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Retirement and Postretirement Plans (Qualifed, Non-qualified, and Accumulated Benefit Obligations) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2015
Amounts recognized in accumulated other comprehensive income (loss) on a pre-tax basis noncontrolling interest      
Accumulated other comprehensive income (loss) beginning balance $ 10.5us-gaap_DefinedBenefitPlanAccumulatedOtherComprehensiveIncomeBeforeTax $ (21.2)us-gaap_DefinedBenefitPlanAccumulatedOtherComprehensiveIncomeBeforeTax  
Increase (decrease) in accumulated other comprehensive income (loss):      
Amortization of net actuarial losses recognized during the year 0.3us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIPensionAndOtherPostretirementBenefitPlansForNetGainLossBeforeTax 0.9us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIPensionAndOtherPostretirementBenefitPlansForNetGainLossBeforeTax  
Net actuarial (losses) gains occurring during the year (18.8)us-gaap_OtherComprehensiveIncomeLossPensionAndOtherPostretirementBenefitPlansNetUnamortizedGainLossArisingDuringPeriodBeforeTax 30.8us-gaap_OtherComprehensiveIncomeLossPensionAndOtherPostretirementBenefitPlansNetUnamortizedGainLossArisingDuringPeriodBeforeTax  
Accumulated other comprehensive (loss) income ending balance (8.0)us-gaap_DefinedBenefitPlanAccumulatedOtherComprehensiveIncomeBeforeTax 10.5us-gaap_DefinedBenefitPlanAccumulatedOtherComprehensiveIncomeBeforeTax  
Other Postretirement Benefit Plan, Defined Benefit [Member]      
Information for the Non-qualified Plan, which had accumulated benefit obligations in excess of plan assets      
Projected benefit obligation 27.1us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateProjectedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
24.2us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateProjectedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
 
Accumulated benefit obligation 27.1us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateAccumulatedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
24.2us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateAccumulatedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
 
Fair value of plan assets 0us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateFairValueOfPlanAssets
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
0us-gaap_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsInExcessOfPlanAssetsAggregateFairValueOfPlanAssets
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_OtherPostretirementBenefitPlansDefinedBenefitMember
 
Qualified Plan [Member]      
Information for the Qualified Plan, which had accumulated benefit obligations less than plan assets      
Projected benefit obligation 92.6wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateProjectedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
78.7wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateProjectedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
 
Accumulated benefit obligation 92.6wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateAccumulatedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
78.7wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateAccumulatedBenefitObligation
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
 
Fair value of plan net assets 146.0wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateFairValueOfPlanAssets
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
142.8wtm_DefinedBenefitPlanPensionPlansWithAccumulatedBenefitObligationsLessThanPlanAssetsAggregateFairValueOfPlanAssets
/ us-gaap_DefinedBenefitPlansDisclosuresDefinedBenefitPlansAxis
= us-gaap_PensionPlansDefinedBenefitMember
 
Scenario, Forecast [Member] | OneBeacon Ltd.      
Increase (decrease) in accumulated other comprehensive income (loss):      
Amount expected to be amortized from accumulated other comprehensive income (loss) into net periodic benefit cost during 2012     $ 1.2us-gaap_DefinedBenefitPlanAmountToBeAmortizedFromAccumulatedOtherComprehensiveIncomeLossNextFiscalYear
/ dei_LegalEntityAxis
= wtm_OneBeaconInsuranceGroupLtdMember
/ us-gaap_StatementScenarioAxis
= us-gaap_ScenarioForecastMember