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Investment Securities (Restrictions on Redemption Frequency and Advance Notice Requirements) (Details) (Hedge funds, USD $)
In Millions, unless otherwise specified
Mar. 31, 2015
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Distributions from Inactive Hedge Funds $ 2.1wtm_DistributionsFromInactiveHedgeFunds
Other long-term investments 92.1us-gaap_TradingSecuritiesOther
Redemption requests 6.9wtm_FairValueInvestmentsEntitiesthatCalculateNetAssetValueRedemptionRequest
30-59 days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 36.3us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod30To59DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period60 To89 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 43.0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod60To89DaysMember
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= us-gaap_HedgeFundsMember
Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period90 To119 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 4.7us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod90To119DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
120+ days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 8.1us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriodOver120DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
Monthly  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 4.5us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyMonthlyMember
Monthly | 30-59 days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 4.5us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod30To59DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyMonthlyMember
Monthly | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period60 To89 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod60To89DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyMonthlyMember
Monthly | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period90 To119 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod90To119DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyMonthlyMember
Monthly | 120+ days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriodOver120DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyMonthlyMember
Quarterly  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 59.8us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyQuarterlyMember
Quarterly | 30-59 days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 31.8us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod30To59DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyQuarterlyMember
Quarterly | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period60 To89 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 20.1us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod60To89DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyQuarterlyMember
Quarterly | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period90 To119 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod90To119DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyQuarterlyMember
Quarterly | 120+ days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 7.9us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
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= us-gaap_HedgeFundsMember
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Semi-annual  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 22.9us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencySemiAnnualMember
Semi-annual | 30-59 days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod30To59DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencySemiAnnualMember
Semi-annual | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period60 To89 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 22.9us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod60To89DaysMember
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/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencySemiAnnualMember
Semi-annual | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period90 To119 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod90To119DaysMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencySemiAnnualMember
Semi-annual | 120+ days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriodOver120DaysMember
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= us-gaap_HedgeFundsMember
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= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencySemiAnnualMember
Annual  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 4.9us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAnnualMember
Annual | 30-59 days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod30To59DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAnnualMember
Annual | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period60 To89 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 0us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod60To89DaysMember
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/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAnnualMember
Annual | Fair Value Investments Entities that Calculate Net Asset Value Per Share Investment Redemption Notice Period90 To119 Days [Member]  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments 4.7us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionNoticePeriod90To119DaysMember
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= us-gaap_HedgeFundsMember
/ wtm_RedemptionFrequencyAxis
= wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAnnualMember
Annual | 120+ days notice  
Schedule of Trading Securities and Other Trading Assets [Line Items]  
Other long-term investments $ 0.2us-gaap_TradingSecuritiesOther
/ wtm_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareInvestmentRedemptionFrequencyAxis
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