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Commitments and Contingencies (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Loss Contingencies [Line Items]      
Rent expense $ 19.4us-gaap_OperatingLeasesRentExpenseNet $ 20.2us-gaap_OperatingLeasesRentExpenseNet $ 18.8us-gaap_OperatingLeasesRentExpenseNet
Capital Leases, Future Minimum Payments Due, Fiscal Year Maturity [Abstract]      
Capital lease payments due next year 16.5us-gaap_CapitalLeasesFutureMinimumPaymentsDueCurrent    
Capital lease payments due in two years 15.2us-gaap_CapitalLeasesFutureMinimumPaymentsDueInTwoYears    
Capital lease payments due in three years 13.6us-gaap_CapitalLeasesFutureMinimumPaymentsDueInThreeYears    
Capital Lease payments due in four years and thereafter 54.7us-gaap_CapitalLeasesFutureMinimumPaymentsDueInFourYears    
Commitments to fund other-long term investments 81.7wtm_CommitmentsOtherLongTermInvestments    
Reserve for probable liability from mandatory shared market mechanisms 11.9us-gaap_LossContingencyUndiscountedAmountOfInsuranceRelatedAssessmentLiability    
OB Services      
Capital Leases, Future Minimum Payments Due, Fiscal Year Maturity [Abstract]      
Capital lease payments due next year 5.3us-gaap_CapitalLeasesFutureMinimumPaymentsDueCurrent
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
   
Capital lease payments due in two years 5.3us-gaap_CapitalLeasesFutureMinimumPaymentsDueInTwoYears
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
   
Capital lease payments due in three years 1.8us-gaap_CapitalLeasesFutureMinimumPaymentsDueInThreeYears
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
   
Cash proceeds received a result of entering into the sale-leaseback transactions 23.1us-gaap_SaleLeasebackTransactionNetProceeds
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
   
Capital lease obligation 7.1us-gaap_CapitalLeaseObligations
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
12.5us-gaap_CapitalLeaseObligations
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
 
Capital lease asset $ 7.0us-gaap_CapitalLeasedAssetsGross
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
$ 10.9us-gaap_CapitalLeasedAssetsGross
/ dei_LegalEntityAxis
= wtm_OneBeaconServicesLlcMember
 
Furniture and equipment | OB Services      
Capital Leases, Future Minimum Payments Due, Fiscal Year Maturity [Abstract]      
Capital lease term (in years) 5 years    
Capitalized software | OB Services      
Capital Leases, Future Minimum Payments Due, Fiscal Year Maturity [Abstract]      
Capital lease term (in years) 4 years