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Senior Debt (Details) - USD ($)
3 Months Ended
Jun. 30, 2020
Mar. 31, 2020
Dec. 31, 2019
Debt Instrument [Line Items]      
Drawn balance outstanding $ 217,300,000   $ 158,300,000
2013 Facility      
Debt Instrument [Line Items]      
Amount drawn   $ 60,000,000.0  
Unsecured Debt | 2013 Facility      
Debt Instrument [Line Items]      
Line of credit (up to)   212,500,000  
Drawn balance outstanding 163,300,000    
Line of Credit | 2013 Facility      
Debt Instrument [Line Items]      
Line of credit (up to)   315,000,000.0  
Repaid amount 30,000,000.0    
JRG Reinsurance Company, Ltd. | 2013 Facility      
Debt Instrument [Line Items]      
Amount of letters of credit issued 74,700,000    
JRG Reinsurance Company, Ltd. | 2017 Facility      
Debt Instrument [Line Items]      
Amount drawn   $ 59,000,000.0  
Line of credit (up to) 100,000,000.0    
Repaid amount 30,000,000.0    
Amount of letters of credit issued 17,800,000    
JRG Reinsurance Company, Ltd. | Unsecured Debt | 2017 Facility      
Debt Instrument [Line Items]      
Drawn balance outstanding $ 39,000,000.0