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Discontinued Operations (Loss from Discontinued Operations) (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended 12 Months Ended
Dec. 31, 2014
Sep. 30, 2014
Jun. 30, 2014
Mar. 31, 2014
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Revenues                      
Earned insurance premiums                 $ 2,058.9us-gaap_PremiumsEarnedNet $ 1,987.3us-gaap_PremiumsEarnedNet $ 2,063.6us-gaap_PremiumsEarnedNet
Other revenue                 62.4us-gaap_OtherIncome 57.5us-gaap_OtherIncome 100.3us-gaap_OtherIncome
Revenues (including realized gains and losses) 689.7us-gaap_Revenues 589.4us-gaap_Revenues 652.8us-gaap_Revenues 578.3us-gaap_Revenues 626.6us-gaap_Revenues 574.1us-gaap_Revenues 489.3us-gaap_Revenues 627.4us-gaap_Revenues 2,510.2us-gaap_Revenues 2,317.4us-gaap_Revenues 2,435.7us-gaap_Revenues
Expenses                      
Loss and loss adjustment expenses                 1,169.3us-gaap_PolicyholderBenefitsAndClaimsIncurredNet 1,040.5us-gaap_PolicyholderBenefitsAndClaimsIncurredNet 1,193.9us-gaap_PolicyholderBenefitsAndClaimsIncurredNet
Insurance and reinsurance acquisition expenses                 399.8wtm_InsuranceAndReinsuranceAcquisitionExpenses 376.9wtm_InsuranceAndReinsuranceAcquisitionExpenses 430.2wtm_InsuranceAndReinsuranceAcquisitionExpenses
Other underwriting expenses                 309.3us-gaap_OtherUnderwritingExpense 331.3us-gaap_OtherUnderwritingExpense 321.8us-gaap_OtherUnderwritingExpense
Total expenses 643.5us-gaap_BenefitsLossesAndExpenses 555.0us-gaap_BenefitsLossesAndExpenses 543.8us-gaap_BenefitsLossesAndExpenses 466.2us-gaap_BenefitsLossesAndExpenses 492.4us-gaap_BenefitsLossesAndExpenses 518.8us-gaap_BenefitsLossesAndExpenses 485.7us-gaap_BenefitsLossesAndExpenses 475.6us-gaap_BenefitsLossesAndExpenses 2,208.5us-gaap_BenefitsLossesAndExpenses 1,972.5us-gaap_BenefitsLossesAndExpenses 2,172.9us-gaap_BenefitsLossesAndExpenses
Net loss from discontinued operations, net of tax (12.2)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 6.7us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 2.6us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (0.5)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (0.3)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 0.4us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 3.9us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 0.5us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (1.8)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (42.1)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (24.0)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax
(Loss) gain on sale of discontinued operations, net of tax                 (1.6)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax 46.6us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax (91.0)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
Discontinued Operations                      
Revenues                      
Earned insurance premiums                 0.1us-gaap_PremiumsEarnedNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
0.8us-gaap_PremiumsEarnedNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
10.6us-gaap_PremiumsEarnedNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Other revenue                 0us-gaap_OtherIncome
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
10.8us-gaap_OtherIncome
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
0us-gaap_OtherIncome
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Revenues (including realized gains and losses)                 0.1us-gaap_Revenues
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
11.6us-gaap_Revenues
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
10.6us-gaap_Revenues
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Expenses                      
Loss and loss adjustment expenses                 (0.7)us-gaap_PolicyholderBenefitsAndClaimsIncurredNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
78.9us-gaap_PolicyholderBenefitsAndClaimsIncurredNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
48.4us-gaap_PolicyholderBenefitsAndClaimsIncurredNet
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Insurance and reinsurance acquisition expenses                 0.1wtm_InsuranceAndReinsuranceAcquisitionExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
0wtm_InsuranceAndReinsuranceAcquisitionExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(2.1)wtm_InsuranceAndReinsuranceAcquisitionExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Other underwriting expenses                 3.5us-gaap_OtherUnderwritingExpense
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(0.2)us-gaap_OtherUnderwritingExpense
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
1.7us-gaap_OtherUnderwritingExpense
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Total expenses                 2.9us-gaap_BenefitsLossesAndExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
78.7us-gaap_BenefitsLossesAndExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
48.0us-gaap_BenefitsLossesAndExpenses
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Loss from discontinued operations                 (2.8)us-gaap_DiscontinuedOperationIncomeLossFromDiscontinuedOperationBeforeIncomeTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(67.1)us-gaap_DiscontinuedOperationIncomeLossFromDiscontinuedOperationBeforeIncomeTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(37.4)us-gaap_DiscontinuedOperationIncomeLossFromDiscontinuedOperationBeforeIncomeTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Income tax benefit                 1.0us-gaap_DiscontinuedOperationTaxEffectOfDiscontinuedOperation
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
25.0us-gaap_DiscontinuedOperationTaxEffectOfDiscontinuedOperation
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
13.4us-gaap_DiscontinuedOperationTaxEffectOfDiscontinuedOperation
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Net loss from discontinued operations, net of tax                 (1.8)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(42.1)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(24.0)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(Loss) gain on sale of discontinued operations, net of tax                 (1.6)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
46.6us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
(91.0)us-gaap_DiscontinuedOperationGainLossOnDisposalOfDiscontinuedOperationNetOfTax
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
Net (loss) income from discontinued operations                 $ (3.4)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxAttributableToReportingEntity
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
$ 4.5us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxAttributableToReportingEntity
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember
$ (115.0)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxAttributableToReportingEntity
/ us-gaap_StatementOperatingActivitiesSegmentAxis
= us-gaap_SegmentDiscontinuedOperationsMember