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Investment Securities (Investment Holdings Fixed Maturity Table) (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
U.S. Government and agency obligations    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 165.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
184.7us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
Trading Securities, Unrealized Holding Gain 0.3us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
0.1us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
Trading Securities, Unrealized Holding Loss (0.1)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
(0.3)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
Net foreign currency gains (losses) 0.2wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
3.6wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
Fixed maturity investments, at fair value 165.7us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
188.1us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_USTreasuryAndGovernmentMember
Debt securities issued by corporations    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 2,103.8us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
2,221.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
Trading Securities, Unrealized Holding Gain 46.7us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
45.2us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
Trading Securities, Unrealized Holding Loss (1.0)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
(5.1)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
Net foreign currency gains (losses) 66.2wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
49.8wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
Fixed maturity investments, at fair value 2,215.7us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
2,311.2us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CorporateDebtSecuritiesMember
Municipal obligations    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 96.0us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
82.0us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
Trading Securities, Unrealized Holding Gain 1.8us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
1.4us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
Trading Securities, Unrealized Holding Loss (0.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
(0.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
Net foreign currency gains (losses) 0wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
0wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
Fixed maturity investments, at fair value 97.6us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
83.2us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MunicipalBondsMember
Mortgage-backed and asset-backed securities    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 2,049.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
1,811.1us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Trading Securities, Unrealized Holding Gain 11.9us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
7.6us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Trading Securities, Unrealized Holding Loss (2.6)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
(3.5)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Net foreign currency gains (losses) 39.5wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
25.7wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Fixed maturity investments, at fair value 2,098.1us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
1,840.9us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Foreign government, agency and provincial obligations    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 106.9us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
274.6us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
Trading Securities, Unrealized Holding Gain 1.2us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
4.2us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
Trading Securities, Unrealized Holding Loss (0.2)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
(1.0)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
Net foreign currency gains (losses) 0.9wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
(2.7)wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
Fixed maturity investments, at fair value 108.8us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
275.1us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForeignGovernmentDebtSecuritiesMember
Preferred Stock    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 79.5us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
79.6us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Trading Securities, Unrealized Holding Gain 6.3us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
6.1us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Trading Securities, Unrealized Holding Loss 0us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
0us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Net foreign currency gains (losses) 0.2wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
0.1wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Fixed maturity investments, at fair value 86.0us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
85.8us-gaap_TradingSecuritiesDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Fixed Income Investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Cost or amortized cost 4,600.8us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
4,653.3us-gaap_TradingSecuritiesCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
Trading Securities, Unrealized Holding Gain 68.2us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
64.6us-gaap_TradingSecuritiesUnrealizedHoldingGain
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
Trading Securities, Unrealized Holding Loss (4.1)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
(10.1)us-gaap_TradingSecuritiesUnrealizedHoldingLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
Net foreign currency gains (losses) 107.0wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
76.5wtm_TradingSecuritiesNetUnrealizedForeignCurrencyGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
Total fixed maturity investments including assets held for sale $ 4,771.9wtm_TradingSecuritiesDebtIncludingAssetsHeldForSale
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember
$ 4,784.3wtm_TradingSecuritiesDebtIncludingAssetsHeldForSale
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedIncomeInvestmentsMember