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Investment Securities (Non-agency Commercial Mortgage-backed Securities) (Details) (USD $)
In Millions, unless otherwise specified
Mar. 31, 2015
Dec. 31, 2014
Mar. 31, 2014
Dec. 31, 2013
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments $ 5,957.2us-gaap_InvestmentsFairValueDisclosure $ 5,991.4us-gaap_InvestmentsFairValueDisclosure $ 6,736.7us-gaap_InvestmentsFairValueDisclosure $ 6,766.5us-gaap_InvestmentsFairValueDisclosure
Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 292.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
236.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
   
Commercial Mortgage Backed Securities | Super Senior        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 18.6us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
     
Commercial Mortgage Backed Securities | Senior        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 76.2us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
     
Commercial Mortgage Backed Securities | Subordinate        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments $ 197.4us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember