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Investment Securities (Cost or Amortized Cost, Gross Unrealized Investment Gains and Losses) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Fixed maturity investments, at fair value $ 4,784.3us-gaap_TradingSecuritiesDebt $ 5,030.5us-gaap_TradingSecuritiesDebt  
Sales and maturities of investment securities 6,238.1wtm_ProceedsfromSaleandMaturityofTradingSecuritiesHeldforinvestmentExcludingShortTermSecurities 4,924.8wtm_ProceedsfromSaleandMaturityofTradingSecuritiesHeldforinvestmentExcludingShortTermSecurities 6,997.5wtm_ProceedsfromSaleandMaturityofTradingSecuritiesHeldforinvestmentExcludingShortTermSecurities
Common Stock      
Investment securities      
Trading Securities, Cost 633.6us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
890.2us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
 
Net foreign currency gains (losses) (1.9)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
(0.8)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
 
Fixed maturity investments, at fair value 801.6us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
1,156.8us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
 
Trading Securities, Unrealized Holding Gain 175.1us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
271.0us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
 
Trading Securities, Unrealized Holding Loss (5.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
(3.6)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
 
Convertible fixed maturity investments      
Investment securities      
Trading Securities, Cost 19.1us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
71.7us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
 
Net foreign currency gains (losses) 0.7wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
(0.2)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
 
Fixed maturity investments, at fair value 20.5us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
80.5us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
 
Trading Securities, Unrealized Holding Gain 0.9us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
9.9us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
 
Trading Securities, Unrealized Holding Loss (0.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
(0.9)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
 
Other long-term investments      
Investment securities      
Trading Securities, Cost 344.5us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
238.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
 
Net foreign currency gains (losses) 1.6wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
(2.4)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
 
Fixed maturity investments, at fair value 408.2us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
288.9us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
 
Trading Securities, Unrealized Holding Gain 73.0us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
79.6us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
 
Trading Securities, Unrealized Holding Loss $ (10.9)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember
$ (26.6)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_OtherLongTermInvestmentsExcludingEquityMethodInvestmentsMember