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Investment Securities (Net Realized and Unrealized Investment Gains (Losses) (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended
Mar. 31, 2015
Mar. 31, 2014
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total $ 52.8wtm_TradingSecuritiesRealizedGainLossTotal $ 21.7wtm_TradingSecuritiesRealizedGainLossTotal
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 50.6wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 42.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Net Realized and Unrealized Gain (Loss) on Trading Securities 103.4us-gaap_NetRealizedOrUnrealizedGainLossOnTradingSecurities 63.8us-gaap_NetRealizedOrUnrealizedGainLossOnTradingSecurities
Income tax expense attributable to net realized and unrealized investment gains (26.3)wtm_Taxonnetrealizedandunrealizedgainslosstradingsecurities (15.7)wtm_Taxonnetrealizedandunrealizedgainslosstradingsecurities
Realized and unrealized gain 77.1wtm_NetRealizedandUnrealizedGainLossonTradingSecuritiesNetofTax 48.1wtm_NetRealizedandUnrealizedGainLossonTradingSecuritiesNetofTax
Fixed maturity investments.    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total 31.0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
0.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 52.3wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
31.6wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Short-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total 3.5wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 0wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Common equity securities    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total 25.5wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
18.8wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities (3.4)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
4.5wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Convertible fixed maturity investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total (4.2)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
2.4wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 0.8wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0.7wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Other long-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total (3.0)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
(0.3)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 0.9wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
5.3wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Forward Contracts    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss), Total 0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
(0.1)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities $ 0wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
$ 0wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember