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Investment Securities (Non-agency Residential Mortgage-backed Securities) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Fair value investments $ 5,991.4us-gaap_InvestmentsFairValueDisclosure $ 6,766.5us-gaap_InvestmentsFairValueDisclosure $ 6,950.7us-gaap_InvestmentsFairValueDisclosure
Residential      
Investment securities      
Fair value investments 131.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
125.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
 
Residential | Prime      
Investment securities      
Fair value investments 119.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialPrimeFinancingReceivableMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Non-prime      
Investment securities      
Fair value investments 9.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= wtm_ResidentialNonprimeFinancingReceivableMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Sub-prime      
Investment securities      
Fair value investments 2.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialSubprimeFinancingReceivableMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Super Senior      
Investment securities      
Fair value investments 74.1us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Super Senior | Prime      
Investment securities      
Fair value investments 71.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialPrimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Super Senior | Non-prime      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= wtm_ResidentialNonprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Super Senior | Sub-prime      
Investment securities      
Fair value investments 2.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialSubprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Senior      
Investment securities      
Fair value investments 57.1us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Senior | Prime      
Investment securities      
Fair value investments 47.8us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialPrimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Senior | Non-prime      
Investment securities      
Fair value investments 9.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= wtm_ResidentialNonprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Senior | Sub-prime      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialSubprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Subordinate      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Subordinate | Prime      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialPrimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Subordinate | Non-prime      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= wtm_ResidentialNonprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Residential | Subordinate | Sub-prime      
Investment securities      
Fair value investments $ 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_FinancingReceivableRecordedInvestmentByClassOfFinancingReceivableAxis
= us-gaap_ResidentialSubprimeFinancingReceivableMember
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember