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Goodwill and Other Intangibles - Narrative (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended 12 Months Ended
Aug. 31, 2018
Feb. 28, 2019
Feb. 28, 2018
May 31, 2018
May 31, 2017
Goodwill and Other Intangibles (Details) [Line Items]          
Goodwill, Impaired, Accumulated Impairment Loss   $ 39.6 $ 39.6 $ 39.6 $ 39.6
Amortizable intangible assets acquired   0.6 1.5 3.3  
Amortization expense   $ 2.0 $ 1.6 $ 2.1  
Useful life   3 years 6 months      
U.K. Based Book Business [Member]          
Goodwill and Other Intangibles (Details) [Line Items]          
Amortizable intangible assets acquired $ 0.6