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Employee Share-Based Incentive Compensation Plans (OneBeacon Performance Shares Outstanding) (Details) (USD $)
In Millions, except Share data, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Share-based compensation arrangement by share-based payment award        
Accrued incentive compensation $ 184.6wtm_IncentiveCompensationPayable $ 218.3wtm_IncentiveCompensationPayable    
OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 526,090wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
     
Incentive compensation payable before forfeitures 3.4wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
     
forfeitures (8,620)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAssumedForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
     
Assumed forfeitures in period amount 0wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAssumedForfeituresAmount
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
     
Shares outstanding (in shares) 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
642,667us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Accrued incentive compensation 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
9.7wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
Unamortized grant date fair value 1.6us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
     
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 14.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
13.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
10.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
 
Range Of Performance Cycle From 2014-2016 [Member] | OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 165,800wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Incentive compensation payable before forfeitures 0.5wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Performance Cycle From 2013 to 2015 | OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 179,000wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Incentive compensation payable before forfeitures 1.4wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Performance Cycle From 2012 to 2014 | OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 181,290wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Incentive compensation payable before forfeitures $ 1.5wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Maximum | OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 21.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
20.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
17.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
 
Percentage of performance shares earned 200.00%wtm_Percentageofperformancesharesearned
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
200.00%wtm_Percentageofperformancesharesearned
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
200.00%wtm_Percentageofperformancesharesearned
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
 
Minimum | OneBeacon | Performance Shares | Long Term Incentive Plan        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 7.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
6.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
3.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_PlanNameAxis
= wtm_LongTermIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember