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Income Taxes (Valuation Allowance) (Details) (USD $)
3 Months Ended 12 Months Ended 3 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
Dec. 31, 2012
Valuation Allowance [Line Items]                        
Valuation allowance $ 274,600,000us-gaap_DeferredTaxAssetsValuationAllowance       $ 289,800,000us-gaap_DeferredTaxAssetsValuationAllowance       $ 274,600,000us-gaap_DeferredTaxAssetsValuationAllowance $ 289,800,000us-gaap_DeferredTaxAssetsValuationAllowance    
Valuation allowance                 18,100,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance 33,600,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance 14,100,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance  
Income Tax Expense (Benefit) (8,700,000)us-gaap_IncomeTaxExpenseBenefit 7,800,000us-gaap_IncomeTaxExpenseBenefit 23,900,000us-gaap_IncomeTaxExpenseBenefit 30,300,000us-gaap_IncomeTaxExpenseBenefit 27,400,000us-gaap_IncomeTaxExpenseBenefit 8,200,000us-gaap_IncomeTaxExpenseBenefit (600,000)us-gaap_IncomeTaxExpenseBenefit 41,600,000us-gaap_IncomeTaxExpenseBenefit 53,300,000us-gaap_IncomeTaxExpenseBenefit 76,600,000us-gaap_IncomeTaxExpenseBenefit (15,700,000)us-gaap_IncomeTaxExpenseBenefit  
Net operating losses in Luxembourg subsidiaries                        
Valuation Allowance [Line Items]                        
Valuation allowance 164,800,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesInLuxembourgSubsidiariesMember
      195,800,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesInLuxembourgSubsidiariesMember
      164,800,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesInLuxembourgSubsidiariesMember
195,800,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesInLuxembourgSubsidiariesMember
   
U.S. losses and other federal deferred tax benefits                        
Valuation Allowance [Line Items]                        
Valuation allowance 107,600,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_USLossesAndOtherFederalDeferredTaxBenefitsMember
      93,700,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_USLossesAndOtherFederalDeferredTaxBenefitsMember
      107,600,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_USLossesAndOtherFederalDeferredTaxBenefitsMember
93,700,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_USLossesAndOtherFederalDeferredTaxBenefitsMember
   
Net Operating Losses in Israel Subsidiaries [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance 1,900,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinIsraelSubsidiariesMember
              1,900,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinIsraelSubsidiariesMember
     
Net Operating Losses in Netherlands Subsidiaries [Member] [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance 300,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinNetherlandsSubsidiariesMemberMember
      300,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinNetherlandsSubsidiariesMemberMember
      300,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinNetherlandsSubsidiariesMemberMember
300,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_NetOperatingLossesinNetherlandsSubsidiariesMemberMember
   
Luxembourg                        
Valuation Allowance [Line Items]                        
Valuation allowance                 1,200,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
1,400,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
  (41,300,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
Luxembourg | Tax Benefit [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                 (14,300,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxBenefitMember
(16,700,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxBenefitMember
   
Luxembourg | Tax Expense [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                 15,500,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxExpenseMember
18,100,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxExpenseMember
   
Sirius Re Holdings Inc.                        
Valuation Allowance [Line Items]                        
Valuation allowance 100,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
              100,000us-gaap_DeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
     
Foreign tax credit carryforwards, subject to expiration 12,100,000us-gaap_DeferredTaxAssetsTaxCreditCarryforwardsForeign
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
              12,100,000us-gaap_DeferredTaxAssetsTaxCreditCarryforwardsForeign
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
     
Sirius Re Holdings Inc. | Tax Benefit [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                 (3,800,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxBenefitMember
     
Sirius Re Holdings Inc. | Tax Expense [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                       3,900,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= wtm_SiriusReHoldingsIncMember
/ us-gaap_ValuationAllowanceByDeferredTaxAssetAxis
= wtm_TaxExpenseMember
Guilford Holdings, Inc. | UNITED STATES                        
Valuation Allowance [Line Items]                        
Valuation allowance                 7,200,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_GuilfordHoldingsIncMember
/ us-gaap_StatementGeographicalAxis
= country_US
16,600,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_GuilfordHoldingsIncMember
/ us-gaap_StatementGeographicalAxis
= country_US
   
BAM                        
Valuation Allowance [Line Items]                        
Valuation allowance                 8,500,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_BamMember
21,300,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_BamMember
   
Income Tax Expense (Benefit)                 4,900,000us-gaap_IncomeTaxExpenseBenefit
/ dei_LegalEntityAxis
= wtm_BamMember
5,400,000us-gaap_IncomeTaxExpenseBenefit
/ dei_LegalEntityAxis
= wtm_BamMember
   
Houston General Insurance [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                 (100,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
6.0us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_HoustonGeneralInsuranceExchangeMember
   
Star & Shield Insurance Exchange [Member]                        
Valuation Allowance [Line Items]                        
Valuation allowance                 $ (3,200,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember