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Related Parties - Itasca Capital Ltd. (Details)
$ / shares in Units, $ / shares in Units, $ in Millions, $ in Millions
9 Months Ended 12 Months Ended
Nov. 19, 2019
USD ($)
$ / shares
shares
Oct. 31, 2019
CAD ($)
$ / shares
shares
Oct. 09, 2019
CAD ($)
$ / shares
shares
Sep. 30, 2019
USD ($)
$ / shares
shares
Sep. 05, 2018
shares
Nov. 17, 2017
USD ($)
Jun. 10, 2016
USD ($)
Sep. 30, 2019
shares
Dec. 31, 2018
shares
Dec. 31, 2019
shares
Jul. 26, 2017
Sep. 21, 2015
Related Party Transaction [Line Items]                        
Consideration received, cash | $       $ 0.6                
Consideration received (in shares)       594,750                
Consideration received, warrants (in shares)       400,000                
Warrant exercise price (in dollars per share) | $ / shares       $ 15                
Equity Method Investee                        
Related Party Transaction [Line Items]                        
Equity method investment, ownership percentage       47.60%       47.60% 47.60%   0.00% 33.30%
Board of Directors Chairman                        
Related Party Transaction [Line Items]                        
Equity method investment, ownership percentage       40.60%       40.60% 40.60%      
Chief Financial Officer                        
Related Party Transaction [Line Items]                        
Payments to acquire management contract rights | $           $ 0.0 $ 0.0          
Affiliated Entity                        
Related Party Transaction [Line Items]                        
Equity method investment, ownership percentage       0.00%       0.00% 0.00%      
Corporate Segment                        
Related Party Transaction [Line Items]                        
Equity method investment, ownership percentage       22.90%       22.90% 22.90%      
Fundamental Global Investors, LLC | Kingsway Financial Services, Inc                        
Related Party Transaction [Line Items]                        
Ownership percentage (less than at March 31, 2019)               5.00% 5.00%      
Restricted Stock                        
Related Party Transaction [Line Items]                        
Shares unvested (in shares)       976,950       976,950 1,092,450      
2018 Restricted Stock Awards | Restricted Stock                        
Related Party Transaction [Line Items]                        
Shares unvested (in shares)       500,000       500,000        
Former Chief Executive Officer | 2018 Restricted Stock Awards | Restricted Stock                        
Related Party Transaction [Line Items]                        
Shares granted (in shares)         350,000              
Shares withheld for tax obligation (in shares)         102,550              
Shares unvested (in shares)         247,450              
Subsequent Event                        
Related Party Transaction [Line Items]                        
Consideration received, cash | $ $ 0.6                      
Consideration received (in shares) 594,750                      
Consideration received, warrants (in shares) 400,000                      
Warrant exercise price (in dollars per share) | $ / shares $ 15                      
Subsequent Event | ICL | ICL | Affiliated Entity                        
Related Party Transaction [Line Items]                        
Number of shares to be sold (in shares)   3,011,447 1,974,113                  
Share price (in dollars per share) | $ / shares   $ 0.35 $ 0.35                  
Subsequent Event | ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party                        
Related Party Transaction [Line Items]                        
Amount of related party transaction | $   $ 1.1 $ 0.7                  
Number of shares (in shares)   247,450                    
Subsequent Event | ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party, Portion Received in Cash                        
Related Party Transaction [Line Items]                        
Amount of related party transaction | $   $ 0.2                    
Subsequent Event | Former Chief Executive Officer | 2018 Restricted Stock Awards | Restricted Stock                        
Related Party Transaction [Line Items]                        
Shares unvested (in shares)                   247,450