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    <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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_019caf59-221a-7152-b30e-74dd28797c46_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">Finite-Lived Intangible Assets, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill_019caf59-221a-70d1-b8fa-eb90bafef9c4_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-20260331.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_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems_019caf59-221a-76c9-bcb4-508b9afc7011_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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsLineItems"/>
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    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_019caf59-221a-7954-b317-9f70692b11df_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/2025/elts/us-gaap-2025.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_dei_EntityListingsExchangeAxis_019caf59-229d-710f-a590-29fe11a06e8a_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/2025/dei-2025.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_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_019caf59-2168-7f75-b5b5-b6336e71a832_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/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract"/>
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    <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/2025/ecd-2025.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_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019caf59-221a-75c2-857a-af75e3475952_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">Indefinite-Lived Intangible Assets [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">Indefinite-Lived Intangible Assets [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
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    <link:label id="lab_dei_EntityFileNumber_019caf59-2168-7c14-9df7-c7d5b13b0426_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/2025/dei-2025.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_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_019caf59-2312-7156-a79d-d99ae3777e22_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>
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    <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_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>
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    <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_OtherSignificantTransactionsTable_019caf59-229c-7971-9485-6eaffadff013_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-20260331.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_us-gaap_SecuredOvernightFinancingRateSofrMember_019caf59-221a-73ce-8588-8b77b7fa457d_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/2025/elts/us-gaap-2025.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_NumberOfInvestments_019caf59-2312-7d3c-ac15-d5534673b21f_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-20260331.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_us-gaap_FairValueByBalanceSheetGroupingTextBlock_019caf59-229d-7265-9118-b2db13144d7b_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/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueByBalanceSheetGroupingTextBlock"/>
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    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_019caf59-229d-7fb2-bd90-1c77c62f1f34_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/2025/elts/us-gaap-2025.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_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived_019dc3c2-01ef-7c72-a743-80c5ffbaf2bd_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-20260331.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_RedeemableNoncontrollingInterestEquityRedemptionValue_019caf59-221a-773f-a8c1-42c284adba7b_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/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities_019cff12-e87e-733e-a999-59a4c41b957c_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-20260331.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_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/2025/ecd-2025.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_DeferredTaxLiabilityReversal_019cff90-2f4d-7551-8d3d-4aa92831d87c_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-20260331.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_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/2025/ecd-2025.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_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate_019caf59-2168-7707-977d-f2810629b187_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/2025/elts/us-gaap-2025.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_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember_019caf59-229d-7d61-871c-244cfcdc38aa_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/2025/elts/us-gaap-2025.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_OtherLongTermInvestmentsUnrealizedLoss_019caf59-229d-78fb-a080-4536191cbea4_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-20260331.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_019caf59-229c-7049-bdaa-2a7213ffce5d_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-20260331.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_InterestRateCapMember_019caf59-221a-7973-983e-101cca0f7bae_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/2025/elts/us-gaap-2025.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_AssetsOfDisposalGroupIncludingDiscontinuedOperation_019caf59-221a-7a01-98d4-1aad921b090e_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_019dd888-5bc0-7707-9006-71897404aa28_verboseLabel_en-US" xlink:label="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Assets held for sale</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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_ConcentrationRiskPercentage1_019caf59-229d-766d-8950-c143ba1c02bb_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/2025/elts/us-gaap-2025.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_wtm_NotesReceivableNominalFairValueDisclosure_019caf59-221a-7702-bcb6-9238776d5ee2_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_019caf59-221a-73a9-9b67-4c55b02b89fa_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-20260331.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_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_019caf59-229d-7885-822e-d4878f5c5c78_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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensation_019caf59-221a-7907-ab97-e0f59cf9e2b6_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/2025/elts/us-gaap-2025.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_us-gaap_CollateralizedCreditCardSecuritiesMember_019caf59-229c-7b6d-9ae8-0467823fc275_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/2025/elts/us-gaap-2025.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_us-gaap_DerivativeAssetNotionalAmount_019caf59-229d-79b3-9695-5cece552f4cc_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/2025/elts/us-gaap-2025.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_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/2025/elts/us-gaap-2025.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_wtm_PercentageOfParValueOfPolicyReinsured_019caf59-221a-7181-9dbb-a93b6d05bae4_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-20260331.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_Ark2021SubordinatedNotesTranche2Member_019caf59-221a-78b1-9985-8a96865d3674_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-20260331.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_us-gaap_DividendsCommonStockCash_019caf59-221a-70fa-a843-2b7030f10f79_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/2025/elts/us-gaap-2025.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_019caf59-221a-7494-858b-549cfc4b1df5_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_019caf59-221a-79e9-8f29-5de605b94f5f_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueByMeasurementFrequencyAxis_019caf59-229d-7c2a-a744-746490344cde_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/2025/elts/us-gaap-2025.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_DebtSecuritiesAvailableForSaleTable_019cff20-6439-7bef-8663-47b101d22a86_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis_019caf59-229d-71bf-be3f-ceaba3b0fc58_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-20260331.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_CommonStockSharesAuthorized_019caf59-229d-7745-b563-e906f0030ad3_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/2025/elts/us-gaap-2025.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_PaymentsForProceedsFromOtherShortTermInvestments_019caf59-2168-73ef-8973-26f4953925af_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-20260331.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_us-gaap_MinorityInterestLineItems_019caf59-229d-759d-99b9-506a60195293_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/2025/elts/us-gaap-2025.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_FairValueMeasurementsRecurringMember_019caf59-221a-7418-8215-878e755670d4_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_019caf59-221a-7c33-99c3-a3bc3d080643_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_019caf59-221a-73e0-a4cf-e48216e8b6e6_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-20260331.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_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_019caf59-221a-7b4e-97f4-09606dc34e8f_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/2025/elts/us-gaap-2025.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_PremiumsReceivableAtCarryingValue_019caf59-229d-7763-b4a8-2a36f1171ed6_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/2025/elts/us-gaap-2025.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_dei_CoverAbstract_019caf59-221a-7364-a00a-77afb3438ab3_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/2025/dei-2025.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_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock_019caf59-221a-7b5c-993b-dfa5281123a1_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/2025/elts/us-gaap-2025.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_srt_MaximumMember_019caf59-229d-7dfd-8799-d41767fa1104_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/2025/elts/srt-2025.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_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_019caf59-221a-7e4a-b82a-acdb85e5f924_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/2025/elts/us-gaap-2025.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_us-gaap_FiniteLivedIntangibleAssetsNet_019caf59-221a-7b25-b296-f8d51020c432_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">Finite-Lived Intangible Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_DebtInstrumentCollateralAmount_019caf59-221a-7694-9a7d-401ab2a7c862_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/2025/elts/us-gaap-2025.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_us-gaap_RestrictedStockMember_019caf59-229c-777a-a2fd-99905aed1dbd_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/2025/elts/us-gaap-2025.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_IncomeTaxContingencyLineItems_019cff90-d42c-79ed-b6f4-3fd58a23fedc_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_DebtInstrumentLineItems_019caf59-221a-7344-84b7-7fb09bb28f46_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/2025/elts/us-gaap-2025.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_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_019caf59-229c-7e78-bcba-d5cebad65f8d_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesForfeitedInPeriod_019caf59-229d-7bd0-99ab-e8aaa97d4a96_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-20260331.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_wtm_RestrictedCashHeldForSale_019caf59-221a-750a-9fdd-c59883f599b0_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-20260331.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_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/2025/ecd-2025.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_DirectPremiumsEarned_019caf59-229d-7d85-845e-10e8f98ca992_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_019caf59-229d-77fc-9f56-c266ffe19bc7_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/2025/elts/us-gaap-2025.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_srt_ExternalCreditRatingStandardPoorsMember_019caf59-229d-725b-8a10-2416f37fb7d4_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/2025/elts/srt-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_DebtSecuritiesWeightedAveragePortfolioPeriodExcludingShortTermInvestments_019ddc37-4877-7e3a-ad4b-d40b5e77ac8e_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-20260331.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_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019caf59-229d-78e7-ba33-8b807d7ba53a_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/2025/elts/us-gaap-2025.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_dei_EntityShellCompany_019caf59-229d-7789-92c6-aa5dc999690a_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/2025/dei-2025.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_wtm_WTMCreditFacilityMember_019caf59-2312-725a-87d7-9dccfb725d3f_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-20260331.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_019caf59-2312-72ab-9c74-88e777b71b49_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-20260331.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_DebtInstrumentTable_019caf59-221a-78bf-811e-412745a8acc3_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/2025/elts/us-gaap-2025.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_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019caf59-2312-7e18-9e7f-8a09f57aa124_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/2025/elts/us-gaap-2025.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_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum_019caf59-221a-7d3e-87cc-5299b2876a6d_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-20260331.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_us-gaap_StatementOfStockholdersEquityAbstract_019caf59-2168-77cd-9b7d-d1217024335d_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/2025/elts/us-gaap-2025.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_OperatingSegmentsMember_019caf59-221a-765a-b843-89b9ae0294d9_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/2025/elts/us-gaap-2025.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_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest_019caf59-221a-727c-bf9c-a1e682d0e96c_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/2025/elts/us-gaap-2025.xsd#us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest"/>
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    <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/2025/ecd-2025.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_EffectsOfReinsuranceFootnotesAbstract_019caf59-221a-71b9-a723-a44a1228994c_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-20260331.xsd#wtm_EffectsOfReinsuranceFootnotesAbstract"/>
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    <link:label id="lab_us-gaap_LetterOfCreditMember_019caf59-221a-72f5-909d-5ee3d1047908_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/2025/elts/us-gaap-2025.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_us-gaap_PaymentsToMinorityShareholders_019caf59-221a-7d17-97c3-d4e220e8f883_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/2025/elts/us-gaap-2025.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_srt_AMBestAMinusRatingMember_019caf59-221a-7cc4-ae15-c9b7298ae489_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/2025/elts/srt-2025.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_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock_019caf59-221a-7280-bbd9-272318f0cc01_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-20260331.xsd#wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock"/>
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    <link:label id="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember_019caf59-221a-7328-b304-923636e2e496_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/2025/elts/us-gaap-2025.xsd#us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember"/>
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    <link:label id="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate_019caf59-229d-73d4-a6c1-32a0a277ef0d_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>
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    <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_dei_DocumentFiscalPeriodFocus_019caf59-221a-7733-8547-4f539b3c0f62_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/2025/dei-2025.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_us-gaap_IntangibleAssetsNetIncludingGoodwill_019caf59-229d-7a82-ae70-a614b61c28f0_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_019caf59-229d-73b0-9611-0f4da6efe77c_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_019caf59-229d-7323-ab3b-4189f59b3a18_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_019caf59-229d-758b-a1f5-603ed6b3c690_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 Assets, Net (Including Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019caf59-221a-784c-838f-a6451c08053b_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-20260331.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_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/2025/ecd-2025.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_IncomeLossFromContinuingOperationsPerBasicShare_019caf59-221a-770e-bcc8-8545afbe2a03_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/2025/elts/us-gaap-2025.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_AwardTypeAxis_019caf59-229d-7d7b-8acb-d53719f77d59_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/2025/elts/us-gaap-2025.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_wtm_OtherLongTermInvestmentsNetForeignCurrencyGainLoss_019caf59-221a-7ce3-a70f-64945575986d_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-20260331.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_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019caf59-221a-7291-a69d-788f59a41ec1_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/2025/elts/us-gaap-2025.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_GoodwillImpairedAbstract_019caf59-2168-7242-a788-f218926aee5b_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/2025/elts/us-gaap-2025.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_DistinguishedManagementMember_019caf59-229c-7f5b-8f6b-79d7e7579ba4_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-20260331.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_srt_EquityMethodInvesteeNameDomain_019caf59-229c-7561-a66a-445fec0bef66_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/2025/elts/srt-2025.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_dei_TradingSymbol_019caf59-229c-76fd-a2f9-11c935532037_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/2025/dei-2025.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_PolicyholderBenefitsAndClaimsIncurredGross_019caf59-2168-7001-b301-9f345066e985_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/2025/elts/us-gaap-2025.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_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019caf59-229c-78a9-92fb-3dccfcda7256_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">Schedule of Intangible Assets 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/2025/elts/us-gaap-2025.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_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember_019caf59-221a-74ae-9516-e6b5087c9e67_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-20260331.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_dei_EntityAddressCityOrTown_019caf59-221a-74c1-b8ad-ab7aa837da2e_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/2025/dei-2025.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_TechnologySectorMember_019caf59-2312-7215-8336-e7f7f48ef09c_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_IncomeStatementLocationDomain_019caf59-229d-7dfa-a3cf-31c571095c2f_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Statement Location [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementLocationDomain_label_en-US" xlink:label="lab_us-gaap_IncomeStatementLocationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Income Location, Balance [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementLocationDomain" xlink:to="lab_us-gaap_IncomeStatementLocationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherDisposalGroupMember_019caf59-221a-724f-97b5-1b31dc52bc9a_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-20260331.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_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/2025/ecd-2025.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_BusinessCombinationConsiderationTransferred1_019caf59-229d-792e-ad0b-733231002890_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/2025/elts/us-gaap-2025.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_EntityEmergingGrowthCompany_019caf59-2168-7ad9-b26c-6818c8c59869_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/2025/dei-2025.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_wtm_PaymentsToAcquireSurplusNotes_019caf59-229d-7390-ab24-c9aec96a8b4f_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-20260331.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_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic_019caf59-2168-7418-80eb-a10a03b2f80c_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/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets_019cff12-e87e-7ec5-9fdc-3565d5ffd0fe_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-20260331.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_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/2025/ecd-2025.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_DeferredFinanceCostsNet_019d6bb2-05ae-72e3-8c90-2de687c10a67_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/2025/elts/us-gaap-2025.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_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne_019caf59-221a-7a9e-b4be-eaf637963790_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-20260331.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_RestrictedCashAndCashEquivalents_019caf59-229d-7208-82ad-2e896d7a9196_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/2025/elts/us-gaap-2025.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_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019caf59-221a-7f6b-a065-9a5571d50229_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">Indefinite-Lived Intangible Assets (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_CommonStockSharesOutstanding_019caf59-221a-7b7f-8469-13cb8459234e_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/2025/elts/us-gaap-2025.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_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/2025/elts/us-gaap-2025.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_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate_019cffb7-93fb-72f7-a4ab-381efd46d298_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">April 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/2025/elts/us-gaap-2025.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_us-gaap_CollateralizedAutoLoansMember_019caf59-229d-74ad-8d9e-0d9bd9900cc1_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/2025/elts/us-gaap-2025.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_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_019caf59-229d-7a66-bfb9-a5d1d8266332_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>
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    <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_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution_019caf59-229d-7e54-866a-150961a0362b_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-20260331.xsd#wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_019caf59-221a-7241-9be5-247031040e36_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/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod"/>
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    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment_019cff07-6b93-7334-a21e-9b1ab9da2477_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-20260331.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_019caf59-229d-7a98-be46-2b7d0be03514_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-20260331.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_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/2025/ecd-2025.xsd#ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember"/>
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    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract_019caf59-229d-7668-bad8-24bd4984594a_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss_019caf59-229c-77b0-9876-bbc6c268641d_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>
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    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears_019caf59-221a-7039-a892-7480346bccb7_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-20260331.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_019caf59-229c-706b-b2e2-5824232dda79_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_019caf59-229c-7187-88cf-52bf640802d4_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/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward"/>
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    <link:label id="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage_019caf59-229d-77e9-938a-6e929a72a29d_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>
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    <link:label id="lab_us-gaap_PledgedStatusDomain_019caf59-229d-7f91-8a0f-8ff93b34089a_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/2025/elts/us-gaap-2025.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_dei_EntityAddressPostalZipCode_019caf59-229d-7974-8682-a3aaf5fdb392_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>
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    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressPostalZipCode"/>
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    <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/2025/ecd-2025.xsd#ecd_RestatementDeterminationDate"/>
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    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_019caf59-221a-724e-86c8-29227800d3c2_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/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
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    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_019caf59-2168-7edf-95f5-e00157b9284e_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/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
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    <link:label id="lab_wtm_OtherAssetBackedSecuritiesMember_019caf59-229d-716e-9468-5a39ac9f33af_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-20260331.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_OtherAssets_019caf59-229c-76bb-ba97-31ddc845f43e_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019caf59-2312-7ae3-b0d6-9d2ca6551d62_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_019caf59-2312-7d69-81d2-dbbbc72c1cd1_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/2025/elts/us-gaap-2025.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_srt_CreditRatingStandardPoorsAxis_019caf59-229c-7bd1-8195-e157ed48ea32_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/2025/elts/srt-2025.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_dei_DocumentInformationLineItems_019caf59-229d-725d-abcf-4277c03f601c_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/2025/dei-2025.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_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/2025/ecd-2025.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_RealEstateSectorMember_019caf59-221a-7c49-b64b-f0fe801c1e83_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/2025/elts/us-gaap-2025.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_SubsegmentsAxis_019caf59-221a-7100-b1fa-b40e1a95a6f5_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/2025/elts/us-gaap-2025.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_FairValueByFairValueHierarchyLevelAxis_019caf59-221a-788a-87da-68db0404b387_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/2025/elts/us-gaap-2025.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_wtm_InsuranceLinkedSecuritiesFundsMember_019caf59-221a-716f-b569-a179569d85eb_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-20260331.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019caf59-221a-7745-8ac6-1199db39d513_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/2025/elts/us-gaap-2025.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_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract_019caf59-229d-76d9-954f-b449c377fb34_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/2025/elts/us-gaap-2025.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_wtm_DebtInstrumentIncreaseInInterestRatePeriod_019caf59-221a-70dc-90fe-c691d080dfc9_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-20260331.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_019caf59-2312-7c60-8d63-b51787645206_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-20260331.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_us-gaap_ScheduleOfGuaranteeObligationsTable_019caf59-229d-7d5b-b6ae-d45fd987119e_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_GoodwillAcquiredDuringPeriod_019caf59-2312-719e-a535-377b51c32fb6_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/2025/elts/us-gaap-2025.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_SubsidiaryDistinguishedMember_019caf59-229c-73a1-8daa-0c042bfb2e1a_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedMember_label_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryDistinguishedMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryDistinguishedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Distinguished</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryDistinguishedMember" xlink:href="wtm-20260331.xsd#wtm_SubsidiaryDistinguishedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryDistinguishedMember" xlink:to="lab_wtm_SubsidiaryDistinguishedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired_019caf59-221a-7ce8-9bc3-50e34281d01a_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-20260331.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_DerivativePremiumPaid_019caf59-229d-7d90-a80d-c5bc3c202836_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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_019caf59-229c-7dd4-899b-23679920210d_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_019caf59-229c-748d-a2b0-9906abda0282_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/2025/elts/us-gaap-2025.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_us-gaap_CededCreditRiskSecuredMember_019caf59-229d-7739-b684-fcb0363f7b2d_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/2025/elts/us-gaap-2025.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_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_019caf59-221a-706d-a86c-5147b66c735b_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/2025/elts/us-gaap-2025.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_us-gaap_ReinsurancePayable_019caf59-221a-7d9d-8ff4-199174f09805_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/2025/elts/us-gaap-2025.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_GrossPremiumsEarned_019caf59-229d-75dd-949d-fcb561ba902b_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_019caf59-229d-7d55-a7f9-129110d607b5_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-20260331.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_019caf59-2168-7b50-9718-239a82a71dfc_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-20260331.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_NetCashProvidedByUsedInOperatingActivities_019caf59-229c-7ae3-bdc5-a0e779394c2e_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/2025/elts/us-gaap-2025.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_PrivateDebtInstrumentMember_019caf59-229c-76ca-a3de-44d220b880a8_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-20260331.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage_019ddc32-0125-745b-863b-d71388541c70_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Targeted performance goal (as a percent)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" 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, Targeted Performance Goal, Average Annual Growth, Percentage</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" 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, Targeted Performance Goal, Average Annual Growth, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" xlink:href="wtm-20260331.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardTargetedPerformanceGoalAverageAnnualGrowthPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod_019caf59-221a-758e-8674-40dbe396cbf3_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-20260331.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_019caf59-229d-702e-ab55-4649aa473f34_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-20260331.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_EquityMethodInvestmentsAndJointVenturesAbstract_019caf59-229c-76c7-9b3e-a62d8ad84949_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/2025/elts/us-gaap-2025.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019caf59-2168-77ca-880f-66e899a79c41_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_us-gaap_LongtermDebtTypeAxis_019caf59-221a-732e-a0d3-f0a1f6787f44_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/2025/elts/us-gaap-2025.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_wtm_OtherOperationsDebtMember_019caf59-229d-70ee-9b53-994344da0c33_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-20260331.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_WeightedAverageNumberOfSharesOutstandingBasicAbstract_019caf59-229c-7535-907a-e0a126139cc4_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/2025/elts/us-gaap-2025.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_us-gaap_StatementEquityComponentsAxis_019caf59-221a-713f-b313-030da2d41030_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/2025/elts/us-gaap-2025.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_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember_019de451-e81b-73a4-b0d6-86a1b650c19b_terseLabel_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">P&amp;C Insurance Distribution (Bamboo), net</link:label>
    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember_label_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Bamboo Insurance Services, LLC - Segment, Net of Reconciling Items [Member]</link:label>
    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember_documentation_en-US" xlink:label="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Bamboo Insurance Services, LLC - Segment, Net of Reconciling Items</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:href="wtm-20260331.xsd#wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:to="lab_wtm_BambooInsuranceServicesLLCSegmentNetOfReconcilingItemsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock_019caf59-2168-7e33-bb38-31975559d33b_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-20260331.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_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/2025/ecd-2025.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_us-gaap_NumberOfReportableSegments_019caf59-229c-700a-b813-cc05dfce6cdd_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/2025/elts/us-gaap-2025.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_wtm_SignificantTransactionsAbstract_019caf59-221a-732d-b19a-f409bcedb6d2_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-20260331.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_wtm_A2024InterestRateCapMember_019dc2d5-8ea7-7342-a3f2-0a109ca267f5_terseLabel_en-US" xlink:label="lab_wtm_A2024InterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2024 Interest Rate Cap</link:label>
    <link:label id="lab_wtm_A2024InterestRateCapMember_label_en-US" xlink:label="lab_wtm_A2024InterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">2024 Interest Rate Cap [Member]</link:label>
    <link:label id="lab_wtm_A2024InterestRateCapMember_documentation_en-US" xlink:label="lab_wtm_A2024InterestRateCapMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">2024 Interest Rate Cap</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_A2024InterestRateCapMember" xlink:href="wtm-20260331.xsd#wtm_A2024InterestRateCapMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_A2024InterestRateCapMember" xlink:to="lab_wtm_A2024InterestRateCapMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_019caf59-221a-7bc1-a209-1ab962c1e000_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/2025/elts/us-gaap-2025.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_dei_EntityAddressStateOrProvince_019caf59-229c-76e9-869f-31d86cbad94f_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/2025/dei-2025.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_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition_019caf59-221a-76c2-b2dd-f41db3a29ae6_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/2025/elts/us-gaap-2025.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_DelayedDrawTermLoanMember_019caf59-229d-771e-84b6-020598026c60_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/2025/elts/us-gaap-2025.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_us-gaap_EffectsOfReinsuranceLineItems_019caf59-229c-7503-8b33-6928d06864db_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/2025/elts/us-gaap-2025.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_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue_019dfa45-296f-77df-a952-5b48fdcf3ef1_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-20260331.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_CommercialAndIndustrialSectorMember_019caf59-229c-7864-8bdb-5748538c968e_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/2025/elts/us-gaap-2025.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_wtm_OutriggerReMember_019caf59-2312-7f62-9e5a-e3d59936ac79_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-20260331.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_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/2025/ecd-2025.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_EquityMethodInvestmentAggregateCost_019caf59-2312-7eec-94b5-55cfc124a0bc_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/2025/elts/us-gaap-2025.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_wtm_OtherIncomeAdjusted_019caf59-221a-7124-934b-54d4d3fa47ad_terseLabel_en-US" xlink:label="lab_wtm_OtherIncomeAdjusted" 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_OtherIncomeAdjusted_label_en-US" xlink:label="lab_wtm_OtherIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income, Adjusted</link:label>
    <link:label id="lab_wtm_OtherIncomeAdjusted_documentation_en-US" xlink:label="lab_wtm_OtherIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Income, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherIncomeAdjusted" xlink:href="wtm-20260331.xsd#wtm_OtherIncomeAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherIncomeAdjusted" xlink:to="lab_wtm_OtherIncomeAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_019cff90-2f4d-7cb5-b0d0-c772ee3d5516_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/2025/elts/us-gaap-2025.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_us-gaap_PaymentsOfDividendsCommonStock_019caf59-229c-7e4f-b8a1-cb926108a2f7_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/2025/elts/us-gaap-2025.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_wtm_LimitedPartnershipsMember_019caf59-229d-72c8-a10f-6997a4d1b928_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-20260331.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_InsuranceDisclosureTextBlock_019caf59-229c-7fcc-b407-f4a57ef9ea57_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/2025/elts/us-gaap-2025.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_ProceedsFromMinorityShareholders_019caf59-221a-7267-a9c8-61d925ebd4d3_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/2025/elts/us-gaap-2025.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_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_019caf59-229d-716e-8bec-00888417efca_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_DeferredOtherTaxExpenseBenefit_019cff8f-3a55-7c07-a059-cc14503c7c69_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/2025/elts/us-gaap-2025.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_MinorityInterestOwnershipPercentageByNoncontrollingOwners_019caf59-229d-75f9-ae36-82c1ab8c69ed_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/2025/elts/us-gaap-2025.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_us-gaap_RepaymentsOfLongTermDebt_019caf59-221a-7530-9565-c06ba491a1c1_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_019caf59-221a-751a-9f6b-2657db9423fe_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/2025/elts/us-gaap-2025.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_dei_EntityInteractiveDataCurrent_019caf59-229d-70f3-8c39-c5d837b5a886_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/2025/dei-2025.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_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember_019caf59-229c-7194-b555-336fea841f01_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-20260331.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_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued_019caf59-221a-7bf2-aa03-bfb1be857d6b_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-20260331.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_wtm_DebtInstrumentLoanToValuePercentage_019caf59-2168-7107-9a88-72a8aebb1288_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-20260331.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_019dc3be-52c5-76f9-9ffb-3df6351fa9e4_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-20260331.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_us-gaap_HealthcareSectorMember_019caf59-229d-71ce-b1f0-884d4a93040d_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/2025/elts/us-gaap-2025.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_DebtInstrumentPeriodicPaymentPrincipal_019caf59-229d-72bb-89a6-d0cdda979af6_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/2025/elts/us-gaap-2025.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_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes_019caf59-229c-7281-a7df-7978b13c989e_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-20260331.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_019caf59-2312-70a8-8801-122f23181f70_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-20260331.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_TemporaryEquityOtherChanges_019caf59-229c-7a27-a4a0-53f0eb5ac816_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/2025/elts/us-gaap-2025.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_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow_019dc3c2-01ef-7a06-8bed-d4ac77b2f624_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-20260331.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_srt_OwnershipDomain_019caf59-221a-74cb-ac3b-a33f50dd6d6d_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/2025/elts/srt-2025.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_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested_019caf59-221a-7718-8cf7-de68e5528047_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-20260331.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_019caf59-2168-75d7-9dbe-695aa8d81393_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-20260331.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_GovernmentNationalMortgageAssociationCertificatesAndObligationsGNMAMember_019caf59-2312-77b5-b5b9-36ac48b946f2_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/2025/elts/us-gaap-2025.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_TradingSecuritiesDebtAmortizedCost_019caf59-221a-7b18-9534-6c85cb81a891_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_019caf59-221a-7a29-b578-861c8c83f221_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/2025/elts/us-gaap-2025.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_dei_EntityCentralIndexKey_019caf59-221a-7938-b661-7f0176741c0e_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/2025/dei-2025.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_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/2025/ecd-2025.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_Revenues_019caf59-221a-7e8f-a0f1-a093c7ed7df1_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/2025/elts/us-gaap-2025.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_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax_019caf59-229c-75f6-8c47-dc69d541b9cc_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/2025/elts/us-gaap-2025.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_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet_019caf59-229c-797e-a133-d10295162c92_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>
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    <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>
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    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_019caf59-221a-7d21-b0fd-9f01df443e81_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019caf59-221a-78a7-8ddf-dd3acd6619db_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_019caf59-221a-7e9a-8cc6-3b1aef10db23_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_019caf59-221a-768b-8e89-3bae4693b69c_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/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
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    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019caf59-229d-70d9-b0c8-c7c8e7e80a64_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">Schedule of Segment Reporting Information, by Segment [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">Schedule of Segment Reporting Information, by Segment [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_ChangeInLongTermDebtRollForward_019caf59-2168-7c9f-b4ce-e84b1084fa4a_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-20260331.xsd#wtm_ChangeInLongTermDebtRollForward"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenNet_019caf59-221a-7234-849c-4e38b135200c_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_dei_EntityFilerCategory_019caf59-221a-76b9-bb24-f1cd6c88acd3_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/2025/dei-2025.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_HGGlobalBAMSegmentMember_019caf59-229d-70e9-b67f-94e630188685_terseLabel_en-US" xlink:label="lab_wtm_HGGlobalBAMSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Guarantee (HG Global)</link:label>
    <link:label id="lab_wtm_HGGlobalBAMSegmentMember_label_en-US" xlink:label="lab_wtm_HGGlobalBAMSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global/BAM - Segment [Member]</link:label>
    <link:label id="lab_wtm_HGGlobalBAMSegmentMember_documentation_en-US" xlink:label="lab_wtm_HGGlobalBAMSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global/BAM - Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobalBAMSegmentMember" xlink:href="wtm-20260331.xsd#wtm_HGGlobalBAMSegmentMember"/>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_019caf59-221a-7189-a1f1-88af23c80b17_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_019caf59-221a-720a-b719-5c6e1a6f6120_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_019caf59-221a-78de-be88-f7c08278474f_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/2025/elts/us-gaap-2025.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
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    <link:label id="lab_wtm_KuduInvestmentManagementLLCSegmentMember_019caf59-221a-7cc9-8332-9cf33a29d627_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-20260331.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures_019caf59-2312-7f08-b451-5d825b81b750_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-20260331.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019caf59-2168-7557-8114-195be6d960be_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">Finite-Lived Intangible Assets, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
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    <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/2025/ecd-2025.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_BenefitsLossesAndExpenses_019caf59-229d-7cac-9988-dc9f16b8f94b_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_019caf59-229d-7197-97c1-54c073f3d568_terseLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" 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/2025/elts/us-gaap-2025.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_wtm_NotesReceivableInterestRateFairValueDiscount_019caf59-2168-71f1-8c1d-776031f81e4f_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_019caf59-2168-7cfc-8dfa-9efb9dff105d_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-20260331.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_019caf59-221a-734c-b08a-0a16f358eddb_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-20260331.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_us-gaap_PremiumsWrittenGross_019caf59-229d-728e-9552-02b5988a65ec_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_019caf59-229d-75de-8a37-969366abcaba_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/2025/elts/us-gaap-2025.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_dei_EntityAddressAddressLine1_019caf59-229d-712d-ae29-dde7a7738143_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/2025/dei-2025.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_wtm_DebtInstrumentBorrowingBasePercentage_019caf59-2168-78de-a19e-8036baf26e46_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-20260331.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_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_019caf59-2168-7293-955b-310228e3ab0c_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_019caf59-2168-7267-a3c2-d536338f5074_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/2025/elts/us-gaap-2025.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_AccumulatedOtherComprehensiveIncomeMember_019caf59-229d-7e4c-b60d-6c6a4cfa50c8_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/2025/elts/us-gaap-2025.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_019caf59-229d-771b-835f-b39286c3a807_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-20260331.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_us-gaap_InvestmentTypeCategorizationMember_019caf59-221a-764a-b817-dc2823b0d0bb_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/2025/elts/us-gaap-2025.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_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019caf59-221a-7ec2-91cd-5244342d985a_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_019df8d0-b412-73c1-8282-ea989eedfe4b_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_019caf59-221a-7dd8-b4a6-7be08c337853_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/2025/elts/us-gaap-2025.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_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived_019caf59-2312-75b4-99f7-52e392dfb52e_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-20260331.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_RedeemableNoncontrollingInterestEquityCarryingAmount_019caf59-221a-7afc-bb2b-ec5bfc48bca6_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/2025/elts/us-gaap-2025.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_srt_OwnershipAxis_019caf59-229c-768c-910f-cdf31d050fca_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/2025/elts/srt-2025.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_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019caf59-221a-77ef-b1cd-2efd71371eca_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/2025/elts/us-gaap-2025.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_ProceedsFromSaleAndMaturityOfOtherInvestments_019caf59-229d-7a46-a1c2-b7bb5a3d6698_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/2025/elts/us-gaap-2025.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_EquitySecuritiesByIndustryAxis_019caf59-221a-76be-9f0e-627e31a2ad0a_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/2025/elts/us-gaap-2025.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_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems_019caf59-221a-70d4-8b13-0ded8351f87e_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">Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, 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">Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, 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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_EquitySecuritiesFvNiCost_019caf59-2312-7d99-a8fa-bf27c2617966_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/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill_019caf59-2312-7009-ac07-c815181bcb60_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-20260331.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_019caf59-221a-7b43-aec2-a33bd9238355_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-20260331.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_019caf59-221a-762a-9484-b9a81737af21_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-20260331.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_FairValueInputsLevel12And3Member_019caf59-229c-7881-ad57-4039018806ce_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/2025/elts/us-gaap-2025.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_ScheduleOfDebtInstrumentsTextBlock_019caf59-2168-7831-9c7f-9ea4f5e86b07_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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_019caf59-221a-7a84-a922-4c954a42d61e_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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_019caf59-2168-784f-ba06-eb34274a437e_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/2025/elts/us-gaap-2025.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_wtm_DebtInstrumentFundingDateAnniversary_019caf59-221a-7463-b21f-b4def2e4278e_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentFundingDateAnniversary" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Anniversary of funding date</link:label>
    <link:label id="lab_wtm_DebtInstrumentFundingDateAnniversary_label_en-US" xlink:label="lab_wtm_DebtInstrumentFundingDateAnniversary" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Funding Date Anniversary</link:label>
    <link:label id="lab_wtm_DebtInstrumentFundingDateAnniversary_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentFundingDateAnniversary" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Funding Date Anniversary</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentFundingDateAnniversary" xlink:href="wtm-20260331.xsd#wtm_DebtInstrumentFundingDateAnniversary"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentFundingDateAnniversary" xlink:to="lab_wtm_DebtInstrumentFundingDateAnniversary" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentQuarterlyReport_019caf59-229d-7f3a-a58b-8e1b3cc56f0e_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/2025/dei-2025.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_wtm_FidusReLtd.Member_019caf59-229d-7973-9e4a-bcfde774f6a5_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-20260331.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_us-gaap_DeferredIncomeTaxesAndTaxCredits_019caf59-221a-7d22-9953-351473bdc1d6_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/2025/elts/us-gaap-2025.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_LongTermDebtFairValue_019caf59-229d-70d1-b3e3-6337a9cbacdd_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/2025/elts/us-gaap-2025.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_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019caf59-229d-7a36-aac0-0f3b737bb5cb_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss_019caf59-221a-73a0-91fe-9221f976bec8_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-20260331.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_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/2025/ecd-2025.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_AccruedInvestmentIncomeReceivable_019caf59-2168-713e-a1ce-e0caabf787a5_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/2025/elts/us-gaap-2025.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_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock_019caf59-221a-7076-a568-d53d95e2bbca_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/2025/elts/us-gaap-2025.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_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses_019caf59-221a-7b27-8efa-661adb630b8a_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-20260331.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_InvestmentTypeAxis_019caf59-221a-7649-acc9-34ecefa0ba34_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/2025/elts/us-gaap-2025.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_srt_AMBestBPlusPlusRatingMember_019caf59-229d-7a5e-8bd8-b9ba248cd92e_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/2025/elts/srt-2025.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_Investments_019caf59-221a-7fc3-9f88-41390d1f3ced_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_019caf59-221a-79e9-972e-733df133bfab_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_wtm_MandatorilyRedeemablePreferredSecuritiesMember_019caf59-229d-7dd5-8563-06765097ec25_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-20260331.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_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/2025/ecd-2025.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_us-gaap_LettersOfCreditOutstandingAmount_019caf59-229c-70c7-82b7-dbe47762785b_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/2025/elts/us-gaap-2025.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_us-gaap_DebtSecuritiesTradingUnrealizedGain_019caf59-2312-7845-8bed-e511830004d6_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/2025/elts/us-gaap-2025.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_wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable_019caf59-229d-7077-a465-dfe63b911472_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-20260331.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_OtherIntangibleAssetsMember_019caf59-221a-7663-8f0c-a3c933014a95_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019caf59-221a-7503-b01e-b8cc86028bd5_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/2025/elts/us-gaap-2025.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_BusinessCombinationRecognizedAssetsAcquiredOtherAssets_019cff12-e87e-76da-a63d-80d0432080b8_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-20260331.xsd#wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets"/>
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    <link:label id="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments_019cff59-f044-759a-8f02-469daaed30e7_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-20260331.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_MinorityInterest_019caf59-221a-764b-990a-e06f0209e5f7_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_019caf59-221a-7d06-b459-279c6d25facc_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_OtherIncome_019caf59-221a-79c8-bf79-d4888db9ebd1_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/2025/elts/us-gaap-2025.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_country_CA_019df169-7292-7ebf-bee3-467e2b6190d8_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/2025/country-2025.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_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/2025/ecd-2025.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_us-gaap_SubsegmentsDomain_019caf59-2312-79ae-8308-d61b2ce834b4_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/2025/elts/us-gaap-2025.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_us-gaap_DebtInstrumentNameDomain_019caf59-2312-7feb-88b0-30fecd0de250_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/2025/elts/us-gaap-2025.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_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019caf59-229c-7ce4-a48d-5337db8e9ff5_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems_019caf59-221a-7a76-8ac1-e23753469102_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/2025/elts/us-gaap-2025.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_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments_019caf59-2168-76db-896b-f91b1874f0e7_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-20260331.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_019caf59-2312-7d20-9e61-f42e8149608c_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-20260331.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_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_019caf59-229d-7ea5-a0fa-0e41ad5acee8_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_019caf59-229d-7ee8-bd53-b9485a029934_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 Ark&#8217;s contingent consideration</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/2025/elts/us-gaap-2025.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_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal_019cfefb-18e7-770a-93b5-0024ac078042_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-20260331.xsd#wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal"/>
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    <link:label id="lab_wtm_UtilitiesSectorMember_019caf59-2168-7263-bdb9-fc36bc10c7b6_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-20260331.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_RevenuesAbstract_019caf59-221a-7d84-b039-aa8f61a4bb07_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/2025/elts/us-gaap-2025.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_wtm_DavidShieldPassportCardMember_019caf59-229c-74a6-b3b5-4dfbdd37c540_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-20260331.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_wtm_DividendsCommonStockCashNetOfRestrictedStock_019caf59-2168-7596-9ceb-8c10216eebf9_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-20260331.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_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019caf59-2168-731c-9ba8-7d50dcf053e2_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_019caf59-2168-7269-b744-ddaa8e687d7c_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_019caf59-2168-795d-bc08-1b7d2b69acf1_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/2025/elts/us-gaap-2025.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_PerformanceSharesMember_019caf59-229c-7d88-8d89-923ec30a6b73_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/2025/elts/us-gaap-2025.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_country_BM_019caf59-229d-75b8-9597-e9d7e4bc619a_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/2025/country-2025.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_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019caf59-2312-7f25-9f22-c199d41eb2b0_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019caf59-221a-7ba3-9ca6-ede11bcdc074_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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
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    <link:label id="lab_us-gaap_DevelopedTechnologyRightsMember_019caf59-221a-7870-a7e6-251af9b0cd0d_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/2025/elts/us-gaap-2025.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_IncreaseDecreaseInAccruedBonuses_019caf59-229d-7afd-a4dd-71664176947d_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 from 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-20260331.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_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019caf59-229d-75b4-8599-c415dc74ec5e_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">Finite-Lived Intangible Assets by Major 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">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
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    <link:label id="lab_srt_MinimumMember_019caf59-2168-72cf-93db-7e88ec882734_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/2025/elts/srt-2025.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_wtm_DebtCovenantPeriodDomain_019caf59-2168-79b1-a9d2-5e316f101bf2_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-20260331.xsd#wtm_DebtCovenantPeriodDomain"/>
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    <link:label id="lab_us-gaap_GoodwillPurchaseAccountingAdjustments_019caf59-2168-7e48-9714-4add9da2f301_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019caf59-229d-77a0-89f1-e3efd141e5ff_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-20260331.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_019de1cf-ad44-79fa-8305-2cb15774a2a7_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-20260331.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_019caf59-229d-7b12-adec-7706710b77bc_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-20260331.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_us-gaap_GainLossOnSaleOfInvestments_019caf59-221a-7cf8-8684-f9bb0c643822_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/2025/elts/us-gaap-2025.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_us-gaap_DebtDisclosureTextBlock_019caf59-229d-78aa-80dd-f113af7bafd8_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_CitibankLOCFacilityMember_019caf59-229d-77dd-9052-9b3137205b8b_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-20260331.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_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/2025/elts/us-gaap-2025.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_DividendsPayableCurrentAndNoncurrent_019caf59-229d-7664-b78c-08df4a2c3c07_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/2025/elts/us-gaap-2025.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_NetIncomeLossAvailableToCommonStockholdersDiluted_019caf59-2168-75de-a0d3-87f9f4146bfb_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryDistinguishedManagingMember_019caf59-221a-7538-af01-ee5d30a0dd92_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-20260331.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_MeasurementInputLongTermRevenueGrowthRateMember_019caf59-2312-7c3e-8c37-855da00c22a0_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/2025/elts/us-gaap-2025.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_GoodwillRollForward_019caf59-229d-777e-ad6a-cb9b5c0e0972_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/2025/elts/us-gaap-2025.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_CommitmentsAndContingenciesDisclosureTextBlock_019caf59-229d-7076-8073-f634a314e36f_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/2025/elts/us-gaap-2025.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_wtm_BAMSurplusNotesMember_019caf59-221a-7ec4-aebb-49b61cff4672_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-20260331.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_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019caf59-229d-728f-be90-d2c1adf6fa49_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/2025/elts/us-gaap-2025.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_us-gaap_SegmentReportingPolicyPolicyTextBlock_019caf59-2168-7e6d-b2f2-35d40e1bba36_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_DerivativeTable_019caf59-2312-7c9b-8269-971eb433f4c1_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/2025/elts/us-gaap-2025.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_TotalEquityIncludingNoncontrollingInterestMember_019caf59-221a-74fe-a52d-ecfd3eb5a2ae_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-20260331.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_dei_EntitySmallBusiness_019caf59-229d-770a-b744-d6e7ea3ad3c1_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/2025/dei-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage_019ddc32-0125-7c83-9b7c-b92288aef843_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payout range for growth target percentage</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" 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, Average Annual Growth Rate, Percentage</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the percentage growth in intrinsic business value per share to achieve payment.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" xlink:href="wtm-20260331.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardAverageAnnualGrowthRatePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_019caf59-221a-7cb4-a1b8-047e2e670aec_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/2025/elts/us-gaap-2025.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_wtm_AerospaceDefenseGovernmentSectorMember_019caf59-2168-7d84-a448-70893cb3964c_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-20260331.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_dei_DocumentTransitionReport_019caf59-229d-7508-87af-ba0f2b73bab0_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/2025/dei-2025.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_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountOfExpenseRecognized_019caf59-221a-7b19-b187-b389a6b6b564_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-20260331.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_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition_019caf59-221a-7f30-906a-8dc5d4a14259_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/2025/elts/us-gaap-2025.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_wtm_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock_019caf59-2168-7c18-baf3-cb26823eee2b_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-20260331.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_wtm_ProceedsFromReturnOfCapitalOnSubsidiaries_019caf59-229c-7636-8df5-b233262fce49_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-20260331.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_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/2025/ecd-2025.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_EquityComponentDomain_019caf59-229c-7849-bae3-aa617e2875f5_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/2025/elts/us-gaap-2025.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_dei_DocumentPeriodEndDate_019caf59-2312-7bcb-a346-892e97216ce9_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/2025/dei-2025.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_us-gaap_IncomeTaxDisclosureTextBlock_019caf59-229c-7dc5-899d-9d203b459a71_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/2025/elts/us-gaap-2025.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_CededCreditRiskCollateralizationDomain_019caf59-2312-7614-9b34-02897b6d442c_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/2025/elts/us-gaap-2025.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_wtm_StockholdersEquityAdjustmentsToTemporaryEquity_019df177-550a-73a4-b6f3-f3934fb0d68d_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-20260331.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_us-gaap_WeightedAverageNumberOfSharesRestrictedStock_019caf59-229c-7ad9-99e2-ecb54e4ed255_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/2025/elts/us-gaap-2025.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_us-gaap_GeographicDistributionDomain_019caf59-229d-7d89-acbd-0d2b2014bd9c_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/2025/elts/us-gaap-2025.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_country_GB_019caf59-221a-7fc8-8342-1b416feafd02_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/2025/country-2025.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_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_019caf59-2168-7d92-bdd3-d4ba631bc5b3_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-20260331.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_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/2025/ecd-2025.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_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage_019caf59-229c-7efa-a226-bfa9dbcb9abd_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-20260331.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_wtm_IntangibleAssetsGrossIncludingGoodwill_019caf59-221a-7fa6-85ca-3f7aa0b31253_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-20260331.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_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_019caf59-229d-7a21-aee6-817789c846f9_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_019caf59-229d-75d7-8a9e-aba8c87b85b6_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_019caf59-229d-7bff-9732-e93c7a15ebf9_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/2025/elts/us-gaap-2025.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_wtm_PerformancePeriodOneMember_019caf59-221a-788b-a90e-fe688fc8a2ee_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-20260331.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_019caf59-229d-7833-a6d6-6bd85711f974_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-20260331.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_dei_DocumentType_019caf59-229d-760a-a8c7-0b2b1f75aa13_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/2025/dei-2025.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_EquityMethodInvestmentsFairValueDisclosure_019caf59-221a-7d6f-a778-f572f3cad762_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_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueInputsLevel3Member_019caf59-2168-77c5-9f2a-9389036af10d_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/2025/elts/us-gaap-2025.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_us-gaap_EarningsPerShareTextBlock_019caf59-221a-7768-91e6-0490cbd81def_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_AdditionalPaidInCapital_019caf59-221a-7941-b6cf-b41cbb7ffa41_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited_019caf59-2168-735e-8420-6838b805be28_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-20260331.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_us-gaap_CededCreditRiskReinsurerDomain_019caf59-221a-7c9c-a2bd-843b60f744b6_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/2025/elts/us-gaap-2025.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_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10_019caf59-2168-7af6-86f6-55a90f7f4f4f_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-20260331.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_019cff12-e87e-78f0-a9e2-62abcd345cae_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-20260331.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_wtm_DebtInstrumentCovenantDebtToCapitalMaximum_019caf59-229c-71d8-87bd-85279d96e14c_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-20260331.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_us-gaap_AssumedPremiumsEarned_019caf59-221a-73f4-a668-08badaeb9119_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/2025/elts/us-gaap-2025.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_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019caf59-2168-7b09-b3bf-42f6624d20a9_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/2025/elts/us-gaap-2025.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_wtm_DebtInstrumentNumberOfTransactions_019caf59-2168-73fe-901f-f8494b0a27cc_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-20260331.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_RangeAxis_019caf59-221a-71b1-9f25-2571875a7624_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/2025/elts/srt-2025.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_wtm_ShortTermInvestmentsInterestReserve_019caf59-229c-75c5-abee-eb55e35001a2_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-20260331.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_wtm_BambooCRVMember_019caf59-229d-7da2-b84d-b22771690d25_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-20260331.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_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_019caf59-229d-7e52-8eeb-17d4d4057bb7_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_019caf59-229d-7d04-80fa-2b338364961d_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/2025/elts/us-gaap-2025.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_AccruedExpenseRollForward_019caf59-221a-7bd9-bd70-687f3075fcc6_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-20260331.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_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/2025/ecd-2025.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_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_019caf59-221a-74ab-90da-e983d8ae82b4_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10_019caf59-221a-77d6-b681-4445e7acc574_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-20260331.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_NetIncomeLossAvailableToCommonStockholdersBasic_019caf59-229c-7a05-86fa-14c5f85a523c_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_019caf59-229c-7a14-ae0a-2a1517a99abd_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/2025/elts/us-gaap-2025.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_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019caf59-221a-79fb-98f3-1a8b20203f08_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/2025/elts/us-gaap-2025.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_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019caf59-229d-7604-9550-f5ccc6f95485_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-20260331.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_us-gaap_PaymentsToAcquireLimitedPartnershipInterests_019caf59-221a-7d01-8f2a-aa3c14569e4e_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/2025/elts/us-gaap-2025.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_BroadStreetMember_019caf59-221a-77ff-8f95-7b4fccacf973_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-20260331.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_FairValueInputsLevel1Member_019caf59-221a-79e4-b990-1784207265de_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/2025/elts/us-gaap-2025.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_srt_StandardPoorsAAARatingMember_019caf59-2312-755c-b8c2-9794c7fe75d6_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/2025/elts/srt-2025.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_us-gaap_EarningsPerShareDiluted_019caf59-229d-792e-af12-bb8a1a5aee9c_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/2025/elts/us-gaap-2025.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_StandardPoorsOtherMember_019caf59-2168-71ab-b535-4cb0e29fee67_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-20260331.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_wtm_OtherFundsMember_019caf59-229c-7299-a7bf-52a6e9249475_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-20260331.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_019caf59-221a-794a-9690-75436b69caa9_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-20260331.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_wtm_RevenuesAdjusted_019caf59-221a-7238-9e9d-8a89b4a2a438_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-20260331.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_srt_ConsolidationItemsDomain_019caf59-221a-71aa-a6ef-53dca23ed614_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/2025/elts/srt-2025.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_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_019caf59-229d-7807-8533-b3ef19e03e85_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/2025/elts/us-gaap-2025.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_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember_019caf59-221a-741a-8647-3f71cb870d53_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/2025/elts/us-gaap-2025.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_EquityMethodInvestmentsDisclosureTextBlock_019caf59-229d-7821-bbb5-3132aa19db66_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/2025/elts/us-gaap-2025.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_CededCreditRiskAxis_019caf59-221a-7ff5-b02d-d23276fd0853_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives_019caf59-221a-756f-b566-a387bae3471e_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-20260331.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_StockRepurchasedAndRetiredDuringPeriodValue_019caf59-221a-79c9-8d96-b4ccdd2bed5b_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/2025/elts/us-gaap-2025.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_ReinsuranceRecoverables_019caf59-2168-7907-ada3-7a3790dec315_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_019caf59-2168-7294-8edf-c77d76e53f86_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_019caf59-2168-7384-b532-8f37f31516e3_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/2025/elts/us-gaap-2025.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_country_LU_019d041e-754f-7c18-8874-32d8d164bcb4_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/2025/country-2025.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_NoncontrollingInterestAbstract_019caf59-229d-716d-a473-fd7c71f1b1c9_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/2025/elts/us-gaap-2025.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_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems_019caf59-221a-7693-af47-46ff2f99936a_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/2025/elts/us-gaap-2025.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_ProceedsFromSaleOfEquitySecuritiesFvNi_019caf59-229d-73da-b7f6-f22a358b70cb_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
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    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsDistributionReceived_019caf59-221a-73f6-aa69-71a11c726670_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-20260331.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_us-gaap_IncomeTaxesPaidNet_019caf59-221a-745a-a201-572dcfe441c9_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 Taxes Paid, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_FinancialServicesSectorMember_019caf59-221a-798d-9294-9563211a2eb7_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_019caf59-221a-7f1b-86b7-77b346270de3_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/2025/elts/us-gaap-2025.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_us-gaap_DebtInstrumentCarryingAmount_019caf59-229d-7d00-99ed-ff2c0725fb72_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_019caf59-229d-7be5-b723-73053fce1af8_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_019caf59-229d-79df-a86b-f3c2d1d08563_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/2025/elts/us-gaap-2025.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_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders_019caf59-2168-7124-844f-459d9ebb7d26_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/2025/elts/us-gaap-2025.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_TradeNamesMember_019caf59-221a-7f6b-8eab-5d23fd39b22a_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/2025/elts/us-gaap-2025.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_InvestmentOwnedBalanceShares_019caf59-221a-712e-a1e0-d01dec92cd45_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_VariableInterestEntityOwnershipPercentage_019caf59-229d-79eb-93c4-639c74b4cde2_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/2025/elts/us-gaap-2025.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_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract_019caf59-229d-76ab-a621-0c74d4f58bbd_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/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract"/>
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    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_019caf59-221a-7abd-8426-ce9be14f0f7a_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/2025/elts/us-gaap-2025.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_us-gaap_EquityMethodInvestmentsTextBlock_019caf59-229d-75c9-9bb6-953d354788ed_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>
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    <link:label id="lab_us-gaap_InvestmentsMember_019caf59-229d-7102-bd63-6cf8eb256dfd_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/2025/elts/us-gaap-2025.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_us-gaap_CededPremiumsWritten_019caf59-221a-7976-a600-70287c78b5fb_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_019caf59-221a-79b6-ac76-bd25628ecb66_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/2025/elts/us-gaap-2025.xsd#us-gaap_CededPremiumsWritten"/>
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    <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/2025/ecd-2025.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
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    <link:label id="lab_wtm_TotalUnconsolidatedEntitiesMember_019caf59-2168-751a-8299-b19d9468d01d_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-20260331.xsd#wtm_TotalUnconsolidatedEntitiesMember"/>
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    <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/2025/dei-2025.xsd#dei_EntityCurrentReportingStatus"/>
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    <link:label id="lab_us-gaap_DerivativeLineItems_019caf59-229c-7beb-80a9-f795f3eae52d_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired_019caf59-221a-7e1d-bf26-3e5d16c12404_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-20260331.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_srt_ConsolidatedEntitiesDomain_019caf59-221a-7b58-a22a-9b8b84a13c1b_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/2025/elts/srt-2025.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_wtm_InvestmentOwnedChangeInValuePerShare_019caf59-229d-7da7-b231-03db49966bb4_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-20260331.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_EarningsPerShareDilutedDistributed_019caf59-221a-7ad4-8782-b935a675082f_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/2025/elts/us-gaap-2025.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_us-gaap_FinancialInstrumentAxis_019caf59-229d-74d6-a405-8135a31412ac_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/2025/elts/us-gaap-2025.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_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_019caf59-2168-7019-abd3-99244ee2f607_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/2025/elts/us-gaap-2025.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_us-gaap_BenefitsLossesAndExpensesAbstract_019caf59-2168-78a6-a1b7-7a1346991b08_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/2025/elts/us-gaap-2025.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_us-gaap_StatementOfFinancialPositionAbstract_019caf59-221a-7091-a16e-186c21e4e3a6_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_HedgeFundsMember_019caf59-229d-7341-89a5-7ca314b5d15e_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/2025/elts/us-gaap-2025.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_wtm_ValuationTechniqueRecentOrExpectedTransactionPricesMember_019caf59-221a-76b9-a0f6-a51239dd3c32_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-20260331.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_019caf59-229c-7230-9b62-6e21f419cd20_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-20260331.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_DebtInstrumentFloatingInterestRatePercentage_019caf59-2312-705d-97c8-e859d62bf408_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-20260331.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_HGGlobalSeniorNotesMember_019caf59-229c-7c8f-b97a-c3917e8f0f56_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 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-20260331.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_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock_019caf59-2168-7652-bed7-078948e53543_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-20260331.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_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember_019caf59-229d-77d3-a032-da8dce5a7c9e_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-20260331.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_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_019caf59-229c-7532-ab59-c1ec8dcd7756_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/2025/elts/us-gaap-2025.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_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019caf59-229d-7664-bf3b-e844bb7982bd_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_019caf59-229d-7b24-a88c-bb28c4b88c84_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/2025/elts/us-gaap-2025.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_us-gaap_InterestExpense_019caf59-221a-7dd2-9bc0-1daae7cb33ac_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_019caf59-221a-7e09-938e-b43e937675c4_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/2025/elts/us-gaap-2025.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_dei_CurrentFiscalYearEndDate_019caf59-229c-751a-86a1-2b4018dd80fb_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/2025/dei-2025.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_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019caf59-221a-770c-8a03-39eb9494e632_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">Finite-Lived Intangible Assets, Major Class Name [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">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_KuduParticipationContractsMember_019caf59-229d-7670-9413-0e873e2f0844_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_019caf59-229d-7c39-b7fc-1c181f013ddc_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-20260331.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_IncreaseDecreaseInReinsurancePayables_019caf59-229d-7e3e-9cc6-5c52c8661757_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/2025/elts/us-gaap-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate_019caf59-229d-77d9-a990-4fa3078d45b0_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/2025/elts/us-gaap-2025.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019caf59-221a-7a25-988e-b2ac1611c1db_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures_019caf59-221a-7ae5-b2c1-aefeb053f41d_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-20260331.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_wtm_EnterpriseSolutionMember_019caf59-229d-725e-8591-21005e7e8e8b_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-20260331.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_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/2025/ecd-2025.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_us-gaap_MinorityInterestDisclosureTextBlock_019caf59-229d-7c4d-b523-37072a8106d0_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/2025/elts/us-gaap-2025.xsd#us-gaap_MinorityInterestDisclosureTextBlock"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentDividendsOrDistributions_019caf59-221a-7eaa-a673-ffe6a2fedd58_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/2025/elts/us-gaap-2025.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_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_019caf59-2168-75ae-aa14-875fdb73f273_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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
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    <link:label id="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral_019caf59-221a-72f2-b650-6d53765dacc6_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-20260331.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_ProceedsFromDebtNetOfIssuanceCosts_019caf59-221a-7f06-82f8-bb4a4f633536_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember_019caf59-221a-79bd-8918-157b9da24073_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-20260331.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_WeightedAverageNumberOfSharesOutstandingAbstract_019caf59-221a-7de8-a997-1d362dd03ae0_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/2025/elts/us-gaap-2025.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_FairValueByBalanceSheetGroupingTable_019caf59-229d-74e6-b342-8cc9d9108e09_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/2025/elts/us-gaap-2025.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_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue_019caf59-229c-7f2b-9b1e-3eed39f5dc70_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/2025/elts/us-gaap-2025.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_us-gaap_EnergySectorMember_019caf59-221a-7c6c-a16c-ac7ba645b924_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/2025/elts/us-gaap-2025.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_DebtSecuritiesWeightedAveragePortfolioPeriod_019ddc36-5137-746c-b3cd-f3bec6696ae1_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-20260331.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_NetCashProvidedByUsedInFinancingActivities_019caf59-221a-74e7-84f9-6d800f2dc509_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_MaterialsSectorMember_019caf59-2168-7e96-b1cc-6e61a4497639_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-20260331.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_us-gaap_UndistributedContinuingOperationEarningsLossBasic_019caf59-229c-7c78-a29e-628b9f0181ce_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/2025/elts/us-gaap-2025.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_wtm_PrivateEquitySecuritiesMember_019caf59-2168-728e-acce-2fab087c33f0_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-20260331.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_us-gaap_ValuationTechniqueAxis_019caf59-221a-7178-a98a-8f817366ecc0_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/2025/elts/us-gaap-2025.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_us-gaap_CostOfGoodsAndServicesSold_019caf59-2168-75db-b489-745e571ce95c_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/2025/elts/us-gaap-2025.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_us-gaap_DisposalGroupClassificationDomain_019caf59-229d-77f1-ba28-0cf7c75c02eb_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/2025/elts/us-gaap-2025.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_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier_019caf59-229c-72fe-9efb-c901fa7d4cf3_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest accrued multiplier</link:label>
    <link:label id="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier_label_en-US" xlink:label="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Reserve, Interest Accrued Multiplier</link:label>
    <link:label id="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Reserve, Interest Accrued Multiplier</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" xlink:href="wtm-20260331.xsd#wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" xlink:to="lab_wtm_DebtInstrumentInterestReserveInterestAccruedMultiplier" 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/2025/ecd-2025.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_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/2025/ecd-2025.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
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    <link:label id="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember_019caf59-221a-7450-83b7-9cc0ce50b8af_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/2025/elts/us-gaap-2025.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_us-gaap_InvestmentIncomeInvestmentExpense_019caf59-2168-7577-a34a-dd4ae107b1bc_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/2025/elts/us-gaap-2025.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_dei_EntityTaxIdentificationNumber_019caf59-221a-7ce9-bf3d-26ea9209fb86_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/2025/dei-2025.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_us-gaap_ValuationTechniqueDiscountedCashFlowMember_019caf59-229d-7521-8775-663de8005a27_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/2025/elts/us-gaap-2025.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_EquitySecuritiesFvNiUnrealizedGain_019caf59-229c-797d-aa6c-06f6fb102a3b_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/2025/elts/us-gaap-2025.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_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019caf59-229d-7d94-ab77-f3ff9228f1c3_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-20260331.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_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets_019caf59-221a-7808-aa0e-9ffa8ffc0df2_terseLabel_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" 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_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Amortization of Intangible Assets</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets_documentation_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Amortization of Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" xlink:href="wtm-20260331.xsd#wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" xlink:to="lab_wtm_GeneralAndAdministrativeExpenseAmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019caf59-221a-7c0b-86ad-eb68adaafbc3_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/2025/elts/us-gaap-2025.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_LossesAndLossAdjustmentExpenseAbstract_019caf59-229d-7467-ba44-082db4196a0c_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-20260331.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_RedeemableNoncontrollingInterestTableTextBlock_019caf59-221a-758a-b67a-e15dcb8be967_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/2025/elts/us-gaap-2025.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_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock_019caf59-229d-7372-93ea-43aa63f7357e_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/2025/elts/us-gaap-2025.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_GoodwillAndIntangibleAssetsDisclosureTextBlock_019caf59-2312-776e-a284-ea4c5e204c30_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">Goodwill and Intangible Assets Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember_019caf59-221a-7783-9a80-ace80c6d6a4c_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/2025/elts/us-gaap-2025.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_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate_019caf59-229d-7faf-a7fd-faba04d1e2cc_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-20260331.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_us-gaap_DebtInstrumentMeasurementInput_019caf59-2168-73ca-91fd-d6fc626eb4ed_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/2025/elts/us-gaap-2025.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_wtm_HedgeFundLongShortAllCapGlobalMember_019caf59-2168-7916-9116-efc590eb74d3_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-20260331.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_019caf59-229d-7186-9ffc-5c8ed85bd695_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-20260331.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_us-gaap_CorporateNonSegmentMember_019caf59-229c-733b-b44c-f0007e6b45a2_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/2025/elts/us-gaap-2025.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_dei_SecurityExchangeName_019caf59-221a-704b-8d9e-116f653f12d3_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/2025/dei-2025.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_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent_019caf59-229d-76dd-8f08-169db78a6bcc_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-20260331.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_GoodwillAndIntangibleAssetImpairment_019cff4a-35af-7b6d-b8b4-3e2f5552868e_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">Goodwill and Intangible Asset Impairment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_EquitySecuritiesFVNIAbstract_019caf59-229c-72f6-8105-a0ae08a2d914_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/2025/elts/us-gaap-2025.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_us-gaap_MortgageBackedSecuritiesMember_019caf59-221a-7715-ab72-aec528074536_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/2025/elts/us-gaap-2025.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_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_019caf59-221a-7e8d-ad7d-f372e3d0103f_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod_019caf59-2168-790e-a1f4-5996a93df93c_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-20260331.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_019caf59-221a-77ad-951a-10048957b51e_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_019caf59-221a-7035-9153-3832ccdb7aba_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_019caf59-221a-7de4-bbb8-29f5440f06f7_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-20260331.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_CededPremiumsEarned_019caf59-229d-7c02-8d61-1b7448cd2f19_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_019caf59-229d-7f65-a1a0-9169689e83ad_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/2025/elts/us-gaap-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityAbstract_019cffb9-205a-7129-a830-bfe8c31e2353_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/2025/elts/us-gaap-2025.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_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019caf59-2312-7713-8135-55619528afb6_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">Indefinite-Lived Intangible Assets, Major Class Name [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">Indefinite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_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/2025/elts/us-gaap-2025.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_us-gaap_ProceedsFromMaturitiesRepaymentsAndCallsOfTradingSecuritiesHeldforinvestment_019caf59-2168-7591-9db3-33c555464823_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/2025/elts/us-gaap-2025.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019caf59-221a-716b-8877-72a9ffe6758f_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/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_019caf59-221a-7557-b51c-a36bf9b2265f_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/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInTemporaryEquityRollForward"/>
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    <link:label id="lab_wtm_PremiumsAndCommissionsReceivable_019caf59-2312-73d5-8f25-a8d8688dec52_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-20260331.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_wtm_DerivativeMaximumInterestRate_019caf59-229c-7c96-9dbf-c71c583f32fa_terseLabel_en-US" xlink:label="lab_wtm_DerivativeMaximumInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maximum interest rate</link:label>
    <link:label id="lab_wtm_DerivativeMaximumInterestRate_label_en-US" xlink:label="lab_wtm_DerivativeMaximumInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Maximum Interest Rate</link:label>
    <link:label id="lab_wtm_DerivativeMaximumInterestRate_documentation_en-US" xlink:label="lab_wtm_DerivativeMaximumInterestRate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Derivative, Maximum Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DerivativeMaximumInterestRate" xlink:href="wtm-20260331.xsd#wtm_DerivativeMaximumInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DerivativeMaximumInterestRate" xlink:to="lab_wtm_DerivativeMaximumInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_019caf59-221a-7acd-ac61-e04ef82566f3_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_019caf59-221a-7c25-84b2-50e559621d3c_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/2025/elts/us-gaap-2025.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_wtm_LondonInterbankOfferedRateLIBOR1Member_019caf59-229c-7e7e-96bd-11df0cf8bfe6_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-20260331.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_CommonStockMember_019caf59-221a-7f98-ab3d-a019e53c8d36_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_019caf59-221a-7009-bc7f-4cfd147dfa94_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_019caf59-229d-77de-99f2-7d5b962575df_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout_019caf59-221a-7a35-90a1-1fe1920d0e3d_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-20260331.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_UnrealizedGainLossOnInvestments_019caf59-2168-7ef0-a57d-ab6c2daa4f18_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_019caf59-2168-7d44-b24c-3b30f0042467_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/2025/elts/us-gaap-2025.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_us-gaap_CommonStockDividendsPerShareCashPaid_019caf59-229d-7f07-99ad-343f9c5cee67_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 usd 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/2025/elts/us-gaap-2025.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_us-gaap_GuaranteeObligationsLineItems_019caf59-2312-73fa-a26c-21d29df555a5_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/2025/elts/us-gaap-2025.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_wtm_ReleaseOfCashPreFundingsForManagedFunds_019ddaf4-d3ba-79c6-b098-bd9d4be1da21_negatedTerseLabel_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">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-20260331.xsd#wtm_ReleaseOfCashPreFundingsForManagedFunds"/>
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    <link:label id="lab_srt_RangeMember_019caf59-221a-7b53-b3c3-b394e641e30e_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/2025/elts/srt-2025.xsd#srt_RangeMember"/>
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    <link:label id="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember_019caf59-2168-7801-a1a7-be900185a8df_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-20260331.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_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019caf59-221a-7122-a9c2-a85bfd44bfcb_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_019cff66-6e49-77a5-b603-cddfb8d5692b_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/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019caf59-221a-7750-8f91-0a52f00613fc_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 Assets, Gross (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_ValuationTechniqueDomain_019caf59-2168-7a07-ad89-85e9180ee29e_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/2025/elts/us-gaap-2025.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_wtm_PerformancePeriodThreeMember_019caf59-221a-7991-a06b-e376d27d0f45_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-20260331.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_wtm_OtherLongTermInvestmentsMeasurementInput_019caf59-221a-7d6e-9630-c70c6925c0d6_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-20260331.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_019caf59-2168-76b5-8032-d2728169ba61_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-20260331.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_UnearnedPremiums_019caf59-221a-7e6a-891b-7ea816c18196_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/2025/elts/us-gaap-2025.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_us-gaap_EarningsPerShareBasicAbstract_019caf59-221a-7340-8310-2c293ae2c604_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/2025/elts/us-gaap-2025.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_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember_019caf59-2168-7ae0-ba24-6a0343f76142_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-20260331.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_srt_StandardPoorsBBRatingMember_019caf59-2312-7257-b389-03cf32bc3ba4_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/2025/elts/srt-2025.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_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems_019caf59-229d-7db6-8eb1-12d2d89e3d58_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, Acquired, Finite-Lived [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, Acquired, Finite-Lived [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsTextBlock_019caf59-221a-77b6-858a-0800be4b5eae_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 Insurance</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/2025/elts/us-gaap-2025.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_wtm_DebtCovenantPeriod4Member_019caf59-221a-7a68-bae1-eb5cd4475124_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-20260331.xsd#wtm_DebtCovenantPeriod4Member"/>
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    <link:label id="lab_us-gaap_PledgedStatusAxis_019caf59-229c-7e14-b0d0-85dc4031cb17_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_EarningsPerShareBasic_019caf59-2168-7490-8b53-73c7f9ff579d_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/2025/elts/us-gaap-2025.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_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_019caf59-221a-7f03-a64f-6275eb26c7df_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/2025/elts/us-gaap-2025.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_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember_019caf59-229d-727e-91d1-d3bdbc5dc914_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-20260331.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_MeasurementInputDiscountRateMember_019caf59-229c-7bde-a658-6dbb78174701_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/2025/elts/us-gaap-2025.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_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019caf59-229d-774b-b408-9e57dbc577c2_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/2025/elts/us-gaap-2025.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_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_019caf59-229d-7d08-80f3-b0d52dd276c5_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">Schedule of Segment Reporting Information, by Segment [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_MeasurementInputTypeDomain_019caf59-221a-7414-8707-893fca7ec802_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/2025/elts/us-gaap-2025.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_wtm_PerformancePeriodAxis_019caf59-221a-71bb-a4f0-0c3eaab8151c_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-20260331.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_019caf59-229d-7c16-827f-bd4ebf5ef804_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-20260331.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_019caf59-229d-7289-849d-79e15903857b_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-20260331.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_wtm_SupplementalTrustMember_019caf59-221a-7289-9551-0a8dc9c4a211_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-20260331.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_us-gaap_InsuranceCommissionsAndFees_019caf59-229c-75b7-94be-2af00cd283bd_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_019caf59-229c-7d4c-a6b1-698ef0ecb385_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/2025/elts/us-gaap-2025.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_ScheduleOfCededCreditRiskByReinsurerTextBlock_019caf59-229c-79d5-a47c-8d8c3579c784_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/2025/elts/us-gaap-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_019caf59-229d-7e03-94fd-c13ad0798162_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_019caf59-229d-7a7e-80e3-d46e4f293895_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_GainOnSaleOfInvestments_019ddc29-c5f7-7ea3-8485-ba0021dc9234_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/2025/elts/us-gaap-2025.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_wtm_DistinguishedTransactionMember_019caf59-229d-7a89-bedc-823a5c29083d_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-20260331.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_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable_019cff12-e87e-71c5-92d3-ea62a8afb344_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-20260331.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_GoodwillAndIntangibleAssetsDisclosureAbstract_019caf59-2312-7588-82d0-f3322962cb34_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">Goodwill and Intangible Assets Disclosure [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">Goodwill and Intangible Assets Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_LiabilitiesAndStockholdersEquity_019caf59-221a-796f-9659-2a030160e49e_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/2025/elts/us-gaap-2025.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_srt_StandardPoorsAARatingMember_019caf59-229d-74d0-846b-2eecffe4d696_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/2025/elts/srt-2025.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_DeferredPolicyAcquisitionCosts_019caf59-229d-7921-923d-0bcea32ba5c4_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/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
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    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_019caf59-221a-7165-9b77-eb12be12f88e_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/2025/elts/us-gaap-2025.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_us-gaap_TemporaryEquityNetIncome_019caf59-229d-76f4-863e-18dab0195852_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/2025/elts/us-gaap-2025.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_us-gaap_GuaranteesAbstract_019caf59-2168-7246-82e4-5985b8ab96a9_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/2025/elts/us-gaap-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate_019caf59-2168-765d-995e-eefc6f177aaf_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/2025/elts/us-gaap-2025.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_ConcentrationRiskTypeDomain_019caf59-221a-7868-970a-8efd34363ac7_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/2025/elts/us-gaap-2025.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_PaymentsToAcquireOtherInvestments_019caf59-221a-7840-9bdf-b94802e21327_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/2025/elts/us-gaap-2025.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_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment_019caf59-229c-73be-b25f-bdc8ffaaa642_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment_019ddc3b-49e2-7715-9534-2bc2cbc9c4de_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-20260331.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_us-gaap_IncreaseDecreaseInUnearnedPremiums_019caf59-2168-7146-a6ef-c56906682bd7_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/2025/elts/us-gaap-2025.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_us-gaap_EffectsOfReinsuranceTable_019caf59-221a-7b0e-bf2b-38f9f55965ed_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/2025/elts/us-gaap-2025.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_LiabilitiesAbstract_019caf59-229c-743c-8589-f3b5ef29a734_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/2025/elts/us-gaap-2025.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_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination_019caf59-229d-7319-8fd6-3f595da9377e_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/2025/elts/us-gaap-2025.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_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage_019caf59-221a-7b8d-ba8e-f9af45b02caa_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-20260331.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_wtm_OtherLongTermInvestmentsUnrealizedGain_019caf59-229c-79d6-8761-7e6134e8ce35_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-20260331.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_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_019caf59-229d-7298-8ab8-b59aa656390a_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/2025/elts/us-gaap-2025.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_wtm_OtherLongTermInvestmentsCost_019caf59-2168-7fe5-80b1-6028f3c99c24_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-20260331.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_GoodwillImpairmentLoss_019cff40-b779-7a5f-9f47-e97e381f9cfc_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/2025/elts/us-gaap-2025.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_ScheduleOfVariableInterestEntitiesTable_019caf59-229c-79d4-9f2e-01a68c9834f9_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/2025/elts/us-gaap-2025.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_StatementOfCashFlowsAbstract_019caf59-221a-7d21-b3ef-da907932ae7a_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/2025/elts/us-gaap-2025.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_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>
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    <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_Cash_019caf59-221a-743c-8000-22e06a423682_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/2025/elts/us-gaap-2025.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_ComprehensiveIncomeNetOfTax_019caf59-221a-7193-aa90-1785e7221609_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/2025/elts/us-gaap-2025.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_MeasurementInputTypeAxis_019caf59-221a-7751-92ab-a9ba81bbe773_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/2025/elts/us-gaap-2025.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_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain_019caf59-229d-7038-b236-d9875408c476_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_SecuredDebtMember_019caf59-229d-786c-9306-e21dfa199a22_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/2025/elts/us-gaap-2025.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_us-gaap_EquitySecuritiesIndustryMember_019caf59-229c-7d8b-abf8-89eeb2b0958f_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/2025/elts/us-gaap-2025.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_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable_019caf59-221a-7133-959a-007a6ced895d_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/2025/elts/us-gaap-2025.xsd#us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable"/>
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    <link:label id="lab_us-gaap_AssumedPremiumsWritten_019caf59-2312-7431-bda6-359f44704aa8_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/2025/elts/us-gaap-2025.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_ArkInsuranceHoldingsLimitedMember_019caf59-229d-790e-a8bb-74e6af49be9d_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>
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    <link:label id="lab_us-gaap_IncomeTaxContingencyTable_019cff90-d42c-776d-a0a3-dbe6e0cdc00b_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/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxContingencyTable"/>
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    <link:label id="lab_us-gaap_LongTermDebt_019caf59-229c-7423-a822-fde7c8bf0c60_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_019caf59-229c-7756-b4a5-725924e39f06_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_019caf59-229c-7703-94fd-5a1ebea029f9_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>
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    <link:label id="lab_dei_LegalEntityAxis_019caf59-229c-7426-9e11-1bbba507c92a_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>
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    <link:label id="lab_us-gaap_Assets_019caf59-229d-70fd-ab26-82d21c9bc518_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_019caf59-229d-7ad7-af36-980058b2a920_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>
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    <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>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019cfee5-546a-7e35-a029-c33a5d2133e2_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>
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    <link:label id="lab_us-gaap_ConsumerSectorMember_019caf59-221a-77b3-af7b-3fa36f7dfd2c_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/2025/elts/us-gaap-2025.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_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019caf59-229d-769e-86f5-4fd0c76f90ef_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">Acquired Finite-Lived Intangible Assets, Weighted Average Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_PrivateEquityFundsAndHedgeFundsMember_019caf59-229d-7166-ad69-8b748ff5da10_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_019caf59-229d-75fb-99c0-9b2a9ba4f058_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-20260331.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_ConcentrationRiskByTypeAxis_019caf59-221a-703e-afd4-d0d0d85d58bf_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/2025/elts/us-gaap-2025.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_PrivateEquityFundsMember_019caf59-2168-7540-a08b-2faa4160e1bc_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/2025/elts/us-gaap-2025.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_us-gaap_ReinsuranceRecoverableMember_019caf59-229d-7be5-bfbd-5c2076c7382b_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/2025/elts/us-gaap-2025.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_VariableInterestEntityLineItems_019caf59-221a-7da4-9280-c8c788271d28_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/2025/elts/us-gaap-2025.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_wtm_DistinguishedOtherDebtMember_019caf59-229d-78ff-bba1-c5dfb9ef72ef_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_019caf59-229d-7fff-a081-498a6e94fe1b_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-20260331.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_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable_019caf59-2312-7a7f-9454-2f5aa456df3f_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-20260331.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_us-gaap_CommonStockDividendsPerShareDeclared_019caf59-229d-7b1e-a779-37391dae0539_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 usd 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/2025/elts/us-gaap-2025.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_EntityCommonStockSharesOutstanding_019caf59-221a-7e48-8a4b-d5b1ab228e74_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/2025/dei-2025.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_wtm_KuduCreditFacilityMember_019caf59-221a-74d3-b1b8-8af2942c6408_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-20260331.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_019caf59-221a-7408-b3b8-c72fdf3325ff_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-20260331.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_019caf59-221a-70bc-9707-038f08db083e_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_019caf59-221a-74a8-9769-0d1304e8c2e4_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-20260331.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_us-gaap_PrepaidReinsurancePremiums_019caf59-2168-7dd8-8a12-8243d76740ec_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueInputsLevel2Member_019caf59-221a-7c19-8124-824927a96195_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/2025/elts/us-gaap-2025.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_us-gaap_EquityMethodInvestments_019caf59-229d-7007-84a7-2fb78a2b283a_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_019caf59-229d-781a-bf75-e99b688acbd8_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_BusinessAcquisitionAcquireeDomain_019caf59-221a-72c4-bbbf-7a896495f8e5_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/2025/elts/us-gaap-2025.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_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_019dc304-ca46-73f5-a547-8d560e959e3e_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_019ddaef-fc99-79ce-9e35-a3bd73bd4506_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/2025/elts/us-gaap-2025.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_EquityMethodInvestmentsMember_019caf59-221a-7e44-afed-a9137588bd47_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/2025/elts/us-gaap-2025.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_AssetPledgedAsCollateralMember_019caf59-229d-7de5-8234-ec8e5895c729_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/2025/elts/us-gaap-2025.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_wtm_ForeignRegulatoryDepositsMember_019caf59-2168-7614-b529-83c2e7590bfb_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-20260331.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_dei_DocumentInformationTable_019caf59-2168-7632-8315-e39af28d26f0_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/2025/dei-2025.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_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/2025/ecd-2025.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_UnrestrictedCashHeldForSale_019caf59-221a-7cc0-8d53-7295c5596d2b_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-20260331.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_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_019caf59-221a-7b79-80ba-157e8e1d1098_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/2025/elts/us-gaap-2025.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_wtm_OtherLongTermInvestmentsAbstract_019caf59-2168-715f-905d-2d3fcbe7b017_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-20260331.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_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_019caf59-2168-7176-9a26-1c5fe86c541b_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/2025/elts/us-gaap-2025.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_TradingSecuritiesDebt_019caf59-2168-7f87-9ef6-c15fa797b83c_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_019caf59-2168-7b11-a92a-10d30ca23d83_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_019cff24-d211-7bb5-9263-073ec239eff4_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryWMOutriggerReMember_019caf59-221a-7e87-96ab-35d21066c51d_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-20260331.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_ReinsuranceRecoverablesGross_019caf59-2312-7e2d-921f-7d3bd1498b56_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/2025/elts/us-gaap-2025.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_country_US_019caf59-229d-712b-b63f-2dda8c711cb9_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/2025/country-2025.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_IncreaseDecreaseInOperatingCapitalAbstract_019caf59-2168-76e2-bde0-5a5ed34b2516_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/2025/elts/us-gaap-2025.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_LossOnSaleOfInvestments_019ddc2a-bac2-777c-a5c6-a68ae1e5dd4a_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/2025/elts/us-gaap-2025.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_us-gaap_RetainedEarningsMember_019caf59-221a-776f-beef-a1087afbbfab_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod_019caf59-221a-7c36-ba2e-c8722ea97375_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-20260331.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_PaymentsForLossesAndLossAdjustmentExpense_019caf59-221a-7414-9609-507acfc98cdf_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/2025/elts/us-gaap-2025.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_IncomeTaxAuthorityAxis_019cff90-2f4d-7fc7-a878-11fa6ce6dbec_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/2025/elts/us-gaap-2025.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_IntangibleAssetsGrossExcludingGoodwillAbstract_019caf59-229c-7cfd-9003-8d73bcd59cae_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 Assets, Gross (Excluding Goodwill) [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_019caf59-229d-7fbe-aecc-4617306e94e6_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/2025/elts/us-gaap-2025.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_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019caf59-229d-79e9-862f-d2bc2aee7af8_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_019caf59-229d-7038-bdc1-de37781c1468_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 $3.1 and $0.0, unrestricted cash held for sale of $1.1 and $23.0 and restricted cash held for sale of $&#8212; and $77.0)</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/2025/elts/us-gaap-2025.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_us-gaap_IncomeStatementAbstract_019caf59-221a-7989-beea-037e3fa2257d_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/2025/elts/us-gaap-2025.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_DerivativeAssets_019caf59-221a-760e-889b-a4c70c48be3c_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/2025/elts/us-gaap-2025.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_wtm_PercentageofRiskPremiumCeded_019caf59-229d-7ee6-88e8-e20de80411b1_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-20260331.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_us-gaap_PremiumsWrittenNetConsolidatedAbstract_019caf59-221a-7bbf-9620-96c52b9538e9_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/2025/elts/us-gaap-2025.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_us-gaap_InterestExpenseMember_019caf59-229d-7e2b-ad3e-af94ac01ab6f_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpenseMember" 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_InterestExpenseMember_label_en-US" xlink:label="lab_us-gaap_InterestExpenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Expense [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestExpenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpenseMember" xlink:to="lab_us-gaap_InterestExpenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_019caf59-229d-734b-8b6b-1f6e4c8f2d45_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/2025/elts/us-gaap-2025.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_IntangibleAssetsNetExcludingGoodwill_019caf59-229c-701f-bdfb-80c564aac918_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_019caf59-229c-708b-8756-3285fe3e96df_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_019caf59-229c-71c3-a369-24414444bde9_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 Assets, Net (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember_019cff1d-ec85-7d16-aa4b-f0a5730aef0e_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-20260331.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_019caf59-229d-7d42-887a-a42ec51e00cf_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-20260331.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_ReinsurerConcentrationRiskMember_019caf59-229d-7fda-9bc5-a3cccae1979f_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/2025/elts/us-gaap-2025.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_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts_019caf59-2312-7f52-abb8-feda1a04408a_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/2025/elts/us-gaap-2025.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_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare_019caf59-221a-70a3-9b57-ca588604eeb5_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_NetInvestmentIncome_019caf59-229d-70e2-ad7a-e041e7a73de3_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_019caf59-229d-7f93-aaf4-34b376fcdd3c_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/2025/elts/us-gaap-2025.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_us-gaap_ParentMember_019caf59-229d-7430-ab76-6dfb487525f4_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/2025/elts/us-gaap-2025.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_ProfitLoss_019caf59-221a-77ed-9143-7d2dc2824723_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_019caf59-221a-7092-bc7a-fecf6b8aee89_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/2025/elts/us-gaap-2025.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_wtm_DistinguishedPartnersSegmentMember_019caf59-221a-7909-b866-8ad19748c4e3_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_019caf59-221a-7f03-82e4-d7d6d27d6a41_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-20260331.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_019caf59-221a-71cd-81f9-a3c979a2b56d_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-20260331.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_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/2025/ecd-2025.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_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_019caf59-221a-7252-9315-e2729e344e76_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/2025/elts/us-gaap-2025.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_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019cff09-d7b5-7831-a3e2-9fb0c3e82672_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/2025/elts/us-gaap-2025.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_dei_CityAreaCode_019caf59-229c-7fbd-9a73-36e3a2d1f7d1_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/2025/dei-2025.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_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/2025/ecd-2025.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_us-gaap_ReinsuranceRecoverablesOnPaidLosses_019caf59-2312-7eb3-b871-c2de884cc506_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/2025/elts/us-gaap-2025.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_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears_019caf59-229c-7bcf-825b-cb7b37534d10_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-20260331.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_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments_019dc3c2-01ef-7332-90bf-d10a81f9ed3b_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-20260331.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments"/>
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    <link:label id="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax_019caf59-221a-796e-9c2a-2587d2871ca4_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-20260331.xsd#wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax"/>
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    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable_019caf59-229d-7a0f-8de1-f727c955232b_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/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable"/>
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    <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-20260331.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_019cfefb-18e7-7e81-a553-41cf8e8eea51_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-20260331.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_019caf59-2168-717c-8767-961f0053bcd6_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-20260331.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_019caf59-221a-7728-82e0-30118293ff13_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-20260331.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_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_019caf59-221a-7e4c-901c-ca5e5f0d8570_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/2025/elts/us-gaap-2025.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_us-gaap_GeneralAndAdministrativeExpense_019caf59-221a-7a36-b58c-b6d27a292778_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" 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_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_srt_StandardPoorsARatingMember_019caf59-221a-783a-b8fa-2d6f04611897_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/2025/elts/srt-2025.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_InterestReceivable_019caf59-2312-71d4-a4ce-3deecdb48f4a_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/2025/elts/us-gaap-2025.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_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember_019cfefb-18e7-7597-a20b-31dccf75d108_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/2025/elts/us-gaap-2025.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_EquityMethodInvestmentSharePrice_019caf59-221a-7050-9299-de6419e2e711_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-20260331.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_wtm_OtherNoncontrollingInterestMember_019caf59-221a-736d-9107-6e148fbd48e4_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</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-20260331.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_Goodwill_019caf59-229c-7bbd-b06d-7faba0fdb864_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_019caf59-229c-7ac9-af40-fa4bb94a8b9d_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_019caf59-229c-73e8-b933-a8de0cb9e73d_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_019caf59-229c-7285-a88c-8bac117a29dc_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/2025/elts/us-gaap-2025.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_us-gaap_OtherLiabilities_019caf59-221a-7948-8fa8-04f7569f880d_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/2025/elts/us-gaap-2025.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_EquitySecuritiesFvNiCurrentAndNoncurrent_019caf59-229c-790e-a966-8a208e006006_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_019caf59-229c-73d1-8f62-639e028ac74f_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/2025/elts/us-gaap-2025.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019caf59-229c-70ae-95dc-d01609b3fa86_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/2025/elts/us-gaap-2025.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_us-gaap_GainLossOnInvestments_019caf59-2168-76a7-85bd-8152f4d595e8_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_019caf59-2168-7dc5-9c63-b5fa9daa828b_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_019caf59-2168-7b40-87e5-4f32248a5929_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/2025/elts/us-gaap-2025.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_NotesReceivableFairValueDisclosure_019caf59-221a-7c56-99bd-3b37cfbd71bc_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_019caf59-221a-7273-91ff-87a8deaa0d21_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/2025/elts/us-gaap-2025.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersOutOfLevel3_019caf59-221a-7af6-aa4f-e37f416fdfce_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/2025/elts/us-gaap-2025.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_ConcentrationRiskTable_019caf59-229d-7feb-98aa-4fd760890c95_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/2025/elts/us-gaap-2025.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_wtm_DistinguishedTransactionScaleCoProgramMember_019cff09-038f-79d3-8cae-1f4323480005_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-20260331.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_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock_019caf59-221a-7571-91bd-cd073a5c2bc5_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/2025/elts/us-gaap-2025.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_us-gaap_SupplementalCashFlowInformationAbstract_019caf59-2168-7b05-9557-72ac44ac5b52_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/2025/elts/us-gaap-2025.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_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember_019caf59-229d-76ad-b500-17bb6ed02d71_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-20260331.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_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/2025/ecd-2025.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_us-gaap_USTreasuryAndGovernmentMember_019caf59-221a-7c93-9998-24a083796025_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/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationRightToSellRedemptionValue_019caf59-2312-721a-bcfb-16c35c2cb036_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-20260331.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_wtm_PassportCardDavidShieldMember_019caf59-221a-73dd-be05-1369abac1a95_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-20260331.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_us-gaap_DerivativeInstrumentRiskAxis_019caf59-2168-78f0-88b8-9dac38443af9_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/2025/elts/us-gaap-2025.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_RestrictedCash_019caf59-2168-72d1-9d20-15e5b6b9905f_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/2025/elts/us-gaap-2025.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_dei_EntityDomain_019caf59-2168-774d-89ce-5f1e376a5b2c_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/2025/dei-2025.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_us-gaap_NetCashProvidedByUsedInInvestingActivities_019caf59-221a-7012-8bda-80d3c3c5ee80_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/2025/elts/us-gaap-2025.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_us-gaap_EarningsPerShareBasicDistributed_019caf59-2168-7f50-a67a-51292609d6cb_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_PaymentsForParticipationContracts_019caf59-221a-711b-99ac-0daaa0e1b31b_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-20260331.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_019caf59-221a-7acb-972e-449533bd6c49_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-20260331.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_us-gaap_InterestPaidNet_019caf59-229d-7d3d-804f-b69dc297dd09_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>
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    <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"/>
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    <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>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_019caf59-221a-76f0-95b9-d7a267717356_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/2025/elts/us-gaap-2025.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_BasisOfAccountingPolicyPolicyTextBlock_019caf59-221a-70dc-bbcc-0f2a56454552_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod_019caf59-221a-7705-a7de-25731b0b6f08_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-20260331.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_EffectiveIncomeTaxRateContinuingOperations_019caf59-2312-7d69-b799-827736636542_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/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
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    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract_019caf59-229d-7447-b2c0-d5de4387b42a_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 Assets, Net (Including Goodwill) [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier_019caf59-229c-7c2d-a7e9-ddc8b6d84682_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-20260331.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_wtm_DistinguishedCreditFacilityMember_019caf59-221a-7961-80ce-580a08cce98a_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_019caf59-221a-7644-8d18-b3bd0c509d2d_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-20260331.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_wtm_ReinsurerTypeAxis_019caf59-229c-76a6-850c-2b06de21044e_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-20260331.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_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_019caf59-2168-737a-80c9-cd51b619b6b8_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/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
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    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_019caf59-221a-799a-ad43-f55329ff0bfa_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 Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_BusinessCombinationConsiderationTransferredCashOnHand_019cff07-6b93-71ff-9c2d-dffa91da1bd0_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>
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    <link:label id="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable_019caf59-2168-7ffb-a89d-c62cafaa0251_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">Schedule of Acquired Finite-Lived Intangible Asset by Major Class [Table]</link:label>
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    <link:label id="lab_srt_AMBestAPlusRatingMember_019caf59-229c-7b09-acff-8d4ff2d13778_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>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_019caf59-221a-75b6-837f-06e0ecd9565d_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>
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    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_019caf59-229d-7806-a1b1-c7924f31176c_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>
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    <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-20260331.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_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/2025/ecd-2025.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_CommonStockOtherMember_019caf59-221a-7515-b74f-cc111cdd8ee8_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-20260331.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_us-gaap_BusinessCombinationContingentConsiderationLiability_019caf59-221a-74f5-bd24-dce699b506fc_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_019caf59-229c-74a9-853a-77a5f79d52de_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/2025/elts/us-gaap-2025.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_AmortizationOfIntangibleAssets_019caf59-2312-7b95-af0f-3af8439b74f3_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">Amortization of Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_dei_ExchangeDomain_019caf59-221a-7658-b03d-49016f6b3be9_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/2025/dei-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward_019caf59-221a-7d07-8824-5c8f72aced6f_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-20260331.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_wtm_AdjustmentForRedeemableNoncontrollingInterest_019cffbf-8c39-722c-8495-8a9f1831ed0b_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-20260331.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_019caf59-221a-7338-82a2-e639455b17dc_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-20260331.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_RevolvingCreditFacilityMember_019caf59-221a-72d5-a225-74a927f52f24_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage_019ddc32-0125-7629-8085-ba0a74f011e7_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payout maximum growth target percentage</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" 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 for Maximum Growth Target Percentage</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the percentage of target achieved, high end of range.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" xlink:href="wtm-20260331.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_019caf59-221a-794d-9617-a3bcfdf86a80_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_GainLossOnFairValueAdjustmentOfSurplusNotes_019caf59-229d-78d7-94dc-19ce9e6652b3_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-20260331.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_TradingSecuritiesAndCertainTradingAssetsTextBlock_019caf59-229d-7ff4-bd0a-bac4ec7534d1_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/2025/elts/us-gaap-2025.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_us-gaap_StatementBusinessSegmentsAxis_019caf59-229c-75e0-a787-90d634e88c1a_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/2025/elts/us-gaap-2025.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_dei_LocalPhoneNumber_019caf59-2168-79cb-9769-22d74f28a07e_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/2025/dei-2025.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_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_019caf59-221a-75a1-bde0-298c30821f37_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</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-20260331.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_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/2025/ecd-2025.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_NoncontrollingInterestNetContributionAndDilutionDuringPeriod_019caf59-229c-7ad2-9a0a-3f95d5347c7d_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-20260331.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_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_019caf59-221a-7435-870a-1405f2f5322e_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/2025/elts/us-gaap-2025.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_wtm_PerformancePeriodTwoMember_019caf59-229c-741c-86b2-c9f31e242c2c_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-20260331.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_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_019caf59-229d-7363-b295-234ff929db06_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/2025/elts/us-gaap-2025.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_SubsidiaryOwnershipPercentageEconomicInterest_019caf59-221a-7e3c-bb9f-7296903a713e_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-20260331.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019caf59-229d-703d-b2bb-9747718ee0e5_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/2025/elts/us-gaap-2025.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019cff12-e87e-70ab-8274-601c39b8a87d_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/2025/elts/us-gaap-2025.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_us-gaap_AssetsAbstract_019caf59-2312-7a9a-9bee-8edbd84ad696_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/2025/elts/us-gaap-2025.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_us-gaap_CreditFacilityAxis_019caf59-229d-7055-ab71-af1e296d7bed_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_DebtInstrumentAxis_019caf59-229c-78a6-829c-1081227d73ea_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/2025/elts/us-gaap-2025.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_DebtInstrumentAnnualPrincipalPayment_019caf59-221a-7c33-aa2e-7c8e69c115cd_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAnnualPrincipalPayment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Annual payments</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAnnualPrincipalPayment_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAnnualPrincipalPayment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Annual Principal Payment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAnnualPrincipalPayment" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentAnnualPrincipalPayment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAnnualPrincipalPayment" xlink:to="lab_us-gaap_DebtInstrumentAnnualPrincipalPayment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_019caf59-2312-7b4a-8f93-010c6256faca_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/2025/elts/us-gaap-2025.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_CreditFacilityDomain_019caf59-2168-762e-86ce-c02380efb38b_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/2025/elts/us-gaap-2025.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_StockholdersEquityAbstract_019caf59-229d-7b5b-ade5-3faf5ef25761_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/2025/elts/us-gaap-2025.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_wtm_WMOutriggerReSegmentMember_019caf59-221a-748c-a246-4d14f64f6d87_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-20260331.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_019caf59-229c-70e1-b133-66936556c76d_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-20260331.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_us-gaap_DebtInstrumentInterestRateStatedPercentage_019caf59-229c-765d-929e-84e5030c654a_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/2025/elts/us-gaap-2025.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_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_019caf59-229d-723c-b7fe-22f23a01a2e5_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/2025/elts/srt-2025.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_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod_019caf59-229c-7237-83c9-ef27b0fedfe8_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-20260331.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_us-gaap_OtherLongTermInvestments_019caf59-229c-735e-86dd-4edf1aebbc2e_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_019caf59-229c-7cf9-b698-11efb550e1a8_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_019caf59-229c-7e1b-8b86-e30ed7e3185d_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/2025/elts/us-gaap-2025.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_DepreciationAmortizationAndAccretionNet_019caf59-2168-75b6-96ce-8907ae9eb6a5_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/2025/elts/us-gaap-2025.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_dei_EntityRegistrantName_019caf59-2168-79b4-99f7-8c7092ed8e31_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/2025/dei-2025.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_CommunicationsSectorMember_019caf59-2168-74d1-8f05-078141c6f55e_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-20260331.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_us-gaap_CededCreditRiskCollateralizationAxis_019caf59-229d-7bcc-b8e5-7081dee2c1a6_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_KuduInvestmentManagementLLCMember_019caf59-221a-7409-8598-40ba6bc0249d_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-20260331.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_019caf59-229d-7fc1-8d24-163bde87cc7e_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-20260331.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_019caf59-229c-72d2-822c-d24434c93940_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-20260331.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_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation_019caf59-229c-793b-a2b4-adef75276cad_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod_019caf59-221a-7ae0-8e9b-79687c17f4a0_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-20260331.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_019caf59-221a-7ef4-89b6-0193b9f04b1e_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-20260331.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_019caf59-2168-75d9-b4d7-883cfa735fae_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-20260331.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_us-gaap_EarningsPerShareDilutedUndistributed_019caf59-221a-72f8-a869-77cfd4ac4460_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/2025/elts/us-gaap-2025.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_LargestInvestmentMember_019caf59-221a-71d9-af8b-d28acfae17e8_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-20260331.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_wtm_EquityMethodInvestmentsAbstract_019caf59-2168-701e-a1b9-926ad287aefe_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-20260331.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_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/2025/ecd-2025.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_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019caf59-221a-7f46-b0be-f772da5cce86_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/2025/elts/us-gaap-2025.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_wtm_Ark2021SubordinatedNotesTranche3Member_019caf59-229d-7902-bfe2-70582f773888_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-20260331.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_019caf59-229c-7bcf-a0e4-932eafabcd7a_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-20260331.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_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/2025/ecd-2025.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_wtm_CommonStockExchangeTradedFundsMember_019caf59-229d-791e-a226-9a7f99bf1b52_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-20260331.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_019caf59-221a-7d6f-b547-207d2361aa63_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-20260331.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_019caf59-2312-7cb2-94fb-26099bf6b047_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-20260331.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_DebtInstrumentFaceAmount_019caf59-229d-7aa1-b7cf-bf5b8f213222_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/2025/elts/us-gaap-2025.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_wtm_SubsidiaryDistinguishedPartnersMember_019caf59-229c-7804-b177-31c52cae41c1_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-20260331.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_019caf59-229c-7ebf-a738-e6d49f12c478_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-20260331.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_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract_019caf59-229d-72a1-be55-3c1175f5ef25_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/2025/elts/us-gaap-2025.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_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable_019caf59-221a-7de5-ad6e-0adb9e5d8333_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-20260331.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_PreferredStockMember_019caf59-229c-7d7f-a3e0-7b4d82d8465f_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_BrokerCommissionExpense_019caf59-221a-720e-9e42-b3e0d658a9e3_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-20260331.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_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>
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    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_019caf59-221a-7faf-b117-d4041d97a9d0_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>
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    <link:label id="lab_us-gaap_SeniorNotesMember_019caf59-229c-7b39-9c59-73ca95e3836d_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>
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    <link:label id="lab_wtm_OtherShortTermInvestmentsMember_019caf59-2168-78bb-8848-0adccbc4845c_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-20260331.xsd#wtm_OtherShortTermInvestmentsMember"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract_019caf59-229c-71ba-8572-a1660cd36a9b_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019caf59-229c-7319-bd58-bbaa6e9bb643_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/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
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    <link:label id="lab_us-gaap_SubordinatedDebtMember_019caf59-221a-70dd-88b0-5acaffc27ddc_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.xsd#ecd_AllExecutiveCategoriesMember"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019caf59-229d-7c24-a33d-41b3dd288202_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/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_019caf59-229c-7bfe-9831-72598b7991a3_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">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/2025/elts/us-gaap-2025.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_OtherOperatingIncome_019caf59-2168-76e8-a8b7-d4471e08ad6b_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/2025/elts/us-gaap-2025.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_us-gaap_CommonStockValue_019caf59-2312-7f84-aea4-03863bc6e80c_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 2,476,670 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/2025/elts/us-gaap-2025.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_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_019caf59-2168-7c7e-93e2-fba87ab86dcd_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/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable"/>
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    <link:label id="lab_us-gaap_PremiumsEarnedNet_019caf59-229c-7235-934e-fd32b5e16b89_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_019caf59-229c-7442-9b1a-cf42ec6bc08d_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>
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    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_019caf59-221a-75b7-a81c-e2463076e76e_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>
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    <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>
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    <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"/>
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    <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>
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    <link:label id="lab_wtm_HGGlobalSegmentMember_019caf59-221a-74d0-8515-baa567393356_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-20260331.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_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod_019de1db-47a4-7558-abf8-79b6d80a474c_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-20260331.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_wtm_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_019caf59-221a-70c8-b06f-7953ba86fd06_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_019caf59-221a-74e4-b48c-f4f51353872b_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-20260331.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_019caf59-229d-7768-b4de-d5ca8f858cf8_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-20260331.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_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived_019caf59-221a-780c-a357-d63e076a432a_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-20260331.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_srt_StatementScenarioAxis_019caf59-229d-7c19-bca0-75026e16a186_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/2025/elts/srt-2025.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_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_019caf59-221a-7a9b-9a41-cfc3e3cee441_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/2025/elts/us-gaap-2025.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_wtm_ReinsuranceAgreementsAssetLimitAmount_019caf59-221a-7bff-b709-4dbaae05b539_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-20260331.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_us-gaap_DerivativeNumberOfInstrumentsHeld_019caf59-229c-77c8-a49a-f3b41711f0fc_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeNumberOfInstrumentsHeld" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of interest rate cap agreements</link:label>
    <link:label id="lab_us-gaap_DerivativeNumberOfInstrumentsHeld_label_en-US" xlink:label="lab_us-gaap_DerivativeNumberOfInstrumentsHeld" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Number of Instruments Held</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeNumberOfInstrumentsHeld" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeNumberOfInstrumentsHeld"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeNumberOfInstrumentsHeld" xlink:to="lab_us-gaap_DerivativeNumberOfInstrumentsHeld" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeContractTypeDomain_019caf59-229c-7106-be00-b5b55d7827b2_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable_019cffb8-e302-7b63-bd96-51e9c79c8aa7_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/2025/elts/us-gaap-2025.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_LongtermDebtTypeDomain_019caf59-221a-7822-b0ff-74c19437c467_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/2025/elts/us-gaap-2025.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_FairValueDisclosuresAbstract_019caf59-229d-7d03-9c52-69f0d6c52c3e_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations_019caf59-221a-77b0-a55f-f27eee611284_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_DisposalGroupClassificationAxis_019caf59-2312-7153-9d2b-0d2e668bbbe8_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod_019caf59-229d-76aa-9f40-b8a9ce8016b5_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-20260331.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_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward_019caf59-2168-73d4-b110-771a527027f8_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-20260331.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_us-gaap_OtherShortTermInvestments_019caf59-221a-712a-95b2-e397ea7156eb_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_srt_StatementGeographicalAxis_019de1cf-ad44-76cd-a7c4-c96030dfc14e_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/2025/elts/srt-2025.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_wtm_GoodwillAcquisitionDateFairValue_019cff40-b779-7001-bb9d-9afb19f8fb8d_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-20260331.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_019caf59-221a-7aca-a471-ae2054c729fc_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-20260331.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_us-gaap_IncreaseDecreaseInOtherOperatingCapitalNet_019caf59-2312-78cd-809e-84b36505410e_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_srt_ScenarioForecastMember_019caf59-221a-71af-a779-6f3232450ec1_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/2025/elts/srt-2025.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_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/2025/ecd-2025.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_ConcentrationRiskBenchmarkDomain_019caf59-221a-7fd2-868c-fe8d614b932c_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/2025/elts/us-gaap-2025.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_dei_Security12bTitle_019caf59-221a-74d6-a789-024f4dcd4b6f_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/2025/dei-2025.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_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable_019caf59-229d-70df-b814-7233f35d37cc_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/2025/elts/us-gaap-2025.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_srt_CreditRatingAMBestDomain_019caf59-229d-7c7f-b65b-7f2e168a0ba2_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/2025/elts/srt-2025.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_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_019caf59-229c-7a8b-9318-72b04a363125_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-20260331.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_us-gaap_EarningsPerShareAbstract_019caf59-2168-7529-bb88-ab4021d74ff0_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/2025/elts/us-gaap-2025.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_us-gaap_DerivativeCapInterestRate_019caf59-229d-756d-a97c-057c70822904_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/2025/elts/us-gaap-2025.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019caf59-2312-7ae1-ba56-bb9d0efc9f7b_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/2025/elts/us-gaap-2025.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_wtm_LloydsLOCFacilityMember_019caf59-229d-7969-ad51-d9e5fc8c912b_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-20260331.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_MinorityInterestOwnershipPercentageByParent_019caf59-2312-7181-914b-e303fae26eec_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/2025/elts/us-gaap-2025.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_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier_019caf59-221a-72c8-add2-71917d5b31d3_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-20260331.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_us-gaap_EquitySecuritiesFvNiUnrealizedLoss_019caf59-221a-756d-b443-f59a4479c1ad_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/2025/elts/us-gaap-2025.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_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember_019caf59-221a-7326-a4ba-e74729104add_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/2025/elts/us-gaap-2025.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_wtm_ChangesInNominalValueOfSurplusNotesRollForward_019caf59-229d-7674-b93a-c24ba15adcc5_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-20260331.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_019caf59-229c-71ef-8927-787b29565b49_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-20260331.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_wtm_MediaAlphaMember_019caf59-221a-7c76-ad45-4057df1ff37e_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_019caf59-221a-76d5-9013-42606c635d10_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-20260331.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_NonvestedRestrictedStockSharesActivityTableTextBlock_019caf59-229d-73ed-9716-7b4fcb9bd222_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_GainLossOnInvestmentsTextBlock_019caf59-229d-7ec5-b208-21b13a52398f_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/2025/elts/us-gaap-2025.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_us-gaap_FairValueMeasurementFrequencyDomain_019caf59-229d-7dd4-a22d-8e4cf84217e5_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/2025/elts/us-gaap-2025.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_wtm_NumberofSecuredCreditFacilities_019caf59-2168-7363-adaf-9155bc71fdad_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-20260331.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_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019caf59-229c-710e-a560-7feb170fdef1_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_019caf59-229c-7a22-9863-dfc59696a413_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/2025/elts/us-gaap-2025.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_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne_019caf59-221a-72cd-9c60-b0bec19f478b_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-20260331.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_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments_019caf59-229c-7359-8b49-bc82632eba44_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/2025/elts/us-gaap-2025.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_srt_CreditRatingAMBestAxis_019caf59-221a-7d1f-a003-2eb6485c3602_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/2025/elts/srt-2025.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_us-gaap_ReinsuranceTextBlock_019caf59-221a-7512-88f7-ef18d7734547_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/2025/elts/us-gaap-2025.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_us-gaap_NetIncomeLoss_019caf59-229d-7cd1-9b29-f8647e143cc1_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_019caf59-229d-7bbc-9c66-b5acb052b57a_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_019caf59-229d-7260-ac68-cb62bc5aa0e5_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/2025/elts/us-gaap-2025.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_SubsidiaryOrEquityMethodInvesteeLineItems_019caf59-229d-7776-aefd-44a6e5f603d2_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/2025/elts/us-gaap-2025.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_wtm_EquityMethodInvestmentUnrealizedLoss_019caf59-229c-7740-b0d5-d8334754b673_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-20260331.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_us-gaap_CollateralizedLoanObligationsMember_019caf59-221a-74b7-9714-59c082116463_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/2025/elts/us-gaap-2025.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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_019caf59-229d-7910-9388-2a798337223e_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/2025/elts/us-gaap-2025.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_wtm_BankLoanFundMember_019caf59-229d-7405-8107-619354d867be_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-20260331.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_us-gaap_SegmentReportingInformationLineItems_019caf59-229d-735b-9907-734ddfefb026_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 Information [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 Information [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_us-gaap_PaymentsForRepurchaseOfCommonStock_019caf59-2168-7bf6-8ce4-646ab1760c40_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_TrustDepositsMember_019caf59-2168-7ef2-942f-045f11ddb92a_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-20260331.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_CustomerRelationshipsMember_019caf59-229d-75d3-b38c-c7e24fc32bd3_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/2025/elts/us-gaap-2025.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_LineOfCreditMember_019caf59-229d-7656-87c4-cebb0f95b3a7_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/2025/elts/us-gaap-2025.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_us-gaap_RetainedEarningsAccumulatedDeficit_019caf59-229d-7983-baf3-d2f743f90382_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/2025/elts/us-gaap-2025.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
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    <link:label id="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember_019caf59-221a-71d1-8980-8dad3c68002f_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-20260331.xsd#wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember"/>
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    <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/2025/ecd-2025.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
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    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche1Member_019caf59-2312-7e34-aa32-5e2a0a54eaca_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-20260331.xsd#wtm_Ark2021SubordinatedNotesTranche1Member"/>
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    <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-20260331.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_019caf59-221a-7480-9bea-bc752f515900_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-20260331.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_ImpairmentOfIntangibleAssetsFinitelived_019caf59-2168-779a-afbc-f519ed2a3a06_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">Impairment of Intangible Assets, Finite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.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_wtm_ReinsurerTypeDomain_019caf59-229d-78e0-9b3f-b52b34b20296_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-20260331.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_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/2025/ecd-2025.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_EarningsPerShareBasicUndistributed_019caf59-2168-70f2-821b-0df41340ff64_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/2025/elts/us-gaap-2025.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_us-gaap_StatementTable_019caf59-229d-79c0-a052-adee550e1546_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/2025/elts/us-gaap-2025.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_019cff12-e87e-7f34-93da-acea772e44e0_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/2025/elts/us-gaap-2025.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_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_019caf59-229d-7422-a813-1bae220e24ed_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/2025/elts/us-gaap-2025.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_019cff12-e87e-78c4-b538-e6ec09dd0ca1_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/2025/elts/us-gaap-2025.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_us-gaap_VariableRateDomain_019caf59-221a-799b-b88d-fe67a624dfee_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/2025/elts/us-gaap-2025.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_wtm_NewYorkStockExchangeMember_019caf59-221a-7960-a89a-5a711f81fe93_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-20260331.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_019caf59-229c-70f3-ac6e-d1f6421361f4_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-20260331.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_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_019caf59-2312-7026-87e8-e6bd9a61f79e_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_dei_AmendmentFlag_019caf59-229d-7a17-a0b9-be09d01a8cf6_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/2025/dei-2025.xsd#dei_AmendmentFlag"/>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019caf59-229d-7026-a020-71e57b9cf823_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_019caf59-229d-7200-afd3-ba8167e1193c_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_019caf59-229d-736f-938b-615bef9f245d_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_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/2025/ecd-2025.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_FinancialGuaranteeInsuranceContractsNumberOfContracts_019caf59-221a-75d8-b94f-22832d56999a_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-20260331.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_WeightedAverageNumberOfSharesOutstandingBasic_019caf59-221a-7c9c-a42b-c2b091bd5744_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/2025/elts/us-gaap-2025.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_FairValueAssetsMeasuredOnRecurringBasisTextBlock_019caf59-229d-7a05-85bb-9a75c63b647c_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/2025/elts/us-gaap-2025.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_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_019caf59-229d-7206-86ac-9800e08b65d3_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/2025/elts/us-gaap-2025.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_SegmentReportingAbstract_019caf59-229c-7034-94f1-d2e3015544ef_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/2025/elts/us-gaap-2025.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_wtm_RevenuesFromExternalCustomers_019caf59-221a-77e5-8966-5411abb74b39_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-20260331.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_DebtDisclosureAbstract_019caf59-229d-7f3a-9da8-76e4447c2de4_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/2025/elts/us-gaap-2025.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_srt_ScenarioUnspecifiedDomain_019caf59-229d-7d0f-98ee-3bb9b7253fb7_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/2025/elts/srt-2025.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_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock_019caf59-2168-70de-a8cc-259f6129874e_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-20260331.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_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/2025/ecd-2025.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_us-gaap_DebtSecuritiesTradingUnrealizedLoss_019caf59-2168-7a4c-829c-73d603e272a6_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/2025/elts/us-gaap-2025.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_019caf59-2312-79a9-abfb-b78927d4041e_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/2025/elts/us-gaap-2025.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_srt_ConsolidatedEntitiesAxis_019caf59-229c-7279-864d-80c4310b4083_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/2025/elts/srt-2025.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_us-gaap_CommonStockParOrStatedValuePerShare_019caf59-229c-7e6b-b7ac-38b5613ac960_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/2025/elts/us-gaap-2025.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_wtm_BambooSPVMember_019cfefb-18e7-7ba6-9269-fd7e5ab662dd_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-20260331.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_wtm_OtherCountryMember_019caf59-229d-7f86-bdc8-fdac208faf29_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-20260331.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_GeographicDistributionAxis_019caf59-229c-7d0c-bf3a-418f22e9499d_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/2025/elts/us-gaap-2025.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_SurplusNotesMember_019caf59-2168-7add-8375-17e513a0ebe4_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-20260331.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_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock_019caf59-229c-7ed7-b0ce-f022bb2673bb_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/2025/elts/us-gaap-2025.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedAndCancelledInPeriod_019caf59-229c-7395-b297-213fc23ad628_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-20260331.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_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/2025/ecd-2025.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_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019caf59-229c-7c5f-8a33-1a7986d910e8_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/2025/elts/us-gaap-2025.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_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest_019cffaf-1517-7bc9-a360-b06835086d97_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-20260331.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_Liabilities_019caf59-221a-7fd2-86f4-6e19d7215d4e_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_019caf59-221a-7c18-9025-839e037aee0e_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/2025/elts/us-gaap-2025.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_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/2025/ecd-2025.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_wtm_BermudaStockExchangeMember_019caf59-229d-7460-9100-00746907f431_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-20260331.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_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/2025/ecd-2025.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_wtm_BambooInsuranceServicesLLCSegmentMember_019caf59-221a-7b10-b5a5-b5899013431b_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-20260331.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_019cff91-d905-708a-941f-3d64b4a6766b_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-20260331.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_019caf59-229d-7611-b6e4-9f89da4f1c86_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-20260331.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_us-gaap_OtherLongTermInvestmentsMember_019caf59-229d-7729-8868-e9b52f1e5458_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/2025/elts/us-gaap-2025.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt_019cff12-e87e-77dc-b27b-61fa33380c8b_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/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_019caf59-221a-74b5-850e-783f9355bab7_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/2025/elts/us-gaap-2025.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_AssetBackedSecuritiesMember_019caf59-221a-74e4-9f29-6394b80124fb_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_019caf59-221a-78a2-9544-cd92eb0888bb_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/2025/elts/us-gaap-2025.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_us-gaap_VariableRateAxis_019caf59-2168-7e76-ad51-7903856b8737_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/2025/elts/us-gaap-2025.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"/>
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    <link:label id="lab_wtm_InfrastructureFundMember_019d6bfc-22bc-7b98-ac60-56c3150cfa04_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>
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    <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>
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    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_019caf59-229d-772f-9d01-9db08dcc1756_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>
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    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_019caf59-229d-7a5b-bf23-b355a9e0c4ee_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>
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    <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>
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    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_019caf59-2312-726d-96d2-fc2ed8e50c7a_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>
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