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Investment Securities (Net Realized and Unrealized Gains (Losses) After Tax) (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 change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates $ 81.2wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio $ (106.4)wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio $ 62.8wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
Income taxes (5.9)wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliatesTaxEffect 8.3wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliatesTaxEffect (5.1)wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliatesTaxEffect
Net change in unrealized gains (losses) on investments in unconsolidated affiliates, after tax 75.3wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliates (98.1)wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliates 57.7wtm_OtherComprehensiveIncomeLossEquityinUnrealizedGainsLossesfromInvestmentsinUnconsolidatedAffiliates
Net realized and unrealized foreign currency (losses) gains on investments through OCI (274.3)wtm_OtherComprehensiveIncomeForeignCurrencyTransactionandTranslationAdjustmentUnrealizedGainLossonInvestmentsNetofTaxPeriodIncreaseDecrease 11.3wtm_OtherComprehensiveIncomeForeignCurrencyTransactionandTranslationAdjustmentUnrealizedGainLossonInvestmentsNetofTaxPeriodIncreaseDecrease 95.5wtm_OtherComprehensiveIncomeForeignCurrencyTransactionandTranslationAdjustmentUnrealizedGainLossonInvestmentsNetofTaxPeriodIncreaseDecrease
Total investment (losses) gains through accumulated other comprehensive income (199.0)wtm_OtherComprehensiveIncomeChangeInUnrealizedHoldingGainLoss (86.8)wtm_OtherComprehensiveIncomeChangeInUnrealizedHoldingGainLoss 153.2wtm_OtherComprehensiveIncomeChangeInUnrealizedHoldingGainLoss
Net Realized and Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax 214.2wtm_NetRealizedAndUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax 139.8wtm_NetRealizedAndUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax 91.4wtm_NetRealizedAndUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax
Total investment gains recorded during the period, after-tax $ 15.2wtm_GainLossOnInvestmentsNetOfTax $ 53.0wtm_GainLossOnInvestmentsNetOfTax $ 244.6wtm_GainLossOnInvestmentsNetOfTax