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Employee Share-Based Incentive Compensation Plans (OneBeason Peformance Shares) (Details) (USD $)
In Millions, except Share data, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Expense Amortized      
Ending December 31, $ 184.6wtm_IncentiveCompensationPayable $ 218.3wtm_IncentiveCompensationPayable  
Long Term Incentive Plan      
Expense Amortized      
Percentage of payout for minimum growth target percentage     138.60%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMinimumGrowthTargetPercentage
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Performance Shares      
Share-based compensation arrangement by share-based payment award      
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding, Number 125,000us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
   
Share-based Compensation Arrangement by Share-based Payment Award, Options Outstanding Amended, Exercise Price $ 742wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingAmendedExercisePrice
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
   
OneBeacon | Performance Shares | Long Term Incentive Plan      
Target options outstanding      
Beginning of period 493,421us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
563,190us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
642,667us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Shares paid or expired (in shares) (142,138)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsTargetSharesPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(238,658)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsTargetSharesPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(258,901)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsTargetSharesPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
New grants 165,800us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
179,000us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
181,290us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Assumed forfeitures and cancellations (in shares) 387us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(10,111)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(1,866)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Ending December 31, 517,470us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
493,421us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
563,190us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Expense Amortized      
Beginning of period 4.0wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
1.2wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
9.7wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Payments and deferrals (1.0)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAmountsPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
0wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAmountsPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(7.7)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAmountsPaidInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Assumed forfeitures and cancellations 0wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(0.1)wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
0wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Expense recognized 0.4us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
2.9us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
(0.8)us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Ending December 31, $ 3.4wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
$ 4.0wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
$ 1.2wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Range of Performance Cycle from 2011 to 2013 [Member] | Long Term Incentive Plan      
Expense Amortized      
Percentage of payout for minimum growth target percentage 37.10%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMinimumGrowthTargetPercentage
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2011To2013Member