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Investment Securities (Other Long-Term Investments) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Other Investments $ 385.0us-gaap_OtherInvestments $ 262.3us-gaap_OtherInvestments  
Other long-term investments      
Investment securities      
Carrying value of investment accounted for using the equity method 23.2us-gaap_EquityMethodInvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
   
Limited Liability Company and Private Equity Securities      
Investment securities      
Other Investments 69.7us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_LimitedliabilitycompaniesandprivateequitysecuritiesMember
20.3us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_LimitedliabilitycompaniesandprivateequitysecuritiesMember
 
Surplus Note      
Investment securities      
Other Investments 65.1us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_SurplusNoteMember
0us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_SurplusNoteMember
 
Total hedge and private equity funds included in other long-term investments      
Investment securities      
Other Investments 242.9us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_HedgeFundsAndPrivateEquityFundsMember
239.0us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_HedgeFundsAndPrivateEquityFundsMember
 
Other Debt Obligations [Member]      
Investment securities      
Other Investments 7.3us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_OtherDebtSecuritiesMember
3.1us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_OtherDebtSecuritiesMember
 
Forward contracts      
Investment securities      
Other Investments 0us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_ForwardContractsMember
(0.1)us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_ForwardContractsMember
 
Fair value measured on a recurring basis | Level 3 Inputs | Other long-term investments      
Investment securities      
Carrying value of investment accounted for using the equity method $ 23.2us-gaap_EquityMethodInvestmentsFairValueDisclosure
/ us-gaap_FairValueByFairValueHierarchyLevelAxis
= us-gaap_FairValueInputsLevel3Member
/ us-gaap_FairValueByMeasurementFrequencyAxis
= us-gaap_FairValueMeasurementsRecurringMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
$ 26.6us-gaap_EquityMethodInvestmentsFairValueDisclosure
/ us-gaap_FairValueByFairValueHierarchyLevelAxis
= us-gaap_FairValueInputsLevel3Member
/ us-gaap_FairValueByMeasurementFrequencyAxis
= us-gaap_FairValueMeasurementsRecurringMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
$ 35.0us-gaap_EquityMethodInvestmentsFairValueDisclosure
/ us-gaap_FairValueByFairValueHierarchyLevelAxis
= us-gaap_FairValueInputsLevel3Member
/ us-gaap_FairValueByMeasurementFrequencyAxis
= us-gaap_FairValueMeasurementsRecurringMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember