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Investment Securities (Other long-term investments) (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]        
Other Investments $ 402.6us-gaap_OtherInvestments $ 407.0us-gaap_OtherInvestments    
Partnership investments [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments 3.8us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_PartnershipinvestmentsMember
5.2us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_PartnershipinvestmentsMember
   
Hedge and private equity funds included in other long-term investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments 242.5us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_HedgeFundsAndPrivateEquityFundsMember
242.9us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_HedgeFundsAndPrivateEquityFundsMember
   
Surplus Note        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments 68.0us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_SurplusNoteMember
65.1us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_SurplusNoteMember
   
Limited Liability Companies and Private Equity Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments 66.6us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_LimitedliabilitycompaniesandprivateequitysecuritiesMember
69.7us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_LimitedliabilitycompaniesandprivateequitysecuritiesMember
   
Affordable Housing Development Fund [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments 16.2us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_AffordableHousingDevelopmentFundMember
16.8us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_AffordableHousingDevelopmentFundMember
18.5us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_AffordableHousingDevelopmentFundMember
19.1us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= wtm_AffordableHousingDevelopmentFundMember
Other        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Other Investments $ 5.5us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_OtherDebtSecuritiesMember
$ 7.3us-gaap_OtherInvestments
/ us-gaap_DebtSecurityAxis
= us-gaap_OtherDebtSecuritiesMember