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Income Taxes (Effective Rate Reconciliation) (Details) (USD $)
3 Months Ended 12 Months Ended 0 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, 2012
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Jan. 02, 2013
Income Tax Contingency [Line Items]                          
U.S. statutory rate (as a percent)                 35.00%us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate        
Tax (expense) benefit at the U.S. statutory rate                   $ (105,600,000)us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate $ (120,700,000)us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate $ (92,000,000)us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate  
Differences in taxes resulting from:                          
Non-U.S. earnings, net of foreign taxes                   77,700,000us-gaap_IncomeTaxReconciliationRepatriationOfForeignEarnings 82,900,000us-gaap_IncomeTaxReconciliationRepatriationOfForeignEarnings 43,000,000us-gaap_IncomeTaxReconciliationRepatriationOfForeignEarnings  
Change in valuation allowance                   (18,100,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance (33,600,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance (14,100,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance  
Effective Income Tax Rate Reconciliation, Deduction, Other, Amount                   (5,600,000)us-gaap_IncomeTaxReconciliationDeductionsOther (1,700,000)us-gaap_IncomeTaxReconciliationDeductionsOther (2,900,000)us-gaap_IncomeTaxReconciliationDeductionsOther  
Tax exempt interest and dividends                   4,400,000us-gaap_IncomeTaxReconciliationTaxExemptIncome 3,200,000us-gaap_IncomeTaxReconciliationTaxExemptIncome 3,100,000us-gaap_IncomeTaxReconciliationTaxExemptIncome  
Tax reserve adjustments                   (2,200,000)us-gaap_IncomeTaxReconciliationTaxContingencies (10,200,000)us-gaap_IncomeTaxReconciliationTaxContingencies (1,300,000)us-gaap_IncomeTaxReconciliationTaxContingencies  
Purchase of subsidiaries                   (300,000)wtm_EffectiveIncomeTaxRateReconciliationPurchaseofSubsidiary 5,300,000wtm_EffectiveIncomeTaxRateReconciliationPurchaseofSubsidiary 5,100,000wtm_EffectiveIncomeTaxRateReconciliationPurchaseofSubsidiary  
Other, net                   (3,600,000)us-gaap_IncomeTaxReconciliationOtherAdjustments (1,800,000)us-gaap_IncomeTaxReconciliationOtherAdjustments 2,200,000us-gaap_IncomeTaxReconciliationOtherAdjustments  
Income tax (expense) benefit 8,700,000us-gaap_IncomeTaxExpenseBenefit (7,800,000)us-gaap_IncomeTaxExpenseBenefit (23,900,000)us-gaap_IncomeTaxExpenseBenefit (30,300,000)us-gaap_IncomeTaxExpenseBenefit (27,400,000)us-gaap_IncomeTaxExpenseBenefit (8,200,000)us-gaap_IncomeTaxExpenseBenefit 600,000us-gaap_IncomeTaxExpenseBenefit (41,600,000)us-gaap_IncomeTaxExpenseBenefit   (53,300,000)us-gaap_IncomeTaxExpenseBenefit (76,600,000)us-gaap_IncomeTaxExpenseBenefit 15,700,000us-gaap_IncomeTaxExpenseBenefit  
Pre-tax loss 46,200,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 34,400,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 109,000,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 112,100,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 134,200,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 55,300,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 3,600,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 151,800,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments   301,700,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 344,900,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 262,800,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments  
Tax Payments and Receipts                          
Net income tax payments to (receipts from) national governments, total                   9,400,000us-gaap_IncomeTaxesPaidNet 13,900,000us-gaap_IncomeTaxesPaidNet 17,500,000us-gaap_IncomeTaxesPaidNet  
Non-US                          
Differences in taxes resulting from:                          
Pre-tax loss                   338,500,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments
/ us-gaap_StatementGeographicalAxis
= wtm_NonUSMember
294,300,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments
/ us-gaap_StatementGeographicalAxis
= wtm_NonUSMember
250,000,000us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments
/ us-gaap_StatementGeographicalAxis
= wtm_NonUSMember
 
SWEDEN                          
Differences in taxes resulting from:                          
Tax rate change enacted                   0us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_SE
0us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_SE
65,400,000us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_SE
 
Luxembourg                          
Differences in taxes resulting from:                          
Change in valuation allowance                 41,300,000us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
(1,200,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
(1,400,000)us-gaap_IncomeTaxReconciliationChangeInDeferredTaxAssetsValuationAllowance
/ us-gaap_StatementGeographicalAxis
= country_LU
   
Tax rate change enacted                   0us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_LU
0us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_LU
7,200,000us-gaap_IncomeTaxReconciliationChangeInEnactedTaxRate
/ us-gaap_StatementGeographicalAxis
= country_LU
 
Sirius Group | SWEDEN                          
Differences in taxes resulting from:                          
Effective income tax                       26.30%us-gaap_EffectiveIncomeTaxRateContinuingOperations
/ us-gaap_IncomeTaxAuthorityAxis
= country_SE
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
22.00%us-gaap_EffectiveIncomeTaxRateContinuingOperations
/ us-gaap_IncomeTaxAuthorityAxis
= country_SE
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
Increase (Decrease) in Deferred Income Taxes                         $ 65,400,000us-gaap_IncreaseDecreaseInDeferredIncomeTaxes
/ us-gaap_IncomeTaxAuthorityAxis
= country_SE
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember