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Goodwill and Intangible Assets, net - Goodwill Rollforward (Details) - USD ($)
$ in Thousands
3 Months Ended 12 Months Ended
Jun. 30, 2019
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Goodwill [Roll Forward]        
Beginning balance   $ 47,396    
Impairment   (28,025) $ 0 $ 0
Acquisitions   29,708    
Ending balance   49,079 47,396  
Property and Casualty        
Goodwill [Roll Forward]        
Beginning balance   9,460    
Impairment   0    
Acquisitions   0    
Ending balance   9,460 9,460  
Supplemental        
Goodwill [Roll Forward]        
Beginning balance   0    
Impairment   0    
Acquisitions   19,621    
Ending balance   19,621 0  
Retirement        
Goodwill [Roll Forward]        
Beginning balance   28,025    
Impairment $ (28,000) (28,025)    
Acquisitions   10,087    
Ending balance   10,087 28,025  
Life        
Goodwill [Roll Forward]        
Beginning balance   9,911    
Impairment   0    
Acquisitions   0    
Ending balance   $ 9,911 $ 9,911