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Reserves for Unpaid Losses and Loss Adjustment Expenses Reserves for Unpaid Losses and Loss Adjustment Expenses (Reserve Development) (Details) (USD $)
In Millions, unless otherwise specified
9 Months Ended 12 Months Ended
Sep. 30, 2014
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Premiums earned        
Current Accident Year   $ 1,175.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear $ 1,088.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear $ 1,235.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
Prior Accident Year   (6.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears (48.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears (41.9)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
Total incurred losses and LAE   1,169.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,040.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,193.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
OneBeacon        
Premiums earned        
Current Accident Year 33.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
33.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year 14.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
75.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
  (7.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Total incurred losses and LAE   109.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
89.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Professional Insurance | OneBeacon        
Premiums earned        
Current Accident Year   22.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   46.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   69.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
59.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Specialty Property | OneBeacon        
Premiums earned        
Current Accident Year   (1.1)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyPropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   5.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyPropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   4.6us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyPropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyPropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Crop | OneBeacon        
Premiums earned        
Current Accident Year   3.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   3.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Other | OneBeacon        
Premiums earned        
Current Accident Year   2.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   (0.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   2.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1.6us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Specialty Products | OneBeacon        
Premiums earned        
Current Accident Year   28.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   51.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   80.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
61.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Entertainment | OneBeacon        
Premiums earned        
Current Accident Year   1.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_EntertainmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   11.6us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_EntertainmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   13.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_EntertainmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
13.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_EntertainmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Accident | OneBeacon        
Premiums earned        
Current Accident Year   0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AccidentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   3.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AccidentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   3.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AccidentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
6.0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AccidentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Government Risks | OneBeacon        
Premiums earned        
Current Accident Year   1.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_GovernmentRisksMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   7.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_GovernmentRisksMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   8.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_GovernmentRisksMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
8.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_GovernmentRisksMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Other | OneBeacon        
Premiums earned        
Current Accident Year   2.6us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   1.6us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   4.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_OtherSpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
 
Specialty Industries | OneBeacon        
Premiums earned        
Current Accident Year   5.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Prior Accident Year   23.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
   
Total incurred losses and LAE   $ 29.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
$ 28.0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyIndustriesMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember