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Investments in Unconsolidated Affiliates (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Investments in unconsolidated affiliates        
Investments in unconsolidated affiliates $ 414.4wtm_InvestmentsInUnconsolidatedAffiliates $ 321.4wtm_InvestmentsInUnconsolidatedAffiliates    
Symetra        
Investments in unconsolidated affiliates        
Unrealized gains (losses) from Symetra’s fixed maturity portfolio 37.6wtm_EquityInUnrealizedGainsLossesFromInvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
(43.6)wtm_EquityInUnrealizedGainsLossesFromInvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
   
Investments in unconsolidated affiliates 411.4wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
317.3wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
381.5wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
273.6wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
Symetra | Common Stock        
Investments in unconsolidated affiliates        
Symetra common shares 373.8wtm_SharesExcludingUnrealizedGainsLosses
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
360.9wtm_SharesExcludingUnrealizedGainsLosses
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
   
Investments in unconsolidated affiliates 411.4wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
317.3wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
351.2wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
261.0wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
Symetra | Warrants        
Investments in unconsolidated affiliates        
Investments in unconsolidated affiliates 0wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
0wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
30.3wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
12.6wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
Hamer, LLC        
Investments in unconsolidated affiliates        
Investments in unconsolidated affiliates $ 3.0wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_HamerLlcMember
$ 4.1wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_HamerLlcMember