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Investment Securities (Net Realized and Unrealized Investement Gains and Losses) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investments, Debt and Equity Securities [Abstract]      
Net realized investment gains, pre-tax $ 233.8wtm_TradingSecuritiesRealizedGainLossTotal $ 104.5wtm_TradingSecuritiesRealizedGainLossTotal $ 68.1wtm_TradingSecuritiesRealizedGainLossTotal
Net unrealized investment gains, pre-tax 50.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 57.2wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 50.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Net realized and unrealized investment gains, pre-tax 283.9us-gaap_NetRealizedOrUnrealizedGainLossOnTradingSecurities 161.7us-gaap_NetRealizedOrUnrealizedGainLossOnTradingSecurities 118.2us-gaap_NetRealizedOrUnrealizedGainLossOnTradingSecurities
Income tax expense attributable to net realized and unrealized investment gains (69.7)wtm_Taxonnetrealizedandunrealizedgainslosstradingsecurities (21.9)wtm_Taxonnetrealizedandunrealizedgainslosstradingsecurities (26.8)wtm_Taxonnetrealizedandunrealizedgainslosstradingsecurities
Net realized and unrealized investment gains, after tax $ 214.2wtm_NetRealizedandUnrealizedGainLossonTradingSecuritiesNetofTax $ 139.8wtm_NetRealizedandUnrealizedGainLossonTradingSecuritiesNetofTax $ 91.4wtm_NetRealizedandUnrealizedGainLossonTradingSecuritiesNetofTax