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Employee Share-Based Incentive Compensation Plans (WTM Performance Shares Granted Under the WTM Incentive Plan) (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    
Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 9.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 200.00%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 8.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 200.00%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Performance Cycle From 2012 to 2014 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 8.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalforPersonnelExpressedasPercentageofGrowthinIntrinsicBusinessValue
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 200.00%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardPayoutForMaximumGrowthTargetPercentage
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
White Mountains | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 126,717wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
     
Incentive compensation payable before forfeitures 49.4wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
     
forfeitures (3,168)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAssumedForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
     
Assumed forfeitures in period amount (1.3)wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsAssumedForfeituresAmount
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
     
Shares outstanding (in shares) 123,549us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
119,220us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
119,357us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
150,064us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
Accrued incentive compensation 48.1wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
60.2wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
29.4wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
66.1wtm_IncentiveCompensationPayable
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
White Mountains | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 41,937wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Incentive compensation payable before forfeitures 4.1wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
White Mountains | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 46,803wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Incentive compensation payable before forfeitures 18.9wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
White Mountains | Performance Cycle From 2012 to 2014 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 37,977wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumberBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Incentive compensation payable before forfeitures 26.4wtm_IncentiveCompensationPayableBeforeForfeitures
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Minimum | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 3.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Minimum | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Minimum | Performance Cycle From 2012 to 2014 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member
     
Maximum | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 15.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
     
Maximum | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 14.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
     
Maximum | Performance Cycle From 2012 to 2014 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 14.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardPerformanceGoalPercentageforPayout
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2012To2014Member