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Senior Debt (Details) - USD ($)
3 Months Ended
Mar. 31, 2020
Dec. 31, 2019
Debt Instrument [Line Items]    
Drawn balance outstanding $ 277,300,000 $ 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 193,300,000  
Line of Credit | 2013 Facility    
Debt Instrument [Line Items]    
Line of credit (up to) 315,000,000.0  
JRG Reinsurance Company, Ltd. | 2013 Facility    
Debt Instrument [Line Items]    
Amount of letters of credit issued 76,000,000.0  
JRG Reinsurance Company, Ltd. | 2017 Facility    
Debt Instrument [Line Items]    
Amount drawn 59,000,000.0  
Line of credit (up to) 100,000,000  
Amount of letters of credit issued 25,700,000  
JRG Reinsurance Company, Ltd. | Unsecured Debt | 2017 Facility    
Debt Instrument [Line Items]    
Drawn balance outstanding $ 69,000,000.0