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Investment Securities (Net 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, Change in Unrealized Holding Gain (Loss) $ 9.5us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss $ 29.0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
Trading Securities, Tax on Unrealized Holding Gain (Loss) on Investments (2.8)wtm_TradingSecuritiesTaxonUnrealizedHoldingGainLossonInvestments (9.1)wtm_TradingSecuritiesTaxonUnrealizedHoldingGainLossonInvestments
Trading Securities Unrealized Holding Gain (Loss) on Investments after Tax 6.7wtm_TradingSecuritiesUnrealizedHoldingGainLossonInvestmentsafterTax 19.9wtm_TradingSecuritiesUnrealizedHoldingGainLossonInvestmentsafterTax
Foreign Currency Transaction Gain (Loss), Unrealized 41.1us-gaap_ForeignCurrencyTransactionGainLossUnrealized 13.1us-gaap_ForeignCurrencyTransactionGainLossUnrealized
Trading Securities, Unrealized Foreign Currency Transaction Gain (Loss) Tax (10.3)wtm_TradingSecuritiesUnrealizedForeignCurrencyTransactionGainLossTax (2.9)wtm_TradingSecuritiesUnrealizedForeignCurrencyTransactionGainLossTax
Trading Securities, Unrealized Foreign Currency Gain (Loss) Net of Tax 30.8wtm_TradingSecuritiesUnrealizedForeignCurrencyGainLossNetOfTax 10.2wtm_TradingSecuritiesUnrealizedForeignCurrencyGainLossNetOfTax
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities 50.6wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities 42.1wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Tax (13.1)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesTax (12.0)wtm_NetUnrealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesTax
Net Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax 37.5wtm_NetUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax 30.1wtm_NetUnrealizedGainLossAndForeignCurrencyGainLossOnTradingSecuritiesNetOfTax
Fixed maturity investments.    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Change in Unrealized Holding Gain (Loss) 12.1us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
19.4us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Foreign Currency Transaction Gain (Loss), Unrealized 40.2us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
12.2us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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, Change in Unrealized Holding Gain (Loss) 0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Unrealized 0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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, Change in Unrealized Holding Gain (Loss) (4.2)us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
4.0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Foreign Currency Transaction Gain (Loss), Unrealized 0.8us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
0.5us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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, Change in Unrealized Holding Gain (Loss) 0.7us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0.7us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Foreign Currency Transaction Gain (Loss), Unrealized 0.1us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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, Change in Unrealized Holding Gain (Loss) 0.9us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
4.9us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Unrealized 0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
0.4us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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, Change in Unrealized Holding Gain (Loss) 0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
0us-gaap_TradingSecuritiesUnrealizedHoldingGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
Foreign Currency Transaction Gain (Loss), Unrealized 0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
0us-gaap_ForeignCurrencyTransactionGainLossUnrealized
/ 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