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Employee Share-Based Incentive Compensation Plans (WTM Restricted Shares) (Details) (USD $)
In Millions, except Share data, unless otherwise specified
12 Months Ended 3 Months Ended
Dec. 31, 2013
Dec. 31, 2014
Dec. 31, 2012
Dec. 31, 2014
Restricted Share Cliff Vesting in January 2016 [Member]        
Target Performance Share activity        
Issued (in shares) 25,720us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareCliffVestingInJanuary2016Member
     
Restricted Share Cliff Vesting in January 2015 [Member]        
Target Performance Share activity        
Issued (in shares) 27,960us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareCliffVestingInJanuary2015Member
     
Restricted Share Vesting Beginning in February 2014 [Member]        
Target Performance Share activity        
Issued (in shares) 3,000us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareVestingBeginningInFebruary2014Member
     
Unamortized grant date fair value        
Number of restricted shares installments 2wtm_NumberOfRestrictedSharesInstallments
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareVestingBeginningInFebruary2014Member
     
Restricted Share Cliff Vesting in July 2015 [Member]        
Target Performance Share activity        
Issued (in shares) 1,200us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareCliffVestingInJuly2015Member
     
W T M Incentive and Phantom Plan [Member] | Restricted Share Cliff Vesting in January 2017 [Member]        
Target Performance Share activity        
Issued (in shares)   23,440us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= wtm_RestrictedShareCliffVestinginJanuary2017Member
/ us-gaap_PlanNameAxis
= wtm_WTMIncentiveAndPhantomPlanMember
   
Restricted Share Vested in December 2012 [Member] | Restricted Stock        
Unamortized grant date fair value        
Number of restricted shares installments     5,000wtm_NumberOfRestrictedSharesInstallments
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ us-gaap_VestingAxis
= wtm_RestrictedShareVestedInDecember2012Member
 
White Mountains | W T M Incentive Plan | Restricted Stock        
Target Performance Share activity        
Beginning of period 69,910us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
94,130us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
72,000us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Issued (in shares) 25,720us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
23,440us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
32,160us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Vested (in shares) (1,500)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(33,205)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(32,945)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Assumed forfeitures and cancellations (in shares) 0us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(1,051)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(1,305)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Ending December 31, 94,130us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
83,314us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
69,910us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
83,314us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
Unamortized grant date fair value        
Beginning balance 16.8us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
17.0us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
$ 13.3us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Issued 14.4wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsIssuedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
13.1wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsIssuedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
15.7wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsIssuedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Assumed forfeitures and cancellations 0wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(0.5)wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(0.2)wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Expense recognized 14.2us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
15.3us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(12.0)us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Ending balance 17.0us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
14.3us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
16.8us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
14.3us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
White Mountains | W T M Incentive Plan | Performance Shares        
Target Performance Share activity        
Beginning of period 119,357us-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
150,064us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Assumed forfeitures and cancellations (in shares) 3us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(4,201)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(782)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Ending December 31, 119,220us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
123,549us-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
123,549us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
Unamortized grant date fair value        
Assumed forfeitures and cancellations (0.6)wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(0.7)wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
0.6wtm_EmployeeServiceShareBasedCompensationNonvestedAwardsForfeitedInPeriodTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Expense recognized (42.4)us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(15.3)us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
(21.0)us-gaap_AllocatedShareBasedCompensationExpense
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
 
Ending balance   16.9us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
  16.9us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognized
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentivePlanMember
Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive and Phantom Plan [Member] | Restricted Stock        
Target Performance Share activity        
Issued (in shares)       3,040us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentiveAndPhantomPlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
Assumed forfeitures and cancellations (in shares)       (3,040)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_RestrictedStockMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentiveAndPhantomPlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive and Phantom Plan [Member] | Performance Shares        
Target Performance Share activity        
Assumed forfeitures and cancellations (in shares)       (3,040)us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod
/ us-gaap_AwardTypeAxis
= us-gaap_PerformanceSharesMember
/ us-gaap_PlanNameAxis
= wtm_WTMIncentiveAndPhantomPlanMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member