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Significant Transactions (Dispositions) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended 3 Months Ended 0 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Mar. 31, 2014
Dec. 23, 2014
Oct. 31, 2014
Significant Transactions            
(Loss) gain on sale of discontinued operations, net of tax $ (1.6)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax $ 46.6us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax $ (91.0)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax      
Gain (Loss) on Disposition of Stock in Subsidiary 0.7us-gaap_GainOrLossOnSaleOfStockInSubsidiary 21.3us-gaap_GainOrLossOnSaleOfStockInSubsidiary 0us-gaap_GainOrLossOnSaleOfStockInSubsidiary      
Premiums Written, Net 2,121.5us-gaap_PremiumsWrittenNet          
OneBeacon Runoff            
Significant Transactions            
Surplus notes         101.0us-gaap_SurplusNotes
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
 
Ashmere [Member] | WM Solutions            
Significant Transactions            
Excess amount over statutory surplus           6.0wtm_Excessamountoverstatutorysurplus
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_AshmereMember
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
Gain (Loss) on Disposition of Stock in Subsidiary 1.0us-gaap_GainOrLossOnSaleOfStockInSubsidiary
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_AshmereMember
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
         
Citation [Member] | WM Solutions            
Significant Transactions            
Gain (Loss) on Disposition of Stock in Subsidiary       0.7us-gaap_GainOrLossOnSaleOfStockInSubsidiary
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_CitationMember
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
   
Essentia | OneBeacon            
Significant Transactions            
Gain (Loss) on Disposition of Stock in Subsidiary   23.0us-gaap_GainOrLossOnSaleOfStockInSubsidiary
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_EssentiaMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
       
Gain (Loss) on Disposition of Stock in Subsidiary, After Tax   15.0wtm_GainLossonDispositionofStockinSubsidiaryAfterTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_EssentiaMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
       
Underwriting Agreement [Member] | Essentia | OneBeacon            
Significant Transactions            
Premiums Written, Net     179.7us-gaap_PremiumsWrittenNet
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_EssentiaMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_TypeOfArrangementAxis
= wtm_UnderwritingAgreementMember
     
Premiums Written, Percentage of Total     8.00%wtm_PremiumsWrittenPercentageOfTotal
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_EssentiaMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_TypeOfArrangementAxis
= wtm_UnderwritingAgreementMember
     
Fair Value [Member] | Other long-term investments | OneBeacon Runoff            
Significant Transactions            
Surplus notes         64.9us-gaap_SurplusNotes
/ us-gaap_FairValueByAssetClassAxis
= wtm_FairValueMember
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= wtm_OnebeaconRunoffMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
 
Discontinued Operations            
Significant Transactions            
(Loss) gain on sale of discontinued operations, net of tax (1.6)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
46.6us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(91.0)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
     
Discontinued Operations | OneBeacon Runoff            
Significant Transactions            
Surplus notes 101.0us-gaap_SurplusNotes
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
         
(Loss) gain on sale of discontinued operations, net of tax (35.9)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
  91.5us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
     
Discontinued Operations | Surplus Note | OneBeacon Runoff            
Significant Transactions            
(Loss) gain on sale of discontinued operations, net of tax (23.5)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ invest_InvestmentAxis
= wtm_SurplusNoteMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
         
Discontinued Operations | Fair Value [Member] | OneBeacon Runoff            
Significant Transactions            
Surplus notes 65.1us-gaap_SurplusNotes
/ us-gaap_FairValueByAssetClassAxis
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/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
         
Surplus Note | Discontinued Operations | OneBeacon Runoff            
Significant Transactions            
(Loss) gain on sale of discontinued operations, net of tax $ 36.1us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_InvestmentTypeAxis
= wtm_SurplusNoteMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
      $ 36.1us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_InvestmentTypeAxis
= wtm_SurplusNoteMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember