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Summary of Significant Accounting Policies (Basis of Presentation) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Basis of Presentation    
Assets held for sale $ 58.1us-gaap_AssetsHeldForSaleAtCarryingValue $ 1,880.1us-gaap_AssetsHeldForSaleAtCarryingValue
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured  
OneBeacon Ltd.    
Basis of Presentation    
Ownership interest (as a percent) 75.30%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
75.20%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
HG Global    
Basis of Presentation    
Surplus notes 503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
 
Star & Shield Insurance Exchange [Member]    
Basis of Presentation    
Surplus notes 17.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
 
Redeemable preferred stocks | HG Global    
Basis of Presentation    
Ownership interest (as a percent) 96.90%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
97.30%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Common Stock | HG Global    
Basis of Presentation    
Ownership interest (as a percent) 88.40%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
88.70%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Wholly Owned Properties [Member] | OneBeacon Ltd.    
Basis of Presentation    
Assets held for sale $ 58.1us-gaap_AssetsHeldForSaleAtCarryingValue
/ us-gaap_FairValueByAssetClassAxis
= us-gaap_WhollyOwnedPropertiesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember