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Investment Securities (Investment Holding Common Equities/ Other Investments) (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended 12 Months Ended
Mar. 31, 2015
Dec. 31, 2014
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Fixed maturity investments, at fair value $ 4,771.9us-gaap_TradingSecuritiesDebt $ 4,784.3us-gaap_TradingSecuritiesDebt
Common Stock    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 623.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
633.6us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Trading Securities, Unrealized Holding Gain 163.4us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
175.1us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Trading Securities, Unrealized Holding Loss (8.8)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
(5.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Net foreign currency gains (losses) 9.0wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
(1.9)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Fixed maturity investments, at fair value 786.9us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
801.6us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
Convertible Debt Securities    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 13.1us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
19.1us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Trading Securities, Unrealized Holding Gain 1.8us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0.9us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Trading Securities, Unrealized Holding Loss (0.3)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
(0.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Net foreign currency gains (losses) 1.2wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0.7wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Fixed maturity investments, at fair value 15.8us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
20.5us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Other long-term investments.    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 339.8us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
343.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
Trading Securities, Unrealized Holding Gain 74.7us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
73.0us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
Trading Securities, Unrealized Holding Loss (13.1)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
(10.9)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
Net foreign currency gains (losses) 1.2wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
1.6wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
Fixed maturity investments, at fair value $ 402.6us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
$ 407.0us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember