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Variable Interest Entities (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended 12 Months Ended 6 Months Ended 12 Months Ended
Dec. 31, 2014
Sep. 30, 2014
Jun. 30, 2014
Mar. 31, 2014
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Jun. 30, 2014
Dec. 31, 2011
Variable Interest Entity [Line Items]                          
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured               15.00%wtm_PercentageOfParValueOfPolicyReinsured        
Accumulated losses $ 3,011.4us-gaap_RetainedEarningsAccumulatedDeficit       $ 2,802.3us-gaap_RetainedEarningsAccumulatedDeficit       $ 3,011.4us-gaap_RetainedEarningsAccumulatedDeficit $ 2,802.3us-gaap_RetainedEarningsAccumulatedDeficit      
Noncontrolling interest in VIE 543.0us-gaap_MinorityInterest       491.9us-gaap_MinorityInterest       543.0us-gaap_MinorityInterest 491.9us-gaap_MinorityInterest      
Non-controlling interest in consolidated subsidiaries (15.0)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (11.2)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 4.6us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (0.5)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 0.3us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (1.1)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (11.1)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (0.5)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (22.1)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (12.4)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (14.0)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest    
Payments to Acquire Other Investments                 137.0us-gaap_PaymentsToAcquireOtherInvestments 36.3us-gaap_PaymentsToAcquireOtherInvestments 96.7us-gaap_PaymentsToAcquireOtherInvestments    
HG Global                          
Variable Interest Entity [Line Items]                          
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
              15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
       
Noncontrolling interest in VIE 17.9us-gaap_MinorityInterest
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
      16.6us-gaap_MinorityInterest
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
      17.9us-gaap_MinorityInterest
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
16.6us-gaap_MinorityInterest
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
     
Star & Shield Insurance Exchange [Member]                          
Variable Interest Entity [Line Items]                          
Surplus notes 17.0us-gaap_SurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
              17.0us-gaap_SurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Total assets related to consolidated VIE's 13.5us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
              13.5us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Total liabilities related to consolidated VIE's 25.9us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
              25.9us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Accumulated losses 12.4us-gaap_RetainedEarningsAccumulatedDeficit
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
              12.4us-gaap_RetainedEarningsAccumulatedDeficit
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Prospector                          
Variable Interest Entity [Line Items]                          
Total assets related to consolidated VIE's 135.8us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      249.2us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      135.8us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
249.2us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
     
Total liabilities related to consolidated VIE's 39.8us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      90.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      39.8us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
90.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
     
Noncontrolling interest in VIE 31.1us-gaap_MinorityInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      46.2us-gaap_MinorityInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
      31.1us-gaap_MinorityInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
46.2us-gaap_MinorityInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
     
Net Income (Loss) Attributable to Parent                 5.6us-gaap_NetIncomeLoss
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
14.5us-gaap_NetIncomeLoss
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
9.3us-gaap_NetIncomeLoss
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
   
Non-controlling interest in consolidated subsidiaries                 1.9us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
4.0us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
2.7us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
   
Captial at risk, investment in the fund 64.9us-gaap_EquityMethodInvestmentAggregateCost
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
              64.9us-gaap_EquityMethodInvestmentAggregateCost
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
       
Variable Interest Entity, Qualitative or Quantitative Information, Ownership Percentage                   67.60%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_ProspectorFundsMember
     
Houston General Insurance [Member]                          
Variable Interest Entity [Line Items]                          
Surplus notes 4.0us-gaap_SurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
              4.0us-gaap_SurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
       
Total assets related to consolidated VIE's 2.4us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
      2.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
      2.4us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
2.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
     
Total liabilities related to consolidated VIE's 4.0us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
      4.2us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
      4.0us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
4.2us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
     
Accumulated losses 1.8us-gaap_RetainedEarningsAccumulatedDeficit
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
              1.8us-gaap_RetainedEarningsAccumulatedDeficit
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
       
Accrued interest on surplus notes 0.2wtm_AccruedInterestOnSurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
              0.2wtm_AccruedInterestOnSurplusNotes
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
       
TaClaro [Member]                          
Variable Interest Entity [Line Items]                          
Payments to Acquire Other Investments 2.0us-gaap_PaymentsToAcquireOtherInvestments
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
  1.5us-gaap_PaymentsToAcquireOtherInvestments
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
          3.0us-gaap_PaymentsToAcquireOtherInvestments
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
       
Variable Interest Entity, Qualitative or Quantitative Information, Ownership Percentage                 49.00%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
27.00%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
  39.00%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
 
Notes Issued 1.7us-gaap_NotesIssued1
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
                       
Tranzutary Holdings LLC [Member]                          
Variable Interest Entity [Line Items]                          
Total assets related to consolidated VIE's 29.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
              29.6us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
       
Total liabilities related to consolidated VIE's 4.1us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
              4.1us-gaap_VariableInterestEntityConsolidatedCarryingAmountLiabilities
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
       
Variable Interest Entity, Qualitative or Quantitative Information, Ownership Percentage                 36.00%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
       
Entities Owned by Tuckerman Fund I [Member]                          
Variable Interest Entity [Line Items]                          
Number Of Manufacturing Companies From Whom Shares Received               2wtm_NumberOfManufacturingCompaniesFromWhomSharesReceived
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_EntitiesOwnedByTuckermanFundIMember
         
Common Stock | BAM                          
Variable Interest Entity [Line Items]                          
Issuance of notes                   503.0us-gaap_ProceedsFromIssuanceOfLongTermDebt
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_BamMember
     
Common Stock | Tuckerman Fund I [Member]                          
Variable Interest Entity [Line Items]                          
Variable Interest Entity, Qualitative or Quantitative Information, Ownership Percentage                         94.00%us-gaap_VariableInterestEntityOwnershipPercentage
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommonStockMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TuckermanFundIMember
BAM                          
Variable Interest Entity [Line Items]                          
Right to elect directors on board number                   2wtm_RightToElectDirectorsOnBoardNumber
/ dei_LegalEntityAxis
= wtm_BamMember
     
HG Global                          
Variable Interest Entity [Line Items]                          
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
              15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
       
Surplus notes 503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
      503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
      503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
503.0us-gaap_SurplusNotes
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
     
Noncontrolling interest in VIE 17.9us-gaap_MinorityInterest
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
      16.6us-gaap_MinorityInterest
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
      17.9us-gaap_MinorityInterest
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
16.6us-gaap_MinorityInterest
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
     
First Loss Reinsurance Treaty [Member] | HG Global                          
Variable Interest Entity [Line Items]                          
Percentage of par value of policy reinsured 15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
              15.00%wtm_PercentageOfParValueOfPolicyReinsured
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
       
First Loss Reinsurance Treaty [Member] | BAM                          
Variable Interest Entity [Line Items]                          
Percentage of Premiums 60.00%wtm_PercentageofPremiums
/ dei_LegalEntityAxis
= wtm_BamMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
              60.00%wtm_PercentageofPremiums
/ dei_LegalEntityAxis
= wtm_BamMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
       
First Loss Reinsurance Treaty [Member] | HG Global                          
Variable Interest Entity [Line Items]                          
Number of Trust 2wtm_NumberOfTrust
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
              2wtm_NumberOfTrust
/ dei_LegalEntityAxis
= wtm_HgGlobalMember
/ us-gaap_TransactionTypeAxis
= wtm_FirstLossReinsuranceTreatyMember
       
Amendment [Member] | Houston General Insurance [Member]                          
Variable Interest Entity [Line Items]                          
Surplus notes 4.0us-gaap_SurplusNotes
/ us-gaap_TransactionTypeAxis
= wtm_AmendmentMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
              4.0us-gaap_SurplusNotes
/ us-gaap_TransactionTypeAxis
= wtm_AmendmentMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
       
Common Stock | TaClaro [Member]                          
Variable Interest Entity [Line Items]                          
Stock Issued 0.3us-gaap_StockIssued1
/ us-gaap_StatementClassOfStockAxis
= us-gaap_CommonStockMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TaClaroMember
                       
Other Intangible Assets [Member] | Tranzutary Holdings LLC [Member]                          
Variable Interest Entity [Line Items]                          
Total assets related to consolidated VIE's $ 28.9us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_FairValueByAssetClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember
              $ 28.9us-gaap_VariableInterestEntityConsolidatedCarryingAmountAssets
/ us-gaap_FairValueByAssetClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ us-gaap_VariableInterestEntitiesByClassificationOfEntityAxis
= wtm_TranzutaryHoldingsLLCMember