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Related Parties - Itasca Capital Ltd. (Details)
$ / shares in Units, $ / shares in Units, $ in Millions, $ in Millions
6 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 ($)
Jun. 10, 2016
USD ($)
Jun. 30, 2019
shares
Dec. 31, 2018
shares
Board of Directors Chairman                  
Related Party Transaction [Line Items]                  
Equity method investment, ownership percentage               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%
Corporate Segment                  
Related Party Transaction [Line Items]                  
Equity method investment, ownership percentage               22.90% 22.90%
Fundamental Global Investors, LLC | Kingsway Financial Services, Inc                  
Related Party Transaction [Line Items]                  
Ownership percentage (less than at June 30, 2019)               5.00% 5.00%
Restricted Stock                  
Related Party Transaction [Line Items]                  
Shares unvested (in shares)               976,950 1,092,450
2018 Restricted Stock Awards | Restricted Stock                  
Related Party Transaction [Line Items]                  
Shares unvested (in shares)               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     $ 0.6          
Consideration received (in shares) 594,750     594,750          
Consideration received, warrants (in shares) 400,000     400,000          
Warrant exercise price (in dollars per share) | $ / shares $ 15     $ 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