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Investment Securities Investment Securities (Net Unrealized Investment Gains (Losses)) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) $ (66.2)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss $ 38.9us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss $ 98.7us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
Foreign Currency Transaction Gain (Loss), Unrealized 116.3us-gaap_ForeignCurrencyTransactionGainLossUnrealized 18.3us-gaap_ForeignCurrencyTransactionGainLossUnrealized (48.6)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
Net unrealized investment gains, pre-tax 50.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 57.2wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 50.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Trading Securities, Tax on Unrealized Holding Gain (Loss) on Investments 6.0wtm_TradingSecuritiesTaxonUnrealizedHoldingGainLossonInvestments 8.2wtm_TradingSecuritiesTaxonUnrealizedHoldingGainLossonInvestments (17.9)wtm_TradingSecuritiesTaxonUnrealizedHoldingGainLossonInvestments
Trading Securities, Unrealized Foreign Currency Transaction Gain (Loss) Tax (28.0)wtm_TradingSecuritiesUnrealizedForeignCurrencyTransactionGainLossTax (5.6)wtm_TradingSecuritiesUnrealizedForeignCurrencyTransactionGainLossTax 12.7wtm_TradingSecuritiesUnrealizedForeignCurrencyTransactionGainLossTax
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Tax (22.0)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesTax 2.6wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesTax (5.2)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesTax
Trading Securities Unrealized Holding Gain (Loss) on Investments after Tax (60.2)wtm_TradingSecuritiesUnrealizedHoldingGainLossonInvestmentsafterTax 47.1wtm_TradingSecuritiesUnrealizedHoldingGainLossonInvestmentsafterTax 80.8wtm_TradingSecuritiesUnrealizedHoldingGainLossonInvestmentsafterTax
Trading Securities, Unrealized Foreign Currency Gain (Loss) Net of Tax 88.3wtm_TradingSecuritiesUnrealizedForeignCurrencyGainLossNetOfTax 12.7wtm_TradingSecuritiesUnrealizedForeignCurrencyGainLossNetOfTax (35.9)wtm_TradingSecuritiesUnrealizedForeignCurrencyGainLossNetOfTax
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax 28.1wtm_NetUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax 59.8wtm_NetUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax 44.9wtm_NetUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax
Fixed maturity investments      
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) 30.9us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(93.9)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
18.5us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Foreign Currency Transaction Gain (Loss), Unrealized 111.7us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
15.3us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(45.9)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Net unrealized investment gains, pre-tax 142.6wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(78.6)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(27.4)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Short-term investments      
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) (0.2)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Unrealized 0.1us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Net unrealized investment gains, pre-tax (0.1)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Common equity securities      
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) (83.0)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
119.2us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
65.9us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Foreign Currency Transaction Gain (Loss), Unrealized (0.1)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
(0.4)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
(0.1)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Net unrealized investment gains, pre-tax (83.1)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
118.8wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
65.8wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Convertible fixed maturity and preferred investments      
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) (8.2)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
3.2us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
1.1us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Foreign Currency Transaction Gain (Loss), Unrealized 0.4us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Net unrealized investment gains, pre-tax (7.8)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
3.2wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
1.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Other long-term investments      
Investment securities      
Trading Securities, Change in Unrealized Holding Gain (Loss) (5.7)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
10.3us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
13.2us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Unrealized 4.2us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
3.4us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
(2.7)us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Net unrealized investment gains, pre-tax $ (1.5)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
$ 13.7wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
$ 10.5wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember