Long-term Debt [Roll Forward]</link:label>
    <link:label id="lab_wtm_ChangeInLongTermDebtRollForward_documentation_en-US" xlink:label="lab_wtm_ChangeInLongTermDebtRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Change in Long-term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ChangeInLongTermDebtRollForward" xlink:href="wtm-20260630.xsd#wtm_ChangeInLongTermDebtRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ChangeInLongTermDebtRollForward" xlink:to="lab_wtm_ChangeInLongTermDebtRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_019e46c4-3a42-7a06-bbb6-0f2686c133fb_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCentralIndexKey"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCentralIndexKey" xlink:to="lab_dei_EntityCentralIndexKey" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfGuaranteeObligationsTable_019e46c4-3969-7f74-ae0d-4eb88a039b64_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Guarantor Obligations [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGuaranteeObligationsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantor Obligation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfGuaranteeObligationsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:to="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year</link:label>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_label_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:to="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation_019e46c4-3969-7ca7-af82-a311adab21c4_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total liabilities held for sale</link:label>
    <link:label id="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation_label_en-US" xlink:label="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation" xlink:to="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCSegmentMember_019e46c4-3a42-740c-a125-87525fdf6b71_terseLabel_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Management (Kudu)</link:label>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCSegmentMember_label_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Kudu Investment Management, LLC - Segment [Member]</link:label>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCSegmentMember_documentation_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Kudu Investment Management, LLC - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:href="wtm-20260630.xsd#wtm_KuduInvestmentManagementLLCSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:to="lab_wtm_KuduInvestmentManagementLLCSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipAxis_019e46c4-3ae4-79a0-a0cf-502a2a868c0d_terseLabel_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:label id="lab_srt_OwnershipAxis_label_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_OwnershipAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipAxis" xlink:to="lab_srt_OwnershipAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_019e46c4-3ae3-7c12-9f11-e222cb537d02_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:to="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_019e46c4-3a42-7a36-985c-1c5225ea1493_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_019e46c4-3969-70d2-83a5-784145f29538_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_019e46c4-3a42-7a49-b825-70b42886ccb6_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FixedMaturitiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FixedMaturitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FixedMaturitiesMember" xlink:to="lab_us-gaap_FixedMaturitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures_019e46c4-3a42-74ad-87d2-1f2935960114_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Target performance shares outstanding (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Nonvested, Number, Before Assumed Forfeitures</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Nonvested, Number, Before Assumed Forfeitures</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_019e46c4-3ae3-7df4-9121-73e998244cea_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_019e46c4-3ae4-7b6a-bb8b-6db04f2b3c13_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis spread on variable rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NotesReceivableInterestRateFairValueDiscount_019e46c4-3ae3-728c-9646-6f345978418e_periodStartLabel_en-US" xlink:label="lab_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning fair value discount</link:label>
    <link:label id="lab_wtm_NotesReceivableInterestRateFairValueDiscount_019e46c4-3ae3-70d8-b217-9e7595a08d4d_periodEndLabel_en-US" xlink:label="lab_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending fair value discount</link:label>
    <link:label id="lab_wtm_NotesReceivableInterestRateFairValueDiscount_label_en-US" xlink:label="lab_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Receivable, Interest Rate Fair Value Discount</link:label>
    <link:label id="lab_wtm_NotesReceivableInterestRateFairValueDiscount_documentation_en-US" xlink:label="lab_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Notes Receivable, Interest Rate Fair Value Discount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:href="wtm-20260630.xsd#wtm_NotesReceivableInterestRateFairValueDiscount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:to="lab_wtm_NotesReceivableInterestRateFairValueDiscount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod2Member_019e46c4-3ae3-7ae9-b796-7df8777ac966_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriod2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 2</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod2Member_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriod2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 2 [Member]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod2Member_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriod2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriod2Member" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriod2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriod2Member" xlink:to="lab_wtm_DebtCovenantPeriod2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentBorrowingBasePercentage_019e46c4-3969-7f79-80af-2b17f48b09b2_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentBorrowingBasePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of borrowing base</link:label>
    <link:label id="lab_wtm_DebtInstrumentBorrowingBasePercentage_label_en-US" xlink:label="lab_wtm_DebtInstrumentBorrowingBasePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Borrowing Base, Percentage</link:label>
    <link:label id="lab_wtm_DebtInstrumentBorrowingBasePercentage_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentBorrowingBasePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Borrowing Base, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentBorrowingBasePercentage" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentBorrowingBasePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentBorrowingBasePercentage" xlink:to="lab_wtm_DebtInstrumentBorrowingBasePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateDomain_019e46c4-3a42-7fa5-806c-4837d606d263_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateDomain" xlink:to="lab_us-gaap_VariableRateDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedStockMember_019e46c4-3a42-7018-b7ee-8accdcc826a1_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted Stock</link:label>
    <link:label id="lab_us-gaap_RestrictedStockMember_label_en-US" xlink:label="lab_us-gaap_RestrictedStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedStockMember" xlink:to="lab_us-gaap_RestrictedStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_019e46c4-3ae3-79d2-bc82-7b41489faf67_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AOCI, after tax</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentsExcludingMediaAlphaMember_019e46c4-3969-75ff-8d03-2a5aacc588a7_terseLabel_en-US" xlink:label="lab_wtm_InvestmentsExcludingMediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments, Excluding MediaAlpha</link:label>
    <link:label id="lab_wtm_InvestmentsExcludingMediaAlphaMember_label_en-US" xlink:label="lab_wtm_InvestmentsExcludingMediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Excluding MediaAlpha [Member]</link:label>
    <link:label id="lab_wtm_InvestmentsExcludingMediaAlphaMember_documentation_en-US" xlink:label="lab_wtm_InvestmentsExcludingMediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investments, Excluding MediaAlpha</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentsExcludingMediaAlphaMember" xlink:href="wtm-20260630.xsd#wtm_InvestmentsExcludingMediaAlphaMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InvestmentsExcludingMediaAlphaMember" xlink:to="lab_wtm_InvestmentsExcludingMediaAlphaMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
    <link:label id="lab_ecd_AllIndividualsMember_label_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Individuals [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllIndividualsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllIndividualsMember" xlink:to="lab_ecd_AllIndividualsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived_019e46c4-3969-78d0-9f0a-dffdae03401b_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash distribution received</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Cash Distribution Received</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Cash Distribution Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_019e46c4-3969-7a40-9d0b-17a98349119e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_019fac60-9b37-7f27-a192-024ff55d6b66_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity contributions</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Equity Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_019e46c4-3a42-7b5d-9c30-44359c904920_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:label id="lab_us-gaap_StatementLineItems_label_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BasesixMember_019f25d1-ee07-7e50-893f-69968308effc_terseLabel_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basesix</link:label>
    <link:label id="lab_wtm_BasesixMember_label_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basesix [Member]</link:label>
    <link:label id="lab_wtm_BasesixMember_documentation_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Basesix</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BasesixMember" xlink:href="wtm-20260630.xsd#wtm_BasesixMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BasesixMember" xlink:to="lab_wtm_BasesixMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_019e46c4-3969-70d4-b9d0-5ec850cc8773_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_019e46c4-3969-76b4-8887-9b62744e245a_terseLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Assets" xlink:to="lab_us-gaap_Assets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrivateEquityFundsMember_019e46c4-3a42-7b6e-a57c-57786570c407_terseLabel_en-US" xlink:label="lab_us-gaap_PrivateEquityFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private equity funds</link:label>
    <link:label id="lab_us-gaap_PrivateEquityFundsMember_label_en-US" xlink:label="lab_us-gaap_PrivateEquityFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity Funds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrivateEquityFundsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrivateEquityFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrivateEquityFundsMember" xlink:to="lab_us-gaap_PrivateEquityFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill_019e46c4-3ae3-7b77-8e8d-5aa7a81cc193_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Including Goodwill</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Including Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodDomain_019e46c4-3969-77ab-8ff1-791f599b207c_terseLabel_en-US" xlink:label="lab_wtm_PerformancePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Period [Domain]</link:label>
    <link:label id="lab_wtm_PerformancePeriodDomain_label_en-US" xlink:label="lab_wtm_PerformancePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Period [Domain]</link:label>
    <link:label id="lab_wtm_PerformancePeriodDomain_documentation_en-US" xlink:label="lab_wtm_PerformancePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">This element represents minimum performance period for right to receive performance share from the entity.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PerformancePeriodDomain" xlink:href="wtm-20260630.xsd#wtm_PerformancePeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PerformancePeriodDomain" xlink:to="lab_wtm_PerformancePeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Regulation114Member_019e46c4-3ae3-776f-9d83-2a94fb15f896_terseLabel_en-US" xlink:label="lab_wtm_Regulation114Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Regulation 114</link:label>
    <link:label id="lab_wtm_Regulation114Member_label_en-US" xlink:label="lab_wtm_Regulation114Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Regulation 114 [Member]</link:label>
    <link:label id="lab_wtm_Regulation114Member_documentation_en-US" xlink:label="lab_wtm_Regulation114Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Regulation 114</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Regulation114Member" xlink:href="wtm-20260630.xsd#wtm_Regulation114Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Regulation114Member" xlink:to="lab_wtm_Regulation114Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_019e46c4-3a42-7898-beeb-227b60a5948c_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesByIndustryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:to="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember_019e46c4-3969-70d8-88bd-e315ece2f62c_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Not Primary Beneficiary</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Not Primary Beneficiary [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:to="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_019e46c4-3ae3-78f0-bf47-e5e9174b417a_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Segments</link:label>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_label_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Segments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingSegmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingSegmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingSegmentsMember" xlink:to="lab_us-gaap_OperatingSegmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019e46c4-3ae4-7b6e-ad48-c20f71b3eac1_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities acquired</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_019e46c4-3969-7468-8595-bdcc51cdbdfe_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Share-Based Incentive Compensation Plans</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FidusReLtd.Member_019e46c4-3a42-7c39-96b1-5ac6f0a11e92_terseLabel_en-US" xlink:label="lab_wtm_FidusReLtd.Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fidus Re Ltd.</link:label>
    <link:label id="lab_wtm_FidusReLtd.Member_label_en-US" xlink:label="lab_wtm_FidusReLtd.Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fidus Re Ltd. [Member]</link:label>
    <link:label id="lab_wtm_FidusReLtd.Member_documentation_en-US" xlink:label="lab_wtm_FidusReLtd.Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fidus Re Ltd. [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FidusReLtd.Member" xlink:href="wtm-20260630.xsd#wtm_FidusReLtd.Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FidusReLtd.Member" xlink:to="lab_wtm_FidusReLtd.Member" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoMember_terseLabel_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO</link:label>
    <link:label id="lab_ecd_PeoMember_label_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoMember" xlink:to="lab_ecd_PeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss_019e46c4-3a42-79d1-a77e-b933dc3f8813_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net&#160;Foreign Currency Gains (Losses)</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Net Foreign Currency Gain (Loss)</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Net Foreign Currency Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:to="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses_019e46c4-3ae3-7e0f-8805-3adf34c49951_terseLabel_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other underwriting expenses</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses_label_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Other Underwriting Expenses</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses_documentation_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Other Underwriting Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:href="wtm-20260630.xsd#wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:to="lab_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_019e46c4-3ae3-7647-b78f-318cdc646cb0_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskReinsurerDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:to="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_019e46c4-3a42-74eb-b37d-5be6a15455c5_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer Concentration Risk</link:label>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurerConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:to="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Goodwill_019e46c4-3969-7412-9fc5-57285e9cd92b_terseLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:label id="lab_us-gaap_Goodwill_019e46c4-3969-7762-b204-6095a8132258_netLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Net Carrying Value</link:label>
    <link:label id="lab_us-gaap_Goodwill_019e46c4-3969-7697-8947-b1c47814926c_periodStartLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Goodwill, beginning Balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_019e46c4-3969-78b1-97df-7296036b6a00_periodEndLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Goodwill, ending balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Goodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestAxis_019e46c4-3a42-73cd-a5a7-3bf275428e23_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestAxis_label_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingAMBestAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestAxis" xlink:to="lab_srt_CreditRatingAMBestAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember_019e46c4-3969-72fc-88b0-6ec41a33114f_terseLabel_en-US" xlink:label="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private preferred securities</link:label>
    <link:label id="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember_label_en-US" xlink:label="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mandatorily Redeemable Preferred Securities [Member]</link:label>
    <link:label id="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember_documentation_en-US" xlink:label="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mandatorily Redeemable Preferred Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:href="wtm-20260630.xsd#wtm_MandatorilyRedeemablePreferredSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:to="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsMember_019e46c4-3a42-7102-9204-6f987c4d782c_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_019e46c4-3ae3-75d2-a0a7-3323e92459a7_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility</link:label>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable_019e46c4-3ae3-7d62-9de1-64e022c0c385_terseLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in premiums and commissions payable</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Premiums and Commissions Payable</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Premiums and Commissions Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:href="wtm-20260630.xsd#wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:to="lab_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_019e46c4-3a42-7d19-9a73-1b7156d48cdb_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Shareholders' Equity</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019e46c4-3ae3-7464-8df2-4343f7a7479d_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, outstanding shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesOutstanding" xlink:to="lab_us-gaap_CommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgDiscLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgDiscLineItems" xlink:to="lab_ecd_AwardTmgDiscLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_019e46c4-3a42-72c7-ae78-bbec80fbf4af_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of the fair value and carrying value of financial instruments</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByBalanceSheetGroupingTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_019e46c4-3a42-74b0-9ef6-0a7d1dbe5bcf_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt securities issued by corporations</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_019e46c4-3ae3-7ec5-a10a-b55770d8ccff_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (loss) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_019f87ef-c075-7e67-a311-5fc510ffaa68_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other equity method eligible investments more than or equal to 50.0%</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_label_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, More Than or Equal to Fifty Percent [Member]</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_documentation_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, More Than Fifty Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:href="wtm-20260630.xsd#wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:to="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets_019e46c4-3969-7d59-a1ec-98c4bc4d1e78_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Assets Acquired, Other Assets</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Assets Acquired, Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments_019e46c4-3a42-7337-8aec-2ba287cf40a2_totalLabel_en-US" xlink:label="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments_label_en-US" xlink:label="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets, Measurement Period Adjustments</link:label>
    <link:label id="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments_documentation_en-US" xlink:label="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets, Measurement Period Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:href="wtm-20260630.xsd#wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:to="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_019e46c4-3ae3-7208-bfeb-bfe0169af036_terseLabel_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net unrealized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_019e46c4-3ae3-769f-bdc6-a17b2211823a_verboseLabel_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total net unrealized investment gains (losses) recognized during the period on Level 3 investments held at the end of period</link:label>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrealizedGainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnrealizedGainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnrealizedGainLossOnInvestments" xlink:to="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AmortizationOfOtherIntangibleAssets_019e46c4-3969-75bb-b25c-0a67f4cb5c72_terseLabel_en-US" xlink:label="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of other intangible assets</link:label>
    <link:label id="lab_wtm_AmortizationOfOtherIntangibleAssets_label_en-US" xlink:label="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Other Intangible Assets</link:label>
    <link:label id="lab_wtm_AmortizationOfOtherIntangibleAssets_documentation_en-US" xlink:label="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amortization of Other Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AmortizationOfOtherIntangibleAssets" xlink:href="wtm-20260630.xsd#wtm_AmortizationOfOtherIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AmortizationOfOtherIntangibleAssets" xlink:to="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019e46c4-3969-7fb8-aa52-8619e7702b19_negatedLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:to="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable_019e46c4-3ae3-702b-8716-16402eac9544_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Table]</link:label>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable_label_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation, Less-than-Wholly-Owned Subsidiary, Parent Ownership Interest, Effect of Change [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:to="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipDomain_019e46c4-3a42-7d2f-9494-ce310df027c6_terseLabel_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:label id="lab_srt_OwnershipDomain_label_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_OwnershipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipDomain" xlink:to="lab_srt_OwnershipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain_019e46c4-3ae3-7316-a0e4-18b4afe8bbdb_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesTradingUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:to="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_019e46c4-3ae3-7a0a-8b3d-fedebdf1d672_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskAxis" xlink:to="lab_us-gaap_CededCreditRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_019e46c4-3ae3-735d-b52a-5bdfb5b62115_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net written premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_019e46c4-3a42-7d61-b0c5-f385cf2f4258_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based Payment Arrangement [Abstract]</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments_019e46c4-3969-7dc9-ae0b-b8ee3a30c9ee_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of fixed maturity investments</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments_label_en-US" xlink:label="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Trading Fixed Maturities Investments</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments_documentation_en-US" xlink:label="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">The cash outflow to acquire fixed maturity and convertible fixed maturity investments classified as trading.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:href="wtm-20260630.xsd#wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:to="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EuroInterbankOfferedRateEURIBORMember_019e46c4-3a42-7269-a0ec-27b8c9a30c26_terseLabel_en-US" xlink:label="lab_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Euro Interbank Offered Rate (EURIBOR)</link:label>
    <link:label id="lab_wtm_EuroInterbankOfferedRateEURIBORMember_label_en-US" xlink:label="lab_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Euro Interbank Offered Rate (EURIBOR) [Member]</link:label>
    <link:label id="lab_wtm_EuroInterbankOfferedRateEURIBORMember_documentation_en-US" xlink:label="lab_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Euro Interbank Offered Rate (EURIBOR)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:href="wtm-20260630.xsd#wtm_EuroInterbankOfferedRateEURIBORMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:to="lab_wtm_EuroInterbankOfferedRateEURIBORMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_019e46c4-3a42-73f2-a624-a3b901581b45_terseLabel_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Limited liability company or limited partnership, members or limited partners, ownership interest</link:label>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_label_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Members or Limited Partners, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:to="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal_019e46c4-3a42-7cfd-a1f7-4bdbafb52edf_terseLabel_en-US" xlink:label="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net gain</link:label>
    <link:label id="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal_label_en-US" xlink:label="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Not Discontinued Operation, Net Gain (Loss) on Disposal</link:label>
    <link:label id="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal_documentation_en-US" xlink:label="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disposal Group, Not Discontinued Operation, Net Gain (Loss) on Disposal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:href="wtm-20260630.xsd#wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:to="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_019e46c4-3ae4-7289-a047-20b96a99b46d_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of significant equity method eligible investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UtilitiesSectorMember_019e46c4-3a42-7d7b-a9bd-c785f97bfb38_terseLabel_en-US" xlink:label="lab_wtm_UtilitiesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Utilities</link:label>
    <link:label id="lab_wtm_UtilitiesSectorMember_label_en-US" xlink:label="lab_wtm_UtilitiesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Utilities Sector [Member]</link:label>
    <link:label id="lab_wtm_UtilitiesSectorMember_documentation_en-US" xlink:label="lab_wtm_UtilitiesSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Utilities Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_UtilitiesSectorMember" xlink:href="wtm-20260630.xsd#wtm_UtilitiesSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_UtilitiesSectorMember" xlink:to="lab_wtm_UtilitiesSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue_019e46c4-3ae3-788f-865f-70a33dbc5de9_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling interest acquired</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquisition of Less than 100 Percent, Noncontrolling Interest, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:to="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:to="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019e46c4-3a42-7b75-803b-698800efa09c_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total other intangible assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember_019e46c4-3969-7f4e-80ff-27f1744eeec0_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total agency</link:label>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember_label_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage-Backed Security, Issued by US Government-Sponsored Enterprise [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:to="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DavidShieldPassportCardMember_019e46c4-3969-7621-b76f-040083df2cfb_terseLabel_en-US" xlink:label="lab_wtm_DavidShieldPassportCardMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PassportCard/DavidShield</link:label>
    <link:label id="lab_wtm_DavidShieldPassportCardMember_label_en-US" xlink:label="lab_wtm_DavidShieldPassportCardMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">DavidShield &amp; PassportCard [Member]</link:label>
    <link:label id="lab_wtm_DavidShieldPassportCardMember_documentation_en-US" xlink:label="lab_wtm_DavidShieldPassportCardMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">DavidShield &amp; PassportCard [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DavidShieldPassportCardMember" xlink:href="wtm-20260630.xsd#wtm_DavidShieldPassportCardMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DavidShieldPassportCardMember" xlink:to="lab_wtm_DavidShieldPassportCardMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsegmentsDomain_019e46c4-3969-725f-acf8-a939828e17d2_terseLabel_en-US" xlink:label="lab_us-gaap_SubsegmentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsegments [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsegmentsDomain_label_en-US" xlink:label="lab_us-gaap_SubsegmentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsegments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsegmentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsegmentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsegmentsDomain" xlink:to="lab_us-gaap_SubsegmentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock_019e46c4-3ae4-783e-a119-10097c55fb0f_negatedNetLabel_en-US" xlink:label="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:role="http://www.xbrl.org/2009/role/negatedNetLabel" xlink:type="resource" xml:lang="en-US">Dividends declared, net of restricted common share amounts</link:label>
    <link:label id="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock_label_en-US" xlink:label="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends, Common Stock, Cash, Net of Restricted Stock</link:label>
    <link:label id="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock_documentation_en-US" xlink:label="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Dividends, Common Stock, Cash, Net of Restricted Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:href="wtm-20260630.xsd#wtm_DividendsCommonStockCashNetOfRestrictedStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:to="lab_wtm_DividendsCommonStockCashNetOfRestrictedStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019e46c4-3ae3-7818-acdc-838abde07b07_negatedLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Sales and distributions</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Sales</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment_019fc6ee-e460-7b71-abe8-420d2ad12235_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_019e46c4-3a42-7ecd-b8c9-e79cfe8e78b0_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_019e46c4-3a42-715e-8846-f088614e6aa1_negatedTerseLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in accrued incentive compensation &#8212; Other Operations</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Accrued Bonuses</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Accrued Bonuses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInAccruedBonuses" xlink:href="wtm-20260630.xsd#wtm_IncreaseDecreaseInAccruedBonuses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IncreaseDecreaseInAccruedBonuses" xlink:to="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AMBestAMinusRatingMember_019e46c4-3969-7f5a-adc0-9bb3eb923d45_terseLabel_en-US" xlink:label="lab_srt_AMBestAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">A- to A</link:label>
    <link:label id="lab_srt_AMBestAMinusRatingMember_label_en-US" xlink:label="lab_srt_AMBestAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AM Best, A- Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AMBestAMinusRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AMBestAMinusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AMBestAMinusRatingMember" xlink:to="lab_srt_AMBestAMinusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriodDomain_019e46c4-3a42-7960-a15e-7975fbc80bd7_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant Period [Domain]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriodDomain_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant Period [Domain]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriodDomain_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant Period [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriodDomain" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriodDomain" xlink:to="lab_wtm_DebtCovenantPeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_019f25b7-31ed-7dd6-aa60-ae3c6b787248_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix</link:label>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_label_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryBasesixMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryBasesixMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryBasesixMember" xlink:to="lab_wtm_SubsidiaryBasesixMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCountryMember_019e46c4-3ae3-7530-8e4c-e54ee9e6e804_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign</link:label>
    <link:label id="lab_us-gaap_ForeignCountryMember_label_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCountryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCountryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCountryMember" xlink:to="lab_us-gaap_ForeignCountryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DelayedDrawTermLoanMember_019e46c4-3ae3-7987-b35b-1c12680fc66a_terseLabel_en-US" xlink:label="lab_us-gaap_DelayedDrawTermLoanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Delayed Draw Term Loan</link:label>
    <link:label id="lab_us-gaap_DelayedDrawTermLoanMember_label_en-US" xlink:label="lab_us-gaap_DelayedDrawTermLoanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Delayed Draw Term Loan (DDTL) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DelayedDrawTermLoanMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DelayedDrawTermLoanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DelayedDrawTermLoanMember" xlink:to="lab_us-gaap_DelayedDrawTermLoanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019e46c4-3ae3-7d7d-9cec-884250cf9ab2_terseLabel_en-US" xlink:label="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage and asset-backed securities and collateralized loan obligations</link:label>
    <link:label id="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember_label_en-US" xlink:label="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities And Collateralized Loan Obligations [Member]</link:label>
    <link:label id="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember_documentation_en-US" xlink:label="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities And Collateralized Loan Obligations</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:href="wtm-20260630.xsd#wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:to="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence_019e46c4-3969-7797-9272-64abad37f2fd_terseLabel_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical presence</link:label>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence_label_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Geographical Presence</link:label>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence_documentation_en-US" xlink:label="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Geographical Presence</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:href="wtm-20260630.xsd#wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:to="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance_019e46c4-3ae3-734c-ab3e-f1c3795e8cf5_terseLabel_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding par value of policies assumed (in millions)</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance_label_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Principal Balance</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance_documentation_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Principal Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:href="wtm-20260630.xsd#wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:to="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CitibankLOCFacilityMember_019e46c4-3a42-7311-91e9-73645fc50b28_terseLabel_en-US" xlink:label="lab_wtm_CitibankLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Citibank LOC Facility</link:label>
    <link:label id="lab_wtm_CitibankLOCFacilityMember_label_en-US" xlink:label="lab_wtm_CitibankLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Citibank LOC Facility [Member]</link:label>
    <link:label id="lab_wtm_CitibankLOCFacilityMember_documentation_en-US" xlink:label="lab_wtm_CitibankLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Citibank LOC Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_CitibankLOCFacilityMember" xlink:href="wtm-20260630.xsd#wtm_CitibankLOCFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_CitibankLOCFacilityMember" xlink:to="lab_wtm_CitibankLOCFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedManagingMember_019e46c4-3969-7249-8394-5db818815932_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedManagingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Managing General Agent</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedManagingMember_label_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedManagingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Managing [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedManagingMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedManagingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Managing General Agent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryDistinguishedManagingMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryDistinguishedManagingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryDistinguishedManagingMember" xlink:to="lab_wtm_SubsidiaryDistinguishedManagingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_019e46c4-3a42-70c6-abd1-04a59a4405b5_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign government and agency obligations</link:label>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Security, Government, Non-US [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BAMSurplusNotesMember_019e46c4-3ae3-7d78-a896-c2c4ca082a80_terseLabel_en-US" xlink:label="lab_wtm_BAMSurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BAM Surplus Notes</link:label>
    <link:label id="lab_wtm_BAMSurplusNotesMember_label_en-US" xlink:label="lab_wtm_BAMSurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BAM Surplus Notes [Member]</link:label>
    <link:label id="lab_wtm_BAMSurplusNotesMember_documentation_en-US" xlink:label="lab_wtm_BAMSurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">BAM Surplus Note [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BAMSurplusNotesMember" xlink:href="wtm-20260630.xsd#wtm_BAMSurplusNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BAMSurplusNotesMember" xlink:to="lab_wtm_BAMSurplusNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:to="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019e46c4-3a42-724a-8f71-e6f5ef420971_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, issued shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember_019e46c4-3969-7b40-80db-1d386210e7f8_terseLabel_en-US" xlink:label="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Equity</link:label>
    <link:label id="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember_label_en-US" xlink:label="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Equity Including Noncontrolling Interest [Member]</link:label>
    <link:label id="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember_documentation_en-US" xlink:label="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Equity Including Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:href="wtm-20260630.xsd#wtm_TotalEquityIncludingNoncontrollingInterestMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:to="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019e46c4-3ae3-76c9-9c9b-a09b4ba7a06d_periodStartLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019e46c4-3ae3-7987-9b83-53cde0eaa698_periodEndLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AerospaceDefenseGovernmentSectorMember_019e46c4-3ae3-7d00-a73a-5b671751a4b6_verboseLabel_en-US" xlink:label="lab_wtm_AerospaceDefenseGovernmentSectorMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Aerospace/Defense/Government</link:label>
    <link:label id="lab_wtm_AerospaceDefenseGovernmentSectorMember_label_en-US" xlink:label="lab_wtm_AerospaceDefenseGovernmentSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aerospace, Defense Government Sector [Member]</link:label>
    <link:label id="lab_wtm_AerospaceDefenseGovernmentSectorMember_documentation_en-US" xlink:label="lab_wtm_AerospaceDefenseGovernmentSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Aerospace Defense Government [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AerospaceDefenseGovernmentSectorMember" xlink:href="wtm-20260630.xsd#wtm_AerospaceDefenseGovernmentSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AerospaceDefenseGovernmentSectorMember" xlink:to="lab_wtm_AerospaceDefenseGovernmentSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized_019e46c4-3a42-7df7-b069-078fd9e973ee_negatedTerseLabel_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Expense recognized</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized_label_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount of Expense Recognized</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized_documentation_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount of Expense Recognized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:href="wtm-20260630.xsd#wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:to="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock_019e46c4-3a42-7bb9-85a8-08820eb296e2_terseLabel_en-US" xlink:label="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of nominal and fair value of notes receivable</link:label>
    <link:label id="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock_label_en-US" xlink:label="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Nominal and Fair Value of Notes Receivable [Table Text Block]</link:label>
    <link:label id="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock_documentation_en-US" xlink:label="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule of Nominal and Fair Value of Notes Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:to="lab_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductsAndServicesDomain_019e46c4-3ae4-794f-8084-3eff1dffbd00_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries_019e46c4-3a42-7909-aa74-090ad3c73346_terseLabel_en-US" xlink:label="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net distributions</link:label>
    <link:label id="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries_label_en-US" xlink:label="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From Return Of Capital On Subsidiaries</link:label>
    <link:label id="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries_documentation_en-US" xlink:label="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From Return Of Capital On Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:href="wtm-20260630.xsd#wtm_ProceedsFromReturnOfCapitalOnSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:to="lab_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_019e46c4-3ae3-79d1-bd4b-eb488fc710d7_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityLineItems" xlink:to="lab_us-gaap_VariableInterestEntityLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsOtherMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet_019e46c4-3ae4-7012-af00-700844fd38af_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain (loss) on fair value of derivative instruments</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments Not Designated as Hedging Instruments, Gain (Loss), Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet" xlink:to="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity_019e46c4-3ae3-7bac-90ae-bddb4a984b45_negatedLabel_en-US" xlink:label="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Adjustments of redeemable noncontrolling interest</link:label>
    <link:label id="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity_label_en-US" xlink:label="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stockholders' Equity, Adjustments To Temporary Equity</link:label>
    <link:label id="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity_documentation_en-US" xlink:label="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stockholders' Equity, Adjustments To Temporary Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:href="wtm-20260630.xsd#wtm_StockholdersEquityAdjustmentsToTemporaryEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:to="lab_wtm_StockholdersEquityAdjustmentsToTemporaryEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrTerminationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Termination Date</link:label>
    <link:label id="lab_ecd_TrdArrTerminationDate_label_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Termination Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrTerminationDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrTerminationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrTerminationDate" xlink:to="lab_ecd_TrdArrTerminationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestTable_019e46c4-3a42-7344-9783-9324fe27faf3_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Table]</link:label>
    <link:label id="lab_us-gaap_MinorityInterestTable_label_en-US" xlink:label="lab_us-gaap_MinorityInterestTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestTable" xlink:to="lab_us-gaap_MinorityInterestTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_019e46c4-3969-7fd0-9f47-bd28a0a4ac1f_terseLabel_en-US" xlink:label="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payments of principal and interest</link:label>
    <link:label id="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_label_en-US" xlink:label="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments of Notes Receivable, Principal and Interest</link:label>
    <link:label id="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_documentation_en-US" xlink:label="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments of Notes Receivable, Principal and Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:href="wtm-20260630.xsd#wtm_PaymentsOfNotesReceivablePrincipalAndInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:to="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_019e46c4-3969-7e39-8b38-b07e22bde36f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock_019e46c4-3ae3-7ec2-8c33-4555c425f16f_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held for Sale</link:label>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations, Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:to="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_019f25c8-eabc-7d98-802e-123507aee6b0_terseLabel_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC</link:label>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_label_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC [Member]</link:label>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_documentation_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HawkeyeElectricLLCMember" xlink:href="wtm-20260630.xsd#wtm_HawkeyeElectricLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HawkeyeElectricLLCMember" xlink:to="lab_wtm_HawkeyeElectricLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage_019e46c4-3a42-7f96-9e46-ad1a0d3909b3_terseLabel_en-US" xlink:label="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Member surplus contributions, insurance premium charges, percentage</link:label>
    <link:label id="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage_label_en-US" xlink:label="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Member Surplus Contributions, Insurance Premium Charges, Percentage</link:label>
    <link:label id="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage_documentation_en-US" xlink:label="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Member Surplus Contributions, Insurance Premium Charges, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:href="wtm-20260630.xsd#wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:to="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019e46c4-3ae3-7052-9e5e-d2c7a6a5089f_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current year losses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IntangibleAssetsGrossIncludingGoodwill_019e46c4-3a42-735e-827f-660fad7580e2_totalLabel_en-US" xlink:label="lab_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total goodwill and other intangible assets</link:label>
    <link:label id="lab_wtm_IntangibleAssetsGrossIncludingGoodwill_label_en-US" xlink:label="lab_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Gross (Including Goodwill)</link:label>
    <link:label id="lab_wtm_IntangibleAssetsGrossIncludingGoodwill_documentation_en-US" xlink:label="lab_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets, Gross (Including Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:href="wtm-20260630.xsd#wtm_IntangibleAssetsGrossIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:to="lab_wtm_IntangibleAssetsGrossIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodOneMember_019e46c4-3a42-7899-a0c8-1645b9f10c75_verboseLabel_en-US" xlink:label="lab_wtm_PerformancePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">2024 &#8211; 2026</link:label>
    <link:label id="lab_wtm_PerformancePeriodOneMember_label_en-US" xlink:label="lab_wtm_PerformancePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Period One [Member]</link:label>
    <link:label id="lab_wtm_PerformancePeriodOneMember_documentation_en-US" xlink:label="lab_wtm_PerformancePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Range Of Performance Cycle From 2017-2019 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PerformancePeriodOneMember" xlink:href="wtm-20260630.xsd#wtm_PerformancePeriodOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PerformancePeriodOneMember" xlink:to="lab_wtm_PerformancePeriodOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember_019e46c4-3a42-7caa-ac18-89b3a0abd53f_terseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">P&amp;C Insurance and Reinsurance (Ark/WM Outrigger)</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember_label_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited/Outrigger [Member]</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember_documentation_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited/Outrigger</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:href="wtm-20260630.xsd#wtm_ArkInsuranceHoldingsLimitedOutriggerMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardGrantDateFairValue_terseLabel_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value as of Grant Date</link:label>
    <link:label id="lab_ecd_AwardGrantDateFairValue_label_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardGrantDateFairValue" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardGrantDateFairValue" xlink:to="lab_ecd_AwardGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited_019e46c4-3969-7027-8c1c-719805caaaf0_negatedLabel_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Forfeited</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited_label_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount Forfeited</link:label>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited_documentation_en-US" xlink:label="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">The total reduction to unamortized compensation cost for performance shares forfeited during the period.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:href="wtm-20260630.xsd#wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:to="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10_019e46c4-3a42-7c46-ad2e-48cb88ef1fbd_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:to="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable_019e46c4-3ae3-77e4-928a-899fd272fc3c_negatedTerseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Premiums and commissions payable</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Premiums and Commissions Payable</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Premiums and Commissions Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:to="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AMBestBPlusPlusRatingMember_019e46c4-3969-755c-8e85-01b441ed92d8_terseLabel_en-US" xlink:label="lab_srt_AMBestBPlusPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">B++ or lower and not rated</link:label>
    <link:label id="lab_srt_AMBestBPlusPlusRatingMember_label_en-US" xlink:label="lab_srt_AMBestBPlusPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AM Best, B++ Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AMBestBPlusPlusRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AMBestBPlusPlusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AMBestBPlusPlusRatingMember" xlink:to="lab_srt_AMBestBPlusPlusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_019e46c4-3969-703b-bcec-6cab9b166436_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Temporary Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Temporary Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInTemporaryEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTableTextBlock" xlink:to="lab_ecd_PvpTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent_019e46c4-3a42-762e-a81b-7bb9caf05e2d_terseLabel_en-US" xlink:label="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued incentive compensation</link:label>
    <link:label id="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accrued Bonuses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedBonusesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum_019e46c4-3a42-7421-804d-6e299ec8ace2_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt to capital requirement</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Debt To Capital, Maximum</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Debt To Capital, Maximum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentCovenantDebtToCapitalMaximum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:to="lab_wtm_DebtInstrumentCovenantDebtToCapitalMaximum" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
    <link:label id="lab_ecd_TrdArrDuration_label_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Duration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrDuration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrDuration" xlink:to="lab_ecd_TrdArrDuration" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentNumberOfTransactions_019e46c4-3a42-7154-b106-4c951b65419a_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentNumberOfTransactions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of transactions</link:label>
    <link:label id="lab_wtm_DebtInstrumentNumberOfTransactions_label_en-US" xlink:label="lab_wtm_DebtInstrumentNumberOfTransactions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Number of Transactions</link:label>
    <link:label id="lab_wtm_DebtInstrumentNumberOfTransactions_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentNumberOfTransactions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Number of Transactions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentNumberOfTransactions" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentNumberOfTransactions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentNumberOfTransactions" xlink:to="lab_wtm_DebtInstrumentNumberOfTransactions" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsAxis_019e46c4-3969-7909-87f9-e85deae8b3bc_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:label id="lab_srt_ConsolidationItemsAxis_label_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsAxis" xlink:to="lab_srt_ConsolidationItemsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_019e46c4-3a42-73c3-8b6b-224d8e05e1a9_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_019e46c4-3ae3-72a9-999d-741d156d23d6_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserve_019e46c4-3a42-7ffb-8ee1-4b2e5c3b9f82_terseLabel_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest reserve account</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserve_label_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserve_documentation_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserve" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShortTermInvestmentsInterestReserve" xlink:href="wtm-20260630.xsd#wtm_ShortTermInvestmentsInterestReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShortTermInvestmentsInterestReserve" xlink:to="lab_wtm_ShortTermInvestmentsInterestReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock_019e46c4-3ae3-7235-a67a-ed28b26bf649_terseLabel_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation and Significant Accounting Policies</link:label>
    <link:label id="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Organization, Consolidation, Basis of Presentation, Business Description and Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BambooCRVMember_019e46c4-3a42-7116-94b2-e82f34742da3_terseLabel_en-US" xlink:label="lab_wtm_BambooCRVMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bamboo CRV</link:label>
    <link:label id="lab_wtm_BambooCRVMember_label_en-US" xlink:label="lab_wtm_BambooCRVMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bamboo CRV [Member]</link:label>
    <link:label id="lab_wtm_BambooCRVMember_documentation_en-US" xlink:label="lab_wtm_BambooCRVMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bamboo CRV</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BambooCRVMember" xlink:href="wtm-20260630.xsd#wtm_BambooCRVMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooCRVMember" xlink:to="lab_wtm_BambooCRVMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:to="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019e46c4-3969-759f-9f0f-101c248c16d2_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, acquisition date fair value</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_019e46c4-3969-79c6-973f-1e5119e8fdf3_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AccruedExpenseRollForward_019e46c4-3ae3-7de4-a012-b79d7e272097_terseLabel_en-US" xlink:label="lab_wtm_AccruedExpenseRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued Expense</link:label>
    <link:label id="lab_wtm_AccruedExpenseRollForward_label_en-US" xlink:label="lab_wtm_AccruedExpenseRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accrued Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AccruedExpenseRollForward" xlink:href="wtm-20260630.xsd#wtm_AccruedExpenseRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AccruedExpenseRollForward" xlink:to="lab_wtm_AccruedExpenseRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestDomain_019e46c4-3ae3-72fc-be2c-e9b3de61c37b_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestDomain_label_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingAMBestDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestDomain" xlink:to="lab_srt_CreditRatingAMBestDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10_019e46c4-3ae3-7c64-a2e1-fc8f43afca51_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_019e46c4-3ae3-7fa7-90df-65801f7276c6_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Vesting Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillRollForward_019e46c4-3969-7846-8b1a-2737a56ff734_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillRollForward" xlink:to="lab_us-gaap_GoodwillRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019e46c4-3a42-74c1-83e5-73fc620a9cdc_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradeNamesMember_019e46c4-3ae3-79d5-bb24-5dc7e92ece0a_terseLabel_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trade names</link:label>
    <link:label id="lab_us-gaap_TradeNamesMember_label_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trade Names [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradeNamesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradeNamesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradeNamesMember" xlink:to="lab_us-gaap_TradeNamesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_019e46c4-3ae3-7f91-8ea7-8e83c43c31d9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of mortgage and asset-backed securities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019e46c4-3a42-79fe-a15e-8d201cce163d_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019e46c4-3969-748d-962f-1b5749e9ee2b_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year 5 through 10</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year 5 through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:to="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_019fd324-4ee2-7366-b5d6-95dc4cc6fc94_terseLabel_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee revenues</link:label>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_label_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions And Fees, Adjusted</link:label>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_documentation_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Insurance Commissions And Fees, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:href="wtm-20260630.xsd#wtm_InsuranceCommissionsAndFeesAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:to="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_019e46c4-3a42-78e7-97b0-91c8e9648738_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value of Financial Instruments</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_019e46c4-3a42-7bb1-bf98-c5770ddaf5fd_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized&#160;Cost</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_019e46c4-3a42-7f25-8c97-827a3d8f0f3f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BroadStreetMember_019e46c4-3a42-7e23-a1d6-83cab18ad9c9_terseLabel_en-US" xlink:label="lab_wtm_BroadStreetMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BroadStreet</link:label>
    <link:label id="lab_wtm_BroadStreetMember_label_en-US" xlink:label="lab_wtm_BroadStreetMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BroadStreet [Member]</link:label>
    <link:label id="lab_wtm_BroadStreetMember_documentation_en-US" xlink:label="lab_wtm_BroadStreetMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">BroadStreet</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BroadStreetMember" xlink:href="wtm-20260630.xsd#wtm_BroadStreetMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BroadStreetMember" xlink:to="lab_wtm_BroadStreetMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetPledgedAsCollateralMember_019e46c4-3a42-7f98-af4c-cd624b45ef89_terseLabel_en-US" xlink:label="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Pledged as Collateral</link:label>
    <link:label id="lab_us-gaap_AssetPledgedAsCollateralMember_label_en-US" xlink:label="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Pledged as Collateral [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetPledgedAsCollateralMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetPledgedAsCollateralMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetPledgedAsCollateralMember" xlink:to="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners_019e46c4-3ae3-719e-a0e0-1416576394f4_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling percentage</link:label>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners_label_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Noncontrolling Owner</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:to="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementGeographicalAxis_019e46c4-3ae3-7361-bbb6-c27093bbd4fb_terseLabel_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:label id="lab_srt_StatementGeographicalAxis_label_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementGeographicalAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StatementGeographicalAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementGeographicalAxis" xlink:to="lab_srt_StatementGeographicalAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCash_019e46c4-3a42-7be0-bc30-8f4c9409bdb5_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCash_label_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCash" xlink:to="lab_us-gaap_RestrictedCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerLiability_019f5951-e064-7d08-8e23-006ef568f3c8_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract liabilities</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerLiability_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerLiability" xlink:to="lab_us-gaap_ContractWithCustomerLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_StandardPoorsOtherMember_019e46c4-3ae3-7261-b84c-9fe110ab800b_terseLabel_en-US" xlink:label="lab_wtm_StandardPoorsOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_wtm_StandardPoorsOtherMember_label_en-US" xlink:label="lab_wtm_StandardPoorsOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, Other [Member]</link:label>
    <link:label id="lab_wtm_StandardPoorsOtherMember_documentation_en-US" xlink:label="lab_wtm_StandardPoorsOtherMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_StandardPoorsOtherMember" xlink:href="wtm-20260630.xsd#wtm_StandardPoorsOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_StandardPoorsOtherMember" xlink:to="lab_wtm_StandardPoorsOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_019e46c4-3a42-7632-8115-36e1d894e9a2_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">NAV</link:label>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:to="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherFundsMember_019e46c4-3969-7265-8b59-93282254ac18_terseLabel_en-US" xlink:label="lab_wtm_OtherFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_wtm_OtherFundsMember_label_en-US" xlink:label="lab_wtm_OtherFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Funds [Member]</link:label>
    <link:label id="lab_wtm_OtherFundsMember_documentation_en-US" xlink:label="lab_wtm_OtherFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherFundsMember" xlink:href="wtm-20260630.xsd#wtm_OtherFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherFundsMember" xlink:to="lab_wtm_OtherFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding_019e46c4-3a42-70de-8162-08619447f06f_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic units outstanding percentage</link:label>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding_label_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Percentage of Basic Units Outstanding</link:label>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Percentage of Basic Units Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:to="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_019e46c4-3969-79aa-bc4e-a1932cb773d9_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LegalEntityAxis_019e46c4-3969-7e05-a1b1-7a1e276bec0d_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:label id="lab_dei_LegalEntityAxis_label_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LegalEntityAxis" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_LegalEntityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LegalEntityAxis" xlink:to="lab_dei_LegalEntityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RevenuesAdjusted_019e46c4-3ae3-7c89-ae52-819f2e736136_totalLabel_en-US" xlink:label="lab_wtm_RevenuesAdjusted" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_wtm_RevenuesAdjusted_label_en-US" xlink:label="lab_wtm_RevenuesAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues, Adjusted</link:label>
    <link:label id="lab_wtm_RevenuesAdjusted_documentation_en-US" xlink:label="lab_wtm_RevenuesAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revenues, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_RevenuesAdjusted" xlink:href="wtm-20260630.xsd#wtm_RevenuesAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_RevenuesAdjusted" xlink:to="lab_wtm_RevenuesAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e46c4-3a42-751f-8862-7e3b86d2441a_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Cash balance at beginning of period (includes restricted cash balances of $1.2 and $14.1, unrestricted cash held for sale of $0.7 and $16.0 and restricted cash held for sale of $0.0 and $59.5)</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e46c4-3a42-7caa-b522-b2f375f98ca7_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Cash balance at end of period (includes restricted cash balances of $28.8 and $4.6, unrestricted cash held for sale of $0.3 and $23.8 and restricted cash held for sale of $&#8212; and $94.9)</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Continuing Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives_019e46c4-3a42-731b-9a27-cb658f325396_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership percentage, after equity incentives</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives_label_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Parent, After Equity Incentives</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives_documentation_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Parent, After Equity Incentives</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:to="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_019e46c4-3ae3-7563-8d4a-6e975ceb56dc_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicUndistributed_019e46c4-3a42-727f-882b-34ef25fe4e63_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Undistributed earnings (losses) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicUndistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic, Undistributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicUndistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicUndistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicUndistributed" xlink:to="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonNeosMember_terseLabel_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-NEOs</link:label>
    <link:label id="lab_ecd_NonNeosMember_label_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-NEOs [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonNeosMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonNeosMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonNeosMember" xlink:to="lab_ecd_NonNeosMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019e46c4-3ae3-7c7c-9de0-88ddb9306f54_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership interest (as a percent)</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019e46c4-3ae3-78f4-820d-de3a8c7f7b8a_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ownership Interest</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax_019e46c4-3ae3-7e25-a031-bd6ed24b995a_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain (loss) on investments, exchange rate effect</link:label>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax_label_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss), Foreign Currency Transaction, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCurrencyTransactionGainLossAfterTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:to="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived_019e46c4-3a42-7eed-b41d-2569f68e390e_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distribution received</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Distribution Received</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Distribution Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_019e46c4-3a42-7dd8-a92d-59b6d122e1ab_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_019e46c4-3969-7265-b1c4-f897d10570e9_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_019e46c4-3969-7c02-ad56-15f50a4a512a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Repurchases and retirements of common shares</link:label>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for Repurchase of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:to="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesMember_019e46c4-3ae3-7794-b953-09c0b0d32f97_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage-backed securities:</link:label>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeAxis_019e46c4-3ae3-7509-945a-c054e02dfb3e_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_019e46c4-3a42-7b3f-8653-6aabf6297a5c_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote</link:label>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_label_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NamedExecutiveOfficersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_019e46c4-3ae3-7a6b-bc55-edf3f2d74efa_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductOrServiceAxis_019e46c4-3a42-75dc-9a45-101af8dbb444_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:label id="lab_srt_ProductOrServiceAxis_label_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductOrServiceAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019e46c4-3a42-7a51-87b4-c9f7ecd434a0_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities, at fair value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019e46c4-3a42-7499-ad86-644a4dbc4a60_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_019e46c4-3ae3-7240-8e3f-ffd47e707cae_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in fair value of contingent consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_019e46c4-3ae3-7470-a48a-cfa321b328b6_verboseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Change in fair value of contingent consideration &#8212; Ark</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Contingent Consideration, Change in Contingent Consideration, Liability, Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:to="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_019e46c4-3969-70a3-831f-d278fadf1089_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_019e46c4-3969-7014-a74b-555219c583fc_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_019e46c4-3969-73cb-85c5-7d23f2fcd4b0_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issued (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Shares Issued in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoncontrollingInterestAbstract_019e46c4-3a42-7580-a38b-334c8920a743_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Abstract]</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestAbstract_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestAbstract" xlink:to="lab_us-gaap_NoncontrollingInterestAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalUnconsolidatedEntitiesMember_019e46c4-3a42-7b2e-9894-550fb174ffb9_terseLabel_en-US" xlink:label="lab_wtm_TotalUnconsolidatedEntitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total unconsolidated entities</link:label>
    <link:label id="lab_wtm_TotalUnconsolidatedEntitiesMember_label_en-US" xlink:label="lab_wtm_TotalUnconsolidatedEntitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Unconsolidated Entities [Member]</link:label>
    <link:label id="lab_wtm_TotalUnconsolidatedEntitiesMember_documentation_en-US" xlink:label="lab_wtm_TotalUnconsolidatedEntitiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Unconsolidated Entities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalUnconsolidatedEntitiesMember" xlink:href="wtm-20260630.xsd#wtm_TotalUnconsolidatedEntitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalUnconsolidatedEntitiesMember" xlink:to="lab_wtm_TotalUnconsolidatedEntitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeContractTypeDomain_019e46c4-3969-78aa-83d1-072b13ff7956_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeContractTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Contract [Domain]</link:label>
    <link:label id="lab_us-gaap_DerivativeContractTypeDomain_label_en-US" xlink:label="lab_us-gaap_DerivativeContractTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Contract [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeContractTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeContractTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeContractTypeDomain" xlink:to="lab_us-gaap_DerivativeContractTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentAggregateCost_019e46c4-3969-7d6f-9f97-d8ed95108549_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentAggregateCost_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Aggregate Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentAggregateCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentAggregateCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentAggregateCost" xlink:to="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_019e46c4-3ae3-76c1-85ff-48745bbb00b0_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskByBenchmarkAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:to="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired_019e46c4-3969-7d7c-a4f0-a42acb5b206a_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable noncontrolling interest</link:label>
    <link:label id="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired_label_en-US" xlink:label="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Redeemable Noncontrolling Interest Acquired</link:label>
    <link:label id="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Redeemable Noncontrolling Interest Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:to="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_019e46c4-3ae3-78fd-b881-2239a317dc16_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities, redeemable noncontrolling interests and equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValuePerShare_019e46c4-3969-7602-bb35-cc2710be73d0_terseLabel_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase in investment owned (in dollars per share)</link:label>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValuePerShare_label_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Owned, Change in Value, Per Share</link:label>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValuePerShare_documentation_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValuePerShare" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investment Owned, Change in Value, Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentOwnedChangeInValuePerShare" xlink:href="wtm-20260630.xsd#wtm_InvestmentOwnedChangeInValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InvestmentOwnedChangeInValuePerShare" xlink:to="lab_wtm_InvestmentOwnedChangeInValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019e46c4-3a42-702a-b8c2-eaea3ed1f6e8_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and other intangible assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019e46c4-3a42-7c7a-a97c-df3b2b069945_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total goodwill and other intangible assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019e46c4-3a42-7ce4-a74c-31493c32e156_periodStartLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Total goodwill and other intangible assets, beginning balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019e46c4-3a42-7d99-aeab-2659d38f4140_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Total goodwill and other intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_019e46c4-3ae3-72b3-b8c9-315121b631cd_terseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net realized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_label_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Gains (Losses)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RealizedInvestmentGainsLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:to="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Stock Option</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_019e46c4-3ae3-7e24-91c2-6df90eb542f7_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases and contributions</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Purchases</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterest_019e46c4-3969-717f-9d7f-a49f3a0213d4_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_MinorityInterest_019e46c4-3969-767e-9ff9-64e41d209802_verboseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable Noncontrolling Equity</link:label>
    <link:label id="lab_us-gaap_MinorityInterest_label_en-US" xlink:label="lab_us-gaap_MinorityInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterest" xlink:to="lab_us-gaap_MinorityInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_019e46c4-3ae3-7a27-bef9-324bdc218a42_terseLabel_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementBusinessSegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:to="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_label_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Additional402vDisclosureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Additional402vDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember_019e46c4-3ae3-7700-8559-645fa9f087ed_terseLabel_en-US" xlink:label="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recent transaction</link:label>
    <link:label id="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember_label_en-US" xlink:label="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Technique, Recent or Expected Transaction Prices [Member]</link:label>
    <link:label id="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember_documentation_en-US" xlink:label="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Valuation Technique, Recent or Expected Transaction Prices</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:href="wtm-20260630.xsd#wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:to="lab_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedGain_019e46c4-3a42-7d4b-b1fa-34d64999632b_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedGain_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Unrealized Gain</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedGain_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentUnrealizedGain" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentUnrealizedGain" xlink:to="lab_wtm_EquityMethodInvestmentUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HGGlobal2022SeniorNotesMember_019fa1a5-f962-781e-8237-61b44fe2d5ba_terseLabel_en-US" xlink:label="lab_wtm_HGGlobal2022SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global 2022 Senior Notes</link:label>
    <link:label id="lab_wtm_HGGlobal2022SeniorNotesMember_label_en-US" xlink:label="lab_wtm_HGGlobal2022SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global 2022 Senior Notes [Member]</link:label>
    <link:label id="lab_wtm_HGGlobal2022SeniorNotesMember_documentation_en-US" xlink:label="lab_wtm_HGGlobal2022SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global 2022 Senior Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobal2022SeniorNotesMember" xlink:href="wtm-20260630.xsd#wtm_HGGlobal2022SeniorNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HGGlobal2022SeniorNotesMember" xlink:to="lab_wtm_HGGlobal2022SeniorNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_019e46c4-3969-7d73-b4b2-94d78c45dc2f_terseLabel_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global 2022 Senior Notes</link:label>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_label_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global Senior Notes [Member]</link:label>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_documentation_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global Senior Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobalSeniorNotesMember" xlink:href="wtm-20260630.xsd#wtm_HGGlobalSeniorNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HGGlobalSeniorNotesMember" xlink:to="lab_wtm_HGGlobalSeniorNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentFloatingInterestRatePercentage_019e46c4-3a42-7a04-821a-8755ad1470e8_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Floating rate</link:label>
    <link:label id="lab_wtm_DebtInstrumentFloatingInterestRatePercentage_label_en-US" xlink:label="lab_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Floating Interest Rate, Percentage</link:label>
    <link:label id="lab_wtm_DebtInstrumentFloatingInterestRatePercentage_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Floating Interest Rate, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentFloatingInterestRatePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:to="lab_wtm_DebtInstrumentFloatingInterestRatePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock_019e46c4-3969-792d-939d-297364526784_terseLabel_en-US" xlink:label="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of insured obligations</link:label>
    <link:label id="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock_label_en-US" xlink:label="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Municipal Guarantee Insured Obligations [Table Text Block]</link:label>
    <link:label id="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock_documentation_en-US" xlink:label="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">[Table Text Block] for Schedule of Municipal Guarantee Insured Obligations [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:to="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_019e46c4-3969-76bc-a863-dc9f170f6ff7_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity investments, at fair value</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_019e46c4-3969-7795-b036-3c64fc99e41a_verboseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_019e46c4-3969-70b3-941b-308fc98437d9_totalLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesDebt" xlink:to="lab_us-gaap_TradingSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TabularListTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tabular List, Table</link:label>
    <link:label id="lab_ecd_TabularListTableTextBlock_label_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tabular List [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TabularListTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TabularListTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TabularListTableTextBlock" xlink:to="lab_ecd_TabularListTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember_019e46c4-3969-7e2b-a9d2-c511c7bdf38f_terseLabel_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement, Input, Pre-Tax Terminal Cash Flow Exit Multiple</link:label>
    <link:label id="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember_label_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement, Input, Pre-Tax Terminal Cash Flow Exit Multiple [Member]</link:label>
    <link:label id="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember_documentation_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Measurement, Input, Pre-Tax Terminal Cash Flow Exit Multiple</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:href="wtm-20260630.xsd#wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:to="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsAARatingMember_019e46c4-3ae3-7023-b16e-64b18976e8b6_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsAARatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AA</link:label>
    <link:label id="lab_srt_StandardPoorsAARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsAARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AA Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsAARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsAARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsAARatingMember" xlink:to="lab_srt_StandardPoorsAARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_019e46c4-3ae3-73a4-a4c5-238dfa90688e_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid-in surplus</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019e46c4-3969-7688-acb6-40119317df63_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xml:lang="en-US">Less: beginning reinsurance recoverable on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019e46c4-3969-73fb-959e-04deead0d5a1_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Plus: ending reinsurance recoverable on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019e46c4-3969-7d6c-a51f-3bca09c6b24e_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019e46c4-3ae3-7a71-ad7c-1494bae6d050_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Reinsurance Recoverable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduParticipationContractsMember_019e46c4-3a42-7160-b2fb-60234fa8ca8c_terseLabel_en-US" xlink:label="lab_wtm_KuduParticipationContractsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Kudu&#8217;s Participation Contracts</link:label>
    <link:label id="lab_wtm_KuduParticipationContractsMember_019e46c4-3a42-72f9-8556-63d500d6c274_verboseLabel_en-US" xlink:label="lab_wtm_KuduParticipationContractsMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Kudu's Participation Contracts</link:label>
    <link:label id="lab_wtm_KuduParticipationContractsMember_label_en-US" xlink:label="lab_wtm_KuduParticipationContractsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Kudu Participation Contracts [Member]</link:label>
    <link:label id="lab_wtm_KuduParticipationContractsMember_documentation_en-US" xlink:label="lab_wtm_KuduParticipationContractsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Kudu Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_KuduParticipationContractsMember" xlink:href="wtm-20260630.xsd#wtm_KuduParticipationContractsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_KuduParticipationContractsMember" xlink:to="lab_wtm_KuduParticipationContractsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss_019e46c4-3ae3-72f6-a41c-2d514678e9ed_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:to="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_label_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:to="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_019e46c4-3ae4-7b51-9a24-9594b62ed866_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_019e46c4-3ae3-7013-b51a-1a8ba9ea7816_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums written</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_019e46c4-3a42-7b7c-b8c9-e3097c9b6493_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of equity securities and other long-term investments</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures_019e46c4-3969-78ca-8a4e-49ab890637b1_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued Expense</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Before Assumed Forfeitures</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Before Assumed Forfeitures</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate_019e46c4-3969-74c7-950f-ace433f2169d_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">July 1, 2026 - December 31, 2026</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, First Quarter</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EnterpriseSolutionMember_019e46c4-3a42-7e1d-bf9c-819f9f78951c_terseLabel_en-US" xlink:label="lab_wtm_EnterpriseSolutionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Enterprise Solution</link:label>
    <link:label id="lab_wtm_EnterpriseSolutionMember_label_en-US" xlink:label="lab_wtm_EnterpriseSolutionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Enterprise Solution [Member]</link:label>
    <link:label id="lab_wtm_EnterpriseSolutionMember_documentation_en-US" xlink:label="lab_wtm_EnterpriseSolutionMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Enterprise Electric, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EnterpriseSolutionMember" xlink:href="wtm-20260630.xsd#wtm_EnterpriseSolutionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EnterpriseSolutionMember" xlink:to="lab_wtm_EnterpriseSolutionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate_019e46c4-3a42-75b6-b9d3-5ce52c48e27e_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentMeasurementInput_019e46c4-3a42-7816-b420-d368eea8208f_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, measurement input</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentMeasurementInput_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentMeasurementInput" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentMeasurementInput" xlink:to="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAxis_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation:</link:label>
    <link:label id="lab_ecd_AdjToCompAxis_label_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToCompAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAxis" xlink:to="lab_ecd_AdjToCompAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral_019e46c4-3a42-7523-99aa-612899d148c1_terseLabel_en-US" xlink:label="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net</link:label>
    <link:label id="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral_label_en-US" xlink:label="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid, Net of Collateral</link:label>
    <link:label id="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral_documentation_en-US" xlink:label="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid, Net of Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:href="wtm-20260630.xsd#wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:to="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CostOfSalesPolicyTextBlock_019f25bd-e4ea-78df-8bf9-c811a38ad478_terseLabel_en-US" xlink:label="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost of Sales</link:label>
    <link:label id="lab_us-gaap_CostOfSalesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cost of Goods and Service [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfSalesPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfSalesPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostOfSalesPolicyTextBlock" xlink:to="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember_019e46c4-3a42-75b6-b05c-dd730b716394_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark - Management Equity Incentive</link:label>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember_label_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Ark Insurance Holdings Limited, Management Equity Incentive [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Ark Insurance Holdings Limited, Management Equity Incentive</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:to="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationAxis_019e46c4-3969-7acb-89a0-ac62867cffd6_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskCollateralizationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskCollateralizationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskCollateralizationAxis" xlink:to="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:to="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_AggtErrCompAmt_label_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompAmt" xlink:to="lab_ecd_AggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPaidNet_019e46c4-3ae3-7043-9983-1a6f103efd0a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Interest paid</link:label>
    <link:label id="lab_us-gaap_InterestPaidNet_label_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Paid, Excluding Capitalized Interest, Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPaidNet" xlink:to="lab_us-gaap_InterestPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019e46c4-3ae3-7a3f-b54c-65d37e01abc4_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive income (loss), after-tax:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod_019e46c4-3969-7d4b-84b5-6d8467693b9b_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment portfolio duration</link:label>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod_label_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period</link:label>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesWeightedAveragePortfolioPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:to="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainOnSaleOfInvestments_019e46c4-3a42-7e78-b05e-4f5ffbf1afd3_terseLabel_en-US" xlink:label="lab_us-gaap_GainOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized investment gains</link:label>
    <link:label id="lab_us-gaap_GainOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_GainOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainOnSaleOfInvestments" xlink:to="lab_us-gaap_GainOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_019e46c4-3a42-750b-9183-712348bc4521_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests_019e46c4-3a42-77e9-8f14-0b3b70e97983_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payments to acquire limited partnership interests</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Limited Partnership Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireLimitedPartnershipInterests"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:to="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MaterialsSectorMember_019e46c4-3a42-7635-a1b7-0869a2c1ece2_terseLabel_en-US" xlink:label="lab_wtm_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Materials</link:label>
    <link:label id="lab_wtm_MaterialsSectorMember_label_en-US" xlink:label="lab_wtm_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Materials Sector [Member]</link:label>
    <link:label id="lab_wtm_MaterialsSectorMember_documentation_en-US" xlink:label="lab_wtm_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Materials Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MaterialsSectorMember" xlink:href="wtm-20260630.xsd#wtm_MaterialsSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MaterialsSectorMember" xlink:to="lab_wtm_MaterialsSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureName" xlink:to="lab_ecd_MeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateEquitySecuritiesMember_019e46c4-3969-7a58-9cec-3529db22f3c6_terseLabel_en-US" xlink:label="lab_wtm_PrivateEquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private common shares and units</link:label>
    <link:label id="lab_wtm_PrivateEquitySecuritiesMember_label_en-US" xlink:label="lab_wtm_PrivateEquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity Securities [Member]</link:label>
    <link:label id="lab_wtm_PrivateEquitySecuritiesMember_documentation_en-US" xlink:label="lab_wtm_PrivateEquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Private Equity Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateEquitySecuritiesMember" xlink:href="wtm-20260630.xsd#wtm_PrivateEquitySecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateEquitySecuritiesMember" xlink:to="lab_wtm_PrivateEquitySecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_019fd323-cbf6-746d-a48f-23e33ce317c7_terseLabel_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned insurance premiums</link:label>
    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_label_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net, Adjusted</link:label>
    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_documentation_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PremiumsEarnedNetAdjusted" xlink:href="wtm-20260630.xsd#wtm_PremiumsEarnedNetAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PremiumsEarnedNetAdjusted" xlink:to="lab_wtm_PremiumsEarnedNetAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PayVsPerformanceDisclosureLineItems_label_en-US" xlink:label="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PayVsPerformanceDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:to="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_019e46c4-3a42-7a60-979e-52c9cf6fbf2e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember_019e46c4-3a42-768a-a782-35872d4c7c91_terseLabel_en-US" xlink:label="lab_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">GNMA</link:label>
    <link:label id="lab_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember_label_en-US" xlink:label="lab_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Government National Mortgage Association Certificates and Obligations (GNMA) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember" xlink:to="lab_us-gaap_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_019e46c4-3a42-76a5-8361-dc3948362c2a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentLineItems" xlink:to="lab_us-gaap_DebtInstrumentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019e46c4-3969-7516-ba96-66f0684d9ade_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sales of common equity securities and investment in MediaAlpha</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019e46c4-3a42-7c3d-b5c5-94e56fb12e76_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in loss and loss adjustment expense reserves</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Liability for Claims and Claims Adjustment Expense Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:to="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019e46c4-3a42-79a6-aa35-0cbfcc6ac967_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_019e46c4-3969-77fe-b82e-37f14201f6c0_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Impairments</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestReceivable_019e46c4-3a42-709d-81d9-2ad3b87fe0de_terseLabel_en-US" xlink:label="lab_us-gaap_InterestReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest receivable</link:label>
    <link:label id="lab_us-gaap_InterestReceivable_label_en-US" xlink:label="lab_us-gaap_InterestReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestReceivable" xlink:to="lab_us-gaap_InterestReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndName_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_TrdArrIndName_label_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndName" xlink:to="lab_ecd_TrdArrIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_019e46c4-3ae3-70ff-8120-7b241aef7f4f_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional compensation cost that would be recognized if all outstanding performance shares vested</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_019e46c4-3ae3-7776-89bc-d1a201fc073f_periodStartLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning of period</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_019e46c4-3ae3-7a51-8784-0c976eb6d577_periodEndLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock_019e46c4-3969-7ead-b69e-bea6be40871c_negatedLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Average unvested restricted common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares, Restricted Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesRestrictedStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019e46c4-3969-75a1-9037-754f66b95918_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations_019e46c4-3ae3-72bc-85f7-deb67adc235a_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net change in cash during the period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Period Increase (Decrease), Including Exchange Rate Effect, Continuing Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash_019fb80b-c1a9-7ba8-a6a8-408924426a40_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_019e46c4-3a42-7c44-80b4-865f88cec820_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR)</link:label>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_label_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuredOvernightFinancingRateSofrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:to="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LossesAndLossAdjustmentExpenseAbstract_019e46c4-3ae4-77b7-8b97-553267918631_terseLabel_en-US" xlink:label="lab_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE:</link:label>
    <link:label id="lab_wtm_LossesAndLossAdjustmentExpenseAbstract_label_en-US" xlink:label="lab_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Losses and Loss Adjustment Expense [Abstract]</link:label>
    <link:label id="lab_wtm_LossesAndLossAdjustmentExpenseAbstract_documentation_en-US" xlink:label="lab_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Losses and Loss Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:href="wtm-20260630.xsd#wtm_LossesAndLossAdjustmentExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:to="lab_wtm_LossesAndLossAdjustmentExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedAutoLoansMember_019e46c4-3969-7ffa-97c4-5a4e5aaa0d82_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedAutoLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vehicle receivables</link:label>
    <link:label id="lab_us-gaap_CollateralizedAutoLoansMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedAutoLoansMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Auto Loans [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedAutoLoansMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedAutoLoansMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedAutoLoansMember" xlink:to="lab_us-gaap_CollateralizedAutoLoansMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate_019e46c4-3969-7e0d-9c90-cbe7d568ea4f_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage and asset-backed securities and collateralized loan obligations</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:to="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoMember_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO</link:label>
    <link:label id="lab_ecd_NonPeoNeoMember_label_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoMember" xlink:to="lab_ecd_NonPeoNeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HedgeFundLongShortAllCapGlobalMember_019e46c4-3ae3-778d-9b8e-0c8eece0f557_terseLabel_en-US" xlink:label="lab_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long/short all cap global</link:label>
    <link:label id="lab_wtm_HedgeFundLongShortAllCapGlobalMember_label_en-US" xlink:label="lab_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedge Fund, Long/Short All Cap Global [Member]</link:label>
    <link:label id="lab_wtm_HedgeFundLongShortAllCapGlobalMember_documentation_en-US" xlink:label="lab_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hedge Fund, Long/Short All Cap Global</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:href="wtm-20260630.xsd#wtm_HedgeFundLongShortAllCapGlobalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:to="lab_wtm_HedgeFundLongShortAllCapGlobalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember_019e46c4-3969-7ae4-b0e9-18c44d216655_terseLabel_en-US" xlink:label="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized investment (losses) gains</link:label>
    <link:label id="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember_label_en-US" xlink:label="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Investments Before TPC Providers - Investments [Member]</link:label>
    <link:label id="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Investments Before TPC Providers - Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:to="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent_019e46c4-3969-7016-bb24-2931a1c9af2c_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership percentage, fully diluted</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent_label_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Fully Diluted, Parent</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent_documentation_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Fully Diluted, Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryOwnershipPercentageFullyDilutedParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:to="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CostOfGoodsAndServicesSold_019e46c4-3969-7249-a99c-dc5a76fb881b_terseLabel_en-US" xlink:label="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost of sales</link:label>
    <link:label id="lab_us-gaap_CostOfGoodsAndServicesSold_label_en-US" xlink:label="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cost of Product and Service Sold</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSold" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfGoodsAndServicesSold"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostOfGoodsAndServicesSold" xlink:to="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMethodTextBlock" xlink:to="lab_ecd_AwardTmgMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProductAndServiceOtherMember_019f8a8e-fa9a-7b90-b8d1-3e3d8f56f949_terseLabel_en-US" xlink:label="lab_us-gaap_ProductAndServiceOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and service revenues</link:label>
    <link:label id="lab_us-gaap_ProductAndServiceOtherMember_label_en-US" xlink:label="lab_us-gaap_ProductAndServiceOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service, Other [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProductAndServiceOtherMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProductAndServiceOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProductAndServiceOtherMember" xlink:to="lab_us-gaap_ProductAndServiceOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioForecastMember_019e46c4-3a42-723d-b128-139f175cefd0_terseLabel_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forecast</link:label>
    <link:label id="lab_srt_ScenarioForecastMember_label_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forecast [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioForecastMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScenarioForecastMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioForecastMember" xlink:to="lab_srt_ScenarioForecastMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:to="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod_019e46c4-3969-7eb0-8880-e3319c308d6c_negatedLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Shares paid or expired</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Shares Paid In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">The amount of performance shares that were paid out (including deposits into a deferred compensation plan) or that expired due to failure to meet performance criteria.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_019e46c4-3969-77cb-984f-b674423084e7_periodStartLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning of period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_019e46c4-3969-733b-802c-284463af0f4e_periodEndLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_019e46c4-3969-7f3d-942c-623c651b7ea0_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Aggregate carrying value as of the balance sheet date of liabilities for incentive compensation arrangements.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_019e46c4-3969-7c15-8253-c39bd86c99c2_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income (loss) attributable to White Mountains&#8217;s common shareholders</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019e46c4-3969-746b-91a9-5ed65fceaed3_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss) attributable to White Mountains&#8217;s common shareholders</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019e46c4-3969-7d22-8499-c5f69eb1fe33_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_019e46c4-3a42-72ff-885f-c8d30b7cc0a9_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeAxis" xlink:to="lab_us-gaap_LongtermDebtTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis</link:label>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_label_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompAnalysisTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompAnalysisTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompAnalysisTextBlock" xlink:to="lab_ecd_ErrCompAnalysisTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsMember_019e46c4-3ae3-78f3-b411-bd770785d7b7_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentsMember_label_en-US" xlink:label="lab_us-gaap_InvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsMember" xlink:to="lab_us-gaap_InvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDateAxis_terseLabel_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date:</link:label>
    <link:label id="lab_ecd_RestatementDateAxis_label_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDateAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDateAxis" xlink:to="lab_ecd_RestatementDateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsBBBRatingMember_019e46c4-3ae3-7055-b98e-528c9aa3c50d_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsBBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BBB</link:label>
    <link:label id="lab_srt_StandardPoorsBBBRatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsBBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, BBB Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsBBBRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsBBBRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsBBBRatingMember" xlink:to="lab_srt_StandardPoorsBBBRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsBBRatingMember_019e46c4-3a42-735b-8517-a72f0f875a04_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BB</link:label>
    <link:label id="lab_srt_StandardPoorsBBRatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, BB Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsBBRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsBBRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsBBRatingMember" xlink:to="lab_srt_StandardPoorsBBRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PremiumsAndCommissionsReceivable_019e46c4-3ae3-7a2c-aa9a-e51a6930ae4d_terseLabel_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums, commissions and fees receivable</link:label>
    <link:label id="lab_wtm_PremiumsAndCommissionsReceivable_label_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums and Commissions Receivable</link:label>
    <link:label id="lab_wtm_PremiumsAndCommissionsReceivable_documentation_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Premiums and Commissions Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PremiumsAndCommissionsReceivable" xlink:href="wtm-20260630.xsd#wtm_PremiumsAndCommissionsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PremiumsAndCommissionsReceivable" xlink:to="lab_wtm_PremiumsAndCommissionsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities_019fc6ef-b3fd-7901-8b6e-419ce23d8408_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsuranceDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceDisclosuresAbstract" xlink:to="lab_us-gaap_ReinsuranceDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LondonInterbankOfferedRateLIBOR1Member_019e46c4-3a42-728d-81a7-db183c58ef98_terseLabel_en-US" xlink:label="lab_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">London Interbank Offered Rate (LIBOR)</link:label>
    <link:label id="lab_wtm_LondonInterbankOfferedRateLIBOR1Member_label_en-US" xlink:label="lab_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">London Interbank Offered Rate (LIBOR) 1 [Member]</link:label>
    <link:label id="lab_wtm_LondonInterbankOfferedRateLIBOR1Member_documentation_en-US" xlink:label="lab_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">London Interbank Offered Rate (LIBOR) 1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:href="wtm-20260630.xsd#wtm_LondonInterbankOfferedRateLIBOR1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:to="lab_wtm_LondonInterbankOfferedRateLIBOR1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_019e46c4-3ae3-761d-b3d8-b05299803c9f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnBnftsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:to="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LossOnSaleOfInvestments_019e46c4-3ae3-7fa2-b52a-4ddeab30940b_terseLabel_en-US" xlink:label="lab_us-gaap_LossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized investment losses</link:label>
    <link:label id="lab_us-gaap_LossOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_LossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LossOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LossOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LossOnSaleOfInvestments" xlink:to="lab_us-gaap_LossOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout_019e46c4-3a42-7469-95ed-858059e1df56_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of target payout - minimum actual</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-Based Payment Award, Percentage of Target Achieved Payout</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the percentage of target achieved, low end of range.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract_019e46c4-3a42-709a-82ed-66d7c24d4bbc_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings per share denominator (in thousands):</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019e46c4-3969-7c3a-a14c-ba5aa72c37f0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of intangible assets and goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_019e46c4-3969-7dc9-b6e8-4f978622f642_negatedTerseLabel_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net release of cash (pre-funding) of investment purchases</link:label>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_label_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Release Of Cash (Pre-Fundings) For Managed Funds</link:label>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_documentation_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Release Of Cash (Pre-Fundings) For Managed Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:href="wtm-20260630.xsd#wtm_ReleaseOfCashPreFundingsForManagedFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:to="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_019e46c4-3969-7fb7-9b82-efa5a4f583d5_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_019e46c4-3969-76d2-88d8-01a83bcc79d1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_019e46c4-3969-77a6-9100-45a0c1a667af_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums earned</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember_019e46c4-3a42-7610-bf65-dcddd6beaa87_terseLabel_en-US" xlink:label="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long/short equity financials and business services</link:label>
    <link:label id="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember_label_en-US" xlink:label="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedge Fund, Long/Short Equity Banks and Financial [Member]</link:label>
    <link:label id="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember_documentation_en-US" xlink:label="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hedge Fund, Long/Short Equity Banks and Financial [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:href="wtm-20260630.xsd#wtm_HedgeFundLongShortEquityBanksAndFinancialMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:to="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalYearFocus_019e46c4-3969-77f1-969e-a81904494aea_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalYearFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalYearFocus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentFiscalYearFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalYearFocus" xlink:to="lab_dei_DocumentFiscalYearFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_019e46c4-3a42-7b84-8062-d500574a7ad8_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Target Performance Shares Outstanding</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_019e46c4-3a42-7943-92d2-1ce8dbc1b2ff_verboseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Restricted Shares</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodThreeMember_019e46c4-3969-7597-898b-8116694b9cd8_terseLabel_en-US" xlink:label="lab_wtm_PerformancePeriodThreeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2026 &#8211; 2028</link:label>
    <link:label id="lab_wtm_PerformancePeriodThreeMember_label_en-US" xlink:label="lab_wtm_PerformancePeriodThreeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Period Three [Member]</link:label>
    <link:label id="lab_wtm_PerformancePeriodThreeMember_documentation_en-US" xlink:label="lab_wtm_PerformancePeriodThreeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Performance Cycle 2019 to 2021 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PerformancePeriodThreeMember" xlink:href="wtm-20260630.xsd#wtm_PerformancePeriodThreeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PerformancePeriodThreeMember" xlink:to="lab_wtm_PerformancePeriodThreeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_019e46c4-3a42-78e8-a701-2bc94b47329a_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">White Mountains&#8217;s common shares at $1 par value per share - authorized 50,000,000 shares; issued and outstanding 2,386,721 and 2,479,677 shares</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockValue" xlink:to="lab_us-gaap_CommonStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsMeasurementInput_019e46c4-3969-78db-b67e-79e79b484a95_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discount rate</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsMeasurementInput_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Measurement Input</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsMeasurementInput_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:to="lab_wtm_OtherLongTermInvestmentsMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MeasurementInputPreTaxDiscountRateMember_019e46c4-3a42-78b5-ae5c-74963b8af59d_terseLabel_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input, Pre-Tax Discount Rate</link:label>
    <link:label id="lab_wtm_MeasurementInputPreTaxDiscountRateMember_label_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Pre-Tax Discount Rate [Member]</link:label>
    <link:label id="lab_wtm_MeasurementInputPreTaxDiscountRateMember_documentation_en-US" xlink:label="lab_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Measurement Input, Pre-Tax Discount Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:href="wtm-20260630.xsd#wtm_MeasurementInputPreTaxDiscountRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:to="lab_wtm_MeasurementInputPreTaxDiscountRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_019e46c4-3969-77a0-a1d2-20f6a4e0b59d_terseLabel_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization (accretion) and depreciation</link:label>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_label_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Depreciation, Amortization and Accretion, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepreciationAmortizationAndAccretionNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:to="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_019e46c4-3a42-7099-a2e6-ee395bc8d70a_netLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_019e46c4-3a42-7b78-8c48-dfb84c57d0b7_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_label_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Expense, Operating and Nonoperating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpense" xlink:to="lab_us-gaap_InterestExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_019e46c4-3a42-76c4-9ae1-772c019b08bc_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of debt outstanding</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember_019e46c4-3a42-77f4-aa10-72b75a015854_terseLabel_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - HG Global</link:label>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember_label_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - HG Global [Member]</link:label>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember_documentation_en-US" xlink:label="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary - HG Global</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:href="wtm-20260630.xsd#wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:to="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditMember_019e46c4-3ae4-732b-8c8d-f57c5e5e1cc0_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditMember" xlink:to="lab_us-gaap_LineOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDeterminationDate_terseLabel_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:label id="lab_ecd_RestatementDeterminationDate_label_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDeterminationDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDeterminationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDeterminationDate" xlink:to="lab_ecd_RestatementDeterminationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod4Member_019e46c4-3969-7b9f-b439-ba333c81781e_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriod4Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 4</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod4Member_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriod4Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 4 [Member]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod4Member_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriod4Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 4</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriod4Member" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriod4Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriod4Member" xlink:to="lab_wtm_DebtCovenantPeriod4Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AmendmentFlag_019e46c4-3ae4-7765-98b4-4a0fe29d6fbf_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:label id="lab_dei_AmendmentFlag_label_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_AmendmentFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AmendmentFlag" xlink:to="lab_dei_AmendmentFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems_019e46c4-3969-7b6f-a541-da8a4ce48bc9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt and Equity Securities, FV-NI [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt and Equity Securities, FV-NI [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems" xlink:to="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember_019e46c4-3ae4-7d9e-921b-9f16e58b28d8_terseLabel_en-US" xlink:label="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity and short-term investments</link:label>
    <link:label id="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember_label_en-US" xlink:label="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities And Other Short-Term Investments [Member]</link:label>
    <link:label id="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturities And Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:to="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupClassificationAxis_019e46c4-3969-762e-9b31-069d473b6b39_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Axis]</link:label>
    <link:label id="lab_us-gaap_DisposalGroupClassificationAxis_label_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupClassificationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupClassificationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupClassificationAxis" xlink:to="lab_us-gaap_DisposalGroupClassificationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019e46c4-3969-703c-a017-a6056584d9c6_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019e46c4-3969-7d06-a9c4-b4dc961a04b1_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodAxis_019e46c4-3ae3-770f-9eec-95cbc30124c1_terseLabel_en-US" xlink:label="lab_wtm_PerformancePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Period [Axis]</link:label>
    <link:label id="lab_wtm_PerformancePeriodAxis_label_en-US" xlink:label="lab_wtm_PerformancePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Period [Axis]</link:label>
    <link:label id="lab_wtm_PerformancePeriodAxis_documentation_en-US" xlink:label="lab_wtm_PerformancePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disclosure of minimum performance period for right to receive performance share from the entity.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PerformancePeriodAxis" xlink:href="wtm-20260630.xsd#wtm_PerformancePeriodAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PerformancePeriodAxis" xlink:to="lab_wtm_PerformancePeriodAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PremiumsAndCommissionsPayable_019e46c4-3969-782b-ba66-8acf134eace1_terseLabel_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums and commissions payable</link:label>
    <link:label id="lab_wtm_PremiumsAndCommissionsPayable_label_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums and Commissions Payable</link:label>
    <link:label id="lab_wtm_PremiumsAndCommissionsPayable_documentation_en-US" xlink:label="lab_wtm_PremiumsAndCommissionsPayable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Premiums and Commissions Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PremiumsAndCommissionsPayable" xlink:href="wtm-20260630.xsd#wtm_PremiumsAndCommissionsPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PremiumsAndCommissionsPayable" xlink:to="lab_wtm_PremiumsAndCommissionsPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LloydsBankMember_019e46c4-3a42-728f-ae50-8a4ad7fc566a_terseLabel_en-US" xlink:label="lab_wtm_LloydsBankMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lloyds Bank</link:label>
    <link:label id="lab_wtm_LloydsBankMember_label_en-US" xlink:label="lab_wtm_LloydsBankMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lloyds Bank [Member]</link:label>
    <link:label id="lab_wtm_LloydsBankMember_documentation_en-US" xlink:label="lab_wtm_LloydsBankMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Lloyds Bank</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LloydsBankMember" xlink:href="wtm-20260630.xsd#wtm_LloydsBankMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LloydsBankMember" xlink:to="lab_wtm_LloydsBankMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_019e46c4-3ae4-78b3-8ce8-69e2e72510e2_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SupplementalTrustMember_019e46c4-3ae3-7bf8-a69a-91112dc92889_terseLabel_en-US" xlink:label="lab_wtm_SupplementalTrustMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental Trust</link:label>
    <link:label id="lab_wtm_SupplementalTrustMember_label_en-US" xlink:label="lab_wtm_SupplementalTrustMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Trust [Member]</link:label>
    <link:label id="lab_wtm_SupplementalTrustMember_documentation_en-US" xlink:label="lab_wtm_SupplementalTrustMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Supplemental Trust [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SupplementalTrustMember" xlink:href="wtm-20260630.xsd#wtm_SupplementalTrustMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SupplementalTrustMember" xlink:to="lab_wtm_SupplementalTrustMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:to="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_019e46c4-3a42-7dc5-b164-5ff346185d51_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transfers in</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Transfers Into Level 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue_019e46c4-3969-78fc-bb46-16222d0d4998_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest, Equity, Redemption Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:to="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_019e46c4-3969-7a43-a108-e2a58ea922d8_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedTransactionMember_019e46c4-3ae4-7955-9a70-fcbaa5cfa5b4_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedTransactionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished Transaction</link:label>
    <link:label id="lab_wtm_DistinguishedTransactionMember_label_en-US" xlink:label="lab_wtm_DistinguishedTransactionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Transaction [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedTransactionMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedTransactionMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedTransactionMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedTransactionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedTransactionMember" xlink:to="lab_wtm_DistinguishedTransactionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoTotalCompAmt_label_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoTotalCompAmt" xlink:to="lab_ecd_PeoTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable_019e46c4-3a42-7da7-bfb4-813fb651fe04_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums, commissions and fees receivable</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Assets Acquired, Premiums and Commissions Receivable</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Assets Acquired, Premiums and Commissions Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019e46c4-3a42-7446-b282-a29e38a98630_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (losses) per share denominator (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxContingencyLineItems_019e46c4-3a42-7f79-9258-ac36f3f55d66_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Line Items]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxContingencyLineItems_label_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxContingencyLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxContingencyLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxContingencyLineItems" xlink:to="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic_019e46c4-3a42-77c5-bc1f-74f37bf8c519_negatedLabel_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Allocation of losses (earnings) to participating restricted common shares</link:label>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic_label_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Undistributed Continuing Operation Earnings (Loss), Allocation to Participating Securities, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:to="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_019e46c4-3ae3-7acc-9c66-0b8b39799561_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByBalanceSheetGroupingTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_019e46c4-3a42-7021-9f8b-c7b4a23c8c3d_verboseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_019e46c4-3a42-74b9-b2f9-e2bc6c6bdba7_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019e46c4-3a42-7d68-bf99-0309aff0486b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in deferred acquisition costs</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Policy Acquisition Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax_019edf08-543d-742d-b525-7715541b6a53_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and service revenues</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer, Including Assessed Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure_019e46c4-3969-7e83-9de7-64feff55eba9_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure_019fa1c3-0041-7bb3-a268-2a9061940f4e_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, fair value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:to="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment_019e46c4-3a42-7945-a33c-c185cfc015ad_terseLabel_en-US" xlink:label="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill, intangible assets and other liabilities acquired, measurement period adjustment</link:label>
    <link:label id="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment_label_en-US" xlink:label="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Intangible Assets and Other Liabilities Acquired, Measurement Period Adjustment</link:label>
    <link:label id="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment_documentation_en-US" xlink:label="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill, Intangible Assets and Other Liabilities Acquired, Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:href="wtm-20260630.xsd#wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:to="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentInformationLineItems_019e46c4-3ae3-7a00-b1c6-75c23158fb2b_terseLabel_en-US" xlink:label="lab_dei_DocumentInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Information [Line Items]</link:label>
    <link:label id="lab_dei_DocumentInformationLineItems_label_en-US" xlink:label="lab_dei_DocumentInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Information [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationLineItems" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentInformationLineItems" xlink:to="lab_dei_DocumentInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember_019e46c4-3a42-7bb5-9d36-43f9480d95e8_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Terminal Revenue Growth Rate</link:label>
    <link:label id="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember_label_en-US" xlink:label="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Long-Term Revenue Growth Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputLongTermRevenueGrowthRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:to="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation_019e46c4-3969-7bea-9e74-3a8390441933_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets held for sale - Other</link:label>
    <link:label id="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation_label_en-US" xlink:label="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:to="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiDiscTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:to="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_019e46c4-3a42-755e-9b02-580c423f2624_negatedLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Vested (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_019e46c4-3a42-78db-b8f9-75d71c5c7839_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e46c4-3a42-72c6-99d8-69f1855de6f5_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (losses) per share numerators, Total</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e46c4-3a42-7414-9d6a-476d261e9a49_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net earnings (losses) available to White Mountains&#8217;s common shareholders, net of restricted common share amounts</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage_019e46c4-3969-722e-8321-122e39dc63d0_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percent over a target trust balance</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Balance Limit, Percentage</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Balance Limit, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_019e46c4-3a42-7ba5-b5ca-2913285e5027_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, accumulated amortization</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_019e46c4-3a42-7aa0-abf0-ed4329902d30_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_019e46c4-3969-722c-bd09-0465ca644e65_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total commitment under revolving credit facility</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Maximum Borrowing Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:to="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedGain_019e46c4-3a42-7faa-9697-e553a0b100ba_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedGain_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Unrealized Gain</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedGain_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:to="lab_wtm_OtherLongTermInvestmentsUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsCost_019e46c4-3ae3-7243-9414-4f7cad5efcb5_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsCost_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Cost</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsCost_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsCost" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsCost" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsCost" xlink:to="lab_wtm_OtherLongTermInvestmentsCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_019e46c4-3ae3-7b7b-99e3-f296eb3e4abe_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee, Sale of Stock by Subsidiary or Equity Investee [Table]</link:label>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_label_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee, Sale of Stock, Type [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:to="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_019e46c4-3a42-7bb5-bbd8-f30ba4b9501a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Third-party investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:to="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoncontrollingInterestMember_019e46c4-3ae4-7cf7-8cf7-bd1b47716463_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestMember_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestMember" xlink:to="lab_us-gaap_NoncontrollingInterestMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_019e46c4-3a42-74ab-9e2c-32041fd5e945_verboseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total average common shares outstanding during the period (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_019e46c4-3a42-7af2-87d7-0996e3adf4d0_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total average common shares outstanding during the period (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Issued, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesIssuedBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_019e46c4-3ae3-78b9-bcad-dccc79d3bed5_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Partners</link:label>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_label_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - WTM Partners [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - WTM Partners</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryWTMPartnersMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryWTMPartnersMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryWTMPartnersMember" xlink:to="lab_wtm_SubsidiaryWTMPartnersMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestDisclosureTextBlock_019e46c4-3a42-7222-9334-aed4c6aa4fa8_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interests</link:label>
    <link:label id="lab_us-gaap_MinorityInterestDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestDisclosureTextBlock" xlink:to="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019e46c4-3969-7982-8c25-882673830d11_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_019e46c4-3ae4-7dcc-b23a-a2450b372f31_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross unearned insurance premiums (in millions)</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_019e46c4-3ae4-79ba-8433-4daebd416988_totalLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total gross unearned insurance premiums</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Unearned Premium Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebt_019e46c4-3ae3-785b-a7e7-ec4e62b6b9cb_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_019e46c4-3ae3-75a3-83bb-51ba138b2392_totalLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_019e46c4-3ae3-7221-9fcb-da6594cf511d_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_label_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebt" xlink:to="lab_us-gaap_LongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_019e46c4-3969-7552-9b91-5d175c7a8ef1_terseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_label_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited [Member]</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_documentation_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ArkInsuranceHoldingsLimitedMember" xlink:href="wtm-20260630.xsd#wtm_ArkInsuranceHoldingsLimitedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgeFundsMember_019e46c4-3969-72df-b3b1-6dae7ac6cfd9_terseLabel_en-US" xlink:label="lab_us-gaap_HedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedge funds</link:label>
    <link:label id="lab_us-gaap_HedgeFundsMember_label_en-US" xlink:label="lab_us-gaap_HedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedge Funds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgeFundsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HedgeFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgeFundsMember" xlink:to="lab_us-gaap_HedgeFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_019e46c4-3969-7e69-9143-248e4a550f88_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other operating items:</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity, Increase (Decrease) in Operating Capital [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInOperatingCapitalAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:to="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e46c4-3a42-71b1-9438-086f22a0a950_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) investing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in the Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:to="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_019e46c4-3a42-7939-9a5d-d1a2a167e97d_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate_019e46c4-3a42-779f-9c99-82b0a433cc61_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_019e46c4-3a42-7cdd-900c-efb8fa4f5faa_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and Loss Adjustment Expense Reserves</link:label>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:to="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_019e46c4-3ae4-7196-b792-af7de30c9837_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Gross written premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_019e46c4-3ae4-75ed-b74e-59d09b35cf95_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums written, gross</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems_019e46c4-3a42-733b-8c11-9e231a0da66e_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments in unconsolidated affiliates</link:label>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems_label_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:to="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationTechniqueAxis_019e46c4-3a42-7fba-9be5-f096558f1358_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueAxis_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueAxis" xlink:to="lab_us-gaap_ValuationTechniqueAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateEquityFundsAndHedgeFundsMember_019e46c4-3a42-7aa9-8f0d-3cc0e6ec5646_terseLabel_en-US" xlink:label="lab_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private equity funds and hedge funds</link:label>
    <link:label id="lab_wtm_PrivateEquityFundsAndHedgeFundsMember_019e46c4-3a42-7750-baec-baa3862f169a_verboseLabel_en-US" xlink:label="lab_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total private equity funds and hedge funds</link:label>
    <link:label id="lab_wtm_PrivateEquityFundsAndHedgeFundsMember_label_en-US" xlink:label="lab_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity Funds and Hedge Funds [Member]</link:label>
    <link:label id="lab_wtm_PrivateEquityFundsAndHedgeFundsMember_documentation_en-US" xlink:label="lab_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investments in hedge funds and private equity funds.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:href="wtm-20260630.xsd#wtm_PrivateEquityFundsAndHedgeFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:to="lab_wtm_PrivateEquityFundsAndHedgeFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock_019e46c4-3969-73f4-91ee-8aae8a181214_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reportable Segments</link:label>
    <link:label id="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract_019e46c4-3969-7f5e-ae27-ac9ab3444d8d_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Comprehensive Income [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Comprehensive Income [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:to="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryIndName" xlink:to="lab_ecd_OutstandingRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedOtherDebtMember_019e46c4-3969-70ac-bfb5-3e7a814c19f1_verboseLabel_en-US" xlink:label="lab_wtm_DistinguishedOtherDebtMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Distinguished other debt, carrying value</link:label>
    <link:label id="lab_wtm_DistinguishedOtherDebtMember_019e46c4-3969-7fca-82eb-53f04ed3d27d_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedOtherDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished other debt</link:label>
    <link:label id="lab_wtm_DistinguishedOtherDebtMember_label_en-US" xlink:label="lab_wtm_DistinguishedOtherDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Other Debt [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedOtherDebtMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedOtherDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Other Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedOtherDebtMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedOtherDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedOtherDebtMember" xlink:to="lab_wtm_DistinguishedOtherDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgHowMnpiCnsdrdTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:to="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable_019e46c4-3ae3-75e0-82c0-cdb2772b8700_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest receivable</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Interest Receivable</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Interest Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduCreditFacilityMember_019e46c4-3969-7cff-9a96-ba76e1dfac3e_terseLabel_en-US" xlink:label="lab_wtm_KuduCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Kudu Credit Facility</link:label>
    <link:label id="lab_wtm_KuduCreditFacilityMember_label_en-US" xlink:label="lab_wtm_KuduCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Kudu Credit Facility [Member]</link:label>
    <link:label id="lab_wtm_KuduCreditFacilityMember_documentation_en-US" xlink:label="lab_wtm_KuduCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Kudu Credit Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_KuduCreditFacilityMember" xlink:href="wtm-20260630.xsd#wtm_KuduCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_KuduCreditFacilityMember" xlink:to="lab_wtm_KuduCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio_019e46c4-3969-7346-adf4-01e6248acb8e_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total leverage ratio</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Total Leverage Ratio</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Total Leverage Ratio</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentCovenantTotalLeverageRatio"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:to="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryHGGlobalMember_019e46c4-3ae3-7274-b6d1-0ab2362d98fa_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - HG Global</link:label>
    <link:label id="lab_wtm_SubsidiaryHGGlobalMember_019e46c4-3ae3-747c-b0bf-64036b6a1491_verboseLabel_en-US" xlink:label="lab_wtm_SubsidiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">HG Global</link:label>
    <link:label id="lab_wtm_SubsidiaryHGGlobalMember_label_en-US" xlink:label="lab_wtm_SubsidiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - HG Global [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryHGGlobalMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryHGGlobalMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - HG Global</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryHGGlobalMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryHGGlobalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryHGGlobalMember" xlink:to="lab_wtm_SubsidiaryHGGlobalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SegmentGeographicalDomain_019e46c4-3969-75af-a2cb-24d7fc1fded8_terseLabel_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:label id="lab_srt_SegmentGeographicalDomain_label_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SegmentGeographicalDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_SegmentGeographicalDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SegmentGeographicalDomain" xlink:to="lab_srt_SegmentGeographicalDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019e46c4-3a42-75d5-b323-9a44554305f1_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, indefinite-lived</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, Indefinite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year</link:label>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_label_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:to="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsPrrSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:to="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract_019e46c4-3969-74ef-bd7c-f37572f6b364_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings per share denominators (in thousands):</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ForeignRegulatoryDepositsMember_019e46c4-3a42-7a94-9497-229b0f23c734_terseLabel_en-US" xlink:label="lab_wtm_ForeignRegulatoryDepositsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lloyd&#8217;s trust deposits</link:label>
    <link:label id="lab_wtm_ForeignRegulatoryDepositsMember_label_en-US" xlink:label="lab_wtm_ForeignRegulatoryDepositsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Foreign Regulatory Deposits [Member]</link:label>
    <link:label id="lab_wtm_ForeignRegulatoryDepositsMember_documentation_en-US" xlink:label="lab_wtm_ForeignRegulatoryDepositsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Foreign Regulatory Deposits</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ForeignRegulatoryDepositsMember" xlink:href="wtm-20260630.xsd#wtm_ForeignRegulatoryDepositsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ForeignRegulatoryDepositsMember" xlink:to="lab_wtm_ForeignRegulatoryDepositsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UnrestrictedCashHeldForSale_019e46c4-3a42-71dc-90c2-eb41d0abdfaa_terseLabel_en-US" xlink:label="lab_wtm_UnrestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrestricted cash held for sale</link:label>
    <link:label id="lab_wtm_UnrestrictedCashHeldForSale_label_en-US" xlink:label="lab_wtm_UnrestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrestricted Cash, Held For Sale</link:label>
    <link:label id="lab_wtm_UnrestrictedCashHeldForSale_documentation_en-US" xlink:label="lab_wtm_UnrestrictedCashHeldForSale" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unrestricted Cash, Held For Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_UnrestrictedCashHeldForSale" xlink:href="wtm-20260630.xsd#wtm_UnrestrictedCashHeldForSale"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_UnrestrictedCashHeldForSale" xlink:to="lab_wtm_UnrestrictedCashHeldForSale" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsAbstract_019e46c4-3ae3-7023-bf3b-fbebf101e847_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsAbstract_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments [Abstract]</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsAbstract_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsAbstract" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsAbstract" xlink:to="lab_wtm_OtherLongTermInvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019e46c4-3ae4-76a3-ab46-90a8638b3e84_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019e46c4-3ae4-72e4-9f24-6ebaee020363_netLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019e46c4-3ae4-760c-ae70-24ec58945aaf_totalLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireOtherInvestments_019e46c4-3ae3-77ea-a7a2-9b6612159b8b_negatedLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Purchases of other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireOtherInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireOtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireOtherInvestments" xlink:to="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByParent_019e46c4-3969-7329-a0a6-1acffc6655b9_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic ownership</link:label>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByParent_label_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestOwnershipPercentageByParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:to="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryWMOutriggerReMember_019e46c4-3a42-7613-b1a6-c67ae7d6ee50_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryWMOutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - WM Outrigger Re</link:label>
    <link:label id="lab_wtm_SubsidiaryWMOutriggerReMember_label_en-US" xlink:label="lab_wtm_SubsidiaryWMOutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - WM Outrigger Re [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryWMOutriggerReMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryWMOutriggerReMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - WM Outrigger Re</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryWMOutriggerReMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryWMOutriggerReMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryWMOutriggerReMember" xlink:to="lab_wtm_SubsidiaryWMOutriggerReMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019e46c4-3969-7a33-8272-d56bd0ebed55_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amount borrowed</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019e46c4-3969-7e25-b1a0-d601ec5d23ff_periodStartLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019e46c4-3969-7b8e-a5cb-8c671bb6eaf1_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod_019e46c4-3ae3-73cd-b4a6-550ebb5d439b_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New grants</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Grants In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Grants In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskSecuredMember_019e46c4-3a42-72b8-b7ff-efe1993bc0f3_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskSecuredMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Secured</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskSecuredMember_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskSecuredMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Secured [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskSecuredMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskSecuredMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskSecuredMember" xlink:to="lab_us-gaap_CededCreditRiskSecuredMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryCompAmt" xlink:to="lab_ecd_OutstandingRecoveryCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_IndividualAxis_terseLabel_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Individual:</link:label>
    <link:label id="lab_ecd_IndividualAxis_label_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_IndividualAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_IndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_IndividualAxis" xlink:to="lab_ecd_IndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e46c4-3a42-77d4-892b-9bc56e5d5504_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (losses) per share denominator (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PercentageofRiskPremiumCeded_019e46c4-3a42-765a-a585-4eefe891aaff_terseLabel_en-US" xlink:label="lab_wtm_PercentageofRiskPremiumCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of risk premium ceded</link:label>
    <link:label id="lab_wtm_PercentageofRiskPremiumCeded_label_en-US" xlink:label="lab_wtm_PercentageofRiskPremiumCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Percentage of Risk Premium Ceded</link:label>
    <link:label id="lab_wtm_PercentageofRiskPremiumCeded_documentation_en-US" xlink:label="lab_wtm_PercentageofRiskPremiumCeded" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Percentage of Risk Premium Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PercentageofRiskPremiumCeded" xlink:href="wtm-20260630.xsd#wtm_PercentageofRiskPremiumCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PercentageofRiskPremiumCeded" xlink:to="lab_wtm_PercentageofRiskPremiumCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_019e46c4-3a42-7af2-8af7-9eb885a73505_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_019e46c4-3a42-7a84-9cd0-5ea6844a04c9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross and net reinsurance recoverables by reinsurers ratings</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:to="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_label_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019e46c4-3ae3-7a97-93f2-9e0c28893ce4_verboseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract_019e46c4-3a42-720e-91a0-b998e2ca78a4_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, before Accumulated Amortization [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember_019e46c4-3a42-76f0-9b73-9137d4e2d489_terseLabel_en-US" xlink:label="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Investments</link:label>
    <link:label id="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember_label_en-US" xlink:label="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Investments After TPC Providers - Investments [Member]</link:label>
    <link:label id="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Investments After TPC Providers - Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:to="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour_019e46c4-3a42-7ccb-aa16-25418b54607c_terseLabel_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2031 and thereafter</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour_label_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Due after Year Four</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour_documentation_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Due after Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:href="wtm-20260630.xsd#wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:to="lab_wtm_FinancialGuaranteeInsuranceContractPremiumRevenueToBeRecognizedDueAfterYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_019e46c4-3ae3-78e7-aab4-cb882d4b845c_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Partnership interest, carrying value</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Reporting Entity Involvement, Maximum Loss Exposure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:to="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentMember_019e46c4-3ae3-7fb8-a8d3-5a064a4c8d02_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Specialty Insurance Distribution (Distinguished)</link:label>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentMember_019e46c4-3ae3-79ca-b0bc-77b25043bb5b_verboseLabel_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Distinguished</link:label>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentMember_label_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Partners - Segment [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Partners - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedPartnersSegmentMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedPartnersSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedPartnersSegmentMember" xlink:to="lab_wtm_DistinguishedPartnersSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UnderwritingCapacityMember_019e46c4-3ae4-739c-ba9b-f58dd08a6b18_terseLabel_en-US" xlink:label="lab_wtm_UnderwritingCapacityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting Capacity</link:label>
    <link:label id="lab_wtm_UnderwritingCapacityMember_label_en-US" xlink:label="lab_wtm_UnderwritingCapacityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Capacity [Member]</link:label>
    <link:label id="lab_wtm_UnderwritingCapacityMember_documentation_en-US" xlink:label="lab_wtm_UnderwritingCapacityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_UnderwritingCapacityMember" xlink:href="wtm-20260630.xsd#wtm_UnderwritingCapacityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_UnderwritingCapacityMember" xlink:to="lab_wtm_UnderwritingCapacityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_019e46c4-3969-7b17-8d3f-b332ef950c57_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">&gt;10&#160;years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Greater than 10 Years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Greater than 10 Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccruedInvestmentIncomeReceivable_019e46c4-3969-75e1-bf17-615e48eb4c28_terseLabel_en-US" xlink:label="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued investment income</link:label>
    <link:label id="lab_us-gaap_AccruedInvestmentIncomeReceivable_label_en-US" xlink:label="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accrued Investment Income Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedInvestmentIncomeReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedInvestmentIncomeReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccruedInvestmentIncomeReceivable" xlink:to="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember_019e46c4-3ae4-7417-b7ad-a21892c6076e_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other asset-backed securities:</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities, Securitized Loans and Receivables [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses_019e46c4-3ae3-7769-902b-49d91f77caac_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables on paid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Paid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_019e46c4-3a42-79c8-ad73-7e0913a0f296_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LettersOfCreditOutstandingAmount_019e46c4-3969-7a22-8f00-98605edc26cf_terseLabel_en-US" xlink:label="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Letters of credit outstanding</link:label>
    <link:label id="lab_us-gaap_LettersOfCreditOutstandingAmount_label_en-US" xlink:label="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Letters of Credit Outstanding, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LettersOfCreditOutstandingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LettersOfCreditOutstandingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LettersOfCreditOutstandingAmount" xlink:to="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears_019e46c4-3969-73ab-aff6-8d32fc48c50d_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">1 &#8211; 3&#160;years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, One to Three Years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, One to Three Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_019e46c4-3969-7510-8a05-9a1aed0fbc46_terseLabel_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Organization, Consolidation and Presentation of Financial Statements [Abstract]</link:label>
    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_label_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Organization, Consolidation and Presentation of Financial Statements [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:to="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019e46c4-3969-7f52-ba65-ff0909a6b4a9_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments_019e46c4-3969-72bf-8218-d2f83c8ed7e8_terseLabel_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase price adjustments</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments_label_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received, Purchase Price Adjustments</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments_documentation_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Incremental Proceeds Received, Purchase Price Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:href="wtm-20260630.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:to="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax_019e46c4-3a42-790a-84eb-257fa240f82f_terseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive income (loss), net of tax</link:label>
    <link:label id="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Comprehensive Income (Loss), Net Of Tax</link:label>
    <link:label id="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Comprehensive Income (Loss), Net Of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:href="wtm-20260630.xsd#wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:to="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_019e46c4-3ae3-70c0-bafb-1be1aa12ba2d_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notional amount</link:label>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_label_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Notional Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeAssetNotionalAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:to="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_019e46c4-3ae3-70d7-88bf-3c17fdf1a01c_terseLabel_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk</link:label>
    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_label_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk [Member]</link:label>
    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_documentation_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:href="wtm-20260630.xsd#wtm_PrivateEquityAndHedgeFundConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:to="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf_019e46c4-3a42-7910-88e5-24b31d393c1b_terseLabel_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity interest percent of ownership sold</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf_label_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Ownership Percentage Disposed Of</link:label>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf_documentation_en-US" xlink:label="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Ownership Percentage Disposed Of</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:href="wtm-20260630.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:to="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage_019e46c4-3ae3-7d65-aabe-848c331be07b_terseLabel_en-US" xlink:label="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percent of shares outstanding</link:label>
    <link:label id="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage_label_en-US" xlink:label="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Management Rollover Shareholders, Additional Shares, Percentage</link:label>
    <link:label id="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage_documentation_en-US" xlink:label="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Management Rollover Shareholders, Additional Shares, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:href="wtm-20260630.xsd#wtm_ManagementRolloverShareholdersAdditionalSharesPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:to="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriodAxis_019e46c4-3ae3-783c-a80e-2696abdc99b9_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant Period [Axis]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriodAxis_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant Period [Axis]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriodAxis_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriodAxis" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriodAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriodAxis" xlink:to="lab_wtm_DebtCovenantPeriodAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_terseLabel_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Executive Categories</link:label>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_label_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Executive Categories [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllExecutiveCategoriesMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllExecutiveCategoriesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllExecutiveCategoriesMember" xlink:to="lab_ecd_AllExecutiveCategoriesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationTechniqueDomain_019e46c4-3ae4-7b9a-b89e-5b93e0720889_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Domain]</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueDomain_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueDomain" xlink:to="lab_us-gaap_ValuationTechniqueDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsSvcCstMember" xlink:to="lab_ecd_PnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate_019e46c4-3a42-7b73-8273-e9a8088a7491_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HGGlobal2026SeniorNotesMember_019fa1a5-a65d-767e-9374-e4ad22d350a0_terseLabel_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes</link:label>
    <link:label id="lab_wtm_HGGlobal2026SeniorNotesMember_label_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes [Member]</link:label>
    <link:label id="lab_wtm_HGGlobal2026SeniorNotesMember_documentation_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobal2026SeniorNotesMember" xlink:href="wtm-20260630.xsd#wtm_HGGlobal2026SeniorNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HGGlobal2026SeniorNotesMember" xlink:to="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentSharePrice_019e46c4-3969-7ad3-a780-81d438da108b_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentSharePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase price (in dollars per share)</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentSharePrice_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentSharePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Share Price</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentSharePrice_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentSharePrice" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Share Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentSharePrice" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentSharePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentSharePrice" xlink:to="lab_wtm_EquityMethodInvestmentSharePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount_019e46c4-3a42-77ed-94b7-3d71d7d2385b_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest, Equity, Carrying Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:to="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_019e46c4-3a42-7f1d-96fb-ea35ce648862_terseLabel_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Operations</link:label>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_label_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Noncontrolling Interest [Member]</link:label>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_documentation_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherNoncontrollingInterestMember" xlink:href="wtm-20260630.xsd#wtm_OtherNoncontrollingInterestMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherNoncontrollingInterestMember" xlink:to="lab_wtm_OtherNoncontrollingInterestMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesDebtAmortizedCost_019e46c4-3a42-780c-9882-1f5df67c3913_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebtAmortizedCost_019e46c4-3a42-7dcd-bb88-860704073802_totalLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebtAmortizedCost_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesDebtAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:to="lab_us-gaap_TradingSecuritiesDebtAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_019e46c4-3a42-763f-a83d-a9d9b438312d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of earnings per share from continuing operations</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureAbstract_019e46c4-3ae3-7644-8e0b-dc86b5acc47d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureAbstract" xlink:to="lab_us-gaap_DebtDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_019fba0f-38c1-7bdf-98f8-2dda478c4f27_terseLabel_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Minimum interest reserve period required</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_label_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve, Minimum Period Required</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_documentation_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve, Minimum Period Required</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:href="wtm-20260630.xsd#wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:to="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_019e46c4-3a42-7156-b3d5-5d1d1aedaa4b_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Information</link:label>
    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:to="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MinimumMember_019e46c4-3a42-7136-8cdb-210cf1184d15_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Minimum</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_019e46c4-3a42-7067-8cba-236cd01d1b0d_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeAxis" xlink:to="lab_us-gaap_InvestmentTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments_019e46c4-3ae3-7089-a12a-84e275491704_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unfunded Commitments</link:label>
    <link:label id="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments_label_en-US" xlink:label="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Unfunded Commitments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments" xlink:to="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedTransactionScaleCoProgramMember_019e46c4-3ae3-7cab-bb4e-bccdf261f063_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished Transaction, ScaleCo Program</link:label>
    <link:label id="lab_wtm_DistinguishedTransactionScaleCoProgramMember_label_en-US" xlink:label="lab_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Transaction, ScaleCo Program [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedTransactionScaleCoProgramMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Transaction, ScaleCo Program</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedTransactionScaleCoProgramMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:to="lab_wtm_DistinguishedTransactionScaleCoProgramMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_019e46c4-3969-78eb-9604-53c82467052d_totalLabel_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:to="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_019e46c4-3ae4-790e-b7ab-bd0b0550c53a_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entities</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:to="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_019e46c4-3969-75dd-be4e-75819f8e50ce_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember_019e46c4-3969-7bf1-bc62-abf89a739201_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished, net</link:label>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember_label_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Partners - Segment, Net of Reconciling Items [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Partners - Segment, Net of Reconciling Items</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:to="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare_019e46c4-3ae3-7869-8947-af9b4c22176a_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (losses) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations, Per Diluted Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare_019e46c4-3a42-74e8-9599-a0843e1cb07a_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (losses) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations, Per Basic Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsPerBasicShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsPerBasicShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfIncomeLocationBalanceAxis_019e46c4-3969-73dc-890d-570beb7cc75b_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Statement Location [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementOfIncomeLocationBalanceAxis_label_en-US" xlink:label="lab_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Location, Statement of Income, Balance [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfIncomeLocationBalanceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:to="lab_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonRule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:to="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember_019e46c4-3969-7654-a7a5-996e56a16958_terseLabel_en-US" xlink:label="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FNMA</link:label>
    <link:label id="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember_label_en-US" xlink:label="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal National Mortgage Association Certificates and Obligations (FNMA) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:to="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRightToSellRedemptionValue_019e46c4-3ae3-7310-9265-22e02b1f0125_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redemption value</link:label>
    <link:label id="lab_wtm_BusinessCombinationRightToSellRedemptionValue_label_en-US" xlink:label="lab_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Right to Sell, Redemption Value</link:label>
    <link:label id="lab_wtm_BusinessCombinationRightToSellRedemptionValue_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Right to Sell, Redemption Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRightToSellRedemptionValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:to="lab_wtm_BusinessCombinationRightToSellRedemptionValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLiabilities_019e46c4-3a42-7b08-bb26-8989bf95be59_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_OtherLiabilities_label_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLiabilities" xlink:to="lab_us-gaap_OtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_019e46c4-3a42-700b-ae20-0901d06966af_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred, liabilities incurred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Liabilities Incurred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_019e46c4-3969-709e-9c1b-397fbb60f217_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, authorized shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PassportCardDavidShieldMember_019e46c4-3a42-7997-abbf-bba67cbbca9f_terseLabel_en-US" xlink:label="lab_wtm_PassportCardDavidShieldMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PassportCard/DavidShield</link:label>
    <link:label id="lab_wtm_PassportCardDavidShieldMember_label_en-US" xlink:label="lab_wtm_PassportCardDavidShieldMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PassportCard/DavidShield [Member]</link:label>
    <link:label id="lab_wtm_PassportCardDavidShieldMember_documentation_en-US" xlink:label="lab_wtm_PassportCardDavidShieldMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">PassportCard/DavidShield</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PassportCardDavidShieldMember" xlink:href="wtm-20260630.xsd#wtm_PassportCardDavidShieldMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PassportCardDavidShieldMember" xlink:to="lab_wtm_PassportCardDavidShieldMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardExrcPrice_terseLabel_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise Price</link:label>
    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardExrcPrice" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardExrcPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardExrcPrice" xlink:to="lab_ecd_AwardExrcPrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsRecurringMember_019e46c4-3ae3-7cf3-acb9-fd0493e3311e_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair value measured on a recurring basis</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsRecurringMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsRecurringMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementsRecurringMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsRecurringMember" xlink:to="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_019e46c4-3969-7627-ae40-47606ab9c4ce_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_label_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingInformationLineItems" xlink:to="lab_us-gaap_SegmentReportingInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsForParticipationContracts_019e46c4-3a42-7c5e-bd92-c22c3a57eb02_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsForParticipationContracts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Contributions to Kudu&#8217;s Participation Contracts</link:label>
    <link:label id="lab_wtm_PaymentsForParticipationContracts_label_en-US" xlink:label="lab_wtm_PaymentsForParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for Participation Contracts</link:label>
    <link:label id="lab_wtm_PaymentsForParticipationContracts_documentation_en-US" xlink:label="lab_wtm_PaymentsForParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments for Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsForParticipationContracts" xlink:href="wtm-20260630.xsd#wtm_PaymentsForParticipationContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsForParticipationContracts" xlink:to="lab_wtm_PaymentsForParticipationContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SignificantTransactionsTextBlock_019e46c4-3969-79ec-9fdd-243375fc445c_terseLabel_en-US" xlink:label="lab_wtm_SignificantTransactionsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Significant Transactions</link:label>
    <link:label id="lab_wtm_SignificantTransactionsTextBlock_label_en-US" xlink:label="lab_wtm_SignificantTransactionsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Significant Transactions [Text Block]</link:label>
    <link:label id="lab_wtm_SignificantTransactionsTextBlock_documentation_en-US" xlink:label="lab_wtm_SignificantTransactionsTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Description of various transactions that are significant to White Mountains financial position, results of operations and/or cash flows.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SignificantTransactionsTextBlock" xlink:href="wtm-20260630.xsd#wtm_SignificantTransactionsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SignificantTransactionsTextBlock" xlink:to="lab_wtm_SignificantTransactionsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentQuarterlyReport_019e46c4-3a42-7b18-bb84-9867246fb43a_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentQuarterlyReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentQuarterlyReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_label_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:to="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember_019e46c4-3969-7993-9fdf-4b5c5cdfea59_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares and paid-in surplus</link:label>
    <link:label id="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock Including Additional Paid in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod_019e46c4-3a42-7b06-9859-7ec7c3bbdceb_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New grants (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Grants In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Grants In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019e46c4-3a42-76f0-93a6-822266383bf0_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Prior year losses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019e46c4-3969-7b6a-bca5-17ad3b27f8cf_negatedLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Repayment of debt and revolving lines of credit</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019e46c4-3969-7b92-a1f2-f0cae203de12_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Repayments</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier_019e46c4-3ae3-7e51-b271-a684e707a87d_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based compensation arrangement by share-based payment award, multiplier</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-based Payment Award, Payout Multiplier</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-based Payment Award, Payout Multiplier</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_019e46c4-3969-7e00-8fe6-af27c03a6368_negatedLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Unamortized discount and issuance cost</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Unamortized Discount (Premium) and Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:to="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedCreditFacilityMember_019e46c4-3ae4-72d5-8ae7-a7aa2978d553_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished Credit Facility</link:label>
    <link:label id="lab_wtm_DistinguishedCreditFacilityMember_019e46c4-3ae4-7e68-a018-4655895d34c5_verboseLabel_en-US" xlink:label="lab_wtm_DistinguishedCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Distinguished Credit Facility</link:label>
    <link:label id="lab_wtm_DistinguishedCreditFacilityMember_label_en-US" xlink:label="lab_wtm_DistinguishedCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Credit Facility [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedCreditFacilityMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Credit Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedCreditFacilityMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedCreditFacilityMember" xlink:to="lab_wtm_DistinguishedCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019e46c4-3a42-7ee1-b9bc-50789f0ac4f4_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in MediaAlpha, at fair value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019e46c4-3a42-7eca-b1b1-38ab0d4cf56a_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestments" xlink:to="lab_us-gaap_EquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_019e46c4-3969-70c7-b417-512d67465d7d_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_019e46c4-3a42-7cc3-965a-9d13e31055ee_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_019e46c4-3969-7249-938e-5e686ec0e24b_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019e46c4-3ae4-7f55-a990-45cce4ea1c0a_verboseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized gains</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsurerTypeAxis_019e46c4-3969-7b42-8713-a754b59f5acb_terseLabel_en-US" xlink:label="lab_wtm_ReinsurerTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Type [Axis]</link:label>
    <link:label id="lab_wtm_ReinsurerTypeAxis_label_en-US" xlink:label="lab_wtm_ReinsurerTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Type [Axis]</link:label>
    <link:label id="lab_wtm_ReinsurerTypeAxis_documentation_en-US" xlink:label="lab_wtm_ReinsurerTypeAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurer, Type</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsurerTypeAxis" xlink:href="wtm-20260630.xsd#wtm_ReinsurerTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsurerTypeAxis" xlink:to="lab_wtm_ReinsurerTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpensesAbstract_019e46c4-3a42-7059-912a-033945d6d262_terseLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expenses:</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Benefits, Losses and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:to="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_019e46c4-3a42-7204-a2c7-9327614e121f_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash on hand</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_label_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Cash on Hand</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Cash on Hand</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationConsiderationTransferredCashOnHand"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:to="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrAdoptionDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_019e46c4-3ae3-7b57-897f-f359cc9361d2_terseLabel_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remaining weighted average contract period (in years)</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_label_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Remaining Weighted Average Contract Period</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_documentation_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Remaining Weighted Average Contract Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:href="wtm-20260630.xsd#wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:to="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_019e46c4-3ae4-78e6-a85f-69b9a855c982_terseLabel_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties</link:label>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_label_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties [Member]</link:label>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_documentation_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:href="wtm-20260630.xsd#wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:to="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TechnologySectorMember_019e46c4-3969-7a59-bd82-aae5e15fc98d_terseLabel_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Technology</link:label>
    <link:label id="lab_us-gaap_TechnologySectorMember_label_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Technology Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TechnologySectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TechnologySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TechnologySectorMember" xlink:to="lab_us-gaap_TechnologySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate_019e46c4-3a42-790f-8906-d2dc35fd278b_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommonStockOtherMember_019e46c4-3ae3-7328-a0fb-ddec30ef1c80_verboseLabel_en-US" xlink:label="lab_wtm_CommonStockOtherMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_wtm_CommonStockOtherMember_label_en-US" xlink:label="lab_wtm_CommonStockOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Other [Member]</link:label>
    <link:label id="lab_wtm_CommonStockOtherMember_documentation_en-US" xlink:label="lab_wtm_CommonStockOtherMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Common Stock, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_CommonStockOtherMember" xlink:href="wtm-20260630.xsd#wtm_CommonStockOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_CommonStockOtherMember" xlink:to="lab_wtm_CommonStockOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
    <link:label id="lab_ecd_TrdArrIndTitle_label_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Title</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndTitle" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_019e46c4-3a42-724b-9136-7f8008f2fcf6_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedUndistributed_019e46c4-3a42-7016-82e4-2f46327e29a2_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Undistributed earnings (losses) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedUndistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted, Undistributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDilutedUndistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDilutedUndistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDilutedUndistributed" xlink:to="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward_019e46c4-3969-77fe-b768-eff5315928b8_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unamortized Issue&#160;Date Fair&#160;Value</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Grant Date Fair Value [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019e46c4-3a42-7901-a74b-8dd3039661f2_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net other financing activities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from (Payment for) Other Financing Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromPaymentsForOtherFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:to="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherOperatingIncome_019e46c4-3969-71ce-a4c6-113e83258c47_terseLabel_en-US" xlink:label="lab_us-gaap_OtherOperatingIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest income from BAM Surplus Notes</link:label>
    <link:label id="lab_us-gaap_OtherOperatingIncome_label_en-US" xlink:label="lab_us-gaap_OtherOperatingIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Operating Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherOperatingIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherOperatingIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherOperatingIncome" xlink:to="lab_us-gaap_OtherOperatingIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest_019e46c4-3ae3-7366-b7e7-4079a405c39e_negatedTerseLabel_en-US" xlink:label="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Adjustment for redeemable noncontrolling interests</link:label>
    <link:label id="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest_label_en-US" xlink:label="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment for Redeemable Noncontrolling Interest</link:label>
    <link:label id="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest_documentation_en-US" xlink:label="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Adjustment for Redeemable Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:href="wtm-20260630.xsd#wtm_AdjustmentForRedeemableNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:to="lab_wtm_AdjustmentForRedeemableNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentAdditionalInterestRate_019e46c4-3a42-7a9c-9e11-2ec8cce6ac74_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentAdditionalInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional interest rate</link:label>
    <link:label id="lab_wtm_DebtInstrumentAdditionalInterestRate_label_en-US" xlink:label="lab_wtm_DebtInstrumentAdditionalInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Additional Interest Rate</link:label>
    <link:label id="lab_wtm_DebtInstrumentAdditionalInterestRate_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentAdditionalInterestRate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Additional Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentAdditionalInterestRate" xlink:href="wtm-20260630.xsd#wtm_DebtInstrumentAdditionalInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentAdditionalInterestRate" xlink:to="lab_wtm_DebtInstrumentAdditionalInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments_019e46c4-3a42-72a2-9c67-70d8b8a8ed7b_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distributions and redemptions of other long-term investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale and Maturity of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019e46c4-3ae3-72d4-a1d4-15011880b3d7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Current year losses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DerivativeAssetAmountReceivedOnCancellation_019fac9d-4e47-72e4-a61f-4aed750b4bf3_terseLabel_en-US" xlink:label="lab_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amount received on cancellation</link:label>
    <link:label id="lab_wtm_DerivativeAssetAmountReceivedOnCancellation_label_en-US" xlink:label="lab_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Amount Received On Cancellation</link:label>
    <link:label id="lab_wtm_DerivativeAssetAmountReceivedOnCancellation_documentation_en-US" xlink:label="lab_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Derivative Asset, Amount Received On Cancellation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:href="wtm-20260630.xsd#wtm_DerivativeAssetAmountReceivedOnCancellation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:to="lab_wtm_DerivativeAssetAmountReceivedOnCancellation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_019e46c4-3ae3-7c0c-91d2-9db9771219fb_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAcquireeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:to="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LetterOfCreditMember_019e46c4-3a42-7f23-beab-2f97e4362d6a_terseLabel_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Letter of Credit</link:label>
    <link:label id="lab_us-gaap_LetterOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Letter of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LetterOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LetterOfCreditMember" xlink:to="lab_us-gaap_LetterOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes_019e46c4-3a42-7923-a150-3a576103b398_terseLabel_en-US" xlink:label="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in fair value of BAM Surplus Notes</link:label>
    <link:label id="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes_label_en-US" xlink:label="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Fair Value Adjustment of Surplus Notes</link:label>
    <link:label id="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes_documentation_en-US" xlink:label="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Fair Value Adjustment of Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:href="wtm-20260630.xsd#wtm_GainLossOnFairValueAdjustmentOfSurplusNotes"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:to="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_019e46c4-3a42-706a-a6b3-158679174b02_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_019e46c4-3a42-7711-843b-f1e7ef85b831_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written premiums:</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNetConsolidatedAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:to="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_019e46c4-3969-7628-b0f4-feab773dc635_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Operations</link:label>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_label_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Reconciling Item, Corporate Nonsegment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateNonSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateNonSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateNonSegmentMember" xlink:to="lab_us-gaap_CorporateNonSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberOfInfrastructureFunds_019fac7b-3ef6-7313-9002-de98be3cfcef_terseLabel_en-US" xlink:label="lab_wtm_NumberOfInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of infrastructure funds</link:label>
    <link:label id="lab_wtm_NumberOfInfrastructureFunds_label_en-US" xlink:label="lab_wtm_NumberOfInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Infrastructure Funds</link:label>
    <link:label id="lab_wtm_NumberOfInfrastructureFunds_documentation_en-US" xlink:label="lab_wtm_NumberOfInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Infrastructure Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberOfInfrastructureFunds" xlink:href="wtm-20260630.xsd#wtm_NumberOfInfrastructureFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NumberOfInfrastructureFunds" xlink:to="lab_wtm_NumberOfInfrastructureFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_019e46c4-3ae3-7803-91ce-0c68872a9fb2_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAxis" xlink:to="lab_us-gaap_BusinessAcquisitionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_019e46c4-3ae3-756e-80b5-d433c59ee875_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other equity method eligible investments less than 50.0%</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_label_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, Less Than Fifty Percent [Member]</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_documentation_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, Less Than Fifty Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:href="wtm-20260630.xsd#wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:to="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e46c4-3ae3-72fe-9c0d-ea4fb6996f0b_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) operations</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod_019e46c4-3969-7ee7-b8ff-7ced69bfc34a_terseLabel_en-US" xlink:label="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net contributions (distributions) and dilution from other noncontrolling interests</link:label>
    <link:label id="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod_label_en-US" xlink:label="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Net Contribution and Dilution During Period</link:label>
    <link:label id="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod_documentation_en-US" xlink:label="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Net Contribution and Dilution During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:href="wtm-20260630.xsd#wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:to="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodTwoMember_019e46c4-3a42-7b0f-9df1-725813b68426_terseLabel_en-US" xlink:label="lab_wtm_PerformancePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2025 &#8211; 2027</link:label>
    <link:label id="lab_wtm_PerformancePeriodTwoMember_label_en-US" xlink:label="lab_wtm_PerformancePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Period Two [Member]</link:label>
    <link:label id="lab_wtm_PerformancePeriodTwoMember_documentation_en-US" xlink:label="lab_wtm_PerformancePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Performance Cycle 2018 to 2020 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PerformancePeriodTwoMember" xlink:href="wtm-20260630.xsd#wtm_PerformancePeriodTwoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PerformancePeriodTwoMember" xlink:to="lab_wtm_PerformancePeriodTwoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019e46c4-3a42-79cc-b12e-c627d2ed747e_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior year losses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019e46c4-3a42-70dc-831b-ab0ad5fa6d70_verboseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Favorable prior loss reserve development</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EnergySectorMember_019e46c4-3a42-767c-9150-136c97e0f426_terseLabel_en-US" xlink:label="lab_us-gaap_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy</link:label>
    <link:label id="lab_us-gaap_EnergySectorMember_label_en-US" xlink:label="lab_us-gaap_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EnergySectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EnergySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EnergySectorMember" xlink:to="lab_us-gaap_EnergySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest_019e46c4-3ae4-7683-8d33-a7fe7aad94d0_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary, ownership percentage economic interest falls</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest_label_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Economic Interest</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest_documentation_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Economic Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryOwnershipPercentageEconomicInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:to="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_019e46c4-3ae3-73e6-936d-7c9503b55dc6_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_019e46c4-3ae4-76d0-8ab1-debc60238927_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">White Mountains&#8217;s common shareholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityAbstract" xlink:to="lab_us-gaap_StockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_019e46c4-3969-7374-84a6-e4444fd9c2c4_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems_019e46c4-3ae4-7d72-8831-d8b54cfb44a8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Quantitative information for Level 3 Fair Value Measurements Assets</link:label>
    <link:label id="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Option, Quantitative Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueOptionQuantitativeDisclosuresLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:to="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e46c4-3a42-7df7-98be-7600340a84b5_verboseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e46c4-3a42-7b2a-b138-4357170d66a7_negatedLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized investment (gains) losses</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e46c4-3a42-736c-9614-0301a52b882a_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_terseLabel_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs)</link:label>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_label_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockAppreciationRightsSARSMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:to="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable_019e46c4-3969-7531-91c7-00f47f5196a4_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:to="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_019e46c4-3a42-7af5-a17b-ad14f086c2b1_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_019e46c4-3a42-7229-b1e9-6c30df2d8a3a_totalLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_019e46c4-3a42-71e4-8c81-9c58ec322140_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Collateral</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverables" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverables" xlink:to="lab_us-gaap_ReinsuranceRecoverables" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_019e46c4-3ae4-7cda-83f8-44917d4050a1_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IncreaseDecreaseInShortTermInvestments_019fc6e4-80a4-743c-a5e4-8361a5b52585_negatedLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net change in short-term investments &#8212; Kudu</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInShortTermInvestments_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Short Term Investments</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInShortTermInvestments_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Short Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInShortTermInvestments" xlink:href="wtm-20260630.xsd#wtm_IncreaseDecreaseInShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IncreaseDecreaseInShortTermInvestments" xlink:to="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_WMOutriggerReSegmentMember_019e46c4-3a42-7a08-aa8a-dfe2af54fd8a_terseLabel_en-US" xlink:label="lab_wtm_WMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WM Outrigger Re</link:label>
    <link:label id="lab_wtm_WMOutriggerReSegmentMember_label_en-US" xlink:label="lab_wtm_WMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">WM Outrigger Re - Segment [Member]</link:label>
    <link:label id="lab_wtm_WMOutriggerReSegmentMember_documentation_en-US" xlink:label="lab_wtm_WMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">WM Outrigger Re - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_WMOutriggerReSegmentMember" xlink:href="wtm-20260630.xsd#wtm_WMOutriggerReSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_WMOutriggerReSegmentMember" xlink:to="lab_wtm_WMOutriggerReSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember_019e46c4-3ae3-79b3-895d-b8203684ae7a_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Kudu - Management Equity Incentive</link:label>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember_label_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Kudu Investment Management, Management Equity Incentive [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Kudu Investment Management, Management Equity Incentive</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:to="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentInformationTable_019e46c4-3a42-7db8-85c3-aa8f4c977e41_terseLabel_en-US" xlink:label="lab_dei_DocumentInformationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Information [Table]</link:label>
    <link:label id="lab_dei_DocumentInformationTable_label_en-US" xlink:label="lab_dei_DocumentInformationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Information [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationTable" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentInformationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentInformationTable" xlink:to="lab_dei_DocumentInformationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod_019e46c4-3a42-7f00-8337-7f49837f1517_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written notice period</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Redemption, Written Notice Period</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments, Redemption, Written Notice Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:to="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryIndName" xlink:to="lab_ecd_ForgoneRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description</link:label>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_label_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:to="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommunicationsSectorMember_019e46c4-3969-73c3-923f-4dc66565365b_terseLabel_en-US" xlink:label="lab_wtm_CommunicationsSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Communications</link:label>
    <link:label id="lab_wtm_CommunicationsSectorMember_label_en-US" xlink:label="lab_wtm_CommunicationsSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Communications Sector [Member]</link:label>
    <link:label id="lab_wtm_CommunicationsSectorMember_documentation_en-US" xlink:label="lab_wtm_CommunicationsSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Communications Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_CommunicationsSectorMember" xlink:href="wtm-20260630.xsd#wtm_CommunicationsSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_CommunicationsSectorMember" xlink:to="lab_wtm_CommunicationsSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityDomain_019e46c4-3a42-7a85-b1c4-8ae6d04ae97a_terseLabel_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity [Domain]</link:label>
    <link:label id="lab_dei_EntityDomain_label_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityDomain" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityDomain" xlink:to="lab_dei_EntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCMember_019e46c4-3ae3-7456-b79f-4f553cd0a6b9_verboseLabel_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Asset Management (Kudu)</link:label>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCMember_label_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Kudu Investment Management, LLC [Member]</link:label>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCMember_documentation_en-US" xlink:label="lab_wtm_KuduInvestmentManagementLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Kudu Investment Management, LLC [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_KuduInvestmentManagementLLCMember" xlink:href="wtm-20260630.xsd#wtm_KuduInvestmentManagementLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_KuduInvestmentManagementLLCMember" xlink:to="lab_wtm_KuduInvestmentManagementLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate_019e46c4-3a42-7dc8-a917-315bfc2f09f0_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage and asset-backed securities and collateralized loan obligations</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod3Member_019e46c4-3a42-763a-8248-66ce2a35bf9a_terseLabel_en-US" xlink:label="lab_wtm_DebtCovenantPeriod3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 3</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod3Member_label_en-US" xlink:label="lab_wtm_DebtCovenantPeriod3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 3 [Member]</link:label>
    <link:label id="lab_wtm_DebtCovenantPeriod3Member_documentation_en-US" xlink:label="lab_wtm_DebtCovenantPeriod3Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Covenant, Period 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtCovenantPeriod3Member" xlink:href="wtm-20260630.xsd#wtm_DebtCovenantPeriod3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriod3Member" xlink:to="lab_wtm_DebtCovenantPeriod3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod_019e46c4-3ae3-7ad0-b498-a76f023f442a_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance cycle period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Cycle Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the performance cycle on conclusion of which shares become payable.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentMeasurementInput_019e46c4-3ae3-7eec-99a1-f217b5a45dd9_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discount rate</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentMeasurementInput_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Measurement Input</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentMeasurementInput_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentMeasurementInput" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentMeasurementInput" xlink:to="lab_wtm_EquityMethodInvestmentMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember_019e46c4-3ae3-7a00-90bd-b90e131f72e3_terseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember_label_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited - Segment [Member]</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember_documentation_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:href="wtm-20260630.xsd#wtm_ArkInsuranceHoldingsLimitedSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LargestInvestmentMember_019e46c4-3a42-71e2-a35f-907103df56d4_terseLabel_en-US" xlink:label="lab_wtm_LargestInvestmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Largest Investment</link:label>
    <link:label id="lab_wtm_LargestInvestmentMember_label_en-US" xlink:label="lab_wtm_LargestInvestmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Largest Investment [Member]</link:label>
    <link:label id="lab_wtm_LargestInvestmentMember_documentation_en-US" xlink:label="lab_wtm_LargestInvestmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Largest Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LargestInvestmentMember" xlink:href="wtm-20260630.xsd#wtm_LargestInvestmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LargestInvestmentMember" xlink:to="lab_wtm_LargestInvestmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_019e46c4-3ae3-7f7e-bc61-529f41e10c15_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_label_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:to="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentsAbstract_019e46c4-3ae3-79f1-affe-667fdd9bb0bf_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in MediaAlpha</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentsAbstract_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Abstract]</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentsAbstract_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentsAbstract" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentsAbstract" xlink:to="lab_wtm_EquityMethodInvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Investments_019e46c4-3a42-7c22-aa44-55daea13344a_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_019e46c4-3a42-7228-94d2-570c4e540416_terseLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_019e46c4-3ae3-70b6-b752-87c4e6dd113b_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019e46c4-3ae4-78f2-8f0a-45028da35ede_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash (restricted $0.4)</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompRecoveryTable_terseLabel_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery</link:label>
    <link:label id="lab_ecd_ErrCompRecoveryTable_label_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompRecoveryTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompRecoveryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompRecoveryTable" xlink:to="lab_ecd_ErrCompRecoveryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019e46c4-3ae4-7648-9524-a50785bdcbbe_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of significant unobservable inputs used in estimating the fair value of investment securities</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche3Member_019e46c4-3a42-78f4-b106-de34bd4927f0_terseLabel_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes Tranche 3</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche3Member_label_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 3 [Member]</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche3Member_documentation_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:href="wtm-20260630.xsd#wtm_Ark2021SubordinatedNotesTranche3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:to="lab_wtm_Ark2021SubordinatedNotesTranche3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare_019e46c4-3ae3-726f-a0f2-9538e4d40cc5_terseLabel_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase in book value per share (in dollars per share)</link:label>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare_label_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Owned, Change in Value, Book Value Per Share</link:label>
    <link:label id="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare_documentation_en-US" xlink:label="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investment Owned, Change in Value, Book Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:href="wtm-20260630.xsd#wtm_InvestmentOwnedChangeInValueBookValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:to="lab_wtm_InvestmentOwnedChangeInValueBookValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss_019e46c4-3ae3-765a-8ae4-5c3003a0ecd6_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign currency translation and other adjustments to loss and LAE reserves</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Foreign Currency Translation Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_019e46c4-3a42-7107-8285-8911d1afd401_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCurrentReportingStatus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCurrentReportingStatus" xlink:to="lab_dei_EntityCurrentReportingStatus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e46c4-3969-7b1a-b981-fe2fc8438244_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnAmt" xlink:to="lab_ecd_TotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommonStockExchangeTradedFundsMember_019e46c4-3ae3-71de-a5a0-4de5e59e3274_terseLabel_en-US" xlink:label="lab_wtm_CommonStockExchangeTradedFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exchange-traded funds</link:label>
    <link:label id="lab_wtm_CommonStockExchangeTradedFundsMember_label_en-US" xlink:label="lab_wtm_CommonStockExchangeTradedFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Exchange Traded Funds [Member]</link:label>
    <link:label id="lab_wtm_CommonStockExchangeTradedFundsMember_documentation_en-US" xlink:label="lab_wtm_CommonStockExchangeTradedFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Common Stock, Exchange Traded Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_CommonStockExchangeTradedFundsMember" xlink:href="wtm-20260630.xsd#wtm_CommonStockExchangeTradedFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_CommonStockExchangeTradedFundsMember" xlink:to="lab_wtm_CommonStockExchangeTradedFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember_019e46c4-3a42-7669-bccd-ef28e8a22b5f_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Interest Rate Cap</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember_label_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Interest Rate Cap [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Interest Rate Cap</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryDistinguishedInterestRateCapMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:to="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TradingSecurityFairValue_019e46c4-3a42-7749-b5a2-8a16f4511d13_terseLabel_en-US" xlink:label="lab_wtm_TradingSecurityFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair&#160;Value</link:label>
    <link:label id="lab_wtm_TradingSecurityFairValue_label_en-US" xlink:label="lab_wtm_TradingSecurityFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Security, Fair Value</link:label>
    <link:label id="lab_wtm_TradingSecurityFairValue_documentation_en-US" xlink:label="lab_wtm_TradingSecurityFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Trading Security, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TradingSecurityFairValue" xlink:href="wtm-20260630.xsd#wtm_TradingSecurityFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TradingSecurityFairValue" xlink:to="lab_wtm_TradingSecurityFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax_019e46c4-3969-7d6d-a86b-86439e27def3_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net unrealized gains (losses) from foreign currency translation</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Foreign Currency Translation Adjustment, Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersMember_019e46c4-3a42-7482-a833-9de45135dcf5_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distinguished</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersMember_label_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Partners [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedPartnersMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished Partners</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryDistinguishedPartnersMember" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryDistinguishedPartnersMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryDistinguishedPartnersMember" xlink:to="lab_wtm_SubsidiaryDistinguishedPartnersMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage_019e46c4-3ae3-75f5-818e-74491a7f6b0d_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, basic ownership interest acquired, percentage</link:label>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage_label_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Basic, Percentage</link:label>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Basic, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:to="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable_019e46c4-3a42-74be-8c04-cfde56aef98d_negatedTerseLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in insurance premiums, commissions and fees receivable</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Premiums Commissions and Fees Receivable</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Premiums Commissions and Fees Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:href="wtm-20260630.xsd#wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:to="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_019e46c4-3ae3-73e4-b717-1712d4274f8d_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BrokerCommissionExpense_019e46c4-3969-7bb9-8b35-b8afbd084d25_verboseLabel_en-US" xlink:label="lab_wtm_BrokerCommissionExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Broker commission expenses</link:label>
    <link:label id="lab_wtm_BrokerCommissionExpense_label_en-US" xlink:label="lab_wtm_BrokerCommissionExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Broker Commission Expense</link:label>
    <link:label id="lab_wtm_BrokerCommissionExpense_documentation_en-US" xlink:label="lab_wtm_BrokerCommissionExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Broker Commission Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BrokerCommissionExpense" xlink:href="wtm-20260630.xsd#wtm_BrokerCommissionExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BrokerCommissionExpense" xlink:to="lab_wtm_BrokerCommissionExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019e46c4-3969-727d-b6ae-339546ea6e80_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019e46c4-3ae3-701b-93db-d7c16c57a449_verboseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019e46c4-3ae3-7bbd-bfff-70662c662c7e_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_label_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:to="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_019e46c4-3969-7ea9-98db-216ea3cfd81a_totalLabel_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_label_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Indefinite-Lived Intangible Assets, Acquired During Period</link:label>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_documentation_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill and Indefinite-Lived Intangible Assets, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:href="wtm-20260630.xsd#wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:to="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019e46c4-3ae3-706e-a99d-ea094129ff37_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premiums</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrepaidReinsurancePremiums" xlink:to="lab_us-gaap_PrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019e46c4-3a42-7dad-8336-5a91c9f7e431_periodStartLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning of period (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019e46c4-3a42-7718-a792-224dc2b3da6a_periodEndLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019e46c4-3a42-7062-a1ef-8bc48a96d84b_verboseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total target performance shares outstanding (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract_019e46c4-3ae3-7cc1-b014-050b6d778cb4_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic and diluted earnings per share numerators (in millions):</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeAssets_019e46c4-3ae3-7033-b8d8-0026c7062983_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative, fair value, net</link:label>
    <link:label id="lab_us-gaap_DerivativeAssets_label_en-US" xlink:label="lab_us-gaap_DerivativeAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssets" xlink:to="lab_us-gaap_DerivativeAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_019e46c4-3ae3-7e6a-939e-0ec7264cb501_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other revenues</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment_019e46c4-3ae3-7657-89c3-07f15db43aab_terseLabel_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment_label_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Measurement Period Adjustment</link:label>
    <link:label id="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment_documentation_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets, Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:href="wtm-20260630.xsd#wtm_IntangibleAssetsMeasurementPeriodAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:to="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019e46c4-3a42-71fb-b149-9a793a0ef8fa_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_019e46c4-3969-7068-a88d-5fc6e1892c70_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset and Goodwill [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_terseLabel_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Securities</link:label>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_label_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Underlying Securities Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardUndrlygSecuritiesAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:to="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest_019e46c4-3ae3-7bcd-a7c2-1ff13f24c7c2_negatedLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (income) loss attributable to noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_019e46c4-3a42-78b7-85f7-16af6ae49cd1_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuances of common shares</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Value, New Issues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueNewIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealEstateSectorMember_019e46c4-3ae3-7746-8c9f-1e733fdce8b8_verboseLabel_en-US" xlink:label="lab_us-gaap_RealEstateSectorMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Real estate</link:label>
    <link:label id="lab_us-gaap_RealEstateSectorMember_label_en-US" xlink:label="lab_us-gaap_RealEstateSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Real Estate Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealEstateSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RealEstateSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealEstateSectorMember" xlink:to="lab_us-gaap_RealEstateSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Cash_019e46c4-3ae4-731e-868d-293a6f6dd93b_terseLabel_en-US" xlink:label="lab_us-gaap_Cash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:label id="lab_us-gaap_Cash_label_en-US" xlink:label="lab_us-gaap_Cash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Cash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Cash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Cash" xlink:to="lab_us-gaap_Cash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsegmentsAxis_019e46c4-3a42-7719-8010-43792a8ae992_terseLabel_en-US" xlink:label="lab_us-gaap_SubsegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsegments [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsegmentsAxis_label_en-US" xlink:label="lab_us-gaap_SubsegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsegments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsegmentsAxis" xlink:to="lab_us-gaap_SubsegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockMember_019e46c4-3a42-7fbd-b080-1decea7be23a_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred Stock</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_label_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockMember" xlink:to="lab_us-gaap_PreferredStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_019e46c4-3a42-76dc-9368-3ef322f3349c_negatedLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net other investing activities</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payment for (Proceeds from) Other Investing Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForProceedsFromOtherInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:to="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal_019e46c4-3a42-7a7a-8650-5d2662cd8c13_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, periodic payment, principal</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Periodic Payment, Principal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentPeriodicPaymentPrincipal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:to="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HealthcareSectorMember_019e46c4-3ae4-7ce3-b847-1d5106916f9c_terseLabel_en-US" xlink:label="lab_us-gaap_HealthcareSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Healthcare</link:label>
    <link:label id="lab_us-gaap_HealthcareSectorMember_label_en-US" xlink:label="lab_us-gaap_HealthcareSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Healthcare Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HealthcareSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HealthcareSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HealthcareSectorMember" xlink:to="lab_us-gaap_HealthcareSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock_019e46c4-3ae3-7f58-8b06-e0718f39cae5_terseLabel_en-US" xlink:label="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of unrecognized compensation costs associated with outstanding restricted share awards</link:label>
    <link:label id="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Nonvested Restricted Stock Shares Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:to="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019e46c4-3a42-7076-b96a-1bcd834bd18c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityNetIncome_019e46c4-3a42-7963-8267-c9fe41842994_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityNetIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityNetIncome_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityNetIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityNetIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityNetIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityNetIncome" xlink:to="lab_us-gaap_TemporaryEquityNetIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_019e46c4-3a42-7c40-a83d-cde02c109f97_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expense recognized</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Expense In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Expense In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_019e46c4-3a42-75db-bc56-48ef3e5be2b8_terseLabel_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Renegotiation period</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_label_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement, Renegotiation Period</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_documentation_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement, Renegotiation Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:href="wtm-20260630.xsd#wtm_ReinsuranceAgreementRenegotiationPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:to="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_019e46c4-3969-71e2-a76e-b9823a03086a_negatedTerseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities related to investment basis differences</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill, Deferred Tax Liability</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill, Deferred Tax Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GuaranteesAbstract_019e46c4-3a42-723a-8ee7-e60477bd2a5b_terseLabel_en-US" xlink:label="lab_us-gaap_GuaranteesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Guarantees [Abstract]</link:label>
    <link:label id="lab_us-gaap_GuaranteesAbstract_label_en-US" xlink:label="lab_us-gaap_GuaranteesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantees [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GuaranteesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GuaranteesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GuaranteesAbstract" xlink:to="lab_us-gaap_GuaranteesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_019e46c4-3969-7386-99f6-5606ccb0b16a_terseLabel_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_label_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes [Member]</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_documentation_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Ark2021SubordinatedNotesMember" xlink:href="wtm-20260630.xsd#wtm_Ark2021SubordinatedNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesMember" xlink:to="lab_wtm_Ark2021SubordinatedNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BroadStreetSPVMember_019e46c4-3ae4-7470-b695-a28665eec81b_terseLabel_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BroadStreet SPV</link:label>
    <link:label id="lab_wtm_BroadStreetSPVMember_label_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BroadStreet SPV [Member]</link:label>
    <link:label id="lab_wtm_BroadStreetSPVMember_documentation_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">BroadStreet SPV</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BroadStreetSPVMember" xlink:href="wtm-20260630.xsd#wtm_BroadStreetSPVMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BroadStreetSPVMember" xlink:to="lab_wtm_BroadStreetSPVMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_019e46c4-3969-7235-880e-cf43edadb4cf_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllTradingArrangementsMember_terseLabel_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Trading Arrangements</link:label>
    <link:label id="lab_ecd_AllTradingArrangementsMember_label_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Trading Arrangements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllTradingArrangementsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllTradingArrangementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllTradingArrangementsMember" xlink:to="lab_ecd_AllTradingArrangementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_label_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OtherPerfMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OtherPerfMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OtherPerfMeasureAmt" xlink:to="lab_ecd_OtherPerfMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_019e46c4-3969-73eb-9016-3a37f5211a22_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of common equity securities and investment in MediaAlpha</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_label_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities and Equity Method Investments</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:href="wtm-20260630.xsd#wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:to="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_019e46c4-3ae3-7852-9253-60001f3b312c_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_019e46c4-3ae3-7d01-9148-7838914bec34_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherShortTermInvestmentsMember_019e46c4-3ae3-7527-a8a8-bc56ef7908d1_terseLabel_en-US" xlink:label="lab_wtm_OtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_wtm_OtherShortTermInvestmentsMember_label_en-US" xlink:label="lab_wtm_OtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments [Member]</link:label>
    <link:label id="lab_wtm_OtherShortTermInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_OtherShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherShortTermInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_OtherShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherShortTermInvestmentsMember" xlink:to="lab_wtm_OtherShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentOwnedBalanceShares_019e46c4-3ae3-73ff-982d-26aab0fbe419_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment owned (in shares)</link:label>
    <link:label id="lab_us-gaap_InvestmentOwnedBalanceShares_label_en-US" xlink:label="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Owned, Balance, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentOwnedBalanceShares" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentOwnedBalanceShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentOwnedBalanceShares" xlink:to="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeLineItems_019e46c4-3a42-7095-85c0-30d159b9660f_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative [Line Items]</link:label>
    <link:label id="lab_us-gaap_DerivativeLineItems_label_en-US" xlink:label="lab_us-gaap_DerivativeLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeLineItems" xlink:to="lab_us-gaap_DerivativeLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsARatingMember_019e46c4-3969-763f-a0d6-7859054f4f01_verboseLabel_en-US" xlink:label="lab_srt_StandardPoorsARatingMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">A</link:label>
    <link:label id="lab_srt_StandardPoorsARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, A Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsARatingMember" xlink:to="lab_srt_StandardPoorsARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_019e46c4-3a42-728d-8f09-ac1f78c7ee3f_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financials</link:label>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_019e46c4-3a42-746f-864a-d5e49053f02a_netLabel_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Financial services</link:label>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_label_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Services Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialServicesSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialServicesSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialServicesSectorMember" xlink:to="lab_us-gaap_FinancialServicesSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_019fd325-9029-79ae-8ad3-0b319877ee0b_terseLabel_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance acquisition expenses</link:label>
    <link:label id="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_label_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense, Adjusted</link:label>
    <link:label id="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_documentation_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:href="wtm-20260630.xsd#wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:to="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year</link:label>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:to="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareDeclared_019e46c4-3ae3-7154-86e4-335a292df8f5_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends declared per White Mountains&#8217;s common share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareDeclared_label_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Dividends, Per Share, Declared</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockDividendsPerShareDeclared" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockDividendsPerShareDeclared"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockDividendsPerShareDeclared" xlink:to="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_019e46c4-3a42-7b80-9c19-76806f727da8_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_019e46c4-3ae3-7c59-8f86-b4342bf0009f_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of contractual maturities of fixed maturities</link:label>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019e46c4-3969-7764-a449-31b1b880e076_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Summary of loss and LAE reserve activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders_019e46c4-3ae3-77d0-b83c-0a989fad14c2_negatedLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Dividends declared to noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders_label_en-US" xlink:label="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Decrease from Distributions to Noncontrolling Interest Holders</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:to="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedCreditCardSecuritiesMember_019e46c4-3a42-70db-8d25-2a03415dd3eb_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit card receivables</link:label>
    <link:label id="lab_us-gaap_CollateralizedCreditCardSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Credit Card Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedCreditCardSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_019e46c4-3ae3-7697-bb5b-3d0a253a6b33_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net&#160;Foreign Currency Gains (Losses)</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Net Foreign Currency Gain (Loss)</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Net Foreign Currency Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:to="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_019fc6e0-85bd-7aa3-a6e4-96bd21b89f3d_terseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recognition of equity-based compensation expense of subsidiaries</link:label>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_label_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:href="wtm-20260630.xsd#wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:to="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RecoveryOfErrCompDisclosureLineItems_label_en-US" xlink:label="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Recovery of Erroneously Awarded Compensation Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:to="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_019e46c4-3a42-7695-b047-adbffd1b7c65_terseLabel_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_label_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_documentation_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherSignificantTransactionsLineItems" xlink:href="wtm-20260630.xsd#wtm_OtherSignificantTransactionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherSignificantTransactionsLineItems" xlink:to="lab_wtm_OtherSignificantTransactionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureAxis" xlink:to="lab_ecd_MeasureAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss_019e46c4-3969-70ee-b73a-05325ad3d5c9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesTradingUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_019e46c4-3a42-77be-9850-a4f639901d86_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain_019e46c4-3969-7ba5-a1f6-f9c09294fdb3_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss_019e46c4-3ae3-759f-a478-ba19dc690f2c_terseLabel_en-US" xlink:label="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net&#160;Foreign Currency Gains (Losses)</link:label>
    <link:label id="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss_label_en-US" xlink:label="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FN-NI, Net Foreign Currency Gain (Loss)</link:label>
    <link:label id="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss_documentation_en-US" xlink:label="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Securities, FN-NI, Net Foreign Currency Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:href="wtm-20260630.xsd#wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:to="lab_wtm_EquitySecuritiesFNNINetForeignCurrencyGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019e46c4-3969-7d17-b0d5-f027c715b604_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned insurance premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019e46c4-3969-7f27-afa4-cdae29d79d87_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019e46c4-3969-78fe-8021-0059e5126ab5_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Earned insurance premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedDebtMember_019e46c4-3ae3-76cb-890b-867839603eda_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Distinguished debt</link:label>
    <link:label id="lab_wtm_DistinguishedDebtMember_label_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Debt [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedDebtMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedDebtMember" xlink:href="wtm-20260630.xsd#wtm_DistinguishedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedDebtMember" xlink:to="lab_wtm_DistinguishedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_019e46c4-3a42-7fbe-8e2a-b1d6b0b6ebef_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommonStockAndEquityMethodInvestmentsMember_019e46c4-3969-7d31-a053-858b54cc40ff_terseLabel_en-US" xlink:label="lab_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities and investment in MediaAlpha</link:label>
    <link:label id="lab_wtm_CommonStockAndEquityMethodInvestmentsMember_label_en-US" xlink:label="lab_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock And Equity Method Investments [Member]</link:label>
    <link:label id="lab_wtm_CommonStockAndEquityMethodInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Common Stock And Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_CommonStockAndEquityMethodInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:to="lab_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_019e46c4-3ae3-7c72-a680-01deac9078b4_negatedLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net income tax payments</link:label>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_label_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Paid, after Refund Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxesPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxesPaidNet" xlink:to="lab_us-gaap_IncomeTaxesPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_019e46c4-3ae3-7980-883e-a3699607e620_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_019e46c4-3ae3-7233-84f0-5669cdd64fc8_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateAxis_019e46c4-3a42-7697-b474-e9e1dbb42204_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateAxis" xlink:to="lab_us-gaap_VariableRateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_019e46c4-3a42-771b-83a4-0387a36101ff_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net (income) loss attributable to noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AMBestAPlusRatingMember_019e46c4-3a42-7802-ad57-c1a980b89b9c_terseLabel_en-US" xlink:label="lab_srt_AMBestAPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">A+ or better</link:label>
    <link:label id="lab_srt_AMBestAPlusRatingMember_label_en-US" xlink:label="lab_srt_AMBestAPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AM Best, A+ Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AMBestAPlusRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AMBestAPlusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AMBestAPlusRatingMember" xlink:to="lab_srt_AMBestAPlusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019e46c4-3ae4-7d8c-bc3b-1acd7469c9e5_terseLabel_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturities, Excluding Asset-Backed Securities And Collateralized Loan Obligations</link:label>
    <link:label id="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_label_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities, Excluding Asset-Backed Securities And Collateralized Loan Obligations [Member]</link:label>
    <link:label id="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_documentation_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the fixed maturity investments and convertible fixed maturity investments excluding mortgage-backed securities, asset-backed securities and preferred stock.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:href="wtm-20260630.xsd#wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:to="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HGGlobalSegmentMember_019e46c4-3969-7409-8951-2a82bdbf579a_terseLabel_en-US" xlink:label="lab_wtm_HGGlobalSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global</link:label>
    <link:label id="lab_wtm_HGGlobalSegmentMember_label_en-US" xlink:label="lab_wtm_HGGlobalSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global - Segment [Member]</link:label>
    <link:label id="lab_wtm_HGGlobalSegmentMember_documentation_en-US" xlink:label="lab_wtm_HGGlobalSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobalSegmentMember" xlink:href="wtm-20260630.xsd#wtm_HGGlobalSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HGGlobalSegmentMember" xlink:to="lab_wtm_HGGlobalSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntitySmallBusiness_019e46c4-3a42-782e-a788-b86bc8ff6897_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod_019e46c4-3969-7e6e-a5d8-8d1773b6f7ca_terseLabel_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lock up period</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod_label_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Fund Lock Up Period</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod_documentation_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Funds Lock Up Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:href="wtm-20260630.xsd#wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:to="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_019e46c4-3969-7aa6-ad96-bc895da16f66_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (loss) attributable to White Mountains&#8217;s common shareholders</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnearnedPremiums_019e46c4-3969-7844-87c8-0adfde8e9fb2_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned insurance premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_019e46c4-3969-7741-a63f-db3b97ad64cc_terseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">P&amp;C Insurance and Reinsurance (Ark/WM Outrigger)</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_019e46c4-3969-7c79-a1be-062e86691900_verboseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">P&amp;C Insurance and Reinsurance (Ark/WM Outrigger)</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_label_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited/WM Outrigger Re - Segment [Member]</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_documentation_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited/WM Outrigger Re - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:href="wtm-20260630.xsd#wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BambooGroupMember_019e46c4-3ae4-79c6-9f4d-1057a8e41443_terseLabel_en-US" xlink:label="lab_wtm_BambooGroupMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bamboo Group</link:label>
    <link:label id="lab_wtm_BambooGroupMember_label_en-US" xlink:label="lab_wtm_BambooGroupMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bamboo Group [Member]</link:label>
    <link:label id="lab_wtm_BambooGroupMember_documentation_en-US" xlink:label="lab_wtm_BambooGroupMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bamboo Group</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BambooGroupMember" xlink:href="wtm-20260630.xsd#wtm_BambooGroupMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooGroupMember" xlink:to="lab_wtm_BambooGroupMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019e46c4-3969-7ead-9afc-1413a317c8e7_terseLabel_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, weighted average useful life (in years)</link:label>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_label_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired, Weighted-Average Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:to="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_019fa19c-2b81-7bd5-a44b-6e7e97e136a0_terseLabel_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prefunded commitments</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_label_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Prefunded Commitments</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_documentation_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Prefunded Commitments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:href="wtm-20260630.xsd#wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:to="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived_019e46c4-3ae3-746d-81ff-7063c28d03cc_negatedTerseLabel_en-US" xlink:label="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Interest income from BAM Surplus Notes</link:label>
    <link:label id="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived_label_en-US" xlink:label="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Income, Operating, Net of Interest Payments Received</link:label>
    <link:label id="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived_documentation_en-US" xlink:label="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Interest Income, Operating, Net of Interest Payments Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:href="wtm-20260630.xsd#wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:to="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock_019e46c4-3ae3-77dc-96f0-4005f1d0c82f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of investments and unfunded commitments by investment objective and sector</link:label>
    <link:label id="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock" xlink:to="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_terseLabel_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value</link:label>
    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_label_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MnpiDiscTimedForCompValFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:to="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentType_019e46c4-3969-7519-8121-90c49ed73b5e_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
    <link:label id="lab_dei_DocumentType_label_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentType"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentType" xlink:to="lab_dei_DocumentType" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_019e46c4-3ae3-7c91-8bc4-e925fefe2cbd_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of consolidated subsidiaries, net of cash acquired of $7.3 and $0.8</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Net of Cash Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt_019fac8a-a8cc-7d56-8b0d-a5a1a5c215bb_terseLabel_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss on extinguishment of debt</link:label>
    <link:label id="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt_label_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Extinguishment of Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:to="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceAgreementsAssetLimitAmount_019e46c4-3ae3-71a4-a8e0-1c4a775f0fc2_terseLabel_en-US" xlink:label="lab_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsured amount</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementsAssetLimitAmount_label_en-US" xlink:label="lab_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Agreements, Asset Limit Amount</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementsAssetLimitAmount_documentation_en-US" xlink:label="lab_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Agreements, Asset Limit Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:href="wtm-20260630.xsd#wtm_ReinsuranceAgreementsAssetLimitAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:to="lab_wtm_ReinsuranceAgreementsAssetLimitAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_019e46c4-3ae3-7f6f-8b6b-db890844321d_terseLabel_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from Kudu&#8217;s Participation Contracts sold</link:label>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_label_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Participation Contracts</link:label>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_documentation_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ProceedsFromSaleOfParticipationContracts" xlink:href="wtm-20260630.xsd#wtm_ProceedsFromSaleOfParticipationContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ProceedsFromSaleOfParticipationContracts" xlink:to="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_019e46c4-3a42-7ec0-becb-e75887962ae6_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable_019e46c4-3ae3-7a11-a68d-34d6516643eb_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Trading Securities and Other Trading Assets</link:label>
    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:to="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019e46c4-3ae3-7211-b340-164aad99feb1_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Draw down of debt and revolving lines of credit</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019e46c4-3ae3-7fb7-b199-f4c2a4b8903b_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_019e46c4-3ae3-7ae7-9fa3-e37a45296d50_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_country_CA_019e46c4-3a42-76da-a1f8-6b08df44132b_terseLabel_en-US" xlink:label="lab_country_CA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Canadian</link:label>
    <link:label id="lab_country_CA_label_en-US" xlink:label="lab_country_CA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">CANADA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_CA" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_CA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_CA" xlink:to="lab_country_CA" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_019e46c4-3ae3-7f21-b1fe-21aaf9149417_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherShortTermInvestments" xlink:to="lab_us-gaap_OtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod_019e46c4-3ae3-7ddc-af6c-8abadf3d4ea2_negatedNetLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedNetLabel" xlink:type="resource" xml:lang="en-US">Assumed forfeitures</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Accrued Liability, Forfeited in Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Accrued Liability, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PledgedStatusDomain_019e46c4-3ae3-7ec5-83af-b748b12f5f52_terseLabel_en-US" xlink:label="lab_us-gaap_PledgedStatusDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged Status [Domain]</link:label>
    <link:label id="lab_us-gaap_PledgedStatusDomain_label_en-US" xlink:label="lab_us-gaap_PledgedStatusDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pledged Status [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PledgedStatusDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PledgedStatusDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PledgedStatusDomain" xlink:to="lab_us-gaap_PledgedStatusDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e46c4-3a42-70a8-91b2-07d427f88e7b_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Pre-tax income (loss)</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward_019e46c4-3ae3-7bcc-a023-641b4bb506d9_terseLabel_en-US" xlink:label="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changes In Fair Value Discount Of Surplus Notes [Roll Forward]</link:label>
    <link:label id="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward_label_en-US" xlink:label="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changes In Fair Value Discount Of Surplus Notes [Roll Forward]</link:label>
    <link:label id="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward_documentation_en-US" xlink:label="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Changes In Fair Value Discount Of Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:href="wtm-20260630.xsd#wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:to="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_label_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:to="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems_019e46c4-3a42-7267-8fb8-bcf022413f09_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:to="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxContingencyTable_019e46c4-3ae3-7145-a232-51751fda9c15_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Table]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxContingencyTable_label_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxContingencyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxContingencyTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxContingencyTable" xlink:to="lab_us-gaap_IncomeTaxContingencyTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_019e46c4-3a42-7794-82a9-d6bd356d9e07_terseLabel_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_label_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ExternalCreditRatingStandardPoorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:to="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_terseLabel_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Executive Category:</link:label>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_label_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Executive Category [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ExecutiveCategoryAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ExecutiveCategoryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ExecutiveCategoryAxis" xlink:to="lab_ecd_ExecutiveCategoryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_019e46c4-3ae3-77ca-8fd0-cefd41522284_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets held-in-trust</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_019e46c4-3a42-73f9-9bf5-d5af6e2951b4_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Third-Party Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillAcquisitionDateFairValue_019e46c4-3969-7b15-b64c-85d8793de6c0_terseLabel_en-US" xlink:label="lab_wtm_GoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition Date Fair Value</link:label>
    <link:label id="lab_wtm_GoodwillAcquisitionDateFairValue_label_en-US" xlink:label="lab_wtm_GoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Acquisition Date, Fair Value</link:label>
    <link:label id="lab_wtm_GoodwillAcquisitionDateFairValue_documentation_en-US" xlink:label="lab_wtm_GoodwillAcquisitionDateFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill, Acquisition Date, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAcquisitionDateFairValue" xlink:href="wtm-20260630.xsd#wtm_GoodwillAcquisitionDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAcquisitionDateFairValue" xlink:to="lab_wtm_GoodwillAcquisitionDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NetUnrealizedGainsLossesOnInvestments_019e46c4-3ae3-76eb-a73c-74771fb11c78_totalLabel_en-US" xlink:label="lab_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net unrealized investment gains (losses) recognized during the period on investment securities held at the end of the period</link:label>
    <link:label id="lab_wtm_NetUnrealizedGainsLossesOnInvestments_label_en-US" xlink:label="lab_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Unrealized Gains (Losses) On Investments</link:label>
    <link:label id="lab_wtm_NetUnrealizedGainsLossesOnInvestments_documentation_en-US" xlink:label="lab_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Unrealized Gains (Losses) On Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:href="wtm-20260630.xsd#wtm_NetUnrealizedGainsLossesOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:to="lab_wtm_NetUnrealizedGainsLossesOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgCompActuallyPaidAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:to="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_019e46c4-3969-78b5-b6bf-6667ea838de1_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Variable Interest Entities [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_019e46c4-3969-7e96-a69f-f6955b8704c9_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental cash flows information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoName" xlink:to="lab_ecd_PeoName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019e46c4-3a42-7c92-8684-c9a7e6f424c5_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Net paid loss and LAE</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAcquiredFromAcquisition_019e46c4-3969-754f-81ba-0e388bf58142_terseLabel_en-US" xlink:label="lab_us-gaap_CashAcquiredFromAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash acquired from acquisition</link:label>
    <link:label id="lab_us-gaap_CashAcquiredFromAcquisition_label_en-US" xlink:label="lab_us-gaap_CashAcquiredFromAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Acquired from Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAcquiredFromAcquisition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAcquiredFromAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAcquiredFromAcquisition" xlink:to="lab_us-gaap_CashAcquiredFromAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_country_BM_019e46c4-3969-765d-ae25-988c52131b9d_terseLabel_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bermuda</link:label>
    <link:label id="lab_country_BM_label_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_BM" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_BM"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_BM" xlink:to="lab_country_BM" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_019e46c4-3969-7475-a028-e60074541689_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AAA</link:label>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AAA Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsAAARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsAAARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsAAARatingMember" xlink:to="lab_srt_StandardPoorsAAARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_019e46c4-3ae3-71ae-8a83-0eb47f557311_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_019e46c4-3a42-7c77-a500-e5f7c9cb1136_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year One through Five</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date, after Year One through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:to="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LloydsLOCFacilityMember_019e46c4-3ae3-7a61-a9df-fe48caa33ade_terseLabel_en-US" xlink:label="lab_wtm_LloydsLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lloyds LOC Facility</link:label>
    <link:label id="lab_wtm_LloydsLOCFacilityMember_label_en-US" xlink:label="lab_wtm_LloydsLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lloyds LOC Facility [Member]</link:label>
    <link:label id="lab_wtm_LloydsLOCFacilityMember_documentation_en-US" xlink:label="lab_wtm_LloydsLOCFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Lloyds LOC Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LloydsLOCFacilityMember" xlink:href="wtm-20260630.xsd#wtm_LloydsLOCFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LloydsLOCFacilityMember" xlink:to="lab_wtm_LloydsLOCFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueRecognitionPolicyTextBlock_019f25b9-669c-7fc6-879a-232fba8f296f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenue Recognition</link:label>
    <link:label id="lab_us-gaap_RevenueRecognitionPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueRecognitionPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:to="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross_019e46c4-3ae3-750f-8fde-83843b639038_terseLabel_en-US" xlink:label="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross</link:label>
    <link:label id="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross_label_en-US" xlink:label="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Direct</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PolicyholderBenefitsAndClaimsIncurredGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:to="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier_019e46c4-3a42-7a91-8e7a-0e93159606a3_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, right to purchase units</link:label>
    <link:label id="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier_label_en-US" xlink:label="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Right To Purchase Units, Unit Price Multiplier</link:label>
    <link:label id="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Right To Purchase Units, Unit Price Multiplier</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:href="wtm-20260630.xsd#wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:to="lab_wtm_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_019e46c4-3a42-7e11-a124-e4b3e01dde63_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward_019e46c4-3a42-72ce-ace1-6545bb5cbef8_terseLabel_en-US" xlink:label="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changes In Nominal Value Of Surplus Notes [Roll Forward]</link:label>
    <link:label id="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward_label_en-US" xlink:label="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changes In Nominal Value Of Surplus Notes [Roll Forward]</link:label>
    <link:label id="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward_documentation_en-US" xlink:label="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Changes In Nominal Value Of Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:href="wtm-20260630.xsd#wtm_ChangesInNominalValueOfSurplusNotesRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:to="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AgencyRelationshipsMember_019e46c4-3ae3-7978-be5e-3cdcf428d7a0_terseLabel_en-US" xlink:label="lab_wtm_AgencyRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agency relationships</link:label>
    <link:label id="lab_wtm_AgencyRelationshipsMember_label_en-US" xlink:label="lab_wtm_AgencyRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Agency Relationships [Member]</link:label>
    <link:label id="lab_wtm_AgencyRelationshipsMember_documentation_en-US" xlink:label="lab_wtm_AgencyRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agency Relationships</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AgencyRelationshipsMember" xlink:href="wtm-20260630.xsd#wtm_AgencyRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AgencyRelationshipsMember" xlink:to="lab_wtm_AgencyRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined</link:label>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_label_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompNotYetDeterminedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:to="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_terseLabel_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement</link:label>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_label_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MtrlTermsOfTrdArrTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:to="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year</link:label>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:to="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_019e46c4-3ae3-73ca-960e-d6e7e2a0006f_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_019e46c4-3ae3-7020-9db9-8f40003fe83d_verboseLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_019e46c4-3ae3-78ea-8857-801dfccac0f0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementFrequencyDomain_019e46c4-3a42-7e65-b151-684523ef278c_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementFrequencyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementFrequencyDomain" xlink:to="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensation_019e46c4-3a42-7a98-bfc9-0a2f42cd56fd_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of restricted share awards</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensation" xlink:to="lab_us-gaap_ShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MediaAlphaMember_019e46c4-3ae3-7c01-b259-fc30957641ee_terseLabel_en-US" xlink:label="lab_wtm_MediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">MediaAlpha</link:label>
    <link:label id="lab_wtm_MediaAlphaMember_019e46c4-3ae3-7369-8a9b-94a467b7d077_verboseLabel_en-US" xlink:label="lab_wtm_MediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Investment in MediaAlpha</link:label>
    <link:label id="lab_wtm_MediaAlphaMember_label_en-US" xlink:label="lab_wtm_MediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">MediaAlpha [Member]</link:label>
    <link:label id="lab_wtm_MediaAlphaMember_documentation_en-US" xlink:label="lab_wtm_MediaAlphaMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">MediaAlpha</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_MediaAlphaMember" xlink:href="wtm-20260630.xsd#wtm_MediaAlphaMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MediaAlphaMember" xlink:to="lab_wtm_MediaAlphaMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_019e46c4-3a42-7665-9ac3-111076b18ce6_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_019e46c4-3ae3-7413-a267-623008c33410_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (loss) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_019e46c4-3a42-793e-8b46-6cee34217545_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingArrLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingArrLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingArrLineItems" xlink:to="lab_ecd_InsiderTradingArrLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberofSecuredCreditFacilities_019e46c4-3ae3-70a2-b59b-097bd1e0d4e9_terseLabel_en-US" xlink:label="lab_wtm_NumberofSecuredCreditFacilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured credit facilities</link:label>
    <link:label id="lab_wtm_NumberofSecuredCreditFacilities_label_en-US" xlink:label="lab_wtm_NumberofSecuredCreditFacilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Secured Credit Facilities</link:label>
    <link:label id="lab_wtm_NumberofSecuredCreditFacilities_documentation_en-US" xlink:label="lab_wtm_NumberofSecuredCreditFacilities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Secured Credit Facilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberofSecuredCreditFacilities" xlink:href="wtm-20260630.xsd#wtm_NumberofSecuredCreditFacilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NumberofSecuredCreditFacilities" xlink:to="lab_wtm_NumberofSecuredCreditFacilities" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne_019e46c4-3a42-7aa8-888f-31796bc6577a_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in one year or less</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated And Single Maturity Date, Year One</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated And Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:href="wtm-20260630.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsReceivableNetCurrent_019f44de-36e5-7a3c-b696-af12b8fe95dc_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsReceivableNetCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts receivable</link:label>
    <link:label id="lab_us-gaap_AccountsReceivableNetCurrent_label_en-US" xlink:label="lab_us-gaap_AccountsReceivableNetCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts Receivable, after Allowance for Credit Loss, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsReceivableNetCurrent" xlink:to="lab_us-gaap_AccountsReceivableNetCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees_019fc882-6d46-70f4-86a0-275f7f89b7fb_terseLabel_en-US" xlink:label="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other revenues</link:label>
    <link:label id="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees_label_en-US" xlink:label="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income, Net of Premiums Earned and Insurance Commissions and Fees</link:label>
    <link:label id="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees_documentation_en-US" xlink:label="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Income, Net of Premiums Earned and Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:href="wtm-20260630.xsd#wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:to="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_019e46c4-3969-7558-bcf3-57a9f5172cae_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance acquisition expenses</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedDistributed_019e46c4-3a42-7fde-8e73-65989709b78b_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distributed earnings - dividends declared and paid (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedDistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted, Distributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDilutedDistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDilutedDistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDilutedDistributed" xlink:to="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedLoss_019e46c4-3a42-70cd-8fff-0efd2386938c_negatedTerseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedLoss_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Unrealized Loss</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedLoss_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:href="wtm-20260630.xsd#wtm_EquityMethodInvestmentUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:to="lab_wtm_EquityMethodInvestmentUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_019e46c4-3969-7db8-a303-e61b122abf6b_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industrial</link:label>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_label_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial and Industrial Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommercialAndIndustrialSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:to="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_019e46c4-3a42-724d-991d-019a0fb4a41a_periodStartLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Temporary equity, beginning balance</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_019e46c4-3a42-785c-8cac-9e5a8e527720_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Temporary equity, ending balance</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Including Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:to="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_019e46c4-3969-7df2-88f4-e93d8c1043a1_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net gain on sale of the Bamboo Group</link:label>
    <link:label id="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_019e46c4-3969-74d2-91a0-3010842c9e6c_negatedLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net gain on sale of the Bamboo Group</link:label>
    <link:label id="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_label_en-US" xlink:label="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Not Discontinued Operation, Gain (Loss) on Disposal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:to="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_019e46c4-3a42-72a0-a0e7-a990a9c8374d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contingent consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Contingent Consideration, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationContingentConsiderationLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:to="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BankLoanFundMember_019e46c4-3969-7906-8b24-01baf670021c_terseLabel_en-US" xlink:label="lab_wtm_BankLoanFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bank loan fund</link:label>
    <link:label id="lab_wtm_BankLoanFundMember_label_en-US" xlink:label="lab_wtm_BankLoanFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bank Loan Fund [Member]</link:label>
    <link:label id="lab_wtm_BankLoanFundMember_documentation_en-US" xlink:label="lab_wtm_BankLoanFundMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bank Loan Fund</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BankLoanFundMember" xlink:href="wtm-20260630.xsd#wtm_BankLoanFundMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BankLoanFundMember" xlink:to="lab_wtm_BankLoanFundMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_019e46c4-3969-7e54-9752-7b8a5a09ed2c_terseLabel_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFVNIAbstract_019e46c4-3a42-716d-ab20-2c594aa1b7c2_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFVNIAbstract_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFVNIAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFVNIAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFVNIAbstract" xlink:to="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_country_GB_019e46c4-3969-739d-8f65-ba5ababfe086_terseLabel_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">United Kingdom</link:label>
    <link:label id="lab_country_GB_label_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED KINGDOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_GB" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_GB"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_GB" xlink:to="lab_country_GB" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_019e46c4-3ae3-78b9-864e-543ae634d530_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Inputs Assets Quantitative Information [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_019e46c4-3a42-7ec9-8e57-8b84dbd05b2b_verboseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">% of Total</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskPercentage1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskPercentage1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskPercentage1" xlink:to="lab_us-gaap_ConcentrationRiskPercentage1" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsMember" xlink:to="lab_ecd_EqtyAwrdsAdjsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TrustDepositsMember_019e46c4-3ae3-74c8-8bd9-393e86c46a55_terseLabel_en-US" xlink:label="lab_wtm_TrustDepositsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lloyd&#8217;s trust deposits</link:label>
    <link:label id="lab_wtm_TrustDepositsMember_label_en-US" xlink:label="lab_wtm_TrustDepositsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trust Deposits [Member]</link:label>
    <link:label id="lab_wtm_TrustDepositsMember_documentation_en-US" xlink:label="lab_wtm_TrustDepositsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Trust Deposits</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TrustDepositsMember" xlink:href="wtm-20260630.xsd#wtm_TrustDepositsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TrustDepositsMember" xlink:to="lab_wtm_TrustDepositsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_019e46c4-3ae3-781c-a9be-626b04f4988b_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember_019e46c4-3ae3-74e5-ae82-a7b8f46b77f1_terseLabel_en-US" xlink:label="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other unconsolidated entities</link:label>
    <link:label id="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember_label_en-US" xlink:label="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Unconsolidated Private Equity Investments [Member]</link:label>
    <link:label id="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Unconsolidated Private Equity Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:to="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_019e46c4-3ae3-7d61-afe6-2006674ea347_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Balance Sheet Grouping, Financial Statement Captions</link:label>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:to="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_019e46c4-3969-78c6-8b31-e2368bc11718_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesIndustryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:to="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeographicDistributionDomain_019e46c4-3ae3-7592-9f76-fce7c7456a15_terseLabel_en-US" xlink:label="lab_us-gaap_GeographicDistributionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Domain]</link:label>
    <link:label id="lab_us-gaap_GeographicDistributionDomain_label_en-US" xlink:label="lab_us-gaap_GeographicDistributionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeographicDistributionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeographicDistributionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeographicDistributionDomain" xlink:to="lab_us-gaap_GeographicDistributionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_WTMPartnersLLCSegmentMember_019f44e0-f48a-7ca4-9ec8-b086003a2764_netLabel_en-US" xlink:label="lab_wtm_WTMPartnersLLCSegmentMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Services, Industrial and Consumer (WTM Partners)</link:label>
    <link:label id="lab_wtm_WTMPartnersLLCSegmentMember_019f25ae-f0fe-7386-8e46-4e6711701e5c_verboseLabel_en-US" xlink:label="lab_wtm_WTMPartnersLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Services, Industrial and Consumer (WTM Partners)</link:label>
    <link:label id="lab_wtm_WTMPartnersLLCSegmentMember_019edf00-fc61-7686-beec-b2873330f841_terseLabel_en-US" xlink:label="lab_wtm_WTMPartnersLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Partners</link:label>
    <link:label id="lab_wtm_WTMPartnersLLCSegmentMember_label_en-US" xlink:label="lab_wtm_WTMPartnersLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">WTM Partners LLC - Segment [Member]</link:label>
    <link:label id="lab_wtm_WTMPartnersLLCSegmentMember_documentation_en-US" xlink:label="lab_wtm_WTMPartnersLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">WTM Partners LLC - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_WTMPartnersLLCSegmentMember" xlink:href="wtm-20260630.xsd#wtm_WTMPartnersLLCSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_WTMPartnersLLCSegmentMember" xlink:to="lab_wtm_WTMPartnersLLCSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_019e46c4-3a42-79dc-b4ab-cef1bb1171e0_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:to="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche1Member_019e46c4-3ae3-79f2-9651-e1c8f4906cb4_terseLabel_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes Tranche 1</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche1Member_label_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 1 [Member]</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche1Member_documentation_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes, Tranche 1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:href="wtm-20260630.xsd#wtm_Ark2021SubordinatedNotesTranche1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:to="lab_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentRedemptionNoticePeriod_019e46c4-3a42-7e3c-803c-e44116bacdee_terseLabel_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notice period</link:label>
    <link:label id="lab_wtm_InvestmentRedemptionNoticePeriod_label_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Redemption, Notice Period</link:label>
    <link:label id="lab_wtm_InvestmentRedemptionNoticePeriod_documentation_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investment Redemption, Notice Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentRedemptionNoticePeriod" xlink:href="wtm-20260630.xsd#wtm_InvestmentRedemptionNoticePeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InvestmentRedemptionNoticePeriod" xlink:to="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears_019e46c4-3969-7a2d-b729-ba60a8c185bf_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">3&#160;&#8211;&#160;5&#160;years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Three to Five Years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Three to Five Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:href="wtm-20260630.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ParentMember_019e46c4-3ae3-7782-beda-08aa9008dc44_terseLabel_en-US" xlink:label="lab_us-gaap_ParentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_ParentMember_label_en-US" xlink:label="lab_us-gaap_ParentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ParentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ParentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ParentMember" xlink:to="lab_us-gaap_ParentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_019e46c4-3a42-768c-81de-c4fee3703d5a_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsurerTypeDomain_019e46c4-3a42-71bf-a16e-96720ca1054e_terseLabel_en-US" xlink:label="lab_wtm_ReinsurerTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Type [Domain]</link:label>
    <link:label id="lab_wtm_ReinsurerTypeDomain_label_en-US" xlink:label="lab_wtm_ReinsurerTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Type [Domain]</link:label>
    <link:label id="lab_wtm_ReinsurerTypeDomain_documentation_en-US" xlink:label="lab_wtm_ReinsurerTypeDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurer, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsurerTypeDomain" xlink:href="wtm-20260630.xsd#wtm_ReinsurerTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsurerTypeDomain" xlink:to="lab_wtm_ReinsurerTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract_019e46c4-3a42-7a0e-9480-acd60d91104d_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Including Portion Attributable to Noncontrolling Interest [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:to="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_019e46c4-3ae3-7dcf-ba0c-c8ac952cc1a2_negatedLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Forfeited (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock_019e46c4-3a42-7e13-b02f-7984062afd1a_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:to="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_019f25dd-de06-71e6-83b1-68cf5341e2d4_verboseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">General and administrative expenses</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NewYorkStockExchangeMember_019e46c4-3969-7fce-9b02-73b31550c795_terseLabel_en-US" xlink:label="lab_wtm_NewYorkStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New York Stock Exchange</link:label>
    <link:label id="lab_wtm_NewYorkStockExchangeMember_label_en-US" xlink:label="lab_wtm_NewYorkStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">New York Stock Exchange [Member]</link:label>
    <link:label id="lab_wtm_NewYorkStockExchangeMember_documentation_en-US" xlink:label="lab_wtm_NewYorkStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">New York Stock Exchange</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NewYorkStockExchangeMember" xlink:href="wtm-20260630.xsd#wtm_NewYorkStockExchangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NewYorkStockExchangeMember" xlink:to="lab_wtm_NewYorkStockExchangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments_019e46c4-3ae3-7a95-a642-d974eca15d8a_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Collateral trusts, investments and cash</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Cash And Investments</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Cash And Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_019e46c4-3ae3-7aea-a590-5921594113f0_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_terseLabel_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Available</link:label>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts_019e46c4-3a42-77aa-b352-5fdb9dc83e82_terseLabel_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contracts outstanding</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts_label_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Number of Contracts</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts_documentation_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Municipal bond contracts issued and outstanding.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:href="wtm-20260630.xsd#wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:to="lab_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_019e46c4-3ae3-79a5-8aac-9c1bba417a66_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:to="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract_019e46c4-3ae3-7767-ba42-6461c87d5d44_terseLabel_en-US" xlink:label="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discontinued Operations and Disposal Groups [Abstract]</link:label>
    <link:label id="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract_label_en-US" xlink:label="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Discontinued Operations and Disposal Groups [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:to="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_019e46c4-3969-7acb-9520-4d1761fd7265_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_019e46c4-3a42-7af5-b994-69639f5bed5e_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination_019e46c4-3ae3-78bc-8dcb-136ef9448d31_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Increase from Business Combination</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:to="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTable_terseLabel_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure</link:label>
    <link:label id="lab_ecd_PvpTable_label_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTable" xlink:to="lab_ecd_PvpTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019e46c4-3969-76d7-861f-69fa75c01d76_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferred1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFilerCategory_019e46c4-3a42-788f-b9fb-a085a22f0e9e_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFilerCategory"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFilerCategory" xlink:to="lab_dei_EntityFilerCategory" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RevenuesFromExternalCustomers_019e46c4-3969-7ed3-9fbd-ed762e0eed40_totalLabel_en-US" xlink:label="lab_wtm_RevenuesFromExternalCustomers" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_wtm_RevenuesFromExternalCustomers_label_en-US" xlink:label="lab_wtm_RevenuesFromExternalCustomers" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues From External Customers</link:label>
    <link:label id="lab_wtm_RevenuesFromExternalCustomers_documentation_en-US" xlink:label="lab_wtm_RevenuesFromExternalCustomers" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revenues From External Customers</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_RevenuesFromExternalCustomers" xlink:href="wtm-20260630.xsd#wtm_RevenuesFromExternalCustomers"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_RevenuesFromExternalCustomers" xlink:to="lab_wtm_RevenuesFromExternalCustomers" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicDistributed_019e46c4-3969-7a46-bc3f-5be5ca7ff28b_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Distributed earnings - dividends declared and paid (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicDistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic, Distributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicDistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicDistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicDistributed" xlink:to="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock_019e46c4-3ae3-76ab-a030-a3530ea435d9_terseLabel_en-US" xlink:label="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of credit ratings of debt securities issued</link:label>
    <link:label id="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock_label_en-US" xlink:label="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Fixed Maturity Securities Credit Quality Indicators [Table Text Block]</link:label>
    <link:label id="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock_documentation_en-US" xlink:label="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tabular disclosure of fixed maturity securities by credit quality indicator.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:href="wtm-20260630.xsd#wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:to="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_country_LU_019e46c4-3a42-72f4-ade3-aa54847b8f0b_terseLabel_en-US" xlink:label="lab_country_LU" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">LUXEMBOURG</link:label>
    <link:label id="lab_country_LU_label_en-US" xlink:label="lab_country_LU" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">LUXEMBOURG</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_LU" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_LU"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_LU" xlink:to="lab_country_LU" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_019e46c4-3a42-7761-926f-25c1ed8efdbd_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskBenchmarkDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:to="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityOwnershipPercentage_019e46c4-3969-7c27-a58a-8bf26da96ebe_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership interest</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Qualitative or Quantitative Information, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityOwnershipPercentage" xlink:to="lab_us-gaap_VariableInterestEntityOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions_019e46c4-3969-74c8-a964-ec437bc3051a_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividend and income distributions from equity method eligible investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Equity Method Investment, Distribution</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDividendsOrDistributions" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentDividendsOrDistributions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentDividendsOrDistributions" xlink:to="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_019e46c4-3ae3-70ce-a7b8-e9cf5a6a7554_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:to="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_019e46c4-3a42-7ebe-bba8-e6d94c290369_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:to="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BambooSPVMember_019e46c4-3a42-7ae7-905f-e0171febb1c9_terseLabel_en-US" xlink:label="lab_wtm_BambooSPVMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bamboo SPV</link:label>
    <link:label id="lab_wtm_BambooSPVMember_label_en-US" xlink:label="lab_wtm_BambooSPVMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bamboo SPV [Member]</link:label>
    <link:label id="lab_wtm_BambooSPVMember_documentation_en-US" xlink:label="lab_wtm_BambooSPVMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bamboo SPV</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BambooSPVMember" xlink:href="wtm-20260630.xsd#wtm_BambooSPVMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooSPVMember" xlink:to="lab_wtm_BambooSPVMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_019e46c4-3a42-7c5e-8994-7ef344e9ed98_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned premiums:</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:to="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_019e46c4-3a42-7897-b7aa-79a78b0bece7_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of net realized and unrealized investment gains and losses</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:to="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherCountryMember_019e46c4-3969-7ce5-b62d-38292fcf9708_terseLabel_en-US" xlink:label="lab_wtm_OtherCountryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_wtm_OtherCountryMember_label_en-US" xlink:label="lab_wtm_OtherCountryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other country [Member]</link:label>
    <link:label id="lab_wtm_OtherCountryMember_documentation_en-US" xlink:label="lab_wtm_OtherCountryMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other country</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherCountryMember" xlink:href="wtm-20260630.xsd#wtm_OtherCountryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherCountryMember" xlink:to="lab_wtm_OtherCountryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock_019e46c4-3ae3-7fe7-972f-8460e86c367b_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Municipal Bond Guarantee Reinsurance</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProfitLoss_019e46c4-3969-7f97-8936-83e5d9e59b4d_totalLabel_en-US" xlink:label="lab_us-gaap_ProfitLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_ProfitLoss_019e46c4-3969-76b8-9ed5-b9ec6a45c191_terseLabel_en-US" xlink:label="lab_us-gaap_ProfitLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_ProfitLoss_label_en-US" xlink:label="lab_us-gaap_ProfitLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss), Including Portion Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfitLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProfitLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProfitLoss" xlink:to="lab_us-gaap_ProfitLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_019e46c4-3a42-769a-b587-b0cc314a5c3b_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_label_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Investment Income, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GrossInvestmentIncomeOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:to="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SurplusNotesMember_019e46c4-3ae3-7477-847d-00702222beeb_terseLabel_en-US" xlink:label="lab_wtm_SurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Surplus Notes</link:label>
    <link:label id="lab_wtm_SurplusNotesMember_label_en-US" xlink:label="lab_wtm_SurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Surplus Notes [Member]</link:label>
    <link:label id="lab_wtm_SurplusNotesMember_documentation_en-US" xlink:label="lab_wtm_SurplusNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Surplus Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SurplusNotesMember" xlink:href="wtm-20260630.xsd#wtm_SurplusNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SurplusNotesMember" xlink:to="lab_wtm_SurplusNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityOtherChanges_019e46c4-3a42-7d25-b034-1dbc7164d7c9_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityOtherChanges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments of redeemable noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityOtherChanges_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityOtherChanges" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Other Changes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityOtherChanges" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityOtherChanges"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityOtherChanges" xlink:to="lab_us-gaap_TemporaryEquityOtherChanges" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestRateCapMember_019e46c4-3a42-78d5-8f00-286c8a9aa382_terseLabel_en-US" xlink:label="lab_us-gaap_InterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest Rate Cap</link:label>
    <link:label id="lab_us-gaap_InterestRateCapMember_label_en-US" xlink:label="lab_us-gaap_InterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Rate Cap [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestRateCapMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestRateCapMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestRateCapMember" xlink:to="lab_us-gaap_InterestRateCapMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaRevenue_019e46c4-3ae3-7104-8747-1b4fb42b2403_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pro forma revenue</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaRevenue_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Pro Forma Information, Pro Forma Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionsProFormaRevenue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:to="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SeniorNotesMember_019e46c4-3969-7f18-815d-b903889b1c86_terseLabel_en-US" xlink:label="lab_us-gaap_SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Senior Notes</link:label>
    <link:label id="lab_us-gaap_SeniorNotesMember_label_en-US" xlink:label="lab_us-gaap_SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Senior Notes [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SeniorNotesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SeniorNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SeniorNotesMember" xlink:to="lab_us-gaap_SeniorNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_019e46c4-3969-78d1-978f-6470c9e08cf5_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine1_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived_019e46c4-3969-79a8-be23-e3ec8cc8c121_terseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, impairments</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived_label_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ImpairmentOfIntangibleAssetsFinitelived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:to="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_019e46c4-3969-746d-8df6-d5251be13186_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total expenses</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Benefits, Losses and Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses" xlink:to="lab_us-gaap_BenefitsLossesAndExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract_019e46c4-3ae3-76e9-ad11-07a4d07bf067_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Maturity, Allocated and Single Maturity Date, Fair Value [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_019e46c4-3969-7c63-9754-2c9ee41ae04d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Income tax (expense) benefit</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedLoanObligationsMember_019e46c4-3a42-732f-b2e2-aae7906e66c8_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Collateralized loan obligations</link:label>
    <link:label id="lab_us-gaap_CollateralizedLoanObligationsMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Loan Obligations [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedLoanObligationsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedLoanObligationsMember" xlink:to="lab_us-gaap_CollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod_019e46c4-3969-7451-b2a2-b13f45d1755c_negatedTerseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Forfeitures and cancellations</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Forfeited and Cancelled In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Forfeited and Cancelled In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_019e46c4-3969-7316-ae1d-310a27c0f309_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income to net cash provided from (used for) operations:</link:label>
    <link:label id="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity, Noncash Item [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest_019e46c4-3969-7a88-9d90-8ab2c8c5255e_terseLabel_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued interest</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest_label_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Accrued Interest</link:label>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest_documentation_en-US" xlink:label="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Funds Held Under Reinsurance Agreements, Assets, Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:href="wtm-20260630.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:to="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems_019e46c4-3ae4-7ede-8af0-71dde7912c8b_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems_label_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:to="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_019e46c4-3ae3-758c-89eb-d3a80d4e26a8_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance premiums receivable</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BermudaStockExchangeMember_019e46c4-3ae3-74cd-8b78-080ffac662d9_terseLabel_en-US" xlink:label="lab_wtm_BermudaStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bermuda Stock Exchange</link:label>
    <link:label id="lab_wtm_BermudaStockExchangeMember_label_en-US" xlink:label="lab_wtm_BermudaStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bermuda Stock Exchange [Member]</link:label>
    <link:label id="lab_wtm_BermudaStockExchangeMember_documentation_en-US" xlink:label="lab_wtm_BermudaStockExchangeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bermuda Stock Exchange</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BermudaStockExchangeMember" xlink:href="wtm-20260630.xsd#wtm_BermudaStockExchangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BermudaStockExchangeMember" xlink:to="lab_wtm_BermudaStockExchangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember_019e46c4-3a42-7420-b08d-469996d13175_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discounted cash flow</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Technique, Discounted Cash Flow [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueDiscountedCashFlowMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:to="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_019e46c4-3ae3-7180-901f-e7c2db7645bc_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:label id="lab_us-gaap_StatementTable_label_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementTable" xlink:to="lab_us-gaap_StatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentMember_019e46c4-3a42-7e68-8cf3-44dd90c3f6b4_terseLabel_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">P&amp;C Insurance Distribution (Bamboo)</link:label>
    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentMember_label_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bamboo Insurance Services, LLC - Segment [Member]</link:label>
    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentMember_documentation_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bamboo Insurance Services, LLC - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:href="wtm-20260630.xsd#wtm_BambooInsuranceServicesLLCSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:to="lab_wtm_BambooInsuranceServicesLLCSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit_019e46c4-3969-7394-bba4-05497c1c0c9f_verboseLabel_en-US" xlink:label="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax expense (benefit)</link:label>
    <link:label id="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit_label_en-US" xlink:label="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Economic Transition Adjustment, Tax Expense (Benefit)</link:label>
    <link:label id="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit_documentation_en-US" xlink:label="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Economic Transition Adjustment, Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:href="wtm-20260630.xsd#wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:to="lab_wtm_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod_019e46c4-3969-7be3-877c-ccb43a485188_negatedTerseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Forfeitures and cancellations (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Forfeited and Cancelled In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Performance Shares, Forfeited and Cancelled In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:href="wtm-20260630.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedAndCancelledInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingStandardPoorsAxis_019e46c4-3a42-7437-ba5b-3c8f8896365d_terseLabel_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingStandardPoorsAxis_label_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingStandardPoorsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingStandardPoorsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingStandardPoorsAxis" xlink:to="lab_srt_CreditRatingStandardPoorsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InfrastructureFundMember_019e46c4-3a42-751c-9b6f-6f31c59637fc_terseLabel_en-US" xlink:label="lab_wtm_InfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Infrastructure Fund</link:label>
    <link:label id="lab_wtm_InfrastructureFundMember_label_en-US" xlink:label="lab_wtm_InfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Infrastructure Fund [Member]</link:label>
    <link:label id="lab_wtm_InfrastructureFundMember_documentation_en-US" xlink:label="lab_wtm_InfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Infrastructure Fund</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InfrastructureFundMember" xlink:href="wtm-20260630.xsd#wtm_InfrastructureFundMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InfrastructureFundMember" xlink:to="lab_wtm_InfrastructureFundMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeographicDistributionAxis_019e46c4-3a42-7ead-a5c4-5267ebd0167e_terseLabel_en-US" xlink:label="lab_us-gaap_GeographicDistributionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Axis]</link:label>
    <link:label id="lab_us-gaap_GeographicDistributionAxis_label_en-US" xlink:label="lab_us-gaap_GeographicDistributionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeographicDistributionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeographicDistributionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeographicDistributionAxis" xlink:to="lab_us-gaap_GeographicDistributionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_019e46c4-3ae3-7f3c-96bb-048b1261a69a_terseLabel_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_label_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Other Long-Term Investments [Member]</link:label>
    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalOtherLongTermInvestmentsMember" xlink:href="wtm-20260630.xsd#wtm_TotalOtherLongTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalOtherLongTermInvestmentsMember" xlink:to="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_019e46c4-3969-74d1-b774-05b2af281dad_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership percentage of basic units outstanding</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_label_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Of Basic Units Outstanding, Parent</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_documentation_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Of Basic Units Outstanding, Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:href="wtm-20260630.xsd#wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:to="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestmentsMember_019e46c4-3a42-7cd1-8f30-4c3ad376b965_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLongTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestmentsMember" xlink:to="lab_us-gaap_OtherLongTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract_019e46c4-3969-7af8-80fc-132f6b3e62d2_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:type="arc" order="1"/>
  </link:labelLink>
</link:linkbase>
