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Discontinued Operations (Assets and Liabilities Classified as Held for Sale) (Details) - USD ($)
$ in Millions
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Assets held for sale        
Fixed maturity investments, at fair value $ 4,250.2 $ 2,630.2    
Short-term investments, at amortized cost (which approximates fair value) 287.0 211.2    
Common equity securities, at fair value 474.3 1,113.9    
Other long-term investments 323.3 315.8    
Total investments 5,334.8 4,271.1    
Cash Including Restricted Cash 149.8 173.0    
Reinsurance recoverable on unpaid losses 172.9 186.0    
Reinsurance recoverable on paid losses 6.6 7.5    
Insurance premiums receivable 229.9 220.3    
Deferred acquisition costs 106.9 107.6    
Deferred Income Tax Assets 126.7 112.8    
Ceded unearned insurance premiums 44.2 29.5    
Accounts receivable on unsettled investment sales 6.2 41.9    
Goodwill and intangible assets 55.9 55.4    
Other assets 274.6 273.2    
Assets held for sale 10.1 4,790.4    
Liabilities held for sale        
Loss and loss adjustment expense reserves 1,365.6 1,389.8 $ 1,342.2 $ 1,054.3
Unearned insurance and reinsurance premiums 658.0 610.5    
Debt 285.9 337.6    
Accrued incentive compensation 140.0 140.7    
Funds held under insurance contracts 153.0 137.8    
Other liabilities 199.9 250.8    
Liabilities held for sale 5.1 3,047.4    
Sirius Group, Tranzact, and Star and Shield [Member] | Discontinued Operations, Held-for-sale [Member]        
Assets held for sale        
Fixed maturity investments, at fair value   2,383.5    
Short-term investments, at amortized cost (which approximates fair value)   352.1    
Common equity securities, at fair value   174.4    
Other long-term investments   72.2    
Total investments   2,982.2    
Cash Including Restricted Cash   150.2    
Reinsurance recoverable on unpaid losses   283.6    
Reinsurance recoverable on paid losses   10.2    
Insurance premiums receivable   326.6    
Deferred acquisition costs   74.6    
Deferred Income Tax Assets   303.1    
Ceded unearned insurance premiums   87.7    
Accounts receivable on unsettled investment sales   29.0    
Goodwill and intangible assets   330.5    
Other assets   212.7    
Assets held for sale   4,790.4    
Liabilities held for sale        
Loss and loss adjustment expense reserves   1,650.4    
Unearned insurance and reinsurance premiums   344.3    
Debt   506.4    
Deferred tax liability   270.6    
Accrued incentive compensation   64.2    
Funds held under insurance contracts   52.9    
Other liabilities   158.6    
Liabilities held for sale   3,047.4    
Net assets held for sale   $ 1,743.0    
Star & Shield Insurance Exchange [Member] | Discontinued Operations, Held-for-sale [Member]        
Assets held for sale        
Fixed maturity investments, at fair value 6.6      
Short-term investments, at amortized cost (which approximates fair value) 0.2      
Common equity securities, at fair value 0.0      
Other long-term investments 0.0      
Total investments 6.8      
Cash Including Restricted Cash 0.9      
Reinsurance recoverable on unpaid losses 0.3      
Reinsurance recoverable on paid losses 0.0      
Insurance premiums receivable 1.5      
Deferred acquisition costs 0.0      
Deferred Income Tax Assets 0.0      
Ceded unearned insurance premiums 0.0      
Accounts receivable on unsettled investment sales 0.0      
Goodwill and intangible assets 0.0      
Other assets 0.6      
Assets held for sale 10.1      
Liabilities held for sale        
Loss and loss adjustment expense reserves 5.0      
Unearned insurance and reinsurance premiums 1.2      
Debt 0.0      
Deferred tax liability 0.0      
Accrued incentive compensation 0.0      
Funds held under insurance contracts 0.0      
Other liabilities (1.1)      
Liabilities held for sale 5.1      
Net assets held for sale $ 5.0