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Debt (Details) - USD ($)
3 Months Ended 9 Months Ended
Sep. 30, 2015
Sep. 30, 2015
Sep. 30, 2014
Jul. 23, 2015
Dec. 31, 2014
Nov. 25, 2014
Oct. 10, 2014
Aug. 14, 2013
Debt Instrument                
Total debt $ 383,300,000 $ 383,300,000     $ 343,100,000      
Repayments of Debt   92,900,000 $ 40,200,000          
Draw down of debt and revolving line of credit   $ 134,000,000 $ 40,000,000          
WTM Bank Facility                
Debt Instrument                
Total commitment under revolving credit facility               $ 425,000,000
Proceeds from Issuance of Debt $ 60,000,000              
Debt, Weighted Average Interest Rate 3.65% 3.65%            
Repayments of Debt $ 60,000,000              
OB Bank Facility [Member]                
Debt Instrument                
Total commitment under revolving credit facility 65,000,000 $ 65,000,000            
Other Debt [Member]                
Debt Instrument                
Total debt 0 0     1,000,000      
OneBeacon | 2012 OBH Senior Notes                
Debt Instrument                
Debt instrument at face value 275,000,000 275,000,000     275,000,000      
Unamortized original issue discount (200,000) (200,000)     (300,000)      
Total debt 274,800,000 274,800,000     274,700,000      
White Mountains | WTM Bank Facility                
Debt Instrument                
Total debt 0 0     0      
Tranzact [Member] | Tranzact Bank Facility [Member]                
Debt Instrument                
Long-term Line of Credit 95,800,000 95,800,000     68,700,000      
Unamortized Debt Issuance Expense (2,000,000) (2,000,000)     (1,300,000)      
Line of Credit Facility, Fair Value of Amount Outstanding 93,800,000 93,800,000     67,400,000      
Total commitment under revolving credit facility 116,000,000 116,000,000            
Notional amount 101,000,000 101,000,000         $ 70,000,000  
Line of Credit Facility, Remaining Borrowing Capacity 15,000,000 15,000,000            
Proceeds from Long-term Lines of Credit   13,000,000            
Repayments of Debt 1,300,000 3,900,000            
MediaAlpha | MediaAlpha Bank Facility [Member]                
Debt Instrument                
Long-term Line of Credit 15,000,000 15,000,000     0      
Unamortized Debt Issuance Expense (300,000) (300,000)     0      
Line of Credit Facility, Fair Value of Amount Outstanding 14,700,000 14,700,000     $ 0      
Total commitment under revolving credit facility       $ 20,000,000        
Notional amount 15,000,000 15,000,000            
Line of Credit Facility, Remaining Borrowing Capacity 5,000,000 5,000,000            
Nordea Bank Finland                
Debt Instrument                
Total commitment under revolving credit facility           $ 125,000,000.0    
Lloyds Bank plc [Member]                
Debt Instrument                
Total commitment under revolving credit facility           75,000,000.0    
Unsecured Debt [Member] | Nordea Bank Finland                
Debt Instrument                
Total commitment under revolving credit facility           100,000,000.0    
Unsecured Debt [Member] | Lloyds Bank plc [Member]                
Debt Instrument                
Total commitment under revolving credit facility           $ 25,000,000.0    
TruBridge [Member] | Tranzact [Member] | Tranzact Bank Facility [Member]                
Debt Instrument                
Notional amount $ 31,000,000 $ 31,000,000