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Investment Securities Investment Securities (Net Realized Investment Gain (losses) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Trading Securities, Realized Gain (Loss) $ 208.7us-gaap_TradingSecuritiesRealizedGainLoss $ 121.8us-gaap_TradingSecuritiesRealizedGainLoss $ 76.7us-gaap_TradingSecuritiesRealizedGainLoss
Foreign Currency Transaction Gain (Loss), Realized 25.1us-gaap_ForeignCurrencyTransactionGainLossRealized (17.3)us-gaap_ForeignCurrencyTransactionGainLossRealized (8.6)us-gaap_ForeignCurrencyTransactionGainLossRealized
Net realized investment gains, pre-tax 233.8wtm_TradingSecuritiesRealizedGainLossTotal 104.5wtm_TradingSecuritiesRealizedGainLossTotal 68.1wtm_TradingSecuritiesRealizedGainLossTotal
Trading securities, Tax on Realized Holding Gain (Loss) on Investments (39.7)wtm_TradingsecuritiesTaxonRealizedHoldingGainLossonInvestments (30.0)wtm_TradingsecuritiesTaxonRealizedHoldingGainLossonInvestments (23.8)wtm_TradingsecuritiesTaxonRealizedHoldingGainLossonInvestments
Trading Securities, Tax on Realized Foreign Currency Transaction Gain (Loss) Tax (8.0)wtm_TradingSecuritiesTaxonRealizedForeignCurrencyTransactionGainLossTax 5.5wtm_TradingSecuritiesTaxonRealizedForeignCurrencyTransactionGainLossTax 2.2wtm_TradingSecuritiesTaxonRealizedForeignCurrencyTransactionGainLossTax
Tax on Net Realized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities (47.7)wtm_TaxonNetRealizedGainLossandForeignCurrencyGainLossonTradingSecurities (24.5)wtm_TaxonNetRealizedGainLossandForeignCurrencyGainLossonTradingSecurities (21.6)wtm_TaxonNetRealizedGainLossandForeignCurrencyGainLossonTradingSecurities
Trading Securities Realized Holding Gain (Loss) on Investments after Tax 169.0wtm_TradingSecuritiesRealizedHoldingGainLossonInvestmentsafterTax 91.8wtm_TradingSecuritiesRealizedHoldingGainLossonInvestmentsafterTax 52.9wtm_TradingSecuritiesRealizedHoldingGainLossonInvestmentsafterTax
Trading Securities, Realized Foreign Currency Gain (Loss) Net of Tax 17.1wtm_TradingSecuritiesRealizedForeignCurrencyGainLossNetofTax (11.8)wtm_TradingSecuritiesRealizedForeignCurrencyGainLossNetofTax (6.4)wtm_TradingSecuritiesRealizedForeignCurrencyGainLossNetofTax
Net Realized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax 186.1wtm_NetRealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesNetofTax 80.0wtm_NetRealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesNetofTax 46.5wtm_NetRealizedGainLossandForeignCurrencyGainLossonTradingSecuritiesNetofTax
Fixed maturity investments      
Investment securities      
Trading Securities, Realized Gain (Loss) 23.9us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
8.6us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
82.5us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Foreign Currency Transaction Gain (Loss), Realized 21.0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(15.0)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(2.5)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Net realized investment gains, pre-tax 44.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
(6.4)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
80.0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_FixedMaturitiesMember
Short-term investments      
Investment securities      
Trading Securities, Realized Gain (Loss) 0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Realized 2.9us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
(4.3)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Net realized investment gains, pre-tax 2.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
0.1wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
(4.3)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ShortTermInvestmentsMember
Common equity securities      
Investment securities      
Trading Securities, Realized Gain (Loss) 150.9us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
104.5us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
1.3us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Foreign Currency Transaction Gain (Loss), Realized 0.9us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
(3.7)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Net realized investment gains, pre-tax 151.8wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
100.8wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
1.3wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_EquitySecuritiesMember
Convertible fixed maturity and preferred investments      
Investment securities      
Trading Securities, Realized Gain (Loss) 5.9us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
1.0us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
(8.2)us-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
(1.8)us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Net realized investment gains, pre-tax 5.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
1.0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
(10.0)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ConvertibleDebtSecuritiesMember
Other long-term investments      
Investment securities      
Trading Securities, Realized Gain (Loss) 27.7us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
7.5us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
1.4us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Foreign Currency Transaction Gain (Loss), Realized 0.3us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
1.4us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Net realized investment gains, pre-tax 28.0wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
8.9wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
1.4wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_OtherLongTermInvestmentsMember
Forward contracts      
Investment securities      
Trading Securities, Realized Gain (Loss) 0.3us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
0.1us-gaap_TradingSecuritiesRealizedGainLoss
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
(0.3)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
0us-gaap_ForeignCurrencyTransactionGainLossRealized
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
Net realized investment gains, pre-tax $ 0.3wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
$ 0.1wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember
$ (0.3)wtm_TradingSecuritiesRealizedGainLossTotal
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ForwardContractsMember