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Contingencies (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended 1 Months Ended
Mar. 31, 2015
Mar. 31, 2014
Oct. 31, 2011
Jun. 30, 2007
Oct. 07, 2011
Jan. 22, 2015
Loss Contingencies [Line Items]            
Discontinued Operation, Gain (Loss) on Disposal of Discontinued Operation, Net of Tax $ 8.0us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax $ 0us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax        
Esurance            
Loss Contingencies [Line Items]            
Warranty agreement period     18 months      
Non-solicitation agreement period     3 years      
Percentage of fluctuation in loss reserves of transferred subsidiaries retained         90.00%wtm_PercentageOfFluctuationInLossReservesOfTransferredSubsidiariesRetained
/ dei_LegalEntityAxis
= wtm_EsuranceMember
 
Tribune Company Litigation | Pending Litigation            
Loss Contingencies [Line Items]            
Proceeds from Sale, Maturity and Collection of Investments       39.0wtm_ProceedsFromTribuneCommonStock
/ us-gaap_LitigationCaseAxis
= wtm_TribuneCompanyLitigationMember
/ us-gaap_LitigationStatusAxis
= us-gaap_PendingLitigationMember
   
Segment, Discontinued Operations            
Loss Contingencies [Line Items]            
Discontinued Operation, Gain (Loss) on Disposal of Discontinued Operation, Net of Tax 8.0us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
         
OneBeacon Runoff [Member]            
Loss Contingencies [Line Items]            
Number of insurance holders           3wtm_Numberofinsuranceholders
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
OneBeacon Runoff [Member] | Segment, Discontinued Operations            
Loss Contingencies [Line Items]            
Discontinued Operation, Gain (Loss) on Disposal of Discontinued Operation, Net of Tax $ (0.1)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
$ (0.5)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis
= wtm_OnebeaconRunoffMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember