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Investment Securities (Cost and Amortized Cost Maturity Schedule) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Trading Securities by Maturity Cost or Amortized Cost  
Cost or amortized cost $ 4,664.8wtm_TradingSecuritiesAmortizedCost
Trading Securities by Maturity, Fair Value  
Trading Securities 4,796.5us-gaap_TradingSecurities
Fixed Maturities and Convertible Fixed Maturities Excluding A B S M B S and Preferred Stock  
Trading Securities by Maturity Cost or Amortized Cost  
Due in one year or less 331.2wtm_TradingSecuritiesMaturitiesWithinOneYearCostOrAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after one year through five years 1,968.3wtm_TradingSecuritiesMaturitiesAfterOneThroughFiveYearsCostOrAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after five years through ten years 434.4wtm_TradingSecuritiesMaturitiesAfterFiveThroughTenYearsCostOrAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after ten years 40.2wtm_TradingSecuritiesMaturitiesAfterTenYearsCostOrAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Trading Securities by Maturity, Fair Value  
Due in one year or less 337.5wtm_TradingSecuritiesMaturitiesWithinOneYearNetCarryingAmount
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after one year through five years 2,032.3wtm_TradingSecuritiesMaturitiesAfterOneThroughFiveYearsNetCarryingAmount
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after five years through ten years 453.9wtm_TradingSecuritiesMaturitiesAfterFiveThroughTenYearsNetCarryingAmount
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Due after ten years 46.1wtm_TradingSecuritiesMaturitiesAfterTenYearsNetCarryingAmount
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Mortgage-backed and asset-backed securities  
Trading Securities by Maturity Cost or Amortized Cost  
Trading Securities, Maturities without Single Maturity Date, Amortized Cost 1,811.1wtm_TradingSecuritiesMaturitiesWithoutSingleMaturityDateAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Trading Securities by Maturity, Fair Value  
Trading Securities, Maturities without Single Maturity Date, Carrying Value 1,840.9wtm_TradingSecuritiesMaturitiesWithoutSingleMaturityDateCarryingValue
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_AssetBackedSecuritiesMember
Preferred stocks  
Trading Securities by Maturity Cost or Amortized Cost  
Trading Securities, Maturities without Single Maturity Date, Amortized Cost 79.6wtm_TradingSecuritiesMaturitiesWithoutSingleMaturityDateAmortizedCost
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember
Trading Securities by Maturity, Fair Value  
Trading Securities, Maturities without Single Maturity Date, Carrying Value $ 85.8wtm_TradingSecuritiesMaturitiesWithoutSingleMaturityDateCarryingValue
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PreferredStockMember