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Goodwill and Other Intangibles - Narrative (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended 12 Months Ended
Feb. 29, 2020
Aug. 31, 2018
Feb. 29, 2020
Feb. 28, 2019
May 31, 2018
May 31, 2019
May 31, 2017
Goodwill and Other Intangibles (Details) [Line Items]              
Additions     $ 0.0 $ 0.0 $ 6.3    
Amortizable intangible assets acquired     1.6 0.6 4.5    
Goodwill, Impaired, Accumulated Impairment Loss           $ 39.6 $ 39.6
Amortization expense     $ 2.4 $ 2.0 $ 2.8    
Useful life     5 years 2 months 12 days        
U.S. Based Book Business [Member]              
Goodwill and Other Intangibles (Details) [Line Items]              
Amortizable intangible assets acquired $ 1.6            
U.K. Based Book Business [Member]              
Goodwill and Other Intangibles (Details) [Line Items]              
Amortizable intangible assets acquired   $ 0.6          
Make Believe Ideas Limited (MBI)              
Goodwill and Other Intangibles (Details) [Line Items]              
Goodwill, Impaired, Accumulated Impairment Loss           $ 3.9