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Debt (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2016
Mar. 31, 2015
Dec. 31, 2015
Jul. 23, 2015
Oct. 10, 2014
Aug. 14, 2013
Debt Instrument            
Total debt $ 532.6   $ 440.5      
Repayments of Debt 15.1 $ 1.3        
Draw down of debt and revolving line of credit 107.0 $ 4.5        
WTM Bank Facility            
Debt Instrument            
Total debt 150.0          
Total commitment under revolving credit facility           $ 425.0
Proceeds from Issuance of Debt $ 100.0          
Debt, Weighted Average Interest Rate 3.90%          
OB Bank Facility [Member]            
Debt Instrument            
Total commitment under revolving credit facility $ 65.0          
OneBeacon [Member] | OneBeacon Bank Facility [Member]            
Debt Instrument            
Long-term Line of Credit 0.0          
OneBeacon [Member] | 2012 OBH Senior Notes            
Debt Instrument            
Debt instrument at face value 275.0   275.0      
Unamortized original issue discount (2.1)   (2.1)      
Total debt $ 272.9   $ 272.9      
Debt Instrument, Interest Rate, Effective Percentage 4.70%   4.70%      
White Mountains | WTM Bank Facility            
Debt Instrument            
Total debt $ 150.0   $ 50.0      
Tranzact [Member] | OneBeacon Bank Facility [Member]            
Debt Instrument            
Long-term Line of Credit     0.0      
Tranzact [Member] | Tranzact Bank Facility [Member]            
Debt Instrument            
Long-term Line of Credit $ 94.1   $ 104.7      
Debt Instrument, Interest Rate, Effective Percentage 5.96%   5.60%      
Unamortized Debt Issuance Expense $ (1.6)   $ (1.8)      
Line of Credit Facility, Fair Value of Amount Outstanding 92.5   102.9      
Total commitment under revolving credit facility 116.0          
Notional amount 101.0       $ 70.0  
Line of Credit Facility, Remaining Borrowing Capacity 15.0          
MediaAlpha [Member] | MediaAlpha Bank Facility [Member]            
Debt Instrument            
Total debt 2.5          
Long-term Line of Credit $ 17.5   $ 15.0      
Debt Instrument, Interest Rate, Effective Percentage 6.40%   5.50%      
Unamortized Debt Issuance Expense $ (0.3)   $ (0.3)      
Line of Credit Facility, Fair Value of Amount Outstanding 17.2   $ 14.7      
Total commitment under revolving credit facility       $ 20.0    
Notional amount 15.0          
Proceeds from Issuance of Debt 2.5          
Line of Credit Facility, Remaining Borrowing Capacity 5.0          
Revolving Credit Facility [Member] | Tranzact [Member] | Tranzact Bank Facility [Member]            
Debt Instrument            
Proceeds from Issuance of Debt 4.5          
Repayments of Debt 12.5          
Term Loan [Member] | Tranzact [Member] | Tranzact Bank Facility [Member]            
Debt Instrument            
Repayments of Debt 2.6          
TruBridge [Member] | Tranzact [Member] | Tranzact Bank Facility [Member]            
Debt Instrument            
Notional amount $ 31.0