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SCHEDULE III SUPPLEMENTARY INSURANCE INFORMATION (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
SUPPLEMENTARY INSURANCE INFORMATION      
Net investment income $ 105.0us-gaap_NetInvestmentIncome $ 110.9us-gaap_NetInvestmentIncome $ 153.6us-gaap_NetInvestmentIncome
OneBeacon      
SUPPLEMENTARY INSURANCE INFORMATION      
Deferred acquisition costs 103.2us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
103.7us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
123.9us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Future policy benefits, losses, claims and loss expenses 1,342.2us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,054.3us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,000.0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Unearned premiums 588.3us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
544.9us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
573.8us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Other policy claims and benefits payable 0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Premiums earned 1,177.1us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,120.4us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,132.0us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Net investment income 41.7us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
41.1us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
53.6us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Benefits, claims, losses, and settlement expenses 815.1us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
622.1us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
650.0us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Amortization of deferred policy acquisition costs 203.3us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
208.9us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
249.4us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Other operating expenses 179.2us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
204.8us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
205.2us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Premiums written 1,216.9us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,088.6us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,179.2us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Net investment income 41.7us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
41.1us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
53.6us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Sirius Group      
SUPPLEMENTARY INSURANCE INFORMATION      
Deferred acquisition costs 69.9us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
69.3us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
71.4us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Future policy benefits, losses, claims and loss expenses 1,809.8us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
2,025.0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
2,168.9us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Unearned premiums 338.6us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
343.3us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
350.2us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Other policy claims and benefits payable 0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Premiums earned 873.9us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
866.4us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
931.6us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Net investment income 41.1us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
30.3us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
65.0us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Benefits, claims, losses, and settlement expenses 345.3us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
418.4us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
543.9us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Amortization of deferred policy acquisition costs 193.6us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
166.5us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
180.8us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Other operating expenses 129.7us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
126.1us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
116.4us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Premiums written 882.5us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
876.6us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
947.7us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
HG Global-BAM      
SUPPLEMENTARY INSURANCE INFORMATION      
Deferred acquisition costs 4.0us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
1.7us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Future policy benefits, losses, claims and loss expenses 0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Unearned premiums 27.6us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
13.2us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Other policy claims and benefits payable 0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Premiums earned 1.8us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
0.5us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Net investment income 7.1us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
5.7us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Benefits, claims, losses, and settlement expenses 0us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
0us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Amortization of deferred policy acquisition costs 2.1us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
1.5us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Other operating expenses 0.4us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
0.4us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Premiums written 16.2us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
13.6us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HgGlobalBamMember
 
Other Operations      
SUPPLEMENTARY INSURANCE INFORMATION      
Deferred acquisition costs 0us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Future policy benefits, losses, claims and loss expenses 7.8us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationLiabilityForFuturePolicyBenefitsLossesClaimsAndLossExpenseReserves
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Unearned premiums 0.8us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationUnearnedPremiums
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Other policy claims and benefits payable 0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationOtherPolicyClaimsAndBenefitsPayable
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Premiums earned 6.1us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationPremiumRevenue
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Net investment income 0.2us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0.1us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0.5us-gaap_SupplementaryInsuranceInformationNetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Benefits, claims, losses, and settlement expenses 8.9us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationBenefitsClaimsLossesAndSettlementExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Amortization of deferred policy acquisition costs 0.8us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationAmortizationOfDeferredPolicyAcquisitionCosts
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Other operating expenses 0us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationOtherOperatingExpense
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Premiums written 5.9us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
0us-gaap_SupplementaryInsuranceInformationPremiumsWritten
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OtherOperationsMember
Non-insurance [Member] | Operating Segments      
SUPPLEMENTARY INSURANCE INFORMATION      
Net investment income $ 14.9us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_OperatingSegmentsMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= wtm_NoninsuranceMember
$ 33.7us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_OperatingSegmentsMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= wtm_NoninsuranceMember
$ 32.3us-gaap_NetInvestmentIncome
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_OperatingSegmentsMember
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= wtm_NoninsuranceMember