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Investment Securities (Net Realized 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, Realized Gain (Loss) $ 25.9us-gaap_TradingSecuritiesRealizedGainLoss $ 25.3us-gaap_TradingSecuritiesRealizedGainLoss
Trading securities, tax on realized holding gain (loss) on investments (6.5)wtm_TradingsecuritiesTaxonRealizedHoldingGainLossonInvestments (4.6)wtm_TradingsecuritiesTaxonRealizedHoldingGainLossonInvestments
Trading securities realized holding gain (loss) on investments after tax 19.4wtm_TradingSecuritiesRealizedHoldingGainLossonInvestmentsafterTax 20.7wtm_TradingSecuritiesRealizedHoldingGainLossonInvestmentsafterTax
Foreign Currency Transaction Gain (Loss), Realized 26.9us-gaap_ForeignCurrencyTransactionGainLossRealized (3.6)us-gaap_ForeignCurrencyTransactionGainLossRealized
Trading securities, realized foreign currency transaction gain (loss) t (6.7)wtm_TradingSecuritiesTaxonRealizedForeignCurrencyTransactionGainLossTax 0.9wtm_TradingSecuritiesTaxonRealizedForeignCurrencyTransactionGainLossTax
Trading securities, realized foreign currency gain (loss) net of tax 20.2wtm_TradingSecuritiesRealizedForeignCurrencyGainLossNetofTax (2.7)wtm_TradingSecuritiesRealizedForeignCurrencyGainLossNetofTax
Trading Securities, Realized Gain (Loss), Total 52.8wtm_TradingSecuritiesRealizedGainLossTotal 21.7wtm_TradingSecuritiesRealizedGainLossTotal
Tax on Net Realized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities (13.2)wtm_TaxonNetRealizedGainLossandForeignCurrencyGainLossonTradingSecurities (3.7)wtm_TaxonNetRealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Net Realized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax 39.6wtm_NetRealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesNetofTax 18.0wtm_NetRealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesNetofTax
Fixed maturity investments.    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) 9.8us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
4.4us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Foreign Currency Transaction Gain (Loss), Realized 21.2us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(3.5)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Trading Securities, Realized Gain (Loss), Total 31.0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
0.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Short-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) 0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Realized 3.5us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Trading Securities, Realized Gain (Loss), Total 3.5wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Common equity securities    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) 24.4us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
18.9us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Foreign Currency Transaction Gain (Loss), Realized 1.1us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
(0.1)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Trading Securities, Realized Gain (Loss), Total 25.5wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
18.8wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Convertible fixed maturity investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) (4.2)us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
2.4us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Foreign Currency Transaction Gain (Loss), Realized 0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Trading Securities, Realized Gain (Loss), Total (4.2)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
2.4wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Other long-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) (4.1)us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
(0.3)us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Realized 1.1us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Trading Securities, Realized Gain (Loss), Total (3.0)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
(0.3)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Forward Contracts    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Trading Securities, Realized Gain (Loss) 0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
(0.1)us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
Foreign Currency Transaction Gain (Loss), Realized 0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
Trading Securities, Realized Gain (Loss), Total $ 0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
$ (0.1)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember