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Investment Securities (Fair Value of Hedge Funds Subject to Restrictions on Redemption Frequency) (Details) (USD $)
In Millions, unless otherwise specified
Mar. 31, 2015
Dec. 31, 2014
Hedge funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments $ 92.1us-gaap_TradingSecuritiesOther
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Private equity funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 150.4us-gaap_TradingSecuritiesOther
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Hedge and private equity funds included in other long-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 242.5us-gaap_TradingSecuritiesOther
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242.9us-gaap_TradingSecuritiesOther
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Unfunded Commitments 70.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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81.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= wtm_HedgeFundsAndPrivateEquityFundsMember
Private equity funds | Private Equity Multi Sector    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 24.3us-gaap_TradingSecuritiesOther
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24.2us-gaap_TradingSecuritiesOther
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Unfunded Commitments 4.4us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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5.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Energy Infrastructure and Services    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 51.3us-gaap_TradingSecuritiesOther
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59.6us-gaap_TradingSecuritiesOther
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Unfunded Commitments 10.0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
/ us-gaap_InvestmentTypeAxis
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= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
11.0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= wtm_PrivateEquityEnergyInfrastructureAndServicesMember
Private equity funds | Real Estate Funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 2.0us-gaap_TradingSecuritiesOther
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3.6us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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3.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Secondaries    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 8.0us-gaap_TradingSecuritiesOther
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8.5us-gaap_TradingSecuritiesOther
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Unfunded Commitments 3.2us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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3.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Funds Multi Sector Europe    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 1.2us-gaap_TradingSecuritiesOther
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1.5us-gaap_TradingSecuritiesOther
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Unfunded Commitments 2.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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2.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Funds Manufacturing and Industrial    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 30.5us-gaap_TradingSecuritiesOther
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23.2us-gaap_TradingSecuritiesOther
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Unfunded Commitments 2.9us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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7.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Healthcare    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 8.7us-gaap_TradingSecuritiesOther
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6.1us-gaap_TradingSecuritiesOther
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Unfunded Commitments 1.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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2.8us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Private Equity Insurance    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 2.1us-gaap_TradingSecuritiesOther
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2.1us-gaap_TradingSecuritiesOther
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Unfunded Commitments 41.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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41.2us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Aerospace Defense Government    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 20.9us-gaap_TradingSecuritiesOther
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20.7us-gaap_TradingSecuritiesOther
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Unfunded Commitments 5.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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5.1us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Private equity funds | Venture Capital Funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 1.4us-gaap_TradingSecuritiesOther
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1.4us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0.3us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_VentureCapitalFundsMember
Private equity funds | Private equity funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 150.4us-gaap_TradingSecuritiesOther
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150.9us-gaap_TradingSecuritiesOther
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Unfunded Commitments 70.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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81.7us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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= us-gaap_PrivateEquityFundsMember
Hedge funds | Hedge Funds, Equity Long (Short) [Member]    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 44.3us-gaap_TradingSecuritiesOther
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43.9us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Hedge funds | Hedge Funds Credit and Distressed    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 20.0us-gaap_TradingSecuritiesOther
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21.4us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Hedge funds | Hedge Funds Equity R E I T    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 21.0us-gaap_TradingSecuritiesOther
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20.3us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Hedge funds | Hedge Funds Equity Activist    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 6.6us-gaap_TradingSecuritiesOther
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6.2us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Hedge funds | Hedge Funds Bank Loan    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 0.2us-gaap_TradingSecuritiesOther
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0.2us-gaap_TradingSecuritiesOther
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Unfunded Commitments 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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Hedge funds | Hedge funds    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other long-term investments 92.1us-gaap_TradingSecuritiesOther
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92.0us-gaap_TradingSecuritiesOther
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Unfunded Commitments $ 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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$ 0us-gaap_FairValueInvestmentsEntitiesThatCalculateNetAssetValuePerShareUnfundedCommittments
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