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    <link:label id="lab_srt_MaximumMember_019fd7d0-1bf1-727d-977c-a22f3043f9ed_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_MaximumMember"/>
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    <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>
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    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019fd7d0-1bf1-7958-b2a2-33d4c88c3c60_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>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_019fd7d0-1bf1-7c1a-8465-ec229305d22d_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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsMember" xlink:to="lab_us-gaap_EquityMethodInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_019fd7d0-1bf1-7716-ab85-62fd421a0894_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation, Amount</link:label>
    <link:label id="lab_ecd_AdjToCompAmt_label_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation Amount</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAmt" xlink:to="lab_ecd_AdjToCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PledgedStatusAxis_019fd7d0-1b75-752a-af6c-dab3b6f40499_terseLabel_en-US" xlink:label="lab_us-gaap_PledgedStatusAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged Status [Axis]</link:label>
    <link:label id="lab_us-gaap_PledgedStatusAxis_label_en-US" xlink:label="lab_us-gaap_PledgedStatusAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pledged Status [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PledgedStatusAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PledgedStatusAxis"/>
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    <link:label id="lab_us-gaap_FinancialInstrumentAxis_019fd7d0-1b75-746e-8609-4458092e2283_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>
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    <link:label id="lab_us-gaap_SegmentReportingAbstract_019fd7d0-1b75-75a2-890b-e5b7783e54fb_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingAbstract_label_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingAbstract"/>
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    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets_019fd7d0-1c60-71ce-875f-06b3a8924fe9_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Other Assets</link:label>
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    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust_019fd7d0-1b75-7123-92ad-0b10b7de91ae_terseLabel_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued interest payment held outside of trust</link:label>
    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust_label_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments Of Accrued Interest Held Outside of Trust</link:label>
    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust_documentation_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldOutsideOfTrust" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Repayments Of Accrued Interest Held Outside of Trust</link:label>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisTextBlock_019fd7d0-1c60-7145-987a-648907e66a2a_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>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_019fd7d0-1bf2-7417-b52d-b07f0d06aab1_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>
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    <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>
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    <link:label id="lab_wtm_OtherDisposalGroupMember_019fd7d0-1acb-74bf-b148-cca0a36764b4_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-20260930.xsd#wtm_OtherDisposalGroupMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherDisposalGroupMember" xlink:to="lab_wtm_OtherDisposalGroupMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_019fd7d0-1c60-72fe-9fe0-bca3ccbf35aa_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract assets</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerAssetNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetNet" xlink:to="lab_us-gaap_ContractWithCustomerAssetNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition_019fd7d0-1bf1-7ae3-8f26-5639400c77cf_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of restricted share awards</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Restricted Stock Unit, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationRestrictedStockUnitsRequisiteServicePeriodRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentRiskAxis_019fd7d0-1bf1-7eb3-bf29-8e98a64a38ed_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentRiskAxis_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentRiskAxis" xlink:to="lab_us-gaap_DerivativeInstrumentRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_019fd7d0-1acb-7952-a8ae-97af3f459f67_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance payable</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingNetForeignCurrencyGainLoss_019fd7d0-1bf1-77df-b988-31d66f7c2c8d_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-20260930.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_019fd7d0-1b75-762b-b57a-e4384fc4cb7e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Investment in Debt and Equity Securities, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByMeasurementFrequencyAxis_019fd7d0-1bf1-7856-aaf1-aafe0e04b020_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementFrequencyAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByMeasurementFrequencyAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:to="lab_us-gaap_FairValueByMeasurementFrequencyAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_019fd7d0-1bf1-7ba3-958c-6adf2682d907_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sale of Bamboo Group</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_019fd7d0-1bf1-7236-836a-c8c91d769608_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net cash proceeds</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinesses_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Divestiture of Businesses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDivestitureOfBusinesses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:to="lab_us-gaap_ProceedsFromDivestitureOfBusinesses" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments_019fd7d0-1c60-760e-83d0-64fb80b66da7_terseLabel_en-US" xlink:label="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Attribution of acquisition date fair value estimates between goodwill and other intangible assets</link:label>
    <link:label id="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments_label_en-US" xlink:label="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Attribution of Acquisition Adjustments</link:label>
    <link:label id="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments_documentation_en-US" xlink:label="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill, Attribution of Acquisition Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:href="wtm-20260930.xsd#wtm_GoodwillAttributionOfAcquisitionAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:to="lab_wtm_GoodwillAttributionOfAcquisitionAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_019fd7d0-1b75-733e-802f-dd319a6d648b_terseLabel_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">U.S. Government and agency obligations</link:label>
    <link:label id="lab_us-gaap_USTreasuryAndGovernmentMember_label_en-US" xlink:label="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">US Treasury and Government [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_USTreasuryAndGovernmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USTreasuryAndGovernmentMember" xlink:to="lab_us-gaap_USTreasuryAndGovernmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalInvestmentsAfterTPCProvidersInvestmentsMember_019fd7d0-1bf1-7ef4-a384-934511081b2e_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-20260930.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_srt_ConsolidatedEntitiesAxis_019fd7d0-1bf1-7d7c-8128-bedeed923f35_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentUnrealizedLoss_019fd7d0-1bf1-7659-b9dd-72e4da4ee1c6_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-20260930.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_dei_EntityCommonStockSharesOutstanding_019fd7d0-1b75-7608-97a9-9cce0fa01a3f_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding (in shares)</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DevelopedTechnologyRightsMember_019fd7d0-1bf1-78de-a7d7-daf0d49cf47f_terseLabel_en-US" xlink:label="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Developed technology</link:label>
    <link:label id="lab_us-gaap_DevelopedTechnologyRightsMember_label_en-US" xlink:label="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Developed Technology Rights [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DevelopedTechnologyRightsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DevelopedTechnologyRightsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DevelopedTechnologyRightsMember" xlink:to="lab_us-gaap_DevelopedTechnologyRightsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures_019fd7d0-1b75-7e66-9229-4cf7abf743b3_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-20260930.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityBeforeAssumedForfeitures" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_019fd7d0-1bf1-78df-b29a-6456d91640e6_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_019fd7d0-1bf1-72b3-a7c8-2d8f7d04c07a_verboseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total mortgage and asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_019fd7d0-1c60-7025-925c-b7e4fbe0619a_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix</link:label>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_label_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryBasesixMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryBasesixMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - Basesix</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryBasesixMember" xlink:href="wtm-20260930.xsd#wtm_SubsidiaryBasesixMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryBasesixMember" xlink:to="lab_wtm_SubsidiaryBasesixMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems_019fd7d0-1b75-7fb3-8ca5-2f7e9360de7e_terseLabel_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Line Items]</link:label>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_019fd7d0-1bf1-733c-b3f9-77cf5273bd53_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToMinorityShareholders_019fd7d0-1c60-7ac9-89a1-ecdc4ce756bd_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToMinorityShareholders" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Distributions to other noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_PaymentsToMinorityShareholders_label_en-US" xlink:label="lab_us-gaap_PaymentsToMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Noncontrolling Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToMinorityShareholders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToMinorityShareholders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToMinorityShareholders" xlink:to="lab_us-gaap_PaymentsToMinorityShareholders" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativePremiumPaid_019fd7d0-1b75-7f4a-92cf-66e0bef086a2_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativePremiumPaid" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums paid</link:label>
    <link:label id="lab_us-gaap_DerivativePremiumPaid_label_en-US" xlink:label="lab_us-gaap_DerivativePremiumPaid" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativePremiumPaid" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativePremiumPaid"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativePremiumPaid" xlink:to="lab_us-gaap_DerivativePremiumPaid" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash_01a17fbc-84b9-75e0-9e56-08e8fae88ecf_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Restricted Cash</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Restricted Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:href="wtm-20260930.xsd#wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetAcquiredRestrictedCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_019fd7d0-1bf1-7c5a-a819-56b2f33c350a_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, par value per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_ExchangeDomain_019fd7d0-1bf2-7981-bbb8-a542062f7fde_terseLabel_en-US" xlink:label="lab_dei_ExchangeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exchange [Domain]</link:label>
    <link:label id="lab_dei_ExchangeDomain_label_en-US" xlink:label="lab_dei_ExchangeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Exchange [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_ExchangeDomain" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_ExchangeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_ExchangeDomain" xlink:to="lab_dei_ExchangeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_019fd7d0-1b75-7de2-ab70-6364bf600ff9_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_019fd7d0-1b75-740f-b785-4d70811f5420_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_019fd7d0-1b75-7755-b1c4-19cf865909b3_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets (excluding goodwill), ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_019fd7d0-1acb-7742-9e4c-3e54c7c92f30_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_019fd7d0-1acb-7657-91c8-b1aa77bc0ead_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments_019fd7d0-1bf2-78f7-b351-f3db22cbc5ef_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" 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_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments_label_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period, Including Short-Term Investments</link:label>
    <link:label id="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Weighted Average Portfolio Period, Including Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" xlink:href="wtm-20260930.xsd#wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" xlink:to="lab_wtm_DebtSecuritiesWeightedAveragePortfolioPeriodIncludingShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCollateralAmount_019fd7d0-1c60-7276-84b2-c1bea49c76df_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged collateral</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCollateralAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Collateral Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCollateralAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCollateralAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCollateralAmount" xlink:to="lab_us-gaap_DebtInstrumentCollateralAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_019fd7d0-1c60-785d-b335-0e7b2df0785b_terseLabel_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee revenues</link:label>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_label_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions And Fees, Adjusted</link:label>
    <link:label id="lab_wtm_InsuranceCommissionsAndFeesAdjusted_documentation_en-US" xlink:label="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Insurance Commissions And Fees, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:href="wtm-20260930.xsd#wtm_InsuranceCommissionsAndFeesAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:to="lab_wtm_InsuranceCommissionsAndFeesAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation_019fd7d0-1b75-7136-954d-75ca3268f22a_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Payments of principal received on the BAM Surplus Notes</link:label>
    <link:label id="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation_label_en-US" xlink:label="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments on Long-term Debt Subsequent To Deconsolidation</link:label>
    <link:label id="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation_documentation_en-US" xlink:label="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments on Long-term Debt Subsequent To Deconsolidation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:href="wtm-20260930.xsd#wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:to="lab_wtm_PaymentsOnLongTermDebtSubsequentToDeconsolidation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_019fd7d0-1bf2-764d-abf6-bd9005a51376_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of reportable segments</link:label>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Reportable Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfReportableSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NumberOfReportableSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfReportableSegments" xlink:to="lab_us-gaap_NumberOfReportableSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedTransactionScaleCoProgramMember_019fd7d0-1c60-75ae-81e4-caf987d50ea6_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-20260930.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_CustomerRelationshipsMember_019fd7d0-1acb-7bbb-87d5-46d65e4e97a0_terseLabel_en-US" xlink:label="lab_us-gaap_CustomerRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Customer relationships</link:label>
    <link:label id="lab_us-gaap_CustomerRelationshipsMember_label_en-US" xlink:label="lab_us-gaap_CustomerRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Customer Relationships [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CustomerRelationshipsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CustomerRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CustomerRelationshipsMember" xlink:to="lab_us-gaap_CustomerRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedDebtMember_019fd7d0-1bf2-703c-bfd6-6147f8686d35_terseLabel_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Distinguished debt</link:label>
    <link:label id="lab_wtm_DistinguishedDebtMember_label_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Distinguished Debt [Member]</link:label>
    <link:label id="lab_wtm_DistinguishedDebtMember_documentation_en-US" xlink:label="lab_wtm_DistinguishedDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Distinguished Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DistinguishedDebtMember" xlink:href="wtm-20260930.xsd#wtm_DistinguishedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DistinguishedDebtMember" xlink:to="lab_wtm_DistinguishedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_019fd7d0-1c60-7ebd-8aea-79abc92b06bb_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTable" xlink:to="lab_us-gaap_ConcentrationRiskTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019fd7d0-1bf2-7090-a807-e1d15016224a_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-20260930.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_dei_EntityAddressCityOrTown_019fd7d0-1b75-7ffa-ae4f-a5ce11a66bd4_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPercentageOfTargetAchievedPayout_019fd7d0-1bf1-7fb3-8358-d7e54e754187_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-20260930.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_019fd7d0-1bf1-7fe4-b2a6-4dccdc270022_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New grants (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_019fd7d0-1c60-7c97-81a8-6864bbfb0e5a_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based compensation arrangement by share-based payment award</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodOneMember_019fd7d0-1bf1-71ea-a0f9-1dd399d27498_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-20260930.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_us-gaap_StatementOfFinancialPositionAbstract_019fd7d0-1b75-7425-8476-d1212dd3751e_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_019fd7d0-1c60-76d9-8215-12c380517e5d_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, net carrying value</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019fd7d0-1bf1-7eac-8d7a-aca7a1f92aae_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE incurred relating to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_019fd7d0-1b75-74ff-8adc-68a10f2bbaf6_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnVsPeerGroupTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:to="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember_019fd7d0-1b75-79aa-8524-83c5a195982d_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-20260930.xsd#wtm_TotalEquityIncludingNoncontrollingInterestMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:to="lab_wtm_TotalEquityIncludingNoncontrollingInterestMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax_019fd7d0-1b75-7b0c-a536-13eda04d27a7_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive income (loss), net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonRule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_country_US_019fd7d0-1b75-7c47-83ae-1dd8aec006ce_terseLabel_en-US" xlink:label="lab_country_US" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">United&#160;States</link:label>
    <link:label id="lab_country_US_label_en-US" xlink:label="lab_country_US" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED STATES</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_US" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_US"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_US" xlink:to="lab_country_US" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember_019fd7d0-1bf1-7e40-96ae-5a55304769f3_terseLabel_en-US" xlink:label="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLMC</link:label>
    <link:label id="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember_label_en-US" xlink:label="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal Home Loan Mortgage Corporation Certificates and Obligations (FHLMC) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:to="lab_us-gaap_FederalHomeLoanMortgageCorporationCertificatesAndObligationsFHLMCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_019fd7d0-1bf1-725d-86ce-edceb46f4276_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:to="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_019fd7d0-1c60-7964-9aa6-503e9a7a6881_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Long-term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments_019fd7d0-1bf1-7b4c-8467-2896d14b32c6_terseLabel_en-US" xlink:label="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Attribution of acquisition date fair value estimates between goodwill and other intangible assets</link:label>
    <link:label id="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments_label_en-US" xlink:label="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Attribution of Acquisition Adjustments</link:label>
    <link:label id="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments_documentation_en-US" xlink:label="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Attribution of Acquisition Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:href="wtm-20260930.xsd#wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:to="lab_wtm_FiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedManagementMember_019fd7d0-1bf1-768d-b6d6-732594f89202_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-20260930.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_wtm_FinancialGuaranteeInsuranceContractsNumberOfContracts_019fd7d0-1bf1-7c2c-9a33-ccdb877166c4_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-20260930.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_InsuranceCommissionsAndFees_019fd7d0-1bf1-7cce-b4d7-ed565b7d65c7_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee revenues</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommonStockExchangeTradedFundsMember_019fd7d0-1c60-7f88-a51f-9cd44a4bede6_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-20260930.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_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019fd7d0-1c60-7a9a-b1f1-2f47243d01c6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IntangibleAssetsGrossIncludingGoodwill_019fd7d0-1b75-713f-a480-5224c29701b3_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-20260930.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_ScheduleOfSegmentReportingInformationBySegmentTextBlock_019fd7d0-1bf1-7bf8-9a04-8f42bf417569_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of financial information for segments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberOfPrefundedInfrastructureFunds_019fd7d0-1c60-7060-9cd3-ae047dfa59ea_terseLabel_en-US" xlink:label="lab_wtm_NumberOfPrefundedInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of infrastructure funds</link:label>
    <link:label id="lab_wtm_NumberOfPrefundedInfrastructureFunds_label_en-US" xlink:label="lab_wtm_NumberOfPrefundedInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Prefunded Infrastructure Funds</link:label>
    <link:label id="lab_wtm_NumberOfPrefundedInfrastructureFunds_documentation_en-US" xlink:label="lab_wtm_NumberOfPrefundedInfrastructureFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Prefunded Infrastructure Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberOfPrefundedInfrastructureFunds" xlink:href="wtm-20260930.xsd#wtm_NumberOfPrefundedInfrastructureFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NumberOfPrefundedInfrastructureFunds" xlink:to="lab_wtm_NumberOfPrefundedInfrastructureFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EnterpriseSolutionMember_019fd7d0-1bf1-7da8-99c4-4ea283071e2f_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-20260930.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_wtm_DistinguishedOtherDebtMember_019fd7d0-1b75-7e6a-a5ba-0b281ce22511_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_019fd7d0-1b75-7f1c-af2f-d64711278323_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-20260930.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_us-gaap_ReinsuranceRecoverablesGross_019fd7d0-1b75-724e-93e5-45dbbcaedcd6_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019fd7d0-1bf2-7a71-bf33-487d9fb672f6_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive income (loss), net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CitibankLOCFacilityMember_019fd7d0-1bf1-767c-ac4f-731f8b0c495d_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-20260930.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_NotesReceivableFairValueDisclosure_019fd7d0-1bf1-73a1-9888-cec9061b030f_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_019fd7d0-1bf1-74ff-9ee7-379ed9babd48_terseLabel_en-US" xlink:label="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes receivable, fair value disclosure</link:label>
    <link:label id="lab_us-gaap_NotesReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Receivable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NotesReceivableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesReceivableFairValueDisclosure" xlink:to="lab_us-gaap_NotesReceivableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_019fd7d0-1bf1-7e36-8c05-4655d36196c2_terseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expense recognized</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Expense In Period</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Accrued Liability, Expense In Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:href="wtm-20260930.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityExpenseInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_019fd7d0-1bf1-7635-8f34-20cf950ce103_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Debt, Net of Issuance Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDebtNetOfIssuanceCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:to="lab_us-gaap_ProceedsFromDebtNetOfIssuanceCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationDomain_019fd7d0-1bf1-7e74-99f1-dc3b958cd583_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskCollateralizationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskCollateralizationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskCollateralizationDomain" xlink:to="lab_us-gaap_CededCreditRiskCollateralizationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GuaranteeObligationsLineItems_019fd7d0-1bf2-700b-a3c8-83720f313c4a_terseLabel_en-US" xlink:label="lab_us-gaap_GuaranteeObligationsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Guarantor Obligations [Line Items]</link:label>
    <link:label id="lab_us-gaap_GuaranteeObligationsLineItems_label_en-US" xlink:label="lab_us-gaap_GuaranteeObligationsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantor Obligations [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GuaranteeObligationsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GuaranteeObligationsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GuaranteeObligationsLineItems" xlink:to="lab_us-gaap_GuaranteeObligationsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_019fd7d0-1c60-778e-a6cd-a19171432bcb_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:label id="lab_dei_DocumentPeriodEndDate_label_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentPeriodEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentPeriodEndDate" xlink:to="lab_dei_DocumentPeriodEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentAdditionalInterestRate_019fd7d0-1b75-7f09-8884-6677f35994af_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-20260930.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_DebtInstrumentFaceAmount_019fd7d0-1b75-7644-bd9f-7e460424672c_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Face value</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicAbstract_019fd7d0-1b75-7d74-b985-a31bf01f3df4_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Basic and diluted earnings per share (in dollars):</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicAbstract" xlink:to="lab_us-gaap_EarningsPerShareBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt_019fd7d0-1bf1-7da6-91cc-1dd08653a3a9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Long-Term Debt, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNoncurrentLiabilitiesLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage_019fd7d0-1bf2-7823-b0ec-f5fceb3688c0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective yield (as a percent)</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Effective Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentInterestRateEffectivePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateEffectivePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts_019fd7d0-1b75-7665-bac7-0db1f3fd309a_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transaction costs</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Transaction Cost, Excluding Separately Recognized Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:to="lab_us-gaap_BusinessAcquisitionCostOfAcquiredEntityTransactionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel12And3Member_019fd7d0-1b75-7ec7-a88c-9d46c8a86a00_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1, Level 2, and Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel12And3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1, Level 2, and Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel12And3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel12And3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel12And3Member" xlink:to="lab_us-gaap_FairValueInputsLevel12And3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMinorityShareholders_019fd7d0-1acb-7445-a89c-291397f25ea9_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contributions from other noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMinorityShareholders_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Noncontrolling Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMinorityShareholders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMinorityShareholders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMinorityShareholders" xlink:to="lab_us-gaap_ProceedsFromMinorityShareholders" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_019fd7d0-1c60-7d81-8016-1d4e5101dc44_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableMember" xlink:to="lab_us-gaap_ReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_019fd7d0-1acb-7ca9-bc5c-43d11a424a3a_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in reinsurance payable</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Reinsurance Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod_019fd7d0-1b75-7ad8-bc23-325c6f2e5a60_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-20260930.xsd#wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:to="lab_wtm_NoncontrollingInterestNetContributionAndDilutionDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilitySharesPaidInPeriod_019fd7d0-1b75-7f48-b9ad-bf88c5c3e81b_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-20260930.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_dei_EntityShellCompany_019fd7d0-1c60-7b7e-9a5d-99f8157874d6_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsDomain_019fd7d0-1bf1-7577-9c33-9dfda617a413_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:label id="lab_srt_ConsolidationItemsDomain_label_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsDomain" xlink:to="lab_srt_ConsolidationItemsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodDomain_019fd7d0-1b75-706f-be93-ee2bd624c05c_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-20260930.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_us-gaap_UndistributedContinuingOperationEarningsLossBasic_019fd7d0-1bf2-760d-b8c3-45f28ad56261_totalLabel_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total undistributed net earnings (losses), net of restricted common share amounts</link:label>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic_label_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Undistributed Continuing Operation Earnings (Loss), Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UndistributedContinuingOperationEarningsLossBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:to="lab_us-gaap_UndistributedContinuingOperationEarningsLossBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_019fd7d0-1bf1-7edd-8656-cfa1af755d3a_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_019fd7d0-1c60-7796-bd7c-5adb2b2650a7_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Earnings (loss) per share attributable to White Mountains&#8217;s common shareholders:</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_019fd7d0-1b75-7d20-9850-88ed283b7066_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_019fd7d0-1c60-7aaf-8a74-03471831da66_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_019fd7d0-1c60-798d-a238-1c6c0986889e_terseLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_019fd7d0-1b75-7458-90b7-e6fd59acd189_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ChangeInLongTermDebtRollForward_019fd7d0-1bf1-7c20-bbad-8a3055860a65_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-20260930.xsd#wtm_ChangeInLongTermDebtRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ChangeInLongTermDebtRollForward" xlink:to="lab_wtm_ChangeInLongTermDebtRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputDiscountRateMember_019fd7d0-1c60-7598-9688-ee42e9ab335e_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discount Rate</link:label>
    <link:label id="lab_us-gaap_MeasurementInputDiscountRateMember_label_en-US" xlink:label="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Discount Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputDiscountRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputDiscountRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputDiscountRateMember" xlink:to="lab_us-gaap_MeasurementInputDiscountRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BankLoanFundMember_019fd7d0-1b75-74dc-b328-b215c9755978_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-20260930.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_IntangibleAssetsNetIncludingGoodwillAbstract_019fd7d0-1b75-7c54-a2dc-beec58b328ac_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Goodwill and Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, after Accumulated Amortization [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwillAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ChangesInNominalValueOfSurplusNotesRollForward_019fd7d0-1bf1-7990-8979-a6d587375edf_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-20260930.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_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred_01a1a4b1-6fc3-7cbe-bbc5-d69233e02ee9_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Post closing adjustment, consideration transferred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Provisional Information, Initial Accounting Incomplete, Adjustment, Consideration Transferred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred" xlink:to="lab_us-gaap_BusinessCombinationProvisionalInformationInitialAccountingIncompleteAdjustmentConsiderationTransferred" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears_019fd7d0-1acb-747d-ad11-dc10fb7480c1_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-20260930.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodOneToThreeYears" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019fd7d0-1bf1-7c83-a525-3dca50f878f5_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of assets acquired and liabilities assumed</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired and Liability Assumed [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureName_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureName_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureName" xlink:to="lab_ecd_CoSelectedMeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_019fd7d0-1bf2-7c65-8c41-a382de1962fe_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate_019fd7d0-1b75-75f0-9d3d-3877342e47ae_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed rate</link:label>
    <link:label id="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate_label_en-US" xlink:label="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Percentage Bearing Fixed Interest, Percentage Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtPercentageBearingFixedInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:to="lab_us-gaap_LongTermDebtPercentageBearingFixedInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_019fd7d0-1b75-7f3c-b421-f4a6ab92c0df_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskLineItems" xlink:to="lab_us-gaap_ConcentrationRiskLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsCost_019fd7d0-1c60-719b-8be7-9a09cef9359d_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-20260930.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_wtm_OtherCountryMember_019fd7d0-1b75-7610-b85b-dadd1225cf72_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-20260930.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_EquitySecuritiesFvNiCost_019fd7d0-1bf1-7f89-a32d-8d79a98fc73b_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCost_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PercentageofRiskPremiumCeded_019fd7d0-1b75-73be-a103-d1babfee547e_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-20260930.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_wtm_PrivateEquityFundsAndHedgeFundsMember_019fd7d0-1b75-71b5-943c-833adcfeb513_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_019fd7d0-1b75-7e1a-8297-b345928e688c_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-20260930.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_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019fd7d0-1b75-790f-95f6-5b7cef1822d5_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-20260930.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear5Through10" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityDomain_019fd7d0-1bf1-7b58-8b8e-d6f63a382762_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityDomain" xlink:to="lab_us-gaap_CreditFacilityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fd7d0-1b75-7902-8491-3fd3e9c48ce8_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_019fd7d0-1b75-75ef-b0d8-0a6de431d88b_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_019fd7d0-1b75-77ea-8981-9d35c34cf62c_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Gross ending balance</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019fd7d0-1b75-7d6e-a9cc-8c56083e1be4_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operations:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FixedMaturitiesAndOtherShortTermInvestmentsMember_019fd7d0-1c60-78b6-aeec-a43e211142ff_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-20260930.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_CommonStockDividendsPerShareCashPaid_019fd7d0-1acb-76be-ad33-176013a1dc5c_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends paid per White Mountains&#8217;s common share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareCashPaid_label_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Dividends, Per Share, Cash Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockDividendsPerShareCashPaid"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:to="lab_us-gaap_CommonStockDividendsPerShareCashPaid" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote</link:label>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_label_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EquityValuationAssumptionDifferenceFnTextBlock"/>
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    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_019fd7d0-1b75-72fb-8461-13002b183dab_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019fd7d0-1bf1-7c32-a8af-8b1c6903152a_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_019fd7d0-1bf1-72c9-a5d1-d887e19eb0b7_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net ending balance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_019fd7d0-1c60-7e95-b766-0ebc7c4f4d9f_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 (in percent)</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnSaleOfInvestments_019fd7d0-1bf1-73f7-b903-3457803bfe0b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less: net realized and unrealized gains (losses) on investment securities sold during the period</link:label>
    <link:label id="lab_us-gaap_GainLossOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnSaleOfInvestments" xlink:to="lab_us-gaap_GainLossOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition_019fd7d0-1bf2-7634-94a9-881422ad1266_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recognition of equity-based compensation expense of subsidiaries</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">APIC, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:to="lab_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationOtherLongtermIncentivePlansRequisiteServicePeriodRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment_019fd7d0-1bf2-7128-9350-4e8182c88410_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sales of fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale, Debt Security, Trading, and Equity Security, FV-NI, Held-for-Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:to="lab_us-gaap_ProceedsFromSaleOfTradingSecuritiesHeldforinvestment" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageParentAfterEquityIncentives_019fd7d0-1bf1-7573-96ca-08f3dbb20d8a_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-20260930.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_019fd7d0-1bf2-77b3-aa56-01610bf8a740_negatedLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Repurchases and retirements of common shares</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased and Retired During Period, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedAndRetiredDuringPeriodValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:to="lab_us-gaap_StockRepurchasedAndRetiredDuringPeriodValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAbstract_019fd7d0-1c60-75d6-ba5e-4f7955860b9d_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impaired [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillImpairedAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAbstract" xlink:to="lab_us-gaap_GoodwillImpairedAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_019fd7d0-1b75-7a2b-9885-dcf60f705235_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019fd7d0-1b75-7da8-8fc4-0da4f07182f6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019fd7d0-1b75-7646-83c9-0900902ed51a_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_label_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:to="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedManagementEquityIncentiveMember_019fd7d0-1bf1-7a63-a579-08cdf1d4d9a5_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-20260930.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_wtm_PaymentsToAcquireSurplusNotes_019fd7d0-1b75-7b50-95a6-fdebf7bb01f0_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-20260930.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_srt_ScenarioUnspecifiedDomain_019fd7d0-1bf2-7029-96bd-52ee97f3a839_terseLabel_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_label_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioUnspecifiedDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScenarioUnspecifiedDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioUnspecifiedDomain" xlink:to="lab_srt_ScenarioUnspecifiedDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BroadStreetMember_019fd7d0-1b75-77e1-97e6-61a58ffcb2e6_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-20260930.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_wtm_OtherSignificantTransactionsTable_019fd7d0-1c60-7df9-83c4-95acfefb6165_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-20260930.xsd#wtm_OtherSignificantTransactionsTable"/>
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    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_019fd7d0-1b75-78a8-ba96-0c67ac7a6ff6_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>
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    <link:label id="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock_019fd7d0-1c60-7ab9-a8bd-240778f26de2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of carrying values for other long-term investments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Investments Not Readily Marketable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfOtherInvestmentsNotReadilyMarketableTextBlock"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019fd7d0-1b75-7779-95b7-ae7199bebcf1_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE paid relating to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
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    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_019fd7d0-1c60-7dfd-8956-ed6f97d6b50d_terseLabel_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk</link:label>
    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_label_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk [Member]</link:label>
    <link:label id="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember_documentation_en-US" xlink:label="lab_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Private Equity and Hedge Fund Concentration Risk</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PrivateEquityAndHedgeFundConcentrationRiskMember" xlink:href="wtm-20260930.xsd#wtm_PrivateEquityAndHedgeFundConcentrationRiskMember"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired to Liability Assumed, Excess (Less), and Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet"/>
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    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_019fd7d0-1c60-796f-9fbc-3e9884d12f8f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestLineItems_019fd7d0-1acb-753f-af79-70c0cfec48ca_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Line Items]</link:label>
    <link:label id="lab_us-gaap_MinorityInterestLineItems_label_en-US" xlink:label="lab_us-gaap_MinorityInterestLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestLineItems" xlink:to="lab_us-gaap_MinorityInterestLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_019fd7d0-1bf1-7c82-8be6-368cef9cc83b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock_019fd7d0-1bf2-790e-9e0a-4b86ef33a97e_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Securities</link:label>
    <link:label id="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment in Debt and Equity Securities and Other Trading Assets [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsInDebtAndMarketableEquitySecuritiesAndCertainTradingAssetsDisclosureTextBlock"/>
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    <link:label id="lab_wtm_ScheduleOfUndistributedEarningsTableTextBlock_019fd7d0-1bf1-7591-8882-6b3918c22dcf_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>
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    <link:label id="lab_us-gaap_PaymentsOfDividendsCommonStock_019fd7d0-1c60-7c95-a364-39f50e3d1e80_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>
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    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_019fd7d0-1c60-7622-b5e0-810800045d04_terseLabel_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned insurance premiums</link:label>
    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_label_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net, Adjusted</link:label>
    <link:label id="lab_wtm_PremiumsEarnedNetAdjusted_documentation_en-US" xlink:label="lab_wtm_PremiumsEarnedNetAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net, Adjusted</link:label>
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    <link:label id="lab_wtm_PerformancePeriodThreeMember_019fd7d0-1b75-775c-abed-4445643eb02f_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>
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    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsPremiumReceivedOverContractPeriodTableTextBlock_019fd7d0-1c60-7da0-922b-77b1e74de553_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>
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    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_019fd7d0-1bf1-7cef-870c-fc87ba8fb978_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>
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    <link:label id="lab_wtm_OtherOperationsDebtMember_019fd7d0-1b75-751f-8d7b-f8f929ce6843_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-20260930.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_SubordinatedDebtMember_019fd7d0-1b75-7d30-9fc8-8f9468b73014_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubordinatedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebtMember" xlink:to="lab_us-gaap_SubordinatedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems_019fd7d0-1b75-7270-903d-ed644a73319f_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operations [Line Items]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operations [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsumerSectorMember_019fd7d0-1bf2-7cb8-93c1-39766a77aec2_terseLabel_en-US" xlink:label="lab_us-gaap_ConsumerSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consumer</link:label>
    <link:label id="lab_us-gaap_ConsumerSectorMember_label_en-US" xlink:label="lab_us-gaap_ConsumerSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consumer Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsumerSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsumerSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConsumerSectorMember" xlink:to="lab_us-gaap_ConsumerSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtPnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:to="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeTable_019fd7d0-1acb-7702-95a9-e91c7bee6458_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative [Table]</link:label>
    <link:label id="lab_us-gaap_DerivativeTable_label_en-US" xlink:label="lab_us-gaap_DerivativeTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeTable" xlink:to="lab_us-gaap_DerivativeTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCSegmentMember_019fd7d0-1bf1-74d2-994f-7732d75299c3_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-20260930.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_RevenuesFromExternalCustomers_019fd7d0-1b75-7705-a128-a9d026227154_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-20260930.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_NetCashProvidedByUsedInInvestingActivitiesAbstract_019fd7d0-1b75-78f3-8da5-a15ac846182c_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable_019fd7d0-1c60-789b-89c1-5551f06b0196_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations [Table]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentDomain_019fd7d0-1b75-7e11-920e-7de4b1a93224_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:label id="lab_us-gaap_SegmentDomain_label_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentDomain" xlink:to="lab_us-gaap_SegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_019fd7d0-1bf1-7d7c-87e7-beae98eb7e29_terseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementScenarioAxis_019fd7d0-1bf1-79b2-8a3e-9ba4f57134b1_terseLabel_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:label id="lab_srt_StatementScenarioAxis_label_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementScenarioAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StatementScenarioAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementScenarioAxis" xlink:to="lab_srt_StatementScenarioAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_019fd7d0-1c60-75d4-84b6-1692de2d9d78_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net&#160;Foreign Currency Gains (Losses)</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_label_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Net Foreign Currency Gain (Loss)</link:label>
    <link:label id="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss_documentation_en-US" xlink:label="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Net Foreign Currency Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:href="wtm-20260930.xsd#wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:to="lab_wtm_EquityMethodInvestmentNetForeignCurrencyGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupClassificationDomain_019fd7d0-1bf1-7355-8abf-9cb1a7026a44_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Domain]</link:label>
    <link:label id="lab_us-gaap_DisposalGroupClassificationDomain_label_en-US" xlink:label="lab_us-gaap_DisposalGroupClassificationDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Classification [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupClassificationDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupClassificationDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupClassificationDomain" xlink:to="lab_us-gaap_DisposalGroupClassificationDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_019fd7d0-1b75-76ff-8114-8c14613761f7_negatedLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Unamortized issuance cost</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersMember_019fd7d0-1bf1-713a-b32a-9f7a32362d39_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-20260930.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_ArkInsuranceHoldingsLimitedWMOutriggerReSegmentMember_019fd7d0-1b75-7afb-864d-edf051760359_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_019fd7d0-1b75-7c77-8c9b-22d7e3e955d2_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-20260930.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_OtherLongTermInvestmentsUnrealizedGain_019fd7d0-1bf1-7ba3-a1b1-f1fc1338c213_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-20260930.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_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoActuallyPaidCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoActuallyPaidCompAmt" xlink:to="lab_ecd_PeoActuallyPaidCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredOtherTaxExpenseBenefit_019fd7d0-1bf2-7c07-9c7d-ff38934383c8_verboseLabel_en-US" xlink:label="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net deferred tax benefit</link:label>
    <link:label id="lab_us-gaap_DeferredOtherTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Other Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredOtherTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:to="lab_us-gaap_DeferredOtherTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredDebtMember_019fd7d0-1c60-72a5-9d32-b8898fa97db7_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Debt</link:label>
    <link:label id="lab_us-gaap_SecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredDebtMember" xlink:to="lab_us-gaap_SecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationNonredeemableNoncontrollingInterestAcquired_019fd7d0-1c60-7f8e-a01b-26cf61c47f31_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-20260930.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_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal_019fd7d0-1bf1-70ae-b0bd-78ea21a5ea22_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-20260930.xsd#wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:to="lab_wtm_DisposalGroupNotDiscontinuedOperationNetGainLossOnDisposal" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RestrictedCashHeldForSale_019fd7d0-1bf2-7d6a-9da0-b42171c2d86c_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-20260930.xsd#wtm_RestrictedCashHeldForSale"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_RestrictedCashHeldForSale" xlink:to="lab_wtm_RestrictedCashHeldForSale" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_019fd7d0-1c60-7acd-8867-af8deb304b7b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stated margin</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_019fd7d0-1bf2-7e6a-9e0d-a7c1d39a6f58_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DividendsCommonStockCash_019fd7d0-1b75-70ee-8b43-33c108d1b472_negatedLabel_en-US" xlink:label="lab_us-gaap_DividendsCommonStockCash" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Dividends declared on common shares</link:label>
    <link:label id="lab_us-gaap_DividendsCommonStockCash_label_en-US" xlink:label="lab_us-gaap_DividendsCommonStockCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends, Common Stock, Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DividendsCommonStockCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DividendsCommonStockCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DividendsCommonStockCash" xlink:to="lab_us-gaap_DividendsCommonStockCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquity_019fd7d0-1b75-70e2-8d76-80c1d4c57d75_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_019fd7d0-1b75-7088-adf1-aaef40819c1b_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total White Mountains&#8217;s common shareholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution_019fd7d0-1bf2-7c66-9db0-c7ed24c77e10_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-20260930.xsd#wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:to="lab_wtm_PaymentsToAcquireInterestInSubsidiariesAndAffiliatesAdditionalContribution" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityListingsExchangeAxis_019fd7d0-1c60-709a-b0fc-757ad04bcc95_terseLabel_en-US" xlink:label="lab_dei_EntityListingsExchangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Listings, Exchange [Axis]</link:label>
    <link:label id="lab_dei_EntityListingsExchangeAxis_label_en-US" xlink:label="lab_dei_EntityListingsExchangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Listings, Exchange [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityListingsExchangeAxis" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityListingsExchangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityListingsExchangeAxis" xlink:to="lab_dei_EntityListingsExchangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember_019fd7d0-1bf1-7847-b8ec-e85aefd5b829_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group, Disposed of by Sale, Not Discontinued Operations</link:label>
    <link:label id="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember_label_en-US" xlink:label="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Disposed of by Sale, Not Discontinued Operations [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:to="lab_us-gaap_DisposalGroupDisposedOfBySaleNotDiscontinuedOperationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesGrantsInPeriod_019fd7d0-1b75-7cc0-a6a8-febe3131999c_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-20260930.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_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments_019fd7d0-1b75-72ff-a21c-da6ce0653d3f_terseLabel_en-US" xlink:label="lab_wtm_GoodwillAndIntangibleAssetsMeasurementPeriodAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_wtm_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-20260930.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_AssetsAbstract_019fd7d0-1b75-776c-8dff-79523fa94c9d_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MeasurementInputPreTaxTerminalCashFlowExitMultipleMember_019fd7d0-1b75-7964-8e85-699f324b0096_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-20260930.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_GoodwillAndIntangibleAssetImpairment_019fd7d0-1b75-79fb-a9aa-5031067121a7_totalLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible asset impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetImpairment_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetImpairment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeCapInterestRate_019fd7d0-1b75-7eaa-a5a3-68c9c87b50c8_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeCapInterestRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative, cap interest rate</link:label>
    <link:label id="lab_us-gaap_DerivativeCapInterestRate_label_en-US" xlink:label="lab_us-gaap_DerivativeCapInterestRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Cap Interest Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeCapInterestRate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeCapInterestRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeCapInterestRate" xlink:to="lab_us-gaap_DerivativeCapInterestRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillPurchaseAccountingAdjustments_019fd7d0-1b75-74b5-8178-e9429780edaf_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_us-gaap_GoodwillPurchaseAccountingAdjustments_label_en-US" xlink:label="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillPurchaseAccountingAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:to="lab_us-gaap_GoodwillPurchaseAccountingAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable_019fd7d0-1b75-7566-91de-ad2a40cb485f_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Table]</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Claim Liability [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsClaimLiabilityTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PerformanceSharesMember_019fd7d0-1b75-77a8-b377-1ec9a212e701_terseLabel_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance Share</link:label>
    <link:label id="lab_us-gaap_PerformanceSharesMember_label_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Shares [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PerformanceSharesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PerformanceSharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PerformanceSharesMember" xlink:to="lab_us-gaap_PerformanceSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fd7d0-1bf2-7fda-82cf-7dff3bda6e4b_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_019fd7d0-1bf2-7d8d-8c9b-716f332f437c_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_019fd7d0-1bf2-783b-9cb7-5cc87549682f_netLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InsuranceLinkedSecuritiesFundsMember_019fd7d0-1b75-7b25-bb36-071fa6b79b61_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-20260930.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_wtm_Ark2021SubordinatedNotesTranche1Member_019fd7d0-1bf2-743d-ab8d-2aabfdeacd9d_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-20260930.xsd#wtm_Ark2021SubordinatedNotesTranche1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:to="lab_wtm_Ark2021SubordinatedNotesTranche1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_019fd7d0-1bf1-700e-8d1e-4ab0eaba05f9_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCentralIndexKey"/>
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    <link:label id="lab_wtm_BambooInsuranceServicesLLCSegmentMember_019fd7d0-1b75-7f9c-a523-5c3918d4b4a5_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-20260930.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_us-gaap_ScheduleOfGuaranteeObligationsTable_019fd7d0-1acb-723e-9b13-b4f3ad9fc11e_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Guarantor Obligations [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGuaranteeObligationsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantor Obligation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfGuaranteeObligationsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:to="lab_us-gaap_ScheduleOfGuaranteeObligationsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember"/>
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    <link:label id="lab_wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember_019fd7d0-1b75-713e-9503-41eebfdcfea4_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-20260930.xsd#wtm_DistinguishedPartnersSegmentNetOfReconcilingItemsMember"/>
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    <link:label id="lab_us-gaap_LiabilitiesOfDisposalGroupIncludingDiscontinuedOperation_019fd7d0-1b75-7f96-98a4-3d20c437f9fd_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">Liabilities held for sale - Other</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>
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    <link:label id="lab_srt_OwnershipAxis_019fd7d0-1c60-7d32-a49b-4e0be1b5e396_terseLabel_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:label id="lab_srt_OwnershipAxis_label_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_OwnershipAxis"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_019fd7d0-1b75-7cba-9d7f-31e28560f0fe_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_019fd7d0-1b75-7c14-8b75-af40272066a7_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_019fd7d0-1bf1-7c77-a917-f8bff89aaa12_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FixedMaturitiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FixedMaturitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FixedMaturitiesMember" xlink:to="lab_us-gaap_FixedMaturitiesMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments_label_en-US" xlink:label="lab_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Finite-Lived Intangible Assets, Attribution of Acquisition Adjustments</link:label>
    <link:label id="lab_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments_documentation_en-US" xlink:label="lab_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill and Finite-Lived Intangible Assets, Attribution of Acquisition Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:href="wtm-20260930.xsd#wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:to="lab_wtm_GoodwillAndFiniteLivedIntangibleAssetsAttributionOfAcquisitionAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_019fd7d0-1bf1-756e-8894-0f57a5f93beb_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">Schedule of Effects of reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_019fd7d0-1c60-70cd-8978-ec0872ccf9e0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis spread on variable rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UnderwritingCapacityMember_019fd7d0-1c60-7d77-9096-f1393d05f089_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-20260930.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_us-gaap_VariableRateDomain_019fd7d0-1b75-73df-a67c-b511d6a2fc0d_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateDomain" xlink:to="lab_us-gaap_VariableRateDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedStockMember_019fd7d0-1b75-77d4-8ac1-cfc7f2535bbc_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted Stock</link:label>
    <link:label id="lab_us-gaap_RestrictedStockMember_label_en-US" xlink:label="lab_us-gaap_RestrictedStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedStockMember" xlink:to="lab_us-gaap_RestrictedStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_019fd7d0-1c60-7faf-bde5-d1d67f0afc6f_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AOCI, after tax</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
    <link:label id="lab_ecd_AllIndividualsMember_label_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Individuals [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllIndividualsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllIndividualsMember" xlink:to="lab_ecd_AllIndividualsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FidusReLtd.Member_019fd7d0-1b75-78fd-a3a7-924a688d2f1a_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-20260930.xsd#wtm_FidusReLtd.Member"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
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    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_019fd7d0-1c60-75c0-8e9b-84dc9fc58aa3_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity contributions</link:label>
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    <link:label id="lab_us-gaap_StatementLineItems_019fd7d0-1bf1-7eab-8efd-d8dde13e9111_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>
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    <link:label id="lab_us-gaap_Assets_019fd7d0-1b75-7c3a-937d-b5a46a658b5a_terseLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
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    <link:label id="lab_us-gaap_PrivateEquityFundsMember_019fd7d0-1b75-7027-ae22-499090b7c9fe_terseLabel_en-US" xlink:label="lab_us-gaap_PrivateEquityFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Private equity funds</link:label>
    <link:label id="lab_us-gaap_PrivateEquityFundsMember_label_en-US" xlink:label="lab_us-gaap_PrivateEquityFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Private Equity Funds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrivateEquityFundsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrivateEquityFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrivateEquityFundsMember" xlink:to="lab_us-gaap_PrivateEquityFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_019fd7d0-1bf1-7b6d-9898-98453566984e_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesByIndustryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:to="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember_019fd7d0-1b75-75bc-ab18-10f4a3afff45_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Not Primary Beneficiary</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Not Primary Beneficiary [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:to="lab_us-gaap_VariableInterestEntityNotPrimaryBeneficiaryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_019fd7d0-1bf2-7a26-93d8-d94e414466e1_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Segments</link:label>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_label_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Segments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingSegmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingSegmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingSegmentsMember" xlink:to="lab_us-gaap_OperatingSegmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019fd7d0-1c60-79e3-8042-1c52deffe4ef_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities acquired</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_019fd7d0-1b75-7332-a25f-62020c343528_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Share-Based Incentive Compensation Plans</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoMember_terseLabel_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO</link:label>
    <link:label id="lab_ecd_PeoMember_label_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoMember" xlink:to="lab_ecd_PeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TradingSecurityFairValue_019fd7d0-1bf1-7fd8-9d80-796f8c05dd86_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-20260930.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_wtm_IntangibleAssetsMeasurementPeriodAdjustment_019fd7d0-1c60-70b5-a0a4-f2085813d10e_terseLabel_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement period adjustments</link:label>
    <link:label id="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment_label_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Measurement Period Adjustment</link:label>
    <link:label id="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment_documentation_en-US" xlink:label="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets, Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:href="wtm-20260930.xsd#wtm_IntangibleAssetsMeasurementPeriodAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:to="lab_wtm_IntangibleAssetsMeasurementPeriodAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_019fd7d0-1bf1-7f9e-ac6c-723fd441511a_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskReinsurerDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:to="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_019fd7d0-1b75-7b22-a418-edc4785e0968_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer Concentration Risk</link:label>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurerConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:to="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Goodwill_019fd7d0-1acb-75f4-8b9d-e0b641cf4ffb_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_019fd7d0-1acb-7e2b-bca8-522cf4ea9d68_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_019fd7d0-1acb-7189-bab3-3505b9d18ffb_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_019fd7d0-1acb-7a69-b2e2-1e4985780a5b_periodEndLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Goodwill, ending balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Goodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestAxis_019fd7d0-1b75-7085-9e6d-5f8e62d3cf80_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestAxis_label_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingAMBestAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestAxis" xlink:to="lab_srt_CreditRatingAMBestAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock_019fd7d0-1c60-774f-b588-2399d3eb58fe_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-20260930.xsd#wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:to="lab_wtm_ScheduleOfNonvestedPerformanceShareActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsMember_019fd7d0-1bf1-7318-86b8-729308192428_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow_019fd7d0-1acb-7e43-bcd5-d520fbd70822_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-20260930.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:to="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedHeldInEscrow" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_019fd7d0-1c60-7ce8-9257-bbed8b53b2db_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility</link:label>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_019fd7d0-1c60-7be2-b272-71fdb5b2e06c_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other equity method eligible investments more than or equal to 50.0%</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_label_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, More Than or Equal to Fifty Percent [Member]</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember_documentation_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, More Than Fifty Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:href="wtm-20260930.xsd#wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:to="lab_wtm_EquityMethodEligibleInvestmentsMoreThanOrEqualToFiftyPercentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_019fd7d0-1bf1-7a3b-a3a1-c96a7e075e2b_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Shareholders' Equity</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019fd7d0-1bf2-7751-9313-19539d989321_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, outstanding shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesOutstanding" xlink:to="lab_us-gaap_CommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgDiscLineItems"/>
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    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_019fd7d0-1bf1-7c6f-9ef7-4801817addec_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of the fair value and carrying value of financial instruments</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByBalanceSheetGroupingTextBlock"/>
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    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_019fd7d0-1bf1-755e-ba1b-e743836c7b38_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt securities issued by corporations</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NetUnrealizedGainsLossesOnInvestments_019fd7d0-1bf2-777f-ab06-8cf1671a088e_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-20260930.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_EarningsPerShareDiluted_019fd7d0-1c60-76b1-9275-57ff40aeae4c_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (loss) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PerformancePeriodTwoMember_019fd7d0-1bf1-7840-bd50-8b0a35aa9b62_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-20260930.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_UnrealizedGainLossOnInvestments_019fd7d0-1bf1-7106-a12a-47d2ea64184a_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_019fd7d0-1bf1-72fc-a74b-e6f8fbb71b32_verboseLabel_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total net unrealized investment gains (losses) recognized during the period on Level 3 investments held at the end of period</link:label>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrealizedGainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnrealizedGainLossOnInvestments"/>
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    <link:label id="lab_wtm_EquityMethodInvestmentsAbstract_019fd7d0-1bf1-7bff-8590-08fe523cd32e_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-20260930.xsd#wtm_EquityMethodInvestmentsAbstract"/>
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    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019fd7d0-1acb-7156-b715-cbd8af273628_negatedLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
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    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable_019fd7d0-1c60-7d9b-a9d1-0a8aeab07bef_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Table]</link:label>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable_label_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation, Less-than-Wholly-Owned Subsidiary, Parent Ownership Interest, Effect of Change [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetTable"/>
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    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_019fd7d0-1b75-71ce-8951-36bc3c183d97_negatedTerseLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in accrued incentive compensation &#8212; Other Operations</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Accrued Bonuses</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInAccruedBonuses_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInAccruedBonuses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Accrued Bonuses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInAccruedBonuses" xlink:href="wtm-20260930.xsd#wtm_IncreaseDecreaseInAccruedBonuses"/>
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    <link:label id="lab_srt_OwnershipDomain_019fd7d0-1bf1-712d-a60c-a325775541d9_terseLabel_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:label id="lab_srt_OwnershipDomain_label_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_OwnershipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipDomain" xlink:to="lab_srt_OwnershipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain_019fd7d0-1bf2-73b4-a7b5-86bb3248af18_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesTradingUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:to="lab_us-gaap_DebtSecuritiesTradingUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_019fd7d0-1bf1-7687-9300-73cc6f418506_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskAxis" xlink:to="lab_us-gaap_CededCreditRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_019fd7d0-1bf2-7dda-9f9e-89e8a927578c_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net written premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDate_019fd7d0-1b75-7921-9dec-12616c6373e8_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>
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    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_019fd7d0-1b75-71b5-8fc6-4dc1592beb50_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-based Payment Arrangement [Abstract]</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_019fd7d0-1bf1-74ec-972b-fbf74dc22113_terseLabel_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Limited liability company or limited partnership, members or limited partners, ownership interest</link:label>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_label_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Limited Liability Company or Limited Partnership, Members or Limited Partners, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:to="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_019fd7d0-1c60-7efa-afef-32f1af6b608e_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of significant equity method eligible investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsPrincipalBalance_019fd7d0-1bf1-7aec-9d6c-e6935d37a492_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-20260930.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_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue_019fd7d0-1c60-7fc6-9e00-3adc667c6bc6_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling interest acquired</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquisition of Less than 100 Percent, Noncontrolling Interest, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:to="lab_us-gaap_BusinessCombinationAcquisitionOfLessThan100PercentNoncontrollingInterestFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:to="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019fd7d0-1b75-7f31-a748-7378e72e4e57_totalLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total other intangible assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember_019fd7d0-1b75-7d3b-8f91-e263c3879d10_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total agency</link:label>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember_label_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage-Backed Security, Issued by US Government-Sponsored Enterprise [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:to="lab_us-gaap_MortgageBackedSecuritiesIssuedByUSGovernmentSponsoredEnterprisesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsegmentsDomain_019fd7d0-1b75-7ced-94b7-32fdea8eff37_terseLabel_en-US" xlink:label="lab_us-gaap_SubsegmentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsegments [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsegmentsDomain_label_en-US" xlink:label="lab_us-gaap_SubsegmentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsegments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsegmentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsegmentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsegmentsDomain" xlink:to="lab_us-gaap_SubsegmentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019fd7d0-1c60-706d-9a6c-56317e817ea8_negatedLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Sales and distributions</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Sales</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment_019fd7d0-1c60-74a2-aa00-3e3d07cab824_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Investment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationInvestment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_019fd7d0-1bf1-7f56-af42-7572d7e4daec_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRedemptionWrittenNoticePeriod_019fd7d0-1bf1-7772-9f2b-8d4fb9895bab_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-20260930.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_wtm_OtherShortTermInvestmentsMember_019fd7d0-1bf2-7f48-9c9e-01dfec5e5424_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-20260930.xsd#wtm_OtherShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherShortTermInvestmentsMember" xlink:to="lab_wtm_OtherShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduInvestmentManagementLLCMember_019fd7d0-1bf2-7c4c-bb5b-f15bf65cd723_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-20260930.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_HGGlobal2026SeniorNotesMember_019fd7d0-1c60-7157-a4f9-674e7f40b189_terseLabel_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes</link:label>
    <link:label id="lab_wtm_HGGlobal2026SeniorNotesMember_label_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes [Member]</link:label>
    <link:label id="lab_wtm_HGGlobal2026SeniorNotesMember_documentation_en-US" xlink:label="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global 2026 Senior Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobal2026SeniorNotesMember" xlink:href="wtm-20260930.xsd#wtm_HGGlobal2026SeniorNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HGGlobal2026SeniorNotesMember" xlink:to="lab_wtm_HGGlobal2026SeniorNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AMBestAMinusRatingMember_019fd7d0-1b75-74fc-a775-98ef36570f76_terseLabel_en-US" xlink:label="lab_srt_AMBestAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">A- to A</link:label>
    <link:label id="lab_srt_AMBestAMinusRatingMember_label_en-US" xlink:label="lab_srt_AMBestAMinusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AM Best, A- Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AMBestAMinusRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AMBestAMinusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AMBestAMinusRatingMember" xlink:to="lab_srt_AMBestAMinusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SupplementalTrustMember_019fd7d0-1c60-75bd-84ba-423a759ee1e9_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-20260930.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_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019fd7d0-1c60-7b9b-8274-39a6562bc168_terseLabel_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturities, Excluding Asset-Backed Securities And Collateralized Loan Obligations</link:label>
    <link:label id="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_label_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities, Excluding Asset-Backed Securities And Collateralized Loan Obligations [Member]</link:label>
    <link:label id="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_documentation_en-US" xlink:label="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Represents the fixed maturity investments and convertible fixed maturity investments excluding mortgage-backed securities, asset-backed securities and preferred stock.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:href="wtm-20260930.xsd#wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:to="lab_wtm_FixedMaturitiesExcludingAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCountryMember_019fd7d0-1c60-7cf3-8f6f-0c311cedf9c1_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign</link:label>
    <link:label id="lab_us-gaap_ForeignCountryMember_label_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction, Foreign [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCountryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCountryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCountryMember" xlink:to="lab_us-gaap_ForeignCountryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DelayedDrawTermLoanMember_019fd7d0-1c60-7b6a-a273-554a18f21bd7_terseLabel_en-US" xlink:label="lab_us-gaap_DelayedDrawTermLoanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Delayed Draw Term Loan</link:label>
    <link:label id="lab_us-gaap_DelayedDrawTermLoanMember_label_en-US" xlink:label="lab_us-gaap_DelayedDrawTermLoanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Delayed Draw Term Loan (DDTL) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DelayedDrawTermLoanMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DelayedDrawTermLoanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DelayedDrawTermLoanMember" xlink:to="lab_us-gaap_DelayedDrawTermLoanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedManagingMember_019fd7d0-1acb-7335-b2e5-d8e960d8b14d_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-20260930.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_wtm_DividendsCommonStockCashNetOfRestrictedStock_019fd7d0-1c60-7cdc-baf1-87b601730fa3_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-20260930.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_ForeignGovernmentDebtSecuritiesMember_019fd7d0-1bf1-7084-9f29-fb1624257dea_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign government and agency obligations</link:label>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Security, Government, Non-US [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredPercentageOfBasicUnitsOutstanding_019fd7d0-1bf1-7ef8-9e7f-519df4066e22_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-20260930.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_ecd_Rule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:to="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019fd7d0-1b75-7e13-a80f-b4530b074e42_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, issued shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019fd7d0-1c60-742a-a95e-33c387b0e6ba_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_019fd7d0-1c60-7801-a30f-352cb81693c6_periodEndLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_019fd7d0-1c60-745d-acac-a8c219543a14_terseLabel_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and LAE</link:label>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_label_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Adjusted</link:label>
    <link:label id="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted_documentation_en-US" xlink:label="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:href="wtm-20260930.xsd#wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:to="lab_wtm_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashDistributionReceived_019fd7d0-1acb-742e-bb44-a1790910ab76_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-20260930.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_srt_ProductsAndServicesDomain_019fd7d0-1c60-7b95-9d3b-5362018a293b_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentFixedMaturitySecuritiesCreditQualityIndicatorsTableTextBlock_019fd7d0-1c60-7af7-8c99-ad71da905c1c_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-20260930.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_us-gaap_VariableInterestEntityLineItems_019fd7d0-1c60-7ab5-a04d-3f780cce49c5_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityLineItems" xlink:to="lab_us-gaap_VariableInterestEntityLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsOtherMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsNotDesignatedAsHedgingInstrumentsGainLossNet_019fd7d0-1c60-70af-8278-786d5b31eae3_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_wtm_CommonStockAndEquityMethodInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_CommonStockAndEquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Common Stock And Equity Method Investments</link:label>
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    <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>
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    <link:label id="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees_019fd7d0-1c60-7894-ba37-ba4b1b50a7a9_terseLabel_en-US" xlink:label="lab_wtm_OtherIncomeNetOfPremiumsEarnedAndInsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other revenues</link:label>
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    <link:label id="lab_us-gaap_MinorityInterestTable_019fd7d0-1bf1-700a-adea-56f58b6e925e_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Table]</link:label>
    <link:label id="lab_us-gaap_MinorityInterestTable_label_en-US" xlink:label="lab_us-gaap_MinorityInterestTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Table]</link:label>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
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    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock_019fd7d0-1bf2-7b00-bc12-07d2612f684d_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held for Sale</link:label>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Groups, Including Discontinued Operations, Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupsIncludingDiscontinuedOperationsDisclosureTextBlock"/>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019fd7d0-1c60-7c0d-9bc0-72545e4a245c_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current year losses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_ecd_AwardGrantDateFairValue_terseLabel_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value as of Grant Date</link:label>
    <link:label id="lab_ecd_AwardGrantDateFairValue_label_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardGrantDateFairValue" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardGrantDateFairValue"/>
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    <link:label id="lab_wtm_LossesAndLossAdjustmentExpenseAbstract_019fd7d0-1c60-7327-9ec9-ab5864c9adaf_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>
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    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiability_019fd7d0-1b75-7088-af4a-1c71b74402e6_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>
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    <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>
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    <link:label id="lab_srt_AMBestBPlusPlusRatingMember_019fd7d0-1b75-7d2d-951e-33a23fec8518_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>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInTemporaryEquityRollForward_019fd7d0-1acb-7751-a898-9895e41e5b47_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>
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    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember_019fd7d0-1b75-7019-aab2-0070135f336f_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-20260930.xsd#wtm_ArkInsuranceHoldingsLimitedOutriggerMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedOutriggerMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTableTextBlock" xlink:to="lab_ecd_PvpTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent_019fd7d0-1b75-7a6c-a8cd-53215a3704e1_terseLabel_en-US" xlink:label="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued incentive compensation</link:label>
    <link:label id="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accrued Bonuses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedBonusesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccruedBonusesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
    <link:label id="lab_ecd_TrdArrDuration_label_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Duration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrDuration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrDuration" xlink:to="lab_ecd_TrdArrDuration" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_019fd7d0-1bf2-7a56-b94e-ee781159f856_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Partners</link:label>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_label_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary - WTM Partners [Member]</link:label>
    <link:label id="lab_wtm_SubsidiaryWTMPartnersMember_documentation_en-US" xlink:label="lab_wtm_SubsidiaryWTMPartnersMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary - WTM Partners</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryWTMPartnersMember" xlink:href="wtm-20260930.xsd#wtm_SubsidiaryWTMPartnersMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryWTMPartnersMember" xlink:to="lab_wtm_SubsidiaryWTMPartnersMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_IncreaseDecreaseInPremiumsCommissionsAndFeesReceivable_019fd7d0-1b75-7367-a433-3006f3c94dfa_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-20260930.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_srt_ConsolidationItemsAxis_019fd7d0-1b75-7f19-9999-d5e03aca7d85_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:label id="lab_srt_ConsolidationItemsAxis_label_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsAxis" xlink:to="lab_srt_ConsolidationItemsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_019fd7d0-1b75-71bd-9300-b32f294ae5c3_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_019fd7d0-1c60-7046-96db-6968f7893e3b_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock_019fd7d0-1c60-7595-afc7-5c33e60ae4c9_terseLabel_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation and Significant Accounting Policies</link:label>
    <link:label id="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Organization, Consolidation, Basis of Presentation, Business Description and Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_OrganizationConsolidationBasisOfPresentationBusinessDescriptionAndAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:to="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019fd7d0-1b75-7083-9247-e9bce2f2cb85_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, acquisition date fair value</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_019fd7d0-1acb-7d55-9e2d-08c719f1f959_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestDomain_019fd7d0-1bf1-7c6d-a8e0-35daf4d37733_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestDomain_label_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingAMBestDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestDomain" xlink:to="lab_srt_CreditRatingAMBestDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_019fd7d0-1bf2-75bf-add7-0643c936ac9a_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Vesting Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardVestingPeriod1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYear10_019fd7d0-1bf2-7149-9eb9-cebc9a0bcfd0_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-20260930.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_GoodwillRollForward_019fd7d0-1b75-72ff-ac3d-a727ad413aed_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillRollForward" xlink:to="lab_us-gaap_GoodwillRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019fd7d0-1b75-7cca-9c9e-a2e08462e7d9_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradeNamesMember_019fd7d0-1bf2-7438-b743-da4ccb475c35_terseLabel_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trade names</link:label>
    <link:label id="lab_us-gaap_TradeNamesMember_label_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trade Names [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradeNamesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradeNamesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradeNamesMember" xlink:to="lab_us-gaap_TradeNamesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_019fd7d0-1bf2-785e-a0c4-0de964cd3a74_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of mortgage and asset-backed securities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019fd7d0-1bf1-7519-875c-0a988de9bfdd_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_019fd7d0-1acb-7a93-80db-01fe96df33b5_terseLabel_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_label_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited [Member]</link:label>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedMember_documentation_en-US" xlink:label="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark Insurance Holdings Limited [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ArkInsuranceHoldingsLimitedMember" xlink:href="wtm-20260930.xsd#wtm_ArkInsuranceHoldingsLimitedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommonStockOtherMember_019fd7d0-1bf1-7c16-8cc9-deffdee460a0_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-20260930.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_FairValueDisclosuresTextBlock_019fd7d0-1b75-7af7-865c-0e3ebf1fa217_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value of Financial Instruments</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_019fd7d0-1b75-74ac-a41b-da35f80fe608_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized&#160;Cost</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Amortized Cost, after Allowance for Credit Loss, Maturity, Allocated and Single Maturity Date [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_019fd7d0-1b75-725e-96f6-2ae4853f3dc3_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level&#160;3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetPledgedAsCollateralMember_019fd7d0-1bf1-717e-8ab3-bec3b25aad31_terseLabel_en-US" xlink:label="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Pledged as Collateral</link:label>
    <link:label id="lab_us-gaap_AssetPledgedAsCollateralMember_label_en-US" xlink:label="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Pledged as Collateral [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetPledgedAsCollateralMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetPledgedAsCollateralMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetPledgedAsCollateralMember" xlink:to="lab_us-gaap_AssetPledgedAsCollateralMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Regulation114Member_019fd7d0-1bf2-7d16-947b-379b680fc3fa_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-20260930.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019fd7d0-1bf1-7097-8a4d-7166f54df4bc_periodStartLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning of period (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019fd7d0-1bf1-7ce9-bcab-b287638759d6_periodEndLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">End of period (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_019fd7d0-1bf1-7c96-9c3b-0d93dd56003c_verboseLabel_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total target performance shares outstanding (in shares)</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_label_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares</link:label>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares_documentation_en-US" xlink:label="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Performance Shares, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:href="wtm-20260930.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners_019fd7d0-1c60-74c3-84cf-86f4935ad640_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling percentage</link:label>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners_label_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Noncontrolling Owner</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:to="lab_us-gaap_MinorityInterestOwnershipPercentageByNoncontrollingOwners" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementGeographicalAxis_019fd7d0-1bf2-751d-a382-0eeed4b1d4e0_terseLabel_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:label id="lab_srt_StatementGeographicalAxis_label_en-US" xlink:label="lab_srt_StatementGeographicalAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographical [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementGeographicalAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StatementGeographicalAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementGeographicalAxis" xlink:to="lab_srt_StatementGeographicalAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCash_019fd7d0-1bf1-7d1b-9415-bfc24d361581_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCash_label_en-US" xlink:label="lab_us-gaap_RestrictedCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCash" xlink:to="lab_us-gaap_RestrictedCash" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerLiability_019fd7d0-1c60-7f74-9666-9f46bb0369be_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract liabilities</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerLiability_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerLiability" xlink:to="lab_us-gaap_ContractWithCustomerLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_019fd7d0-1b75-7c1d-964c-b28d661f3507_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">NAV</link:label>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:to="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_019fd7d0-1b75-7507-b905-042db3ce3d4a_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SignificantTransactionsTextBlock_019fd7d0-1b75-7832-8cd9-e8706e4161fb_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-20260930.xsd#wtm_SignificantTransactionsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SignificantTransactionsTextBlock" xlink:to="lab_wtm_SignificantTransactionsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LegalEntityAxis_019fd7d0-1b75-7bef-92ae-d7c6a39f7477_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:label id="lab_dei_LegalEntityAxis_label_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LegalEntityAxis" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_LegalEntityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LegalEntityAxis" xlink:to="lab_dei_LegalEntityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityInfrastructureFundMember_01a17e2a-93ef-705e-90a0-390ddffff745_terseLabel_en-US" xlink:label="lab_wtm_EquityInfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity infrastructure fund</link:label>
    <link:label id="lab_wtm_EquityInfrastructureFundMember_label_en-US" xlink:label="lab_wtm_EquityInfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Infrastructure Fund [Member]</link:label>
    <link:label id="lab_wtm_EquityInfrastructureFundMember_documentation_en-US" xlink:label="lab_wtm_EquityInfrastructureFundMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Infrastructure Fund</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityInfrastructureFundMember" xlink:href="wtm-20260930.xsd#wtm_EquityInfrastructureFundMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityInfrastructureFundMember" xlink:to="lab_wtm_EquityInfrastructureFundMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentLoanToValuePercentage_019fd7d0-1b75-7677-a0c6-cf0ff676c5f8_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-20260930.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_OtherAssetBackedSecuritiesMember_019fd7d0-1bf1-7fa5-9420-7bfecae9f1db_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-20260930.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_wtm_DebtInstrumentCovenantDebtToCapitalMaximum_019fd7d0-1bf1-700d-950d-3ae0f720fff1_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-20260930.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_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fd7d0-1bf1-747b-8e99-3bdaa0ef1abe_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_019fd7d0-1bf1-7153-aa27-2efc688d1947_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 $32.4 and $8.4, unrestricted cash held for sale of $0.4 and $36.6 and restricted cash held for sale of $0.0 and $100.2)</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Continuing Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ManagementRolloverShareholdersAdditionalSharesPercentage_019fd7d0-1c60-7a15-a2ca-e6e01ccd2ac0_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-20260930.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_us-gaap_EffectsOfReinsuranceTable_019fd7d0-1bf2-7e4e-9520-779434faf0a9_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicUndistributed_019fd7d0-1b75-75a0-bc77-09bd7f167e19_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Undistributed earnings (losses) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicUndistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic, Undistributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicUndistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicUndistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicUndistributed" xlink:to="lab_us-gaap_EarningsPerShareBasicUndistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonNeosMember_terseLabel_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-NEOs</link:label>
    <link:label id="lab_ecd_NonNeosMember_label_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-NEOs [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonNeosMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonNeosMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonNeosMember" xlink:to="lab_ecd_NonNeosMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019fd7d0-1c60-7f12-9780-7dcb4b4ec9c4_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership interest (as a percent)</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019fd7d0-1c60-7b74-8aef-ffce124fc375_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ownership Interest</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax_019fd7d0-1c60-7738-a454-b7aea90c6276_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain (loss) on investments, exchange rate effect</link:label>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax_label_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss), Foreign Currency Transaction, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCurrencyTransactionGainLossAfterTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:to="lab_us-gaap_ForeignCurrencyTransactionGainLossAfterTax" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_019fd7d0-1b75-7cb3-b42b-9272e1caa187_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_019fd7d0-1b75-7ce6-b2eb-9cb201423bd6_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_019fd7d0-1acb-7aef-a611-1832e9a0e9cb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Repurchases and retirements of common shares</link:label>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for Repurchase of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:to="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesMember_019fd7d0-1bf2-7426-9fb0-4cc1658397c3_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage-backed securities:</link:label>
    <link:label id="lab_us-gaap_MortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_MortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SignificantTransactionsAbstract_019fd7d0-1acb-7781-9de1-9cf21b9757c7_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-20260930.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_srt_RangeAxis_019fd7d0-1c60-7636-a544-6e3b7ff1987f_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_019fd7d0-1b75-72c6-9dbd-1d38d60ac9e2_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote</link:label>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_label_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NamedExecutiveOfficersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_019fd7d0-1bf2-795b-88ec-dfafc4eb34e8_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductOrServiceAxis_019fd7d0-1bf1-7dc7-bfb1-954ffd12cf8f_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:label id="lab_srt_ProductOrServiceAxis_label_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductOrServiceAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019fd7d0-1bf1-7c78-9353-63c4e2cdc83b_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_019fd7d0-1bf1-7de7-a6a5-7b2548f8d95a_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_019fd7d0-1bf2-78d8-846e-7c2a0dc8d0b9_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_019fd7d0-1bf2-7806-8b75-11863c9f1495_verboseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Change in fair value of contingent consideration &#8212; Ark</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Contingent Consideration, Change in Contingent Consideration, Liability, Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:to="lab_us-gaap_BusinessCombinationContingentConsiderationArrangementsChangeInAmountOfContingentConsiderationLiability1" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_019fd7d0-1b75-79fb-8352-2a469528e8e3_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_019fd7d0-1b75-71e7-825e-64f2cb7b55e5_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipMembersOrLimitedPartnersOwnershipInterestLookThroughBasis_019fd7d0-1b75-7920-8237-fefc2982dd0d_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-20260930.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_019fd7d0-1b75-772c-9847-49f4507c941b_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issued (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Shares Issued in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_019fd7d0-1c60-76df-bf9c-ae91331b8eed_terseLabel_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prefunded commitments</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_label_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Prefunded Commitments</link:label>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments_documentation_en-US" xlink:label="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Prefunded Commitments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:href="wtm-20260930.xsd#wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:to="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerSharePrefundedCommitments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoncontrollingInterestAbstract_019fd7d0-1b75-79c2-ad6f-0dc55d83e8f6_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Abstract]</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestAbstract_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestAbstract" xlink:to="lab_us-gaap_NoncontrollingInterestAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeContractTypeDomain_019fd7d0-1b75-79b3-879e-288718c1ec10_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeContractTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Contract [Domain]</link:label>
    <link:label id="lab_us-gaap_DerivativeContractTypeDomain_label_en-US" xlink:label="lab_us-gaap_DerivativeContractTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Contract [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeContractTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeContractTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeContractTypeDomain" xlink:to="lab_us-gaap_DerivativeContractTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentAggregateCost_019fd7d0-1acb-73e3-9d19-57ede4cc8b53_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost&#160;or Amortized Cost</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentAggregateCost_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Aggregate Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentAggregateCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentAggregateCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentAggregateCost" xlink:to="lab_us-gaap_EquityMethodInvestmentAggregateCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_019fd7d0-1c60-7156-9b01-1796399ad22b_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskByBenchmarkAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:to="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_01a17ff1-b9bc-7b32-809e-20b35e731d9a_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Payments of principal and interest</link:label>
    <link:label id="lab_wtm_PaymentsOfNotesReceivablePrincipalAndInterest_019fd7d0-1b75-7ee0-ab9a-783e280c7ff7_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-20260930.xsd#wtm_PaymentsOfNotesReceivablePrincipalAndInterest"/>
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    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent_019fd7d0-1b75-78a7-a5c6-81c8758e7a34_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>
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    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageFullyDilutedParent" xlink:href="wtm-20260930.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_LiabilitiesAndStockholdersEquity_019fd7d0-1bf2-7533-84f5-2968b6705018_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities, redeemable noncontrolling interests and equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019fd7d0-1bf1-727e-ba25-c283442961d3_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_019fd7d0-1bf1-7962-8642-0941d075fafa_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_019fd7d0-1bf1-79dd-99b4-6afb366a776a_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_019fd7d0-1bf1-7d5e-a064-478a0c0f0106_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Total goodwill and other intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Including Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_019fd7d0-1bf1-72f1-bd5c-4bedcf0c68fb_terseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net realized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_label_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Gains (Losses)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RealizedInvestmentGainsLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:to="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Stock Option</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_019fd7d0-1bf2-71b6-9d46-b716b77fab3f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases and contributions</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Purchases</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterest_019fd7d0-1acb-72d7-9fd0-d2b43579569a_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_019fd7d0-1acb-7388-89f5-0b2c85153c6b_verboseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable Noncontrolling Equity</link:label>
    <link:label id="lab_us-gaap_MinorityInterest_label_en-US" xlink:label="lab_us-gaap_MinorityInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterest" xlink:to="lab_us-gaap_MinorityInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_019fd7d0-1bf2-74de-a124-e39bfc5aafca_terseLabel_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementBusinessSegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:to="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_label_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Additional402vDisclosureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Additional402vDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_019fd7d0-1b75-7d14-863d-23e8b1a10af0_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_019fd7d0-1b75-7045-9a44-484f476446f1_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_019fd7d0-1b75-7ab3-8f25-eb128e1ceaac_totalLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity investments</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesDebt" xlink:to="lab_us-gaap_TradingSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TabularListTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tabular List, Table</link:label>
    <link:label id="lab_ecd_TabularListTableTextBlock_label_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tabular List [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TabularListTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TabularListTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TabularListTableTextBlock" xlink:to="lab_ecd_TabularListTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsAARatingMember_019fd7d0-1bf2-7a48-a737-c988180c9b0d_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsAARatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AA</link:label>
    <link:label id="lab_srt_StandardPoorsAARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsAARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AA Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsAARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsAARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsAARatingMember" xlink:to="lab_srt_StandardPoorsAARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_019fd7d0-1bf2-7322-9add-c836746571a0_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid-in surplus</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fd7d0-1b75-7d83-9f05-ff3e36f8554b_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_019fd7d0-1b75-7ea3-999f-042391fc35fa_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_019fd7d0-1b75-7ded-b6bf-5c03b72bbee2_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables on unpaid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019fd7d0-1bf2-75e4-958c-3743ad698230_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Reinsurance Recoverable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_019fd7d0-1c60-7447-9483-9aa5ae82c025_terseLabel_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties</link:label>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_label_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties [Member]</link:label>
    <link:label id="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember_documentation_en-US" xlink:label="lab_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Additional Investments, Insurance Regulators and Reinsurance Counterparties</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_AdditionalInvestmentsInsuranceRegulatorsAndReinsuranceCounterpartiesMember" xlink:href="wtm-20260930.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_wtm_IndefiniteLivedIntangibleAssetsExcludingGoodwillAcquisitionDateFairValue_019fd7d0-1c60-7b3c-be2d-057f0894a7d7_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-20260930.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_EquitySecuritiesFvNiUnrealizedLoss_019fd7d0-1bf1-7980-ad52-0168e93ee8f5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:to="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_label_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:to="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_019fd7d0-1c60-763e-bd94-87c10e49cfbc_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_019fd7d0-1c60-7eff-acdf-f797634d19c5_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums written</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_019fd7d0-1bf1-7adc-8db8-fd0d6ba88ee9_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of equity securities and other long-term investments</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate_019fd7d0-1b75-7f52-ae4b-2f3c2a9adfdd_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">October 1, 2026 - December 31, 2026</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, First Quarter</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedDuringFirstQuarterFollowingBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate_019fd7d0-1b75-7bb5-9c9d-d74a2de63b41_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedOneYearFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryHGGlobalMember_019fd7d0-1bf1-7ae6-9f39-8824ba44cdab_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-20260930.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_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear10_019fd7d0-1b75-7961-896f-8fc37277194e_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-20260930.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_us-gaap_DebtInstrumentMeasurementInput_019fd7d0-1b75-78c1-81a6-e51705c42945_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, measurement input</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentMeasurementInput_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentMeasurementInput" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentMeasurementInput" xlink:to="lab_us-gaap_DebtInstrumentMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAxis_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation:</link:label>
    <link:label id="lab_ecd_AdjToCompAxis_label_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToCompAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAxis" xlink:to="lab_ecd_AdjToCompAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CostOfSalesPolicyTextBlock_019fd7d0-1c60-7066-b958-1de8b1b9a88d_terseLabel_en-US" xlink:label="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost of Sales</link:label>
    <link:label id="lab_us-gaap_CostOfSalesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cost of Goods and Service [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfSalesPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfSalesPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostOfSalesPolicyTextBlock" xlink:to="lab_us-gaap_CostOfSalesPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantDebtServiceCoverageRatioMinimum_019fd7d0-1bf2-7b34-a883-4585adf4f936_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-20260930.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_wtm_AerospaceDefenseGovernmentSectorMember_019fd7d0-1bf2-74d3-a3b6-55609da85a38_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-20260930.xsd#wtm_AerospaceDefenseGovernmentSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_AerospaceDefenseGovernmentSectorMember" xlink:to="lab_wtm_AerospaceDefenseGovernmentSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_019fd7d0-1bf2-70e0-97b2-8d3a22c4628f_terseLabel_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt covenant, loan to value percent</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_label_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Loan to Value Ratio, Maximum</link:label>
    <link:label id="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum_documentation_en-US" xlink:label="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Loan to Value Ratio, Maximum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:href="wtm-20260930.xsd#wtm_DebtInstrumentCovenantLoanToValueRatioMaximum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:to="lab_wtm_DebtInstrumentCovenantLoanToValueRatioMaximum" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust_019fd7d0-1c60-78ce-9d68-9fb4793392ed_terseLabel_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued interest payment held in trust</link:label>
    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust_label_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments Of Accrued Interest Held In Trust</link:label>
    <link:label id="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust_documentation_en-US" xlink:label="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accrued interest payment on surplus notes issued by VIE. The interest is eliminated in consolidation with the primary beneficiary.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:href="wtm-20260930.xsd#wtm_RepaymentsOfAccruedInterestHeldInTrust"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:to="lab_wtm_RepaymentsOfAccruedInterestHeldInTrust" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationAxis_019fd7d0-1b75-7a77-a394-5e70772c68bf_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskCollateralizationAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Collateralization [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskCollateralizationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskCollateralizationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskCollateralizationAxis" xlink:to="lab_us-gaap_CededCreditRiskCollateralizationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BasesixMember_019fd7d0-1c60-7f0a-910c-935841e498d6_terseLabel_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basesix</link:label>
    <link:label id="lab_wtm_BasesixMember_label_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basesix [Member]</link:label>
    <link:label id="lab_wtm_BasesixMember_documentation_en-US" xlink:label="lab_wtm_BasesixMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Basesix</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BasesixMember" xlink:href="wtm-20260930.xsd#wtm_BasesixMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BasesixMember" xlink:to="lab_wtm_BasesixMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_Rule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:to="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_AggtErrCompAmt_label_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompAmt" xlink:to="lab_ecd_AggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPaidNet_019fd7d0-1bf2-7629-875b-1f255d7ce113_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Interest paid</link:label>
    <link:label id="lab_us-gaap_InterestPaidNet_label_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Paid, Excluding Capitalized Interest, Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPaidNet" xlink:to="lab_us-gaap_InterestPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019fd7d0-1c60-76ce-a3ca-250cde102998_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive income (loss), after-tax:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_VariableInterestEntityPrimaryBeneficiaryBuildAmericaMutualAssuranceCompanyMember_019fd7d0-1acb-79e8-86ee-f36250a73f7f_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-20260930.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_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateYearOne_019fd7d0-1b75-7fff-abb9-f31f58decc61_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-20260930.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_GainOnSaleOfInvestments_019fd7d0-1b75-77c4-81c3-992d8a539b68_terseLabel_en-US" xlink:label="lab_us-gaap_GainOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized investment gains</link:label>
    <link:label id="lab_us-gaap_GainOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_GainOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainOnSaleOfInvestments" xlink:to="lab_us-gaap_GainOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedInterestRateCapMember_019fd7d0-1b75-7f48-8d39-5010ce02c7b3_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-20260930.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_GainLossOnEconomicTransitionAdjustmentTaxExpenseBenefit_019fd7d0-1b75-716e-bf05-4d7ff1435acd_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-20260930.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_us-gaap_CreditFacilityAxis_019fd7d0-1bf1-72b1-acd7-38f74b69a4d5_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests_019fd7d0-1bf1-7f53-bfc6-5cff14b60291_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Payments to acquire limited partnership interests</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Limited Partnership Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireLimitedPartnershipInterests"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:to="lab_us-gaap_PaymentsToAcquireLimitedPartnershipInterests" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_019fd7d0-1b75-79c1-bdc6-bc092f6b7bd5_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash on hand</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_label_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Cash on Hand</link:label>
    <link:label id="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Cash on Hand</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:href="wtm-20260930.xsd#wtm_BusinessCombinationConsiderationTransferredCashOnHand"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:to="lab_wtm_BusinessCombinationConsiderationTransferredCashOnHand" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures_019fd7d0-1bf1-7cf9-8e38-e2677620d08c_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-20260930.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesNonvestedNumberBeforeAssumedForfeitures" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsCashAndInvestments_019fd7d0-1c60-7589-9941-3ce208a53b46_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-20260930.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_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureName"/>
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    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodThreeToFiveYears_019fd7d0-1b75-7898-b6b9-3bb507bff6b9_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>
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    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
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    <link:label id="lab_wtm_AmortizationOfOtherIntangibleAssets_label_en-US" xlink:label="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Other Intangible Assets</link:label>
    <link:label id="lab_wtm_AmortizationOfOtherIntangibleAssets_documentation_en-US" xlink:label="lab_wtm_AmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Amortization of Other Intangible Assets</link:label>
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    <link:label id="lab_wtm_DistinguishedTransactionMember_019fd7d0-1c60-794f-9fa7-a72f72f8dca4_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>
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    <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-20260930.xsd#wtm_DistinguishedTransactionMember"/>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019fd7d0-1bf1-763c-8479-9ade66909d81_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
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    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_019fd7d0-1b75-7582-baef-f6ad2f69a408_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Impairments</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate_019fd7d0-1b75-7d9f-9f08-ef8943da5706_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-20260930.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDate"/>
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    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne_019fd7d0-1bf1-7a38-88ba-bc3b74ccc7d5_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>
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    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne" xlink:href="wtm-20260930.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateYearOne"/>
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    <link:label id="lab_us-gaap_InterestReceivable_019fd7d0-1bf1-7e6f-b92d-db6e65957af1_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>
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    <link:label id="lab_ecd_TrdArrIndName_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_TrdArrIndName_label_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndName"/>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_019fd7d0-1bf2-773d-853b-c288bdb85caa_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
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    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock_019fd7d0-1b75-72f6-aac6-14f9791b37ce_negatedLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Average unvested restricted common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares, Restricted Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesRestrictedStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesRestrictedStock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod_019fd7d0-1b75-7e66-bf10-5d4982783dbc_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-20260930.xsd#wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:to="lab_wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareFundLockUpPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations_019fd7d0-1c60-709c-96e4-216561200763_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net change in cash during the period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Period Increase (Decrease), Including Exchange Rate Effect, Continuing Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffectContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash_019fd7d0-1c60-7037-800a-34936663b7f9_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationCash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationCash" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived_019fd7d0-1bf2-7ea3-9f21-0babf038d63b_terseLabel_en-US" xlink:label="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest payments received</link:label>
    <link:label id="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived_label_en-US" xlink:label="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Income, Operating, Interest Payments Received</link:label>
    <link:label id="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived_documentation_en-US" xlink:label="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Interest Income, Operating, Interest Payments Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:href="wtm-20260930.xsd#wtm_InterestIncomeOperatingInterestPaymentsReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:to="lab_wtm_InterestIncomeOperatingInterestPaymentsReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_019fd7d0-1b75-7462-96a0-ee1d62849476_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR)</link:label>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_label_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SecuredOvernightFinancingRateSofrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:to="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalUnconsolidatedEntitiesMember_019fd7d0-1bf1-714c-9644-e9ab3388163e_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-20260930.xsd#wtm_TotalUnconsolidatedEntitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalUnconsolidatedEntitiesMember" xlink:to="lab_wtm_TotalUnconsolidatedEntitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedAutoLoansMember_019fd7d0-1b75-75ae-9825-e74e0101ff97_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedAutoLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vehicle receivables</link:label>
    <link:label id="lab_us-gaap_CollateralizedAutoLoansMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedAutoLoansMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Auto Loans [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedAutoLoansMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedAutoLoansMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedAutoLoansMember" xlink:to="lab_us-gaap_CollateralizedAutoLoansMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoMember_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO</link:label>
    <link:label id="lab_ecd_NonPeoNeoMember_label_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoMember" xlink:to="lab_ecd_NonPeoNeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EuroInterbankOfferedRateEURIBORMember_019fd7d0-1b75-741b-9038-341751af58c9_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-20260930.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_CostOfGoodsAndServicesSold_019fd7d0-1b75-7dfc-bc3d-3482941aed6b_terseLabel_en-US" xlink:label="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost of sales</link:label>
    <link:label id="lab_us-gaap_CostOfGoodsAndServicesSold_label_en-US" xlink:label="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cost of Product and Service Sold</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSold" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfGoodsAndServicesSold"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostOfGoodsAndServicesSold" xlink:to="lab_us-gaap_CostOfGoodsAndServicesSold" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMethodTextBlock" xlink:to="lab_ecd_AwardTmgMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProductAndServiceOtherMember_019fd7d0-1c60-7864-9b6b-33626264c97b_terseLabel_en-US" xlink:label="lab_us-gaap_ProductAndServiceOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and service revenues</link:label>
    <link:label id="lab_us-gaap_ProductAndServiceOtherMember_label_en-US" xlink:label="lab_us-gaap_ProductAndServiceOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service, Other [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProductAndServiceOtherMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProductAndServiceOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProductAndServiceOtherMember" xlink:to="lab_us-gaap_ProductAndServiceOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioForecastMember_019fd7d0-1b75-79cc-84a3-7e427b663b6e_terseLabel_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forecast</link:label>
    <link:label id="lab_srt_ScenarioForecastMember_label_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forecast [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioForecastMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ScenarioForecastMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioForecastMember" xlink:to="lab_srt_ScenarioForecastMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BroadStreetSPVMember_019fd7d0-1c60-79eb-9798-0e77aa850438_terseLabel_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BroadStreet SPV</link:label>
    <link:label id="lab_wtm_BroadStreetSPVMember_label_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BroadStreet SPV [Member]</link:label>
    <link:label id="lab_wtm_BroadStreetSPVMember_documentation_en-US" xlink:label="lab_wtm_BroadStreetSPVMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">BroadStreet SPV</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BroadStreetSPVMember" xlink:href="wtm-20260930.xsd#wtm_BroadStreetSPVMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BroadStreetSPVMember" xlink:to="lab_wtm_BroadStreetSPVMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:to="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_WTMPartnersDebtMember_019fd7d0-1c60-7862-800d-87340937f4ce_terseLabel_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">WTM Partners Debt</link:label>
    <link:label id="lab_wtm_WTMPartnersDebtMember_label_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">WTM Partners Debt [Member]</link:label>
    <link:label id="lab_wtm_WTMPartnersDebtMember_documentation_en-US" xlink:label="lab_wtm_WTMPartnersDebtMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">WTM Partners Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_WTMPartnersDebtMember" xlink:href="wtm-20260930.xsd#wtm_WTMPartnersDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_WTMPartnersDebtMember" xlink:to="lab_wtm_WTMPartnersDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_019fd7d0-1b75-74fa-9426-160519eabaff_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_019fd7d0-1b75-77e0-8185-4851f4fa54c4_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_019fd7d0-1b75-71c3-8411-92a3f08fb0a4_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_019fd7d0-1bf1-7834-8900-783f8ed08bc2_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeAxis" xlink:to="lab_us-gaap_LongtermDebtTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_019fd7d0-1b75-7b99-96cd-43241acfe4ab_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">&gt;10&#160;years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Greater than 10 Years</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long-term Investments, Remaining Period, Greater than 10 Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:href="wtm-20260930.xsd#wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:to="lab_wtm_OtherLongTermInvestmentsRemainingPeriodGreaterThan10Years" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis</link:label>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_label_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompAnalysisTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompAnalysisTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompAnalysisTextBlock" xlink:to="lab_ecd_ErrCompAnalysisTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsMember_019fd7d0-1c60-770b-8ee7-2f93c52fe544_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentsMember_label_en-US" xlink:label="lab_us-gaap_InvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsMember" xlink:to="lab_us-gaap_InvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDateAxis_terseLabel_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date:</link:label>
    <link:label id="lab_ecd_RestatementDateAxis_label_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDateAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDateAxis" xlink:to="lab_ecd_RestatementDateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsBBBRatingMember_019fd7d0-1c60-7eaa-8531-5ff1998f1cff_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsBBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BBB</link:label>
    <link:label id="lab_srt_StandardPoorsBBBRatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsBBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, BBB Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsBBBRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsBBBRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsBBBRatingMember" xlink:to="lab_srt_StandardPoorsBBBRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NotesReceivableNominalFairValueDisclosure_019fd7d0-1b75-78e0-8c97-1a05d59d3d55_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_019fd7d0-1b75-7713-836d-a56888e14837_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-20260930.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_srt_StandardPoorsBBRatingMember_019fd7d0-1bf1-7f9d-8e60-48f3fde48f8c_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BB</link:label>
    <link:label id="lab_srt_StandardPoorsBBRatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsBBRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, BB Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsBBRatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsBBRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsBBRatingMember" xlink:to="lab_srt_StandardPoorsBBRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities_019fd7d0-1b75-78cc-812a-2314f74376cc_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities_label_en-US" xlink:label="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:to="lab_us-gaap_DisposalGroupIncludingDiscontinuedOperationOtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsuranceDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceDisclosuresAbstract" xlink:to="lab_us-gaap_ReinsuranceDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_019fd7d0-1bf1-7076-adc4-5e0f9b30ce7f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentBorrowingBasePercentage_019fd7d0-1b75-7818-94e4-265670994f98_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-20260930.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_ecd_PnsnBnftsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnBnftsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:to="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LossOnSaleOfInvestments_019fd7d0-1c60-7b08-9c6d-389ff0163d0c_terseLabel_en-US" xlink:label="lab_us-gaap_LossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized investment losses</link:label>
    <link:label id="lab_us-gaap_LossOnSaleOfInvestments_label_en-US" xlink:label="lab_us-gaap_LossOnSaleOfInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss on Sale of Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LossOnSaleOfInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LossOnSaleOfInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LossOnSaleOfInvestments" xlink:to="lab_us-gaap_LossOnSaleOfInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract_019fd7d0-1b75-7072-947f-6862eb68beb5_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings per share denominator (in thousands):</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019fd7d0-1acb-7c7e-9e66-edca56750ff4_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of intangible assets and goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_019fd7d0-1b75-7dd4-ac20-5d389394d838_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GrossPremiumsEarned_019fd7d0-1b75-7797-a422-961698dc88d9_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_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-20260930.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_IncreaseDecreaseInPremiumsAndCommissionsPayable_019fd7d0-1bf1-758b-b47f-5240ec24f25d_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-20260930.xsd#wtm_IncreaseDecreaseInPremiumsAndCommissionsPayable"/>
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    <link:label id="lab_us-gaap_CededPremiumsEarned_019fd7d0-1b75-70b5-91ef-8a0b1eb58281_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EffectsOfReinsuranceFootnotesAbstract_019fd7d0-1c60-74e8-90bb-19cec44608cb_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-20260930.xsd#wtm_EffectsOfReinsuranceFootnotesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:to="lab_wtm_EffectsOfReinsuranceFootnotesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentIncreaseInInterestRatePeriod_019fd7d0-1b75-7055-a4ff-06a90b074e05_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-20260930.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_DebtCovenantPeriodAxis_019fd7d0-1bf2-762b-bf96-da9e1b7327e5_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-20260930.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_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesSharesPaidInPeriod_019fd7d0-1b75-7e55-aed5-0f7cb124a3d7_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-20260930.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_us-gaap_InvestmentTypeCategorizationMember_019fd7d0-1c60-7893-a16a-69d196a8ef8b_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SurplusNotesMember_019fd7d0-1bf2-79d5-849f-e75f0f1ec6dc_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-20260930.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_wtm_SubsidiaryWMOutriggerReMember_019fd7d0-1bf2-77f1-b73c-9850f0bafcec_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-20260930.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_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:to="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_019fd7d0-1bf1-76ce-829e-99dec2ca2c31_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transfers in</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Transfers Into Level 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue_019fd7d0-1b75-7d3c-ae57-9b723ec6bd9d_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest, Equity, Redemption Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:to="lab_us-gaap_RedeemableNoncontrollingInterestEquityRedemptionValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_019fd7d0-1b75-7ba8-acb6-229c74f13434_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoTotalCompAmt_label_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoTotalCompAmt" xlink:to="lab_ecd_PeoTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndGoodwill_019fd7d0-1bf1-774c-8300-98112ab93e5d_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-20260930.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_WeightedAverageNumberOfSharesOutstandingBasic_019fd7d0-1bf1-7230-87c2-165e8986c49c_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (losses) per share denominator (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxContingencyLineItems_019fd7d0-1bf1-72c8-8e65-f78011b23ebe_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Line Items]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxContingencyLineItems_label_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxContingencyLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxContingencyLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxContingencyLineItems" xlink:to="lab_us-gaap_IncomeTaxContingencyLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic_019fd7d0-1b75-7a74-9895-091dfe14f1b1_negatedLabel_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Allocation of losses (earnings) to participating restricted common shares</link:label>
    <link:label id="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic_label_en-US" xlink:label="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Undistributed Continuing Operation Earnings (Loss), Allocation to Participating Securities, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:to="lab_us-gaap_UndistributedContinuingOperationEarningsLossAllocationToParticipatingSecuritiesBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_019fd7d0-1bf2-7ae4-86e7-85a0827276fd_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTable_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByBalanceSheetGroupingTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserve_019fd7d0-1bf1-72c1-8eb4-926e698da91c_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-20260930.xsd#wtm_ShortTermInvestmentsInterestReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShortTermInvestmentsInterestReserve" xlink:to="lab_wtm_ShortTermInvestmentsInterestReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_019fd7d0-1bf1-7b1a-899b-01f6b5ac1da2_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_019fd7d0-1bf1-7630-851e-47bb33329f19_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MeasurementInputPreTaxDiscountRateMember_019fd7d0-1bf1-74e4-9238-4c111abcde5f_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-20260930.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_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019fd7d0-1bf1-7f2e-8315-462634ba47c1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net change in deferred acquisition costs</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Policy Acquisition Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PercentageOfParValueOfPolicyReinsured_019fd7d0-1bf1-7107-ae59-178ae564edf6_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-20260930.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_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_019fd7d0-1acb-7d13-ab6f-c25c4056fadf_negatedTerseLabel_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of common equity securities</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_label_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities and Equity Method Investments</link:label>
    <link:label id="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:href="wtm-20260930.xsd#wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:to="lab_wtm_PaymentsToAcquireEquitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax_019fd7d0-1c60-7c18-9a52-98ced4c6fe0f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and service revenues</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer, Including Assessed Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerIncludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BrokerCommissionExpense_019fd7d0-1b75-7b95-89f2-a20bbed6c915_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-20260930.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_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_019fd7d0-1c60-7ca4-841c-a97d03277374_terseLabel_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance acquisition expenses</link:label>
    <link:label id="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_label_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense, Adjusted</link:label>
    <link:label id="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted_documentation_en-US" xlink:label="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:href="wtm-20260930.xsd#wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:to="lab_wtm_DeferredPolicyAcquisitionCostsAmortizationExpenseAdjusted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure_019fd7d0-1b75-7db4-839c-67dd207fbac6_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_019fd7d0-1b75-7803-9d9c-cd1f58dc1e5a_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, fair value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:to="lab_us-gaap_EquityMethodInvestmentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentInformationLineItems_019fd7d0-1bf2-7b09-960d-fedd7b251240_terseLabel_en-US" xlink:label="lab_dei_DocumentInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Information [Line Items]</link:label>
    <link:label id="lab_dei_DocumentInformationLineItems_label_en-US" xlink:label="lab_dei_DocumentInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Information [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationLineItems" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentInformationLineItems" xlink:to="lab_dei_DocumentInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember_019fd7d0-1bf1-759f-8c6b-7485f027595c_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Terminal Revenue Growth Rate</link:label>
    <link:label id="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember_label_en-US" xlink:label="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Long-Term Revenue Growth Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputLongTermRevenueGrowthRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:to="lab_us-gaap_MeasurementInputLongTermRevenueGrowthRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation_019fd7d0-1b75-76df-82f9-7f0c6cb95aab_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets held for sale - Other</link:label>
    <link:label id="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation_label_en-US" xlink:label="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Including Discontinued Operation, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:to="lab_us-gaap_AssetsOfDisposalGroupIncludingDiscontinuedOperation" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiDiscTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:to="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_019fd7d0-1bf1-7b98-97ec-dc66b0ffc59b_negatedLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Vested (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_019fd7d0-1bf1-7fc0-9ccb-460f2d8f5aa3_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019fd7d0-1b75-7dbf-a434-3403d231faa6_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_019fd7d0-1b75-7c28-8bc2-35f9eea370a8_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net earnings (losses) available to White Mountains&#8217;s common shareholders, net of restricted common share amounts</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_KuduCreditFacilityMember_019fd7d0-1b75-7e2b-8c03-7daa68539a85_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-20260930.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_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_019fd7d0-1bf1-75d1-927e-e7d797c10129_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, finite-lived, accumulated amortization</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_019fd7d0-1b75-72cf-ad21-eba1a3b0abf6_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_019fd7d0-1b75-7198-951b-01976d76c741_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total commitment under revolving credit facility</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Maximum Borrowing Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:to="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TrustDepositsMember_019fd7d0-1bf2-7a83-9af2-bce06a3eefc3_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-20260930.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_wtm_EquityMethodInvestmentUnrealizedGain_019fd7d0-1bf1-797f-bf54-24ca4ba7ddbc_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-20260930.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_HGGlobalSegmentMember_019fd7d0-1acb-7a45-b504-1cfdaa37477a_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-20260930.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_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_019fd7d0-1c60-7591-ae1a-7b1a9b998bf8_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee, Sale of Stock by Subsidiary or Equity Investee [Table]</link:label>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_label_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee, Sale of Stock, Type [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:to="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NumberofSecuredCreditFacilities_019fd7d0-1bf1-7409-bde8-1566e19980a4_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-20260930.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_InvestmentIncomeInvestmentExpense_019fd7d0-1bf1-7426-8786-a4f4877b431f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Third-party investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:to="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember_019fd7d0-1bf1-71c8-957c-562ef15207fd_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-20260930.xsd#wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:to="lab_wtm_MortgageAndAssetBackedSecuritiesAndCollateralizedLoanObligationsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoncontrollingInterestMember_019fd7d0-1c60-70fd-ba81-d0f7dded074d_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Nonredeemable noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestMember_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestMember" xlink:to="lab_us-gaap_NoncontrollingInterestMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_019fd7d0-1b75-7a61-8d8b-543e1dd1db73_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_019fd7d0-1b75-77cb-91ea-e0b35874a253_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total average common shares outstanding during the period (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Issued, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesIssuedBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesIssuedBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRightToSellRedemptionValue_019fd7d0-1bf1-7f3b-a76f-82be1eb3a352_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-20260930.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_DebtCovenantPeriod3Member_019fd7d0-1b75-70ce-a825-159dd11ea116_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-20260930.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_MinorityInterestDisclosureTextBlock_019fd7d0-1b75-71d7-85da-52f14b947d37_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Noncontrolling Interests</link:label>
    <link:label id="lab_us-gaap_MinorityInterestDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestDisclosureTextBlock" xlink:to="lab_us-gaap_MinorityInterestDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019fd7d0-1acb-77fc-9787-229d07bec4f0_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryArkInsuranceHoldingsLimitedMember_019fd7d0-1bf1-77a9-8a5e-15d516dfb5fd_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_019fd7d0-1bf1-7e5e-b32a-5eade9564c40_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-20260930.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_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_019fd7d0-1c60-71b6-910a-7dab791ebaf3_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_019fd7d0-1c60-791c-96f3-343278cd94f4_totalLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total gross unearned insurance premiums</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Unearned Premium Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebt_019fd7d0-1bf2-7b4c-8502-c098931c7227_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_019fd7d0-1bf2-76f0-bc3d-6435e9d27247_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_019fd7d0-1bf2-7b68-91d6-85598dc673c5_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_label_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebt" xlink:to="lab_us-gaap_LongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgeFundsMember_019fd7d0-1b75-7ede-b84e-d7ef4ff8d7da_terseLabel_en-US" xlink:label="lab_us-gaap_HedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedge funds</link:label>
    <link:label id="lab_us-gaap_HedgeFundsMember_label_en-US" xlink:label="lab_us-gaap_HedgeFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedge Funds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgeFundsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HedgeFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgeFundsMember" xlink:to="lab_us-gaap_HedgeFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_019fd7d0-1b75-7c9a-a457-c6d703916d2b_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other operating items:</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity, Increase (Decrease) in Operating Capital [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInOperatingCapitalAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:to="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_019fd7d0-1bf1-753a-bb3a-4e0be2710219_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) investing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in the Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:to="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_019fd7d0-1b75-7167-9bf3-42ea3aab1db8_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UtilitiesSectorMember_019fd7d0-1bf1-762d-be8f-a312cfb66d69_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-20260930.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_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate_019fd7d0-1bf1-7ee0-9315-a223d58826de_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanTwoAndWithinThreeYearsFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_019fd7d0-1bf1-74b6-9963-e14eaead3462_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss and Loss Adjustment Expense Reserves</link:label>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:to="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_019fd7d0-1c60-725b-8c42-fcac6d236a92_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_019fd7d0-1c60-7fab-b493-7cb0e72eb020_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums written, gross</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems_019fd7d0-1b75-7fd3-b5a5-36ea1ee15ae3_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments in unconsolidated affiliates</link:label>
    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems_label_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:to="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationTechniqueAxis_019fd7d0-1b75-7b1e-ab87-80de3976738b_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueAxis_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueAxis" xlink:to="lab_us-gaap_ValuationTechniqueAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LloydsMember_019fd7d0-1bf1-7f54-b519-5076135b6051_terseLabel_en-US" xlink:label="lab_wtm_LloydsMember" 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_LloydsMember_label_en-US" xlink:label="lab_wtm_LloydsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lloyd's [Member]</link:label>
    <link:label id="lab_wtm_LloydsMember_documentation_en-US" xlink:label="lab_wtm_LloydsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Lloyd's</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_LloydsMember" xlink:href="wtm-20260930.xsd#wtm_LloydsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_LloydsMember" xlink:to="lab_wtm_LloydsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantSolvencyCapitalMinimum_019fd7d0-1bf2-7882-b05f-930db38083a5_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-20260930.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_SegmentReportingPolicyPolicyTextBlock_019fd7d0-1b75-7ee4-a674-5c7c2258ee90_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reportable Segments</link:label>
    <link:label id="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_SegmentReportingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract_019fd7d0-1b75-7d51-9d69-eb98cc17a563_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Comprehensive Income [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Comprehensive Income [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:to="lab_us-gaap_StatementOfIncomeAndComprehensiveIncomeAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryIndName" xlink:to="lab_ecd_OutstandingRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgHowMnpiCnsdrdTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:to="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SegmentGeographicalDomain_019fd7d0-1acb-714b-8412-3a2a94330c59_terseLabel_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:label id="lab_srt_SegmentGeographicalDomain_label_en-US" xlink:label="lab_srt_SegmentGeographicalDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographical [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SegmentGeographicalDomain" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_SegmentGeographicalDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SegmentGeographicalDomain" xlink:to="lab_srt_SegmentGeographicalDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019fd7d0-1bf1-71fe-82b0-90f84d90c025_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other intangible assets, indefinite-lived</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, Indefinite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year</link:label>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_label_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:to="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsPrrSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:to="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract_019fd7d0-1b75-72c2-91d5-3ffdebc18634_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings per share denominators (in thousands):</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PassportCardDavidShieldMember_019fd7d0-1b75-7fcb-9229-efb18bbe3c33_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-20260930.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_OtherLongTermInvestments_019fd7d0-1c60-7b6d-9331-01b5d6f664bf_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_019fd7d0-1c60-7263-8de3-915919119364_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_019fd7d0-1c60-71c4-a375-635567c5d049_totalLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireOtherInvestments_019fd7d0-1bf2-7aa1-88fc-1a2035fdc320_negatedLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Purchases of other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireOtherInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireOtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireOtherInvestments" xlink:to="lab_us-gaap_PaymentsToAcquireOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByParent_019fd7d0-1b75-7b78-b7ee-52e06b782332_terseLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic ownership</link:label>
    <link:label id="lab_us-gaap_MinorityInterestOwnershipPercentageByParent_label_en-US" xlink:label="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage, Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestOwnershipPercentageByParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:to="lab_us-gaap_MinorityInterestOwnershipPercentageByParent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019fd7d0-1b75-7667-b852-528358e01111_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_019fd7d0-1b75-74db-b8df-4e4261711958_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_019fd7d0-1b75-7c05-ace9-28800f14c0a3_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentSharePrice_019fd7d0-1b75-7741-a046-7e71a1cdb5ee_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-20260930.xsd#wtm_EquityMethodInvestmentSharePrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityMethodInvestmentSharePrice" xlink:to="lab_wtm_EquityMethodInvestmentSharePrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskSecuredMember_019fd7d0-1bf1-78ca-87ae-913ba2fff8c6_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskSecuredMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Secured</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskSecuredMember_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskSecuredMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk, Secured [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskSecuredMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CededCreditRiskSecuredMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskSecuredMember" xlink:to="lab_us-gaap_CededCreditRiskSecuredMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryCompAmt" xlink:to="lab_ecd_OutstandingRecoveryCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_019fd7d0-1bf1-7412-bd35-07a710df5095_terseLabel_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_label_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:label id="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive_documentation_en-US" xlink:label="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:href="wtm-20260930.xsd#wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:to="lab_wtm_DebtSecuritiesTradingFairValueMaturityAllocatedAndSingleMaturityDateAfterYearOneThroughFive" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_IndividualAxis_terseLabel_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Individual:</link:label>
    <link:label id="lab_ecd_IndividualAxis_label_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_IndividualAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_IndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_IndividualAxis" xlink:to="lab_ecd_IndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019fd7d0-1b75-7d13-b2fa-cff89d3e79aa_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (losses) per share denominator (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_019fd7d0-1b75-71a6-bff3-43bd688af519_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_019fd7d0-1bf1-7c07-a130-038289eba6c5_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">Schedule of Gross and net reinsurance recoverables by reinsurers ratings</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:to="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_CommunicationsSectorMember_019fd7d0-1b75-7b4b-b507-ff474cb676c3_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-20260930.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_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_label_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityMethodInvestmentMeasurementInput_019fd7d0-1bf2-7aad-b326-912fa0c25791_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-20260930.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_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019fd7d0-1c60-7b5f-b8b6-1461f5b04aa5_verboseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract_019fd7d0-1b75-718d-bc99-29bb5a34e982_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, before Accumulated Amortization [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwillAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DeferredTaxLiabilityReversal_019fd7d0-1bf1-7d32-8c4c-877d127342b2_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-20260930.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_wtm_NumberOfInvestments_019fd7d0-1b75-743b-8266-7843b8041165_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-20260930.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_VariableInterestEntityEntityMaximumLossExposureAmount_019fd7d0-1c60-7218-8862-8c064927d208_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Partnership interest, carrying value</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Reporting Entity Involvement, Maximum Loss Exposure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:to="lab_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MediaAlphaMember_019fd7d0-1bf2-7467-9258-d233b5e03d69_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_019fd7d0-1bf2-7609-80c1-6d2cf84990fe_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-20260930.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_wtm_WMOutriggerReSegmentMember_019fd7d0-1b75-7ad1-b019-b113b7893142_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-20260930.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_us-gaap_AccruedInvestmentIncomeReceivable_019fd7d0-1b75-7307-a446-2ff4c205bacd_terseLabel_en-US" xlink:label="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accrued investment income</link:label>
    <link:label id="lab_us-gaap_AccruedInvestmentIncomeReceivable_label_en-US" xlink:label="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accrued Investment Income Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedInvestmentIncomeReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedInvestmentIncomeReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccruedInvestmentIncomeReceivable" xlink:to="lab_us-gaap_AccruedInvestmentIncomeReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember_019fd7d0-1c60-7ec1-8bcf-d383f2fac62a_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other asset-backed securities:</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities, Securitized Loans and Receivables [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesSecuritizedLoansAndReceivablesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses_019fd7d0-1bf2-7acf-8cdc-2dd1125171a0_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables on paid losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Paid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_019fd7d0-1bf1-78a4-81c3-e5e315fc2898_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LettersOfCreditOutstandingAmount_019fd7d0-1b75-7419-95e1-18619681a3c5_terseLabel_en-US" xlink:label="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Letters of credit outstanding</link:label>
    <link:label id="lab_us-gaap_LettersOfCreditOutstandingAmount_label_en-US" xlink:label="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Letters of Credit Outstanding, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LettersOfCreditOutstandingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LettersOfCreditOutstandingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LettersOfCreditOutstandingAmount" xlink:to="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PremiumsAndCommissionsPayable_019fd7d0-1b75-7235-9b0c-2e868bbfb3a6_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-20260930.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_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountVested_019fd7d0-1bf2-7ce9-8ddf-004601bca231_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-20260930.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_us-gaap_RepaymentsOfUnsecuredDebt_019fd7d0-1bf2-7e2d-859f-3f72fc0a6f40_terseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfUnsecuredDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net release of cash (pre-funding) of investment purchases</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfUnsecuredDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfUnsecuredDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Unsecured Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfUnsecuredDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfUnsecuredDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfUnsecuredDebt" xlink:to="lab_us-gaap_RepaymentsOfUnsecuredDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateEquityLockUpPeriodTableTextBlock_019fd7d0-1b75-738f-b83c-5c322be07deb_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>
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    <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>
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    <link:label id="lab_wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward_019fd7d0-1bf2-7a7b-b82c-a6dbbde944af_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-20260930.xsd#wtm_ChangesInFairValueDiscountOfSurplusNotesRollForward"/>
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    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_019fd7d0-1b75-710d-bf2d-ef1ad3566d45_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract"/>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019fd7d0-1b75-7da1-a91d-d0a068888bac_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_019fd7d0-1bf2-7c02-89a4-2189ed21b132_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notional amount</link:label>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_label_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Notional Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeAssetNotionalAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:to="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentCovenantTotalLeverageRatio_019fd7d0-1b75-7a8c-ac21-bcb0a13921e8_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>
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    <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_ecd_AllExecutiveCategoriesMember_terseLabel_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Executive Categories</link:label>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_label_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Executive Categories [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllExecutiveCategoriesMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllExecutiveCategoriesMember"/>
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    <link:label id="lab_us-gaap_ValuationTechniqueDomain_019fd7d0-1c60-7b59-bb23-22899cc3aab3_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Domain]</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueDomain_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Approach and Technique [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueDomain" xlink:to="lab_us-gaap_ValuationTechniqueDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsAbstract_019fd7d0-1bf2-7f31-9a03-c12fe6ef0f02_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-20260930.xsd#wtm_OtherLongTermInvestmentsAbstract"/>
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    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsSvcCstMember" xlink:to="lab_ecd_PnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OutriggerReMember_019fd7d0-1b75-75d5-8295-a3eab880de45_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-20260930.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_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate_019fd7d0-1bf1-7210-b6ac-d2372701e425_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanOneAndWithinTwoYearsFromBalanceSheetDate"/>
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    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount_019fd7d0-1bf1-7d36-b99b-f33ab057a896_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Redeemable noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest, Equity, Carrying Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestEquityCarryingAmount"/>
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    <link:label id="lab_wtm_ForeignRegulatoryDepositsMember_019fd7d0-1b75-74eb-83ff-184c94cd6e4e_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-20260930.xsd#wtm_ForeignRegulatoryDepositsMember"/>
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    <link:label id="lab_wtm_BambooCRVMember_019fd7d0-1bf1-7a27-b627-01f869c634ec_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>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements"/>
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    <link:label id="lab_us-gaap_TradingSecuritiesDebtAmortizedCost_019fd7d0-1bf1-7ed3-9ece-4a08f9fa5978_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_019fd7d0-1bf1-79af-a23a-2f1493edc7c3_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>
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    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtDisclosureAbstract"/>
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    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Text Block]</link:label>
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    <link:label id="lab_us-gaap_InvestmentTypeAxis_019fd7d0-1bf1-741e-91b6-142391d5e923_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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:to="lab_us-gaap_StatementOfIncomeLocationBalanceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonRule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:to="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember_019fd7d0-1b75-74d0-bdb9-8d10354b6f8b_terseLabel_en-US" xlink:label="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FNMA</link:label>
    <link:label id="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember_label_en-US" xlink:label="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal National Mortgage Association Certificates and Obligations (FNMA) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:to="lab_us-gaap_FederalNationalMortgageAssociationCertificatesAndObligationsFNMAMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLiabilities_019fd7d0-1bf1-720d-a9bf-edfc0fd3c5fb_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other liabilities</link:label>
    <link:label id="lab_us-gaap_OtherLiabilities_label_en-US" xlink:label="lab_us-gaap_OtherLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLiabilities" xlink:to="lab_us-gaap_OtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedPartnersSegmentMember_019fd7d0-1bf2-70d7-aede-4f042882ae77_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_019fd7d0-1bf2-7dcc-bacb-f45bd005291c_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-20260930.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_InvestmentRedemptionNoticePeriod_019fd7d0-1b75-741a-9fd8-12a99d79596f_terseLabel_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notice period</link:label>
    <link:label id="lab_wtm_InvestmentRedemptionNoticePeriod_label_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Redemption, Notice Period</link:label>
    <link:label id="lab_wtm_InvestmentRedemptionNoticePeriod_documentation_en-US" xlink:label="lab_wtm_InvestmentRedemptionNoticePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Investment Redemption, Notice Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_InvestmentRedemptionNoticePeriod" xlink:href="wtm-20260930.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_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_019fd7d0-1b75-7ea0-ac2b-e07054c53d4e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred, liabilities incurred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Liabilities Incurred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_019fd7d0-1acb-7fa2-b00c-22f623246395_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares, authorized shares (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsUnrealizedLoss_019fd7d0-1b75-772c-859a-88a888c39081_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-20260930.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_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountIssued_019fd7d0-1c60-7914-9ea5-7968a3a412aa_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-20260930.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_SubsidiaryHGGlobalMember_019fd7d0-1bf2-72d1-8690-ad7be2c0578e_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_019fd7d0-1bf2-7a14-96e5-dde50b467d83_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-20260930.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_wtm_SubsidiaryKuduInvestmentManagementLLCMember_019fd7d0-1c60-7e92-94b6-10dfcffb0cbe_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-20260930.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_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests_01a03335-5b0b-79f7-8b14-e9ef953455af_terseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" 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_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests_label_en-US" xlink:label="lab_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Acquisition of Noncontrolling Interests</link:label>
    <link:label id="lab_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Acquisition of Noncontrolling Interests</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" xlink:href="wtm-20260930.xsd#wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" xlink:to="lab_wtm_TemporaryEquityAcquisitionOfNoncontrollingInterests" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardExrcPrice_terseLabel_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise Price</link:label>
    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardExrcPrice" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardExrcPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardExrcPrice" xlink:to="lab_ecd_AwardExrcPrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsRecurringMember_019fd7d0-1bf2-7fea-b311-43792115cb4f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair value measured on a recurring basis</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsRecurringMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsRecurringMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementsRecurringMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsRecurringMember" xlink:to="lab_us-gaap_FairValueMeasurementsRecurringMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_019fd7d0-1b75-7426-8dd8-c16d046dc377_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_label_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingInformationLineItems" xlink:to="lab_us-gaap_SegmentReportingInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentQuarterlyReport_019fd7d0-1bf1-7984-b87e-d03324aa0649_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentQuarterlyReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentQuarterlyReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_label_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember"/>
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    <link:label id="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember_019fd7d0-1b75-733c-bfcf-3fdbf86b15b8_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares and paid-in surplus</link:label>
    <link:label id="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock Including Additional Paid in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_CommonStockIncludingAdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InvestmentsExcludingMediaAlphaMember_019fd7d0-1b75-7a9f-81f1-88c2db148ff4_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-20260930.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_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment_01a17d9f-33ab-7488-93a6-46c0efb2c71e_terseLabel_en-US" xlink:label="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dispositions of businesses</link:label>
    <link:label id="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment_label_en-US" xlink:label="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Dispositions of Businesses , Measurement Period Adjustment</link:label>
    <link:label id="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment_documentation_en-US" xlink:label="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets, Dispositions of Businesses , Measurement Period Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:href="wtm-20260930.xsd#wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:to="lab_wtm_IntangibleAssetsDispositionsOfBusinessesMeasurementPeriodAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019fd7d0-1bf1-7b91-841b-1dda9920d623_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Prior year losses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019fd7d0-1b75-7a24-a33a-fec7747a353d_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_019fd7d0-1b75-731d-8312-62bc72c78e87_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Repayments</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsTargetBalance_019fd7d0-1b75-7db3-a830-f303b868adbb_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-20260930.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_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_019fd7d0-1b75-760c-8a6c-1ab2fdb5ddb3_negatedLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Unamortized discount and issuance cost</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Unamortized Discount (Premium) and Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:to="lab_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_InterestIncomeOperatingNetOfInterestPaymentsReceived_019fd7d0-1c60-7fdc-8d4e-3507a31f3923_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, net of interest payments received of $2.7 and $2.4</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-20260930.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_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019fd7d0-1b75-7023-b32a-33b53d8878db_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_019fd7d0-1b75-7720-a03b-b0e5d9f9be23_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestments" xlink:to="lab_us-gaap_EquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DistinguishedCreditFacilityMember_019fd7d0-1c60-713a-839b-13469ba465c6_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_019fd7d0-1c60-7ffe-abc0-68e5b35bd382_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-20260930.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_us-gaap_EquityComponentDomain_019fd7d0-1acb-78d2-8405-366799689c45_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_019fd7d0-1bf1-7eeb-bf1e-9442f2ead4d4_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_019fd7d0-1b75-78c2-9439-0c502f493bbd_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019fd7d0-1c60-7592-b00b-eb4d296b76ef_verboseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized gains</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
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    <link:label id="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember_019fd7d0-1c60-745e-b5ca-0bcc1b407fd1_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>
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    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:href="wtm-20260930.xsd#wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:to="lab_wtm_OtherUnconsolidatedPrivateEquityInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillIntangibleAssetsAndOtherLiabilitiesAcquiredMeasurementPeriodAdjustment_019fd7d0-1bf1-7489-91c8-200bb18b7907_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-20260930.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_BenefitsLossesAndExpensesAbstract_019fd7d0-1bf1-702e-afaf-0caf450adc87_terseLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expenses:</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Benefits, Losses and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:to="lab_us-gaap_BenefitsLossesAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentFloatingInterestRatePercentage_019fd7d0-1b75-7496-ac34-48c1678384f9_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-20260930.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_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrAdoptionDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TechnologySectorMember_019fd7d0-1b75-7d2c-9193-c83448298e8d_terseLabel_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Technology</link:label>
    <link:label id="lab_us-gaap_TechnologySectorMember_label_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Technology Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TechnologySectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TechnologySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TechnologySectorMember" xlink:to="lab_us-gaap_TechnologySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_019fd7d0-1c60-77e2-be77-6874ed9d0980_terseLabel_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from Kudu&#8217;s Participation Contracts sold</link:label>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_label_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Participation Contracts</link:label>
    <link:label id="lab_wtm_ProceedsFromSaleOfParticipationContracts_documentation_en-US" xlink:label="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ProceedsFromSaleOfParticipationContracts" xlink:href="wtm-20260930.xsd#wtm_ProceedsFromSaleOfParticipationContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ProceedsFromSaleOfParticipationContracts" xlink:to="lab_wtm_ProceedsFromSaleOfParticipationContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate_019fd7d0-1b75-7911-9586-41c5faebe8fc_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030</link:label>
    <link:label id="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate_label_en-US" xlink:label="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contract, Premium Revenue to be Recognized, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:to="lab_us-gaap_FinancialGuaranteeInsuranceContractsFutureExpectedPremiumRevenueToBeRecognizedMoreThanThreeAndWithinFourYearsFromBalanceSheetDate" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
    <link:label id="lab_ecd_TrdArrIndTitle_label_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Title</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndTitle" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_019fd7d0-1b75-760b-b987-5cae0b3fddd0_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedUndistributed_019fd7d0-1bf1-7722-a4c0-a71271a1c5b9_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Undistributed earnings (losses) (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedUndistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted, Undistributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDilutedUndistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDilutedUndistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDilutedUndistributed" xlink:to="lab_us-gaap_EarningsPerShareDilutedUndistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets_019fd7d0-1b75-7e33-b22d-cd13fdd7c96f_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-20260930.xsd#wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:to="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredOtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019fd7d0-1b75-7f25-87ff-e1315dd6e2bf_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net other financing activities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from (Payment for) Other Financing Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromPaymentsForOtherFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:to="lab_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherOperatingIncome_019fd7d0-1b75-7c5d-8770-f35816f47ea4_terseLabel_en-US" xlink:label="lab_us-gaap_OtherOperatingIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest income from BAM Surplus Notes</link:label>
    <link:label id="lab_us-gaap_OtherOperatingIncome_label_en-US" xlink:label="lab_us-gaap_OtherOperatingIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Operating Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherOperatingIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherOperatingIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherOperatingIncome" xlink:to="lab_us-gaap_OtherOperatingIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments_019fd7d0-1b75-76ff-829f-0678972222a1_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distributions and redemptions of other long-term investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale and Maturity of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleAndMaturityOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsAccruedInterest_019fd7d0-1b75-7bb6-8df4-a7b36f6b3d51_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-20260930.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_wtm_GeneralAndAdministrativeExpenseOtherUnderwritingExpenses_019fd7d0-1c60-7835-b522-0d7857344a4f_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-20260930.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019fd7d0-1c60-71fd-83a4-4e06de5b51f9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Current year losses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_019fd7d0-1c60-7171-9d58-b135b9f2a600_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAcquireeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:to="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LetterOfCreditMember_019fd7d0-1bf1-7149-85f0-f1c642929f83_terseLabel_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Letter of Credit</link:label>
    <link:label id="lab_us-gaap_LetterOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Letter of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LetterOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LetterOfCreditMember" xlink:to="lab_us-gaap_LetterOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_019fd7d0-1bf1-75ac-a936-0ba8c4cad3c9_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_019fd7d0-1b75-714d-9ce1-c76a5a5f43c8_terseLabel_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">HG Global 2022 Senior Notes</link:label>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_label_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">HG Global Senior Notes [Member]</link:label>
    <link:label id="lab_wtm_HGGlobalSeniorNotesMember_documentation_en-US" xlink:label="lab_wtm_HGGlobalSeniorNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">HG Global Senior Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HGGlobalSeniorNotesMember" xlink:href="wtm-20260930.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_LargestInvestmentMember_019fd7d0-1b75-7d79-a69b-99f9cda37976_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-20260930.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_BAMSurplusNotesMember_019fd7d0-1bf2-727d-8d5d-164d2ab304e2_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-20260930.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_wtm_PremiumsAndCommissionsReceivable_019fd7d0-1c60-7eb0-987a-49438eb0e82c_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-20260930.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_DebtSecuritiesWeightedAveragePortfolioPeriod_019fd7d0-1b75-7e1e-96cc-bed8a40d5ee4_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-20260930.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_wtm_Ark2021SubordinatedNotesTranche2Member_019fd7d0-1c60-757b-8e0c-94d28295ad71_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-20260930.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_PremiumsWrittenNetConsolidatedAbstract_019fd7d0-1b75-751b-822b-2ab5908c1515_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written premiums:</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenNetConsolidatedAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:to="lab_us-gaap_PremiumsWrittenNetConsolidatedAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_019fd7d0-1b75-756a-a2bc-6401d1a0e567_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Operations</link:label>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_label_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Reconciling Item, Corporate Nonsegment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateNonSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateNonSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateNonSegmentMember" xlink:to="lab_us-gaap_CorporateNonSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_019fd7d0-1bf1-7f29-81cf-615e884f780e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAxis" xlink:to="lab_us-gaap_BusinessAcquisitionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fd7d0-1bf2-7656-9a4e-c81c1957350c_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) operations</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019fd7d0-1b75-7ec0-91ae-abebaba6f2a5_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_019fd7d0-1b75-7a33-828d-2512a2e1db86_verboseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Favorable prior loss reserve development</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LloydsLOCFacilityMember_019fd7d0-1bf2-7ca7-8aae-23c47492aa0d_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-20260930.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_wtm_BusinessCombinationConsiderationTransferredPostClosingPurchasePriceAdjustment_019fd7d0-1bf2-70fe-8a7f-a4f040849647_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-20260930.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_us-gaap_EnergySectorMember_019fd7d0-1b75-7e5a-9bbf-ea76224d45ad_terseLabel_en-US" xlink:label="lab_us-gaap_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy</link:label>
    <link:label id="lab_us-gaap_EnergySectorMember_label_en-US" xlink:label="lab_us-gaap_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EnergySectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EnergySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EnergySectorMember" xlink:to="lab_us-gaap_EnergySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_019fd7d0-1bf2-7e61-9888-7d10327de0ce_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_019fd7d0-1c60-7b66-9ef9-0fe2bc695fa4_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">White Mountains&#8217;s common shareholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityAbstract" xlink:to="lab_us-gaap_StockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_019fd7d0-1b75-75d0-aabc-505a429ea8a6_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems_019fd7d0-1c60-7c2b-a64c-d6a930eb6b45_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Quantitative information for Level 3 Fair Value Measurements Assets</link:label>
    <link:label id="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Option, Quantitative Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueOptionQuantitativeDisclosuresLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:to="lab_us-gaap_FairValueOptionQuantitativeDisclosuresLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019fd7d0-1bf1-7933-a587-678620364781_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_019fd7d0-1bf1-7cd1-8862-1d790e050798_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_019fd7d0-1bf1-751f-a51c-952efaf2beb4_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net realized and unrealized investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember_019fd7d0-1c60-7bb0-9253-db19b410df24_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-20260930.xsd#wtm_ArkInsuranceHoldingsLimitedSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:to="lab_wtm_ArkInsuranceHoldingsLimitedSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_RevenuesAdjusted_019fd7d0-1bf1-7f79-a76d-e939a9bcd3b0_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-20260930.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_wtm_WTMCreditFacilityMember_019fd7d0-1c60-7432-83f6-3c2024519fee_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-20260930.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_us-gaap_StockAppreciationRightsSARSMember_terseLabel_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs)</link:label>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_label_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockAppreciationRightsSARSMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:to="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_LimitedLiabilityCompanyOrLimitedPartnershipGeographicalPresence_019fd7d0-1b75-72f8-b781-e1ae18b0726a_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-20260930.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_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable_019fd7d0-1acb-78c1-8485-409c4d695eb8_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Acquired [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:to="lab_us-gaap_ScheduleOfAcquiredFiniteLivedIntangibleAssetByMajorClassTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_019fd7d0-1bf1-70f8-85fd-4cb585502398_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_019fd7d0-1bf1-75f0-80e4-c4d88c6f26a9_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_019fd7d0-1bf1-74c8-9eb1-3f562f715a50_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Collateral</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverables" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverables" xlink:to="lab_us-gaap_ReinsuranceRecoverables" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_019fd7d0-1c60-7a7e-b10d-6f54aba00969_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentInformationTable_019fd7d0-1b75-7bb6-bef3-7326a0dd376b_terseLabel_en-US" xlink:label="lab_dei_DocumentInformationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Information [Table]</link:label>
    <link:label id="lab_dei_DocumentInformationTable_label_en-US" xlink:label="lab_dei_DocumentInformationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Information [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentInformationTable" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentInformationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentInformationTable" xlink:to="lab_dei_DocumentInformationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ForgoneRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryIndName" xlink:to="lab_ecd_ForgoneRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesTranche3Member_019fd7d0-1b75-7da4-8c31-4a3da36d989f_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-20260930.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_ecd_NonGaapMeasureDescriptionTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description</link:label>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_label_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:to="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ScheduleOfMunicipalGuaranteeInsuredObligationsTableTextBlock_019fd7d0-1b75-775f-8a5e-09343404169b_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-20260930.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_OtherFundsMember_019fd7d0-1b75-7265-aaa9-518b0493e417_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-20260930.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_dei_EntityDomain_019fd7d0-1bf1-7209-b721-26c6dd8aa0d8_terseLabel_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity [Domain]</link:label>
    <link:label id="lab_dei_EntityDomain_label_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityDomain" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityDomain" xlink:to="lab_dei_EntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_EquityInfrastructureFundsMember_01a17e2c-1234-7e85-800b-17291c25eda1_terseLabel_en-US" xlink:label="lab_wtm_EquityInfrastructureFundsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Infrastructure Funds</link:label>
    <link:label id="lab_wtm_EquityInfrastructureFundsMember_label_en-US" xlink:label="lab_wtm_EquityInfrastructureFundsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Infrastructure Funds [Member]</link:label>
    <link:label id="lab_wtm_EquityInfrastructureFundsMember_documentation_en-US" xlink:label="lab_wtm_EquityInfrastructureFundsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Infrastructure Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityInfrastructureFundsMember" xlink:href="wtm-20260930.xsd#wtm_EquityInfrastructureFundsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_EquityInfrastructureFundsMember" xlink:to="lab_wtm_EquityInfrastructureFundsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_019fd7d0-1bf1-70af-93fd-dbb68d09c341_terseLabel_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Operations</link:label>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_label_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Noncontrolling Interest [Member]</link:label>
    <link:label id="lab_wtm_OtherNoncontrollingInterestMember_documentation_en-US" xlink:label="lab_wtm_OtherNoncontrollingInterestMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherNoncontrollingInterestMember" xlink:href="wtm-20260930.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_wtm_DebtCovenantPeriod4Member_019fd7d0-1acb-74d5-b3f7-bcac481bc363_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-20260930.xsd#wtm_DebtCovenantPeriod4Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriod4Member" xlink:to="lab_wtm_DebtCovenantPeriod4Member" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_019fd7d0-1b75-75eb-b53f-ae5b30834163_terseLabel_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_label_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:label id="lab_wtm_OtherSignificantTransactionsLineItems_documentation_en-US" xlink:label="lab_wtm_OtherSignificantTransactionsLineItems" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Significant Transactions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherSignificantTransactionsLineItems" xlink:href="wtm-20260930.xsd#wtm_OtherSignificantTransactionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherSignificantTransactionsLineItems" xlink:to="lab_wtm_OtherSignificantTransactionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetsAcquiredPremiumsAndCommissionsReceivable_019fd7d0-1b75-74c1-9d92-ddcd136e35ac_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-20260930.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_wtm_TotalOtherLongTermInvestmentsMember_019fd7d0-1bf2-7109-9ad9-b93b45d68fbe_terseLabel_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_label_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Other Long-Term Investments [Member]</link:label>
    <link:label id="lab_wtm_TotalOtherLongTermInvestmentsMember_documentation_en-US" xlink:label="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TotalOtherLongTermInvestmentsMember" xlink:href="wtm-20260930.xsd#wtm_TotalOtherLongTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalOtherLongTermInvestmentsMember" xlink:to="lab_wtm_TotalOtherLongTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_019fd7d0-1bf2-7e20-b616-b2fa7d203935_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_label_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:to="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceAgreementsAssetLimitAmount_019fd7d0-1bf2-74ca-a92b-ef1f6fb65ca4_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-20260930.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_Investments_019fd7d0-1bf1-78d8-a3c0-e1a976430ced_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_019fd7d0-1bf1-76f1-85a4-68688cef824a_terseLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriodDomain_019fd7d0-1bf1-7a34-9d6d-bff8f4eb9cf3_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-20260930.xsd#wtm_DebtCovenantPeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_DebtCovenantPeriodDomain" xlink:to="lab_wtm_DebtCovenantPeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsBalanceLimitPercentage_019fd7d0-1b75-7a5f-803c-b1e3afb60be7_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-20260930.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_GoodwillAcquisitionDateFairValue_019fd7d0-1b75-71be-9a74-87a6378cce8d_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-20260930.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019fd7d0-1c60-7a8b-aa2a-40f78780abb0_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
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    <link:label id="lab_ecd_ErrCompRecoveryTable_terseLabel_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery</link:label>
    <link:label id="lab_ecd_ErrCompRecoveryTable_label_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompRecoveryTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ErrCompRecoveryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompRecoveryTable" xlink:to="lab_ecd_ErrCompRecoveryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019fd7d0-1c60-7ed5-891a-d35eac99a3e8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of significant unobservable inputs used in estimating the fair value of investment securities</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss_019fd7d0-1bf2-78e0-98df-0357582a96e1_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign currency translation and other adjustments to loss and LAE reserves</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Foreign Currency Translation Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseForeignCurrencyTranslationGainLoss"/>
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    <link:label id="lab_dei_EntityCurrentReportingStatus_019fd7d0-1bf1-7a86-935e-a9bb43c26b74_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityCurrentReportingStatus"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_019fd7d0-1b75-7ba9-a949-a985e60622ee_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided from (used for) financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
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    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TotalShareholderRtnAmt"/>
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    <link:label id="lab_wtm_StandardPoorsOtherMember_019fd7d0-1bf1-788a-889b-c8d477cd4377_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-20260930.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_PaymentsForProceedsFromOtherShortTermInvestments_019fd7d0-1bf2-7ca4-b160-67812a5be716_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>
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    <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-20260930.xsd#wtm_PaymentsForProceedsFromOtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:to="lab_wtm_PaymentsForProceedsFromOtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable_019fd7d0-1c60-7f2b-8226-a84f9dbaac3a_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-20260930.xsd#wtm_FundsHeldUnderReinsuranceAgreementsAssetsInterestReceivable"/>
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    <link:label id="lab_wtm_PerformancePeriodAxis_019fd7d0-1c60-7a34-ac27-a3b2b90696bc_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-20260930.xsd#wtm_PerformancePeriodAxis"/>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax_019fd7d0-1b75-7711-b5c8-0f4a89e5582c_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentNetOfTax"/>
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    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_019fd7d0-1c60-7159-9dab-4a85ee6dc328_terseLabel_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of private debt instruments</link:label>
    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_label_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Private Debt Instruments</link:label>
    <link:label id="lab_wtm_NumberOfPrivateDebtInstruments_documentation_en-US" xlink:label="lab_wtm_NumberOfPrivateDebtInstruments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Private Debt Instruments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NumberOfPrivateDebtInstruments" xlink:href="wtm-20260930.xsd#wtm_NumberOfPrivateDebtInstruments"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_019fd7d0-1c60-79c2-808a-c85234c27e7c_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
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    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetIncludingGoodwill_019fd7d0-1bf2-75cd-9891-11e1d504ce27_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>
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    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019fd7d0-1acb-7a66-8405-34cb88cabb56_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>
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    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019fd7d0-1bf2-7a25-99a2-1ec0eb77a750_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>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019fd7d0-1bf2-7eee-8045-95e6c4d8f9fd_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premiums</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrepaidReinsurancePremiums" xlink:to="lab_us-gaap_PrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract_019fd7d0-1c60-7cd4-b2d6-d2fa32b598cf_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic and diluted earnings per share numerators (in millions):</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Basic [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasicAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeAssets_019fd7d0-1c60-7ce2-b2d8-35c673ca3284_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative, fair value, net</link:label>
    <link:label id="lab_us-gaap_DerivativeAssets_label_en-US" xlink:label="lab_us-gaap_DerivativeAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssets" xlink:to="lab_us-gaap_DerivativeAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_019fd7d0-1bf2-7b1b-a990-59293220cf41_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other revenues</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019fd7d0-1bf1-7296-878a-051ea4909d8b_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_019fd7d0-1b75-7020-bc35-469cb9789cf1_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Other Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset and Goodwill [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_terseLabel_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Securities</link:label>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_label_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Underlying Securities Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardUndrlygSecuritiesAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:to="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest_019fd7d0-1bf2-7032-9bae-f475dd7dfcdf_negatedLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (income) loss attributable to noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTaxAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_019fd7d0-1b75-77ad-a27b-8d98ab21e8cc_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuances of common shares</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Value, New Issues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueNewIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealEstateSectorMember_019fd7d0-1bf2-7156-926a-82279eef58ff_verboseLabel_en-US" xlink:label="lab_us-gaap_RealEstateSectorMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Real estate</link:label>
    <link:label id="lab_us-gaap_RealEstateSectorMember_label_en-US" xlink:label="lab_us-gaap_RealEstateSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Real Estate Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealEstateSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RealEstateSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealEstateSectorMember" xlink:to="lab_us-gaap_RealEstateSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Cash_019fd7d0-1c60-7650-a38c-0d8e565c4e3c_terseLabel_en-US" xlink:label="lab_us-gaap_Cash" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:label id="lab_us-gaap_Cash_label_en-US" xlink:label="lab_us-gaap_Cash" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Cash" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Cash"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Cash" xlink:to="lab_us-gaap_Cash" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_019fd7d0-1b75-780c-98d0-c0292195ad1e_totalLabel_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Acquisition of businesses</link:label>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_label_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Indefinite-Lived Intangible Assets, Acquired During Period</link:label>
    <link:label id="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod_documentation_en-US" xlink:label="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Goodwill and Indefinite-Lived Intangible Assets, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:href="wtm-20260930.xsd#wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:to="lab_wtm_GoodwillAndIndefiniteLivedIntangibleAssetsAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_UnrestrictedCashHeldForSale_019fd7d0-1bf1-72dc-b16e-37032b7e5103_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-20260930.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_SubsegmentsAxis_019fd7d0-1b75-76bd-a4ea-47c31a2c1d53_terseLabel_en-US" xlink:label="lab_us-gaap_SubsegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsegments [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsegmentsAxis_label_en-US" xlink:label="lab_us-gaap_SubsegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsegments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsegmentsAxis" xlink:to="lab_us-gaap_SubsegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockMember_019fd7d0-1b75-72af-a78b-127a4ffca455_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred Stock</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_label_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockMember" xlink:to="lab_us-gaap_PreferredStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_019fd7d0-1b75-793e-85d2-e8cde6088ba1_negatedLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net other investing activities</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payment for (Proceeds from) Other Investing Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForProceedsFromOtherInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:to="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal_019fd7d0-1bf1-75e6-b7ae-fc5a9fe7e7a8_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, periodic payment, principal</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Periodic Payment, Principal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentPeriodicPaymentPrincipal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:to="lab_us-gaap_DebtInstrumentPeriodicPaymentPrincipal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HealthcareSectorMember_019fd7d0-1c60-7dc0-b283-27c480eef69d_terseLabel_en-US" xlink:label="lab_us-gaap_HealthcareSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Healthcare</link:label>
    <link:label id="lab_us-gaap_HealthcareSectorMember_label_en-US" xlink:label="lab_us-gaap_HealthcareSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Healthcare Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HealthcareSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HealthcareSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HealthcareSectorMember" xlink:to="lab_us-gaap_HealthcareSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock_019fd7d0-1c60-7e1e-8b32-cec38c6ce3bf_terseLabel_en-US" xlink:label="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of unrecognized compensation costs associated with outstanding restricted share awards</link:label>
    <link:label id="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Nonvested Restricted Stock Shares Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:to="lab_us-gaap_NonvestedRestrictedStockSharesActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019fd7d0-1b75-75d6-b68f-adcbe9f8ce9d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityNetIncome_019fd7d0-1b75-7dcc-835d-596eda32a18d_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityNetIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income (loss)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityNetIncome_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityNetIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityNetIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityNetIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityNetIncome" xlink:to="lab_us-gaap_TemporaryEquityNetIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GuaranteesAbstract_019fd7d0-1b75-74b6-91dc-ce79b55c10b3_terseLabel_en-US" xlink:label="lab_us-gaap_GuaranteesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Guarantees [Abstract]</link:label>
    <link:label id="lab_us-gaap_GuaranteesAbstract_label_en-US" xlink:label="lab_us-gaap_GuaranteesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Guarantees [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GuaranteesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GuaranteesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GuaranteesAbstract" xlink:to="lab_us-gaap_GuaranteesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HedgeFundLongShortEquityBanksAndFinancialMember_019fd7d0-1bf1-73ea-886a-75fe27ffd8f9_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-20260930.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_CommitmentsAndContingenciesDisclosureAbstract_019fd7d0-1b75-704b-966a-3b2ab55acbcc_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllTradingArrangementsMember_terseLabel_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Trading Arrangements</link:label>
    <link:label id="lab_ecd_AllTradingArrangementsMember_label_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Trading Arrangements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllTradingArrangementsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllTradingArrangementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllTradingArrangementsMember" xlink:to="lab_ecd_AllTradingArrangementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_label_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OtherPerfMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OtherPerfMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OtherPerfMeasureAmt" xlink:to="lab_ecd_OtherPerfMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedPremiumsAndCommissionsPayable_019fd7d0-1bf2-79f2-9882-cf2815e69947_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-20260930.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_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_019fd7d0-1c60-7789-944b-71f1d9263d4a_negatedTerseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net contributions (distributions) and dilution from other noncontrolling interests</link:label>
    <link:label id="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_label_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Contribution and Dilution From Noncontrolling Interest During Period</link:label>
    <link:label id="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Net Contribution and Dilution From Noncontrolling Interest During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:href="wtm-20260930.xsd#wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:to="lab_wtm_TemporaryEquityNetContributionAndDilutionFromNoncontrollingInterestDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_019fd7d0-1c60-7790-932a-b495a9598adb_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentOwnedBalanceShares_019fd7d0-1bf1-7c74-bb6c-50e7b9bab3b3_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment owned (in shares)</link:label>
    <link:label id="lab_us-gaap_InvestmentOwnedBalanceShares_label_en-US" xlink:label="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Owned, Balance, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentOwnedBalanceShares" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentOwnedBalanceShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentOwnedBalanceShares" xlink:to="lab_us-gaap_InvestmentOwnedBalanceShares" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsurerTypeDomain_019fd7d0-1bf1-7fcd-a46b-ba4c3153399d_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-20260930.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_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeLineItems_019fd7d0-1bf1-7c0e-9a57-f697c5950413_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative [Line Items]</link:label>
    <link:label id="lab_us-gaap_DerivativeLineItems_label_en-US" xlink:label="lab_us-gaap_DerivativeLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeLineItems" xlink:to="lab_us-gaap_DerivativeLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsARatingMember_019fd7d0-1acb-7d2b-9110-3fe74400e85f_verboseLabel_en-US" xlink:label="lab_srt_StandardPoorsARatingMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">A</link:label>
    <link:label id="lab_srt_StandardPoorsARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, A Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsARatingMember" xlink:to="lab_srt_StandardPoorsARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_019fd7d0-1b75-7daa-a161-f27a25de45b0_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_019fd7d0-1b75-7fbe-b450-21ea041b9aad_netLabel_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Financial services</link:label>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_label_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Services Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialServicesSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FinancialServicesSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialServicesSectorMember" xlink:to="lab_us-gaap_FinancialServicesSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax_019fd7d0-1bf1-7947-b227-c82be82da9de_terseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Comprehensive Income (Loss)</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-20260930.xsd#wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:to="lab_wtm_TemporaryEquityComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year</link:label>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:to="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareDeclared_019fd7d0-1bf2-70de-b4ab-89cba32b26b0_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends declared per White Mountains&#8217;s common share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockDividendsPerShareDeclared_label_en-US" xlink:label="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Dividends, Per Share, Declared</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockDividendsPerShareDeclared" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockDividendsPerShareDeclared"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockDividendsPerShareDeclared" xlink:to="lab_us-gaap_CommonStockDividendsPerShareDeclared" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_019fd7d0-1b75-7e8e-8657-5b56ff2b6777_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PrivateDebtInstrumentMember_019fd7d0-1c60-79cc-8bd2-0513491febe0_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-20260930.xsd#wtm_PrivateDebtInstrumentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_PrivateDebtInstrumentMember" xlink:to="lab_wtm_PrivateDebtInstrumentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_019fd7d0-1bf2-7f1c-bb69-bb3abefb2df5_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of contractual maturities of fixed maturities</link:label>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019fd7d0-1b75-74a9-a253-4a0df814a00b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Summary of loss and LAE reserve activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders_019fd7d0-1c60-77af-862f-04be87377a07_negatedLabel_en-US" xlink:label="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Dividends declared to noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders_label_en-US" xlink:label="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Decrease from Distributions to Noncontrolling Interest Holders</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:to="lab_us-gaap_MinorityInterestDecreaseFromDistributionsToNoncontrollingInterestHolders" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedCreditCardSecuritiesMember_019fd7d0-1b75-77f1-b8f8-d57f9d46054f_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit card receivables</link:label>
    <link:label id="lab_us-gaap_CollateralizedCreditCardSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Credit Card Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CollateralizedCreditCardSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedCreditCardSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_019fd7d0-1b75-7677-b82f-c7a7bb9bbd9f_terseLabel_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership percentage of basic units outstanding</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_label_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Of Basic Units Outstanding, Parent</link:label>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent_documentation_en-US" xlink:label="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subsidiary, Ownership Percentage Of Basic Units Outstanding, Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:href="wtm-20260930.xsd#wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:to="lab_wtm_SubsidiaryOwnershipPercentageOfBasicUnitsOutstandingParent" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RecoveryOfErrCompDisclosureLineItems_label_en-US" xlink:label="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Recovery of Erroneously Awarded Compensation Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:to="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MeasureAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureAxis" xlink:to="lab_ecd_MeasureAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss_019fd7d0-1b75-7050-abc4-0d0dfbece8c5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesTradingUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesTradingUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_019fd7d0-1b75-7da9-8257-bdfa8216bd27_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BambooSPVMember_019fd7d0-1b75-7c14-a50f-9f081a9d68e1_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-20260930.xsd#wtm_BambooSPVMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BambooSPVMember" xlink:to="lab_wtm_BambooSPVMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain_019fd7d0-1b75-770f-89d7-023d01f2a5b6_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019fd7d0-1b75-7aa7-aecf-a7bf0cd8a45a_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_019fd7d0-1b75-7da3-8fae-bd297b92481b_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019fd7d0-1b75-7bd1-aafe-050e4f48f929_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Earned insurance premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsurerTypeAxis_019fd7d0-1acb-7f99-9fc0-97048e99c051_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-20260930.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_StatementEquityComponentsAxis_019fd7d0-1b75-7ca3-abc2-d10c866bd247_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_019fd7d0-1bf2-7871-b5f5-afe3de72226a_negatedLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net income tax payments</link:label>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_label_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Paid, after Refund Received</link:label>
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    <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>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_019fd7d0-1bf2-7acc-8186-449931590713_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateAxis_019fd7d0-1bf1-74e2-a0fd-af28e635701c_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateAxis"/>
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    <link:label id="lab_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_019fd7d0-1b75-7f2f-8794-f03f3b699a08_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAttributableToNoncontrollingInterest"/>
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    <link:label id="lab_srt_AMBestAPlusRatingMember_019fd7d0-1bf1-74a6-8aff-788fa4d6900e_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_wtm_IncreaseDecreaseInShortTermInvestments_019fd7d0-1c60-7043-bd0d-96a130be7989_negatedLabel_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net change in short-term investments &#8212; Kudu</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInShortTermInvestments_label_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Short Term Investments</link:label>
    <link:label id="lab_wtm_IncreaseDecreaseInShortTermInvestments_documentation_en-US" xlink:label="lab_wtm_IncreaseDecreaseInShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Short Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_IncreaseDecreaseInShortTermInvestments" xlink:href="wtm-20260930.xsd#wtm_IncreaseDecreaseInShortTermInvestments"/>
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    <link:label id="lab_dei_EntitySmallBusiness_019fd7d0-1bf1-7a31-a9e5-ef545efd4d5e_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_019fd7d0-1b75-7ceb-b723-291ede8a6a60_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (loss) attributable to White Mountains&#8217;s common shareholders</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnearnedPremiums_019fd7d0-1acb-7715-9ba8-2c295b316f67_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned insurance premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019fd7d0-1acb-7908-8d7b-19b4da493971_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>
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    <link:label id="lab_wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember_019fd7d0-1bf2-72e0-ab19-f001d0d583f7_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>
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    <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-20260930.xsd#wtm_SubsidiaryKuduInvestmentManagementManagementEquityIncentiveMember"/>
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    <link:label id="lab_us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareTableTextBlock_019fd7d0-1bf2-74ab-900d-c8c043563251_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>
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    <link:label id="lab_dei_DocumentType_019fd7d0-1acb-7a24-96d2-82f2923636b0_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>
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    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_019fd7d0-1bf2-7e77-8750-bf5384e3c6ad_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchases of consolidated subsidiaries, net of cash acquired of $7.4 and $1.9</link:label>
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    <link:label id="lab_wtm_PrivateEquitySecuritiesMember_019fd7d0-1b75-7186-a6a9-74b0cf7beb65_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-20260930.xsd#wtm_PrivateEquitySecuritiesMember"/>
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    <link:label id="lab_wtm_LimitedPartnershipsMember_019fd7d0-1b75-761a-9e34-165b1a3c4def_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-20260930.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_GainsLossesOnExtinguishmentOfDebt_019fd7d0-1c60-787a-b1a9-0cf4ee4c5b1e_terseLabel_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss on extinguishment of debt</link:label>
    <link:label id="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt_label_en-US" xlink:label="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Extinguishment of Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:to="lab_us-gaap_GainsLossesOnExtinguishmentOfDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage_019fd7d0-1bf2-7da4-b5a2-5acf1ac698eb_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-20260930.xsd#wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:to="lab_wtm_BusinessCombinationVotingEquityInterestAcquiredBasicPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryOwnershipPercentageEconomicInterest_019fd7d0-1c60-797e-901a-6f2bf8d4c360_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-20260930.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_StatementOfStockholdersEquityAbstract_019fd7d0-1bf1-76a5-bd72-d8fdde11abd4_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod2Member_019fd7d0-1bf1-70ae-969b-982ce9b16dcb_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-20260930.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_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable_019fd7d0-1bf2-7f43-a5a3-70f2edcd1cfe_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Trading Securities and Other Trading Assets</link:label>
    <link:label id="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:to="lab_us-gaap_ScheduleOfTradingSecuritiesAndOtherTradingAssetsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019fd7d0-1c60-7990-ac25-60f53a0be064_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_019fd7d0-1c60-755a-9e08-e263da9911ae_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_019fd7d0-1bf1-7982-8ae8-0638df672ec0_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_country_CA_019fd7d0-1bf2-7c84-b03a-ad7970b0ab73_terseLabel_en-US" xlink:label="lab_country_CA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Canadian</link:label>
    <link:label id="lab_country_CA_label_en-US" xlink:label="lab_country_CA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">CANADA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_CA" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_CA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_CA" xlink:to="lab_country_CA" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_019fd7d0-1c60-7b4a-9db4-fcffc72a5e2a_terseLabel_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">New and existing contracts deployed</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_label_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long Term Investments, Increase (Decrease) in Participation Contracts</link:label>
    <link:label id="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts_documentation_en-US" xlink:label="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Long Term Investments, Increase (Decrease) in Participation Contracts</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:href="wtm-20260930.xsd#wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:to="lab_wtm_OtherLongTermInvestmentsIncreaseDecreaseInParticipationContracts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_019fd7d0-1c60-74d3-aff8-9c237fb616a0_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherShortTermInvestments" xlink:to="lab_us-gaap_OtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PledgedStatusDomain_019fd7d0-1bf2-7ee0-8d60-1138c8223d98_terseLabel_en-US" xlink:label="lab_us-gaap_PledgedStatusDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pledged Status [Domain]</link:label>
    <link:label id="lab_us-gaap_PledgedStatusDomain_label_en-US" xlink:label="lab_us-gaap_PledgedStatusDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pledged Status [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PledgedStatusDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PledgedStatusDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PledgedStatusDomain" xlink:to="lab_us-gaap_PledgedStatusDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fd7d0-1b75-7fdf-b242-4488b54ae034_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Pre-tax income (loss)</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_label_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:to="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems_019fd7d0-1bf1-736d-80ad-8a7f3220a246_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:to="lab_us-gaap_ScheduleOfGainLossOnInvestmentsIncludingMarketableSecuritiesAndInvestmentsHeldAtCostIncomeStatementReportedAmountsSummaryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxContingencyTable_019fd7d0-1c60-706f-a6ba-953ef32e459a_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Table]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxContingencyTable_label_en-US" xlink:label="lab_us-gaap_IncomeTaxContingencyTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Contingency [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxContingencyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxContingencyTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxContingencyTable" xlink:to="lab_us-gaap_IncomeTaxContingencyTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_019fd7d0-1bf1-7aa4-86b2-c9d0e058457d_terseLabel_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:label id="lab_srt_ExternalCreditRatingStandardPoorsMember_label_en-US" xlink:label="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">External Credit Rating, Standard &amp; Poor's [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ExternalCreditRatingStandardPoorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ExternalCreditRatingStandardPoorsMember" xlink:to="lab_srt_ExternalCreditRatingStandardPoorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_terseLabel_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Executive Category:</link:label>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_label_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Executive Category [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ExecutiveCategoryAxis" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_ExecutiveCategoryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ExecutiveCategoryAxis" xlink:to="lab_ecd_ExecutiveCategoryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt_019fd7d0-1bf2-71d3-8cfa-c61193db6312_terseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedLiabilityAssumedLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Borrowings</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-20260930.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_FundsHeldUnderReinsuranceAgreementsAsset_019fd7d0-1bf2-7b1d-b4fa-6d6b3ea0781e_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets held-in-trust</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_019fd7d0-1b75-7d70-98f4-ef22f6afffca_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Third-Party Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_019fd7d0-1c60-7a94-b877-a4d9134bb697_terseLabel_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">General and administrative expenses</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_label_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Including Amortization of Other Intangible Assets</link:label>
    <link:label id="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets_documentation_en-US" xlink:label="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">General and Administrative Expense, Including Amortization of Other Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:href="wtm-20260930.xsd#wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:to="lab_wtm_GeneralAndAdministrativeExpenseIncludingAmortizationOfOtherIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_SubsidiaryDistinguishedPartnersManagementEquityIncentivesMember_019fd7d0-1bf1-7144-be93-c2b638215160_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-20260930.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_wtm_AdjustmentForRedeemableNoncontrollingInterest_019fd7d0-1bf1-70ef-b3ea-59ded34ea55f_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-20260930.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_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonPeoNeoAvgCompActuallyPaidAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:to="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_019fd7d0-1b75-7614-9492-bb73452658a6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Variable Interest Entities [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedPaymentArrangementNonvestedAwardExcludingOptionCostNotYetRecognizedAmountForfeited_019fd7d0-1b75-7244-8142-1996e6ef56c9_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-20260930.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_SupplementalCashFlowInformationAbstract_019fd7d0-1b75-7f91-b7ea-ed603e7dea7c_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental cash flows information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoName" xlink:to="lab_ecd_PeoName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019fd7d0-1bf1-7bd5-a612-b40261bdaeac_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Net paid loss and LAE</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember_019fd7d0-1b75-7b04-b3eb-98199c4a93f6_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-20260930.xsd#wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:to="lab_wtm_TotalInvestmentsBeforeTPCProvidersInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_019fd7d0-1bf2-7378-89f5-7a255cc4cb3f_terseLabel_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remaining weighted average contract period (in years)</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_label_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Remaining Weighted Average Contract Period</link:label>
    <link:label id="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod_documentation_en-US" xlink:label="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Financial Guarantee Insurance Contracts, Remaining Weighted Average Contract Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:href="wtm-20260930.xsd#wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:to="lab_wtm_FinancialGuaranteeInsuranceContractsRemainingWeightedAverageContractPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtCovenantPeriod1Member_019fd7d0-1b75-75f3-9d6a-fe98ef51bdaf_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-20260930.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_CashAcquiredFromAcquisition_019fd7d0-1b75-728b-88c3-0e5b991fd9b6_terseLabel_en-US" xlink:label="lab_us-gaap_CashAcquiredFromAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash acquired from acquisition</link:label>
    <link:label id="lab_us-gaap_CashAcquiredFromAcquisition_label_en-US" xlink:label="lab_us-gaap_CashAcquiredFromAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Acquired from Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAcquiredFromAcquisition" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAcquiredFromAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAcquiredFromAcquisition" xlink:to="lab_us-gaap_CashAcquiredFromAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_country_BM_019fd7d0-1b75-7110-984c-4b4fd7cbf174_terseLabel_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Bermuda</link:label>
    <link:label id="lab_country_BM_label_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_BM" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_BM"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_BM" xlink:to="lab_country_BM" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_019fd7d0-1b75-723f-9549-1270f61130bb_terseLabel_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">AAA</link:label>
    <link:label id="lab_srt_StandardPoorsAAARatingMember_label_en-US" xlink:label="lab_srt_StandardPoorsAAARatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Standard &amp; Poor's, AAA Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StandardPoorsAAARatingMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StandardPoorsAAARatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StandardPoorsAAARatingMember" xlink:to="lab_srt_StandardPoorsAAARatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_019fd7d0-1bf2-7918-9707-06ee2ae4a400_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueRecognitionPolicyTextBlock_019fd7d0-1c60-7bc6-b206-149456f9f9a7_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenue Recognition</link:label>
    <link:label id="lab_us-gaap_RevenueRecognitionPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueRecognitionPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:to="lab_us-gaap_RevenueRecognitionPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross_019fd7d0-1bf1-7874-98fb-f5be956eb7ba_terseLabel_en-US" xlink:label="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross</link:label>
    <link:label id="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross_label_en-US" xlink:label="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Direct</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PolicyholderBenefitsAndClaimsIncurredGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:to="lab_us-gaap_PolicyholderBenefitsAndClaimsIncurredGross" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_019fd7d0-1c60-7572-867c-92ac2618975c_terseLabel_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Minimum interest reserve period required</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_label_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve, Minimum Period Required</link:label>
    <link:label id="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired_documentation_en-US" xlink:label="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short-term Investments, Interest Reserve, Minimum Period Required</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:href="wtm-20260930.xsd#wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:to="lab_wtm_ShortTermInvestmentsInterestReserveMinimumPeriodRequired" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceCyclePeriod_019fd7d0-1bf2-767f-9f92-fc117d6d5668_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-20260930.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_dei_EntityIncorporationStateCountryCode_019fd7d0-1b75-72e0-b171-f2a356b0117e_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationOwnershipPercentageDisposedOf_019fd7d0-1b75-75d2-86c1-7bad422de0cd_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-20260930.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_ecd_AggtErrCompNotYetDeterminedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined</link:label>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_label_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtErrCompNotYetDeterminedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:to="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_terseLabel_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement</link:label>
    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_label_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MtrlTermsOfTrdArrTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:to="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year</link:label>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:to="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceived_019fd7d0-1b75-79d8-a7c9-c5406c589569_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-20260930.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_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_019fd7d0-1bf2-72ec-bf23-2cccbb1d6a94_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_019fd7d0-1bf2-7c2e-b807-3ce56a1acfd0_verboseLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTaxIncludingPortionAttributableToNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_019fd7d0-1bf1-70b7-93a7-0c1ecd2fdb8b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementFrequencyDomain_019fd7d0-1bf1-7714-94a0-a214dc8ec054_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementFrequencyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Frequency [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementFrequencyDomain" xlink:to="lab_us-gaap_FairValueMeasurementFrequencyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DebtInstrumentNumberOfTransactions_019fd7d0-1b75-79b8-8eca-8c0f875b1de1_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-20260930.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_us-gaap_ShareBasedCompensation_019fd7d0-1bf1-7a1d-9b07-0f7cc77e39a5_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of restricted share awards</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensation" xlink:to="lab_us-gaap_ShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_PaymentsToAcquireTradingFixedMaturitiesInvestments_019fd7d0-1b75-7dec-956d-9cbb438161a9_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-20260930.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_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_019fd7d0-1bf1-701a-ba6a-e6e5d4e3bdb8_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRedeemableNoncontrollingInterestAcquired_019fd7d0-1b75-76ca-81fe-36c331946c55_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-20260930.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_wtm_DebtSecuritiesTradingAmortizedCostAfterAllowanceForCreditLossMaturityAllocatedAndSingleMaturityDateAfterYear5Through10_019fd7d0-1b75-7fd8-8554-7fc2069802cb_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-20260930.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_EarningsPerShareBasic_019fd7d0-1bf2-7ee8-bcee-e13ceb028088_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (loss) per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_019fd7d0-1b75-7153-8ae0-d0b2b800524b_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutMultiplier_019fd7d0-1c60-743d-b20a-7bbc30be107d_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-20260930.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_ScheduleOfNominalAndFairValueOfNotesReceivableTableTextBlock_019fd7d0-1bf1-79eb-8301-a8a2f4e455e1_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-20260930.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_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingArrLineItems" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTradingArrLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingArrLineItems" xlink:to="lab_ecd_InsiderTradingArrLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_019fd7d0-1b75-7cc7-8fe1-b1028201f4bb_terseLabel_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_label_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes [Member]</link:label>
    <link:label id="lab_wtm_Ark2021SubordinatedNotesMember_documentation_en-US" xlink:label="lab_wtm_Ark2021SubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Ark 2021 Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_Ark2021SubordinatedNotesMember" xlink:href="wtm-20260930.xsd#wtm_Ark2021SubordinatedNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_Ark2021SubordinatedNotesMember" xlink:to="lab_wtm_Ark2021SubordinatedNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_DavidShieldPassportCardMember_019fd7d0-1b75-7855-85cc-aaba60157762_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-20260930.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_BishopStreetMember_019fd7d0-1c60-7845-a54c-39bcd68e277f_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-20260930.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_AccountsReceivableNetCurrent_019fd7d0-1c60-7244-a391-fd070326451c_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsReceivableNetCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts receivable</link:label>
    <link:label id="lab_us-gaap_AccountsReceivableNetCurrent_label_en-US" xlink:label="lab_us-gaap_AccountsReceivableNetCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts Receivable, after Allowance for Credit Loss, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsReceivableNetCurrent" xlink:to="lab_us-gaap_AccountsReceivableNetCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_019fd7d0-1b75-73b7-8d75-efc75f29ab55_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance acquisition expenses</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedDistributed_019fd7d0-1bf1-7e6f-9abb-b009b1c4fb10_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distributed earnings - dividends declared and paid (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDilutedDistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted, Distributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDilutedDistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareDilutedDistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDilutedDistributed" xlink:to="lab_us-gaap_EarningsPerShareDilutedDistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_019fd7d0-1b75-77de-9f4d-79f4995499bc_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industrial</link:label>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_label_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial and Industrial Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommercialAndIndustrialSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:to="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_019fd7d0-1bf1-7b18-ab3c-e2f04e581cbd_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_019fd7d0-1bf1-7143-8966-bc199bf8aeed_periodEndLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Temporary equity, ending balance</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Including Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:to="lab_us-gaap_TemporaryEquityCarryingAmountIncludingPortionAttributableToNoncontrollingInterests" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MemberSurplusContributionsInsurancePremiumChargesPercentage_019fd7d0-1b75-7820-8cd2-b4d69da513b0_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-20260930.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_BusinessCombinationRightToPurchaseUnitsUnitPriceMultiplier_019fd7d0-1bf1-74da-9d93-3da659072fb5_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-20260930.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_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_019fd7d0-1b75-713a-9911-7f46c3fe9c1f_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_019fd7d0-1b75-7242-9e11-f0927eb24097_negatedLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Net gain on sale of the Bamboo Group</link:label>
    <link:label id="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal_label_en-US" xlink:label="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disposal Group, Not Discontinued Operation, Gain (Loss) on Disposal</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:to="lab_us-gaap_DisposalGroupNotDiscontinuedOperationGainLossOnDisposal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_019fd7d0-1b75-7f1d-bc0a-b413b2551147_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contingent consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Contingent Consideration, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationContingentConsiderationLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:to="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_019fd7d0-1b75-7fd6-88ab-f6e9ca18246a_terseLabel_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFVNIAbstract_019fd7d0-1b75-7cf4-9a20-5e758abe198a_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFVNIAbstract_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFVNIAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFVNIAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFVNIAbstract" xlink:to="lab_us-gaap_EquitySecuritiesFVNIAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_country_GB_019fd7d0-1acb-7b42-b615-5fa4821a51bd_terseLabel_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">United Kingdom</link:label>
    <link:label id="lab_country_GB_label_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED KINGDOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_GB" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_GB"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_GB" xlink:to="lab_country_GB" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_019fd7d0-1c60-7b4d-be11-aa34083f6a67_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Inputs Assets Quantitative Information [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_019fd7d0-1b75-7825-9cc9-2eeb873cfbe0_verboseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">% of Total</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskPercentage1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConcentrationRiskPercentage1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskPercentage1" xlink:to="lab_us-gaap_ConcentrationRiskPercentage1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BermudaStockExchangeMember_019fd7d0-1c60-73eb-92c2-535289a45389_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-20260930.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_wtm_NetInvestmentIncomeAdjusted_019fd7d0-1c60-7794-87ea-2e2bb1162b45_terseLabel_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_wtm_NetInvestmentIncomeAdjusted_label_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income, Adjusted</link:label>
    <link:label id="lab_wtm_NetInvestmentIncomeAdjusted_documentation_en-US" xlink:label="lab_wtm_NetInvestmentIncomeAdjusted" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Investment Income, Adjusted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_NetInvestmentIncomeAdjusted" xlink:href="wtm-20260930.xsd#wtm_NetInvestmentIncomeAdjusted"/>
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    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsMember" xlink:to="lab_ecd_EqtyAwrdsAdjsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_AgencyRelationshipsMember_019fd7d0-1bf2-75d7-b2f9-d1f1ba73f30e_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-20260930.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_us-gaap_AssumedPremiumsEarned_019fd7d0-1bf2-7c53-aa94-5076bc1e2e29_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 Premiums Earned</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod_019fd7d0-1c60-7fd5-93cf-5a610cfe1256_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-20260930.xsd#wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:to="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_019fd7d0-1bf2-7283-82f0-1aca3713f9ec_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Balance Sheet Grouping, Financial Statement Captions</link:label>
    <link:label id="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Balance Sheet Grouping, Financial Statement Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:to="lab_us-gaap_FairValueBalanceSheetGroupingFinancialStatementCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_019fd7d0-1acb-7173-82d5-24310a53fdea_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesIndustryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:to="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_019fd7d0-1c60-7b77-9aa7-4f44763a38b5_terseLabel_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC</link:label>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_label_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC [Member]</link:label>
    <link:label id="lab_wtm_HawkeyeElectricLLCMember_documentation_en-US" xlink:label="lab_wtm_HawkeyeElectricLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hawkeye Electric, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_HawkeyeElectricLLCMember" xlink:href="wtm-20260930.xsd#wtm_HawkeyeElectricLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_HawkeyeElectricLLCMember" xlink:to="lab_wtm_HawkeyeElectricLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities_019fd7d0-1b75-76d2-b0c8-6efe11da415b_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-20260930.xsd#wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:to="lab_wtm_BusinessCombinationRecognizedLiabilitiesAssumedOtherLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeographicDistributionDomain_019fd7d0-1c60-753d-85be-cf23e3860c94_terseLabel_en-US" xlink:label="lab_us-gaap_GeographicDistributionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Domain]</link:label>
    <link:label id="lab_us-gaap_GeographicDistributionDomain_label_en-US" xlink:label="lab_us-gaap_GeographicDistributionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Geographic Distribution [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeographicDistributionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeographicDistributionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeographicDistributionDomain" xlink:to="lab_us-gaap_GeographicDistributionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_019fd7d0-1bf1-75ad-be6f-9a52f4353726_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:to="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_019fd7d0-1b75-71a3-93df-2b2753ce5259_negatedTerseLabel_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net release of cash (pre-funding) of investment purchases</link:label>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_label_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Release Of Cash (Pre-Fundings) For Managed Funds</link:label>
    <link:label id="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds_documentation_en-US" xlink:label="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Release Of Cash (Pre-Fundings) For Managed Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:href="wtm-20260930.xsd#wtm_ReleaseOfCashPreFundingsForManagedFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:to="lab_wtm_ReleaseOfCashPreFundingsForManagedFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ParentMember_019fd7d0-1c60-7337-95d0-b9c271763647_terseLabel_en-US" xlink:label="lab_us-gaap_ParentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_ParentMember_label_en-US" xlink:label="lab_us-gaap_ParentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ParentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ParentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ParentMember" xlink:to="lab_us-gaap_ParentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_019fd7d0-1bf1-7f2f-9042-abb200f86200_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract_019fd7d0-1b75-72bc-a4f4-0a1ff3b67715_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Including Portion Attributable to Noncontrolling Interest [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:to="lab_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_019fd7d0-1c60-75c7-8531-3ee72cb5c97e_terseLabel_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recognition of equity-based compensation expense of subsidiaries</link:label>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_label_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Temporary Equity, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:label id="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition_documentation_en-US" xlink:label="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Temporary Equity, Share-Based Payment Arrangement, Other, Increase for Cost Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:href="wtm-20260930.xsd#wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:to="lab_wtm_TemporaryEquityShareBasedPaymentArrangementOtherIncreaseForCostRecognition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_019fd7d0-1bf1-7c5f-8b64-56a650f86b53_negatedLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Forfeited (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsRemainingPeriodFiveToTenYears_019fd7d0-1b75-76a1-be76-d3c518da04e3_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-20260930.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_RedeemableNoncontrollingInterestTableTextBlock_019fd7d0-1b75-751a-9d53-fec63f71a7a7_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of noncontrolling interest</link:label>
    <link:label id="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock_label_en-US" xlink:label="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Redeemable Noncontrolling Interest [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RedeemableNoncontrollingInterestTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:to="lab_us-gaap_RedeemableNoncontrollingInterestTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_019fd7d0-1bf1-78ea-a261-190297c5774f_verboseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">General and administrative expenses</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_019fd7d0-1bf1-7410-9c98-a75cf33eb544_terseLabel_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Renegotiation period</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_label_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement, Renegotiation Period</link:label>
    <link:label id="lab_wtm_ReinsuranceAgreementRenegotiationPeriod_documentation_en-US" xlink:label="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement, Renegotiation Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:href="wtm-20260930.xsd#wtm_ReinsuranceAgreementRenegotiationPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:to="lab_wtm_ReinsuranceAgreementRenegotiationPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_019fd7d0-1bf2-785c-aa49-56264c83f144_terseLabel_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_terseLabel_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Available</link:label>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_019fd7d0-1c60-7034-9f42-ee495b89e256_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxAuthorityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:to="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember_019fd7d0-1b75-7fcf-9695-9f7e82e29fbb_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-20260930.xsd#wtm_MandatorilyRedeemablePreferredSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:to="lab_wtm_MandatorilyRedeemablePreferredSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract_019fd7d0-1c60-7f69-ba00-4eb0af01808f_terseLabel_en-US" xlink:label="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discontinued Operations and Disposal Groups [Abstract]</link:label>
    <link:label id="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract_label_en-US" xlink:label="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Discontinued Operations and Disposal Groups [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:to="lab_us-gaap_DiscontinuedOperationsAndDisposalGroupsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_FundsHeldUnderReinsuranceAgreementsAssetsSurplusNotes_019fd7d0-1bf2-72f3-8a4b-310ab2f2fc41_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-20260930.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_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_019fd7d0-1b75-7ba5-beac-855f41cf5f65_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_019fd7d0-1bf1-74fa-80b2-568b1893e7cc_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_MaterialsSectorMember_019fd7d0-1b75-78cf-b1a1-aa62400c04a1_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-20260930.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_NoncontrollingInterestIncreaseFromBusinessCombination_019fd7d0-1bf2-75e6-93c0-0c2c479b3522_terseLabel_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisition of noncontrolling interests</link:label>
    <link:label id="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination_label_en-US" xlink:label="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noncontrolling Interest, Increase from Business Combination</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:to="lab_us-gaap_NoncontrollingInterestIncreaseFromBusinessCombination" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_OtherLongTermInvestmentsMeasurementInput_019fd7d0-1acb-77ca-bfec-d4ed238bb6b3_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-20260930.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_ecd_PvpTable_terseLabel_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure</link:label>
    <link:label id="lab_ecd_PvpTable_label_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTable" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PvpTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTable" xlink:to="lab_ecd_PvpTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019fd7d0-1b75-75ce-b219-1e35fd2a8be3_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferred1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_NotesReceivableInterestRateFairValueDiscount_019fd7d0-1bf1-7741-8461-778e7c268b6a_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_019fd7d0-1bf1-7807-ad9a-0fae7b10d3b4_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-20260930.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_dei_EntityFilerCategory_019fd7d0-1bf1-772a-b5d3-53c05bd7fa4b_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityFilerCategory"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFilerCategory" xlink:to="lab_dei_EntityFilerCategory" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes_019fd7d0-1b75-7fa1-8e41-94dbd1d23bca_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_019fd7d0-1b75-7122-83b6-7c09fbf0c966_negatedTerseLabel_en-US" xlink:label="lab_wtm_GainLossOnFairValueAdjustmentOfSurplusNotes" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" 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-20260930.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_EarningsPerShareBasicDistributed_019fd7d0-1b75-7763-bb1f-dc994c758e97_verboseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Distributed earnings - dividends declared and paid (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasicDistributed_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic, Distributed</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasicDistributed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasicDistributed"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasicDistributed" xlink:to="lab_us-gaap_EarningsPerShareBasicDistributed" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral_019fd7d0-1bf1-7f72-acd6-7931fd2a76b6_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-20260930.xsd#wtm_ReinsuranceRecoverablesIncludingReinsurancePremiumPaidNetOfCollateral"/>
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    <link:label id="lab_country_LU_019fd7d0-1b75-7897-b7ba-d3276fa171de_terseLabel_en-US" xlink:label="lab_country_LU" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">LUXEMBOURG</link:label>
    <link:label id="lab_country_LU_label_en-US" xlink:label="lab_country_LU" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">LUXEMBOURG</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_LU" xlink:href="https://xbrl.sec.gov/country/2026/country-2026.xsd#country_LU"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_LU" xlink:to="lab_country_LU" xlink:type="arc" order="1"/>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
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    <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>
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    <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_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_019fd7d0-1b75-79cb-a8e5-e69560d000a4_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income to net cash provided from (used for) operations:</link:label>
    <link:label id="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity, Noncash Item [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_AdjustmentsNoncashItemsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems_019fd7d0-1c60-7c1f-96cc-8adbed526c70_terseLabel_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems_label_en-US" xlink:label="lab_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation, Less than Wholly Owned Subsidiary, Parent Ownership Interest, Effects of Changes, Net [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConsolidationLessThanWhollyOwnedSubsidiaryParentOwnershipInterestEffectsOfChangesNetLineItems"/>
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    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_019fd7d0-1bf2-7338-920d-3052404544ab_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insurance premiums receivable</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantDateFairValueRollForward_019fd7d0-1b75-78bc-abd0-11649b659705_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-20260930.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_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_019fd7d0-1c60-7685-8435-0cc6365c66f3_terseLabel_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other equity method eligible investments less than 50.0%</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_label_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, Less Than Fifty Percent [Member]</link:label>
    <link:label id="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember_documentation_en-US" xlink:label="lab_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Eligible Investments, Less Than Fifty Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_EquityMethodEligibleInvestmentsLessThanFiftyPercentMember" xlink:href="wtm-20260930.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_wtm_MeasurementInputTerminalCashFlowExitMultipleMember_019fd7d0-1bf1-7b5e-b694-32df2afebd8f_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-20260930.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_ValuationTechniqueDiscountedCashFlowMember_019fd7d0-1bf1-73e6-9924-d2a2ecbc915e_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Discounted cash flow</link:label>
    <link:label id="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember_label_en-US" xlink:label="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Valuation Technique, Discounted Cash Flow [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ValuationTechniqueDiscountedCashFlowMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:to="lab_us-gaap_ValuationTechniqueDiscountedCashFlowMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_019fd7d0-1bf2-75cd-9ed5-ba3729de2641_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:label id="lab_us-gaap_StatementTable_label_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementTable" xlink:to="lab_us-gaap_StatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPerformanceSharesAccruedLiabilityGrantsInPeriod_019fd7d0-1c60-714b-838c-041a636051a7_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-20260930.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_wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets_019fd7d0-1b75-7fd4-875c-b31cf57d9e21_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-20260930.xsd#wtm_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNetTangibleAssets"/>
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    <link:label id="lab_wtm_NewYorkStockExchangeMember_019fd7d0-1b75-7e07-8c98-ce3a83f01db7_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-20260930.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_srt_CreditRatingStandardPoorsAxis_019fd7d0-1b75-7240-bc8c-ffa9c36e970c_terseLabel_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingStandardPoorsAxis_label_en-US" xlink:label="lab_srt_CreditRatingStandardPoorsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, Standard &amp; Poor's [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingStandardPoorsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CreditRatingStandardPoorsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingStandardPoorsAxis" xlink:to="lab_srt_CreditRatingStandardPoorsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_019fd7d0-1b75-72ad-9832-82ea95487631_negatedTerseLabel_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities related to investment basis differences</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_label_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill, Deferred Tax Liability</link:label>
    <link:label id="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability_documentation_en-US" xlink:label="lab_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill, Deferred Tax Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability" xlink:href="wtm-20260930.xsd#wtm_BusinessCombinationRecognizedAssetAcquiredIdentifiableIntangibleAssetExcludingGoodwillDeferredTaxLiability"/>
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    <link:label id="lab_wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments_019fd7d0-1b75-74a3-9510-ce4a6575e144_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-20260930.xsd#wtm_DisposalGroupIncludingDiscontinuedOperationIncrementalProceedsReceivedPurchasePriceAdjustments"/>
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    <link:label id="lab_us-gaap_GeographicDistributionAxis_019fd7d0-1b75-702b-88b5-253c1bf4dd35_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>
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