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Municipal Bond Guarantee Insurance (Details)
$ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2015
USD ($)
Contract
Sep. 30, 2015
USD ($)
Jun. 30, 2015
USD ($)
Mar. 31, 2015
USD ($)
Dec. 31, 2014
USD ($)
Contract
Sep. 30, 2014
USD ($)
Jun. 30, 2014
USD ($)
Mar. 31, 2014
USD ($)
Dec. 31, 2015
USD ($)
Contract
Dec. 31, 2014
USD ($)
Contract
Dec. 31, 2013
USD ($)
Dec. 31, 2012
USD ($)
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Percentage of par value of policy reinsured 15.00%               15.00%      
Pre-tax loss $ 258.1 $ (94.6) $ (9.1) $ 0.5 $ (65.7) $ (35.5) $ 33.6 $ 38.6 $ 154.9 $ (29.0) $ 158.6  
Net investment income (loss) - surplus note interest                 0.0 $ 0.0 0.0  
BAM                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Next Quarter 1.1               1.1      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Next Twelve Months 4.4               4.4      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Two 4.3               4.3      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Three 4.1               4.1      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Four 3.8               3.8      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Five 3.6               3.6      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Six Through Ten 30.0               30.0      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Year Two 1.1               1.1      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Third Quarter 1.1               1.1      
Financial Guarantee Insurance Contracts, Future Expected Premium Revenue to be Recognized, Fourth Quarter $ 1.1               $ 1.1      
Municipal bond contract | Contract 3,103       1,750       3,103 1,750    
Insured Financial Obligations with Credit Deterioration, Remaining Weighted Average Contract Period                 12 years 10 months 12 years 10 months    
Municipal bond outstanding principal $ 22,556.0       $ 12,362.5       $ 22,556.0 $ 12,362.5    
Municipal bond outstanding interest 11,984.4       7,086.9       11,984.4 7,086.9    
Financial Guarantee Insurance Contracts, Unearned Premium Revenue $ 50.2       $ 27.6       $ 50.2 $ 27.6    
White Mountains                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Capital contributions                       $ 594.5
HG Global                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Surplus notes                       503.0
Percentage of par value of policy reinsured 15.00%               15.00%      
BAM Management                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Capital contributions                       $ 14.5
Preferred stocks | HG Global                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Ownership interest (as a percent) 96.90%               96.90%      
Common Stock | HG Global                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Ownership interest (as a percent) 88.40%       88.40%       88.40% 88.40%    
BAM                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Surplus notes $ 503.0               $ 503.0      
Pre-tax loss                 (47.3) $ (40.5) (78.6)  
Net investment income (loss) - surplus note interest                 (15.8) (15.7) (40.2)  
HG Re                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Statutory capital and surplus $ 460.8       $ 449.1       $ 460.8 $ 449.1    
Collateral Held in Supplement Trust 136,200,000       120,000,000       136,200,000 120,000,000    
HG Global                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Percentage of par value of policy reinsured 15.00%               15.00%      
Pre-tax loss                 $ 17.9 $ 18.3 38.1  
Net investment income (loss) - surplus note interest                 15.8 $ 15.7 $ 40.2  
Surplus Note | HG Global                        
Schedule of Insured Financial Obligations with Credit Deterioration [Line Items]                        
Interest Receivable $ 90.2               $ 90.2