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Debt and Standby Letter of Credit Facilities (Narrative) (Details) (USD $)
12 Months Ended 1 Months Ended 3 Months Ended 5 Months Ended 7 Months Ended 1 Months Ended 3 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Mar. 31, 2007
Dec. 31, 2013
Dec. 31, 2013
Aug. 13, 2013
Nov. 30, 2012
Dec. 31, 2012
Aug. 14, 2013
Aug. 12, 2011
May 31, 2003
Oct. 10, 2014
Nov. 25, 2014
Debt Instrument                            
Issuance of debt, net of debt issuance costs $ 68,600,000us-gaap_ProceedsFromIssuanceOfDebt $ 0us-gaap_ProceedsFromIssuanceOfDebt $ 271,900,000us-gaap_ProceedsFromIssuanceOfDebt                      
Aggregate purchase price of senior notes purchased and retired (65,000,000)us-gaap_EarlyRepaymentOfSeniorDebt 0us-gaap_EarlyRepaymentOfSeniorDebt 275,900,000us-gaap_EarlyRepaymentOfSeniorDebt                      
Interest expense on debt 41,900,000us-gaap_InterestExpenseDebt 42,500,000us-gaap_InterestExpenseDebt 44,800,000us-gaap_InterestExpenseDebt                      
Draw down of revolving line of credit 0us-gaap_ProceedsFromLinesOfCredit 200,000,000us-gaap_ProceedsFromLinesOfCredit 150,000,000us-gaap_ProceedsFromLinesOfCredit                      
Repayments of debt, principal 66,500,000us-gaap_RepaymentsOfDebt 275,000,000us-gaap_RepaymentsOfDebt 75,000,000us-gaap_RepaymentsOfDebt                      
Interest Paid 42,000,000us-gaap_InterestPaid 42,600,000us-gaap_InterestPaid 44,600,000us-gaap_InterestPaid                      
Debt 746,600,000us-gaap_LongTermDebt 676,400,000us-gaap_LongTermDebt     676,400,000us-gaap_LongTermDebt 676,400,000us-gaap_LongTermDebt                
SIG Senior Notes                            
Debt Instrument                            
Debt instrument at face value       400,000,000us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Percentage of par value at which debt was issued       99.715%wtm_DebtInstrumentIssuePriceAsPercentageOfParValue
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Issuance of debt, net of debt issuance costs       392,000,000us-gaap_ProceedsFromIssuanceOfDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Interest rate (as a percent)       6.375%us-gaap_DebtInstrumentInterestRateStatedPercentage
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Debt issue costs       3,600,000us-gaap_DeferredFinanceCostsGross
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Underwriting discount       2,600,000wtm_DeferredUnderwritingDiscountGross
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Effective yield (as a percent)       6.50%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Loss from interest rate hedge recorded in other comprehensive income       (2,400,000)us-gaap_DerivativeInstrumentsLossRecognizedInOtherComprehensiveIncomeEffectivePortion
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
Unamortized loss remaining in accumulated other comprehensive income 1,000,000us-gaap_AccumulatedOtherComprehensiveIncomeLossCumulativeChangesInNetGainLossFromCashFlowHedgesEffectNetOfTax
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                         
Interest expense on debt 26,200,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
26,200,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
26,200,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                     
Expenses related to issuance, including underwriting fees       3,600,000us-gaap_DeferredFinanceCostsGross
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
                   
WTM Bank Facility                            
Debt Instrument                            
Effective yield (as a percent) 3.65%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
3.65%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
    3.65%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
3.65%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
               
Interest expense on debt 300,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
        300,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
               
Total commitment under revolving credit facility                   425,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
       
Draw down of revolving line of credit 65,000,000us-gaap_ProceedsFromLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
50,000,000us-gaap_ProceedsFromLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
                       
Repayments of lines of credit         50,000,000us-gaap_RepaymentsOfLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
                 
Prior W T M Bank Facility                            
Debt Instrument                            
Effective yield (as a percent)   2.83%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
3.53%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
  2.83%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
2.83%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
    3.53%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
         
Interest expense on debt     1,700,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
      2,900,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
             
Total commitment under revolving credit facility                     375,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
     
Draw down of revolving line of credit   150,000,000us-gaap_ProceedsFromLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
150,000,000us-gaap_ProceedsFromLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
                     
Repayments of debt, principal     75,000,000us-gaap_RepaymentsOfDebt
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
                     
Repayments of lines of credit   225,000,000us-gaap_RepaymentsOfLinesOfCredit
/ us-gaap_DebtInstrumentAxis
= wtm_PriorWTMBankFacilityMember
                       
One Beacon US Holdings Inc. | 2012 OBH Senior Notes                            
Debt Instrument                            
Debt instrument at face value               275,000,000us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Percentage of par value at which debt was issued               99.90%wtm_DebtInstrumentIssuePriceAsPercentageOfParValue
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Issuance of debt, net of debt issuance costs               272,900,000us-gaap_ProceedsFromIssuanceOfDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Interest rate (as a percent)               4.60%us-gaap_DebtInstrumentInterestRateStatedPercentage
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Debt issue costs               2,800,000us-gaap_DeferredFinanceCostsGross
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Underwriting discount               1,800,000wtm_DeferredUnderwritingDiscountGross
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Effective yield (as a percent)               4.70%us-gaap_DebtInstrumentInterestRateEffectivePercentage
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Interest Expense 13,000,000us-gaap_InterestExpense
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
                         
Expenses related to issuance, including underwriting fees               2,800,000us-gaap_DeferredFinanceCostsGross
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
One Beacon US Holdings Inc. | 2003 OBH Senior Notes                            
Debt Instrument                            
Interest Expense   13,000,000us-gaap_InterestExpense
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
16,900,000us-gaap_InterestExpense
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
                     
Guarantee fee basis points per annum on outstanding principal amount of debt (as a percent)                       2.50%wtm_GuarantyFeeAsPercentageOutstandingPrincipalAmountOfDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
   
One Beacon US Holdings Inc. | Senior Notes | 2003 OBH Senior Notes                            
Debt Instrument                            
Interest rate (as a percent)               5.875%us-gaap_DebtInstrumentInterestRateStatedPercentage
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
           
Debt Instrument, Repurchase Amount   269,800,000us-gaap_DebtInstrumentRepurchaseAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
    269,800,000us-gaap_DebtInstrumentRepurchaseAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
269,800,000us-gaap_DebtInstrumentRepurchaseAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
               
Aggregate purchase price of senior notes purchased and retired                 275,900,000us-gaap_EarlyRepaymentOfSeniorDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
         
Loss on retirement of debt                 (6,300,000)us-gaap_GainsLossesOnExtinguishmentOfDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
         
Write off of deferred issuance costs                 200,000us-gaap_WriteOffOfDeferredDebtIssuanceCost
/ us-gaap_DebtInstrumentAxis
= wtm_A2003ObhSeniorNotesMember
/ us-gaap_ExtinguishmentOfDebtAxis
= us-gaap_SeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OneBeaconHoldingsIncMember
         
Tranzact [Member] | Tranzact Bank Facility [Member]                            
Debt Instrument                            
Interest expense on debt 700,000us-gaap_InterestExpenseDebt
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
                         
Line of Credit Facility, Fair Value of Amount Outstanding 67,400,000us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
    0us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
            70,000,000us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
 
Line of Credit Facility, Amount Outstanding 68,700,000us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
    0us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
               
Line of Credit Facility, Remaining Borrowing Capacity 4,500,000us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
                         
Long-term Debt, Percentage Bearing Variable Interest, Percentage Rate 4.15575%us-gaap_LongTermDebtPercentageBearingVariableInterestRate
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
                         
Sirius International | Letter of Credit [Member]                            
Debt Instrument                            
Line of Credit Facility, Fair Value of Amount Outstanding                           200,000,000us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= us-gaap_LetterOfCreditMember
/ dei_LegalEntityAxis
= wtm_SiriusInternationalMember
number of Credit Lines                           2wtm_NumberofCreditLines
/ us-gaap_DebtInstrumentAxis
= us-gaap_LetterOfCreditMember
/ dei_LegalEntityAxis
= wtm_SiriusInternationalMember
Minimum | Tranzact [Member] | Tranzact Bank Facility [Member]                            
Debt Instrument                            
LIBOR rate 2.50%wtm_LIBORrate
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
                         
Maximum | Tranzact [Member] | Tranzact Bank Facility [Member]                            
Debt Instrument                            
LIBOR rate 4.50%wtm_LIBORrate
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
                         
Nordea Bank Finland [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                           125,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_CreditFacilityAxis
= wtm_NordeaBankFinlandMember
Lloyds Bank plc [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                           75,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_CreditFacilityAxis
= wtm_LloydsBankplcMember
Unsecured Debt [Member] | Nordea Bank Finland [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                           100,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_CreditFacilityAxis
= wtm_NordeaBankFinlandMember
/ us-gaap_LongtermDebtTypeAxis
= us-gaap_UnsecuredDebtMember
Unsecured Debt [Member] | Lloyds Bank plc [Member]                            
Debt Instrument                            
Total commitment under revolving credit facility                           $ 25,000,000us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity
/ us-gaap_CreditFacilityAxis
= wtm_LloydsBankplcMember
/ us-gaap_LongtermDebtTypeAxis
= us-gaap_UnsecuredDebtMember