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Retirement and Postretirement Plans (Cash Flow) (Details) (USD $)
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Employee savings plan      
Defined Benefit Plan, Benefit Obligation $ 119,700,000us-gaap_DefinedBenefitPlanBenefitObligation $ 102,900,000us-gaap_DefinedBenefitPlanBenefitObligation $ 119,500,000us-gaap_DefinedBenefitPlanBenefitObligation
Funded status at end of year 26,300,000us-gaap_DefinedBenefitPlanFundedStatusOfPlan 39,900,000us-gaap_DefinedBenefitPlanFundedStatusOfPlan  
OneBeacon Ltd.      
Expected Benefit Payments      
2015 4,900,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsNextTwelveMonths
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
2016 5,300,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsYearTwo
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
2017 5,600,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsYearThree
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
2018 5,900,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsYearFour
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
2019 6,100,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsYearFive
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
2020-2024 34,400,000us-gaap_DefinedBenefitPlanExpectedFutureBenefitPaymentsFiveFiscalYearsThereafter
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
Employee savings plan      
Anticipated contribution to plan 2,200,000us-gaap_DefinedBenefitPlansEstimatedFutureEmployerContributionsInNextFiscalYear
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
   
OneBeacon      
Employee savings plan      
Post-employment benefit liability 4,800,000us-gaap_PostemploymentBenefitsLiabilityNoncurrent
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
5,800,000us-gaap_PostemploymentBenefitsLiabilityNoncurrent
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
 
Sirius Group      
Employee savings plan      
Defined Contribution Plan, Cost Recognized 500,000us-gaap_DefinedContributionPlanCostRecognized
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
700,000us-gaap_DefinedContributionPlanCostRecognized
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
400,000us-gaap_DefinedContributionPlanCostRecognized
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
Government Pension Plans [Member] | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Cost Recognized 10,300,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
9,700,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
7,500,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
Defined Benefit Plan, Benefit Obligation 14,100,000us-gaap_DefinedBenefitPlanBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
13,100,000us-gaap_DefinedBenefitPlanBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
 
Funded status at end of year (1,800,000)us-gaap_DefinedBenefitPlanFundedStatusOfPlan
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
(1,000,000)us-gaap_DefinedBenefitPlanFundedStatusOfPlan
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_UnitedStatesPensionPlansOfUSEntityDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
 
Qualified Plan [Member] | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Cost Recognized 700,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
600,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
600,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
Combination One [Member] | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Employer Matching Contribution, Percent of Employees' Gross Pay 2.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercent
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
/ wtm_MatchingContributionAxis
= wtm_CombinationOneMember
   
Combination Two [Member] | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Employer Matching Contribution, Percent of Employees' Gross Pay 4.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercent
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
/ wtm_MatchingContributionAxis
= wtm_CombinationTwoMember
   
Maximum | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Employer Matching Contribution, Percent of Match 100.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercentOfMatch
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
   
Employer matching contribution variable contributions 7.00%wtm_DefinedContributionPlanEmployerMatchingContributionVariableContributions
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
   
Minimum | Sirius Group      
Employee savings plan      
Defined Contribution Plan, Employer Matching Contribution, Percent of Match 50.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercentOfMatch
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
   
One Beacon Employee Stock Ownership Plan      
Employee savings plan      
Defined Contribution Plan, Cost Recognized 4,400,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
6,300,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
4,800,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
Annual base contribution provided to participants expressed as percentage of salary 3.00%wtm_EmployeeStockOwnershipPlanEsopAnnualBaseContributionProvidedToParticipantsExpressedAsPercentageOfSalary
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
   
Social security wage base amount maximum 117,000wtm_EmployeeStockOwnershipPlanEsopSocialSecurityWageBaseAmountMaximum
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
   
Variable contribution provided to participants (as percentage) 6.00%wtm_EmployeeStockOwnershipPlanEsopVariableContributionProvidedToParticipantsNotEligibleToCertainBenefitsExpressedAsPercentageOfSalary
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
   
One Beacon Employee Stock Ownership Plan | OneBeacon      
Employee savings plan      
Defined Contribution Plan, Employer Matching Contribution, Percent of Match 50.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercentOfMatch
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
Defined Contribution Plan, Employer Matching Contribution, Percent of Employees' Gross Pay 6.00%us-gaap_DefinedContributionPlanEmployerMatchingContributionPercent
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
Defined Contribution Plan, Cost Recognized 2,700,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
2,300,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
2,800,000us-gaap_DefinedContributionPlanCostRecognized
/ us-gaap_EmployeeStockOwnershipPlanESOPDisclosuresByPlanAxis
= wtm_OneBeaconEmployeeStockOwnershipPlanMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
IRS | OneBeacon      
Employee savings plan      
Defined Benefit Plan Compensation LImits 260,000wtm_DefinedBenefitPlanCompensationLImits
/ us-gaap_IncomeTaxAuthorityAxis
= us-gaap_InternalRevenueServiceIRSMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
IRS | Sirius Group      
Employee savings plan      
Defined Benefit Plan Compensation LImits $ 260,000wtm_DefinedBenefitPlanCompensationLImits
/ us-gaap_IncomeTaxAuthorityAxis
= us-gaap_InternalRevenueServiceIRSMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember