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Investment Securities (Fair Value of Hedge Funds Subject to Restrictions on Redemption Frequency) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Private equity funds    
Investment securities    
Number of Investments Held 32wtm_NumberOfInvestmentsHeld
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= us-gaap_PrivateEquityFundsMember
 
Trading Securities, Other $ 150.9us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PrivateEquityFundsMember
 
Hedge funds    
Investment securities    
Number of Investments Held 12wtm_NumberOfInvestmentsHeld
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
 
Trading Securities, Other 92.0us-gaap_TradingSecuritiesOther
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
 
Total hedge and private equity funds included in other long-term investments    
Investment securities    
Trading Securities, Other 242.9us-gaap_TradingSecuritiesOther
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= wtm_HedgeFundsAndPrivateEquityFundsMember
239.0us-gaap_TradingSecuritiesOther
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= wtm_HedgeFundsAndPrivateEquityFundsMember
Fair value unfunded commitments 81.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= wtm_HedgeFundsAndPrivateEquityFundsMember
110.6us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= wtm_HedgeFundsAndPrivateEquityFundsMember
Other Long-term Investments Largest Single Investment 22.0wtm_OtherLongTermInvestmentsLargestSingleInvestment
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= wtm_HedgeFundsAndPrivateEquityFundsMember
18.3wtm_OtherLongTermInvestmentsLargestSingleInvestment
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= wtm_HedgeFundsAndPrivateEquityFundsMember
Private equity funds | Private equity funds    
Investment securities    
Trading Securities, Other 150.9us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PrivateEquityFundsMember
118.2us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PrivateEquityFundsMember
Fair value unfunded commitments 81.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PrivateEquityFundsMember
110.6us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_PrivateEquityFundsMember
Private equity funds | Multi-sector    
Investment securities    
Trading Securities, Other 24.2us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityMultiSectorMember
23.8us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityMultiSectorMember
Fair value unfunded commitments 5.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityMultiSectorMember
6.5us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityMultiSectorMember
Private equity funds | Energy infrastructure & services    
Investment securities    
Trading Securities, Other 59.6us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
45.9us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
Fair value unfunded commitments 11.0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
13.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
Private equity funds | Distressed residential real estate    
Investment securities    
Trading Securities, Other 0us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
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0.4us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityDistressedResidentialRealEstateMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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= wtm_PrivateEquityDistressedResidentialRealEstateMember
Private equity funds | Real estate    
Investment securities    
Trading Securities, Other 3.6us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
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8.2us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_RealEstateFundsMember
Fair value unfunded commitments 3.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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3.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_RealEstateFundsMember
Private equity funds | Private equity secondaries    
Investment securities    
Trading Securities, Other 8.5us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
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9.5us-gaap_TradingSecuritiesOther
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Fair value unfunded commitments 3.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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3.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquitySecondariesMember
Private equity funds | International multi-sector, Europe    
Investment securities    
Trading Securities, Other 1.5us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityFundsMultiSectorEuropeMember
3.9us-gaap_TradingSecuritiesOther
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= wtm_PrivateEquityFundsMultiSectorEuropeMember
Fair value unfunded commitments 2.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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2.8us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityFundsMultiSectorEuropeMember
Private equity funds | Manufacturing/Industrial    
Investment securities    
Trading Securities, Other 23.2us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
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11.2us-gaap_TradingSecuritiesOther
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= wtm_PrivateEquityFundsManufacturingAndIndustrialMember
Fair value unfunded commitments 7.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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15.5us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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= wtm_PrivateEquityFundsManufacturingAndIndustrialMember
Private equity funds | Healthcare    
Investment securities    
Trading Securities, Other 6.1us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
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5.6us-gaap_TradingSecuritiesOther
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= wtm_PrivateEquityHealthcareMember
Fair value unfunded commitments 2.8us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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2.8us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityHealthcareMember
Private equity funds | International multi-sector, Asia    
Investment securities    
Trading Securities, Other 0us-gaap_TradingSecuritiesOther
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0us-gaap_TradingSecuritiesOther
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Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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2.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityFundsMultiSectorAsiaMember
Private equity funds | Insurance    
Investment securities    
Trading Securities, Other 2.1us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityInsuranceMember
2.3us-gaap_TradingSecuritiesOther
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= wtm_PrivateEquityInsuranceMember
Fair value unfunded commitments 41.2us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
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= wtm_PrivateEquityInsuranceMember
41.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_PrivateEquityInsuranceMember
Private equity funds | Aerospace/Defense/Government    
Investment securities    
Trading Securities, Other 20.7us-gaap_TradingSecuritiesOther
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= us-gaap_PrivateEquityFundsMember
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5.8us-gaap_TradingSecuritiesOther
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Fair value unfunded commitments 5.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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19.2us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_AerospaceDefenseGovernmentMember
Private equity funds | Venture capital    
Investment securities    
Trading Securities, Other 1.4us-gaap_TradingSecuritiesOther
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1.6us-gaap_TradingSecuritiesOther
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= us-gaap_VentureCapitalFundsMember
Fair value unfunded commitments 0.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
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= us-gaap_VentureCapitalFundsMember
0.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_PrivateEquityFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_VentureCapitalFundsMember
Hedge funds | Hedge funds    
Investment securities    
Trading Securities, Other 92.0us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
120.8us-gaap_TradingSecuritiesOther
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/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsMember
Hedge funds | Long/short equity    
Investment securities    
Trading Securities, Other 43.9us-gaap_TradingSecuritiesOther
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62.6us-gaap_TradingSecuritiesOther
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= us-gaap_HedgeFundsEquityLongShortMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_HedgeFundsEquityLongShortMember
Hedge funds | Long/short credit & distressed    
Investment securities    
Trading Securities, Other 21.4us-gaap_TradingSecuritiesOther
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/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
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22.8us-gaap_TradingSecuritiesOther
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= wtm_HedgeFundsCreditAndDistressedMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_HedgeFundsMember
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsCreditAndDistressedMember
Hedge funds | Long diversified strategies    
Investment securities    
Trading Securities, Other 0us-gaap_TradingSecuritiesOther
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0.1us-gaap_TradingSecuritiesOther
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= wtm_HedgeFundsDiversifiedStrategiesMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsDiversifiedStrategiesMember
0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_HedgeFundsDiversifiedStrategiesMember
Hedge funds | Long/short equity REIT    
Investment securities    
Trading Securities, Other 20.3us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
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18.3us-gaap_TradingSecuritiesOther
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= wtm_HedgeFundsEquityREITMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsEquityREITMember
0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_HedgeFundsEquityREITMember
Hedge funds | Long/short equity activist    
Investment securities    
Trading Securities, Other 6.2us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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16.8us-gaap_TradingSecuritiesOther
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= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsEquityActivistMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsEquityActivistMember
0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_HedgeFundsEquityActivistMember
Hedge funds | Long bank loan    
Investment securities    
Trading Securities, Other 0.2us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsBankLoanMember
0.2us-gaap_TradingSecuritiesOther
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsBankLoanMember
Fair value unfunded commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
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= wtm_HedgeFundsBankLoanMember
0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_HedgeFundsBankLoanMember
DavidShield [Member]    
Investment securities    
Fair value unfunded commitments $ 21.0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ invest_InvestmentAxis
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