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Business Segments - Segment Net Income (Details) - USD ($)
$ in Millions
 12 Months Ended
Dec. 31, 2021
Dec. 31, 2020
Dec. 31, 2019
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) $ (218.8) $ 438.8 $ 418.3
Loss from Early Extinguishment of Debt 0.0 0.0 (4.6)
Net Income (Loss) (120.5) 409.9 531.1
Operating Segments      
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) (180.4) 401.4 423.7
Operating Segments | Specialty Property & Casualty Insurance      
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) (196.1) 337.9 283.1
Operating Segments | Preferred Property & Casualty Insurance      
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) (12.5) 3.5 41.9
Operating Segments | Life & Health Insurance      
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) 28.2 60.0 98.7
Corporate, Non-Segment      
Segment Reporting Information [Line Items]      
Segment Net Operating Income (Loss) (38.4) 37.4 (5.4)
Partial Satisfaction of Judgment 0.0 70.6 15.9
Other (38.4) (33.2) (21.3)
Segment Reconciling Items      
Segment Reporting Information [Line Items]      
Change in Fair Value of Equity and Convertible Securities 90.5 57.0 109.7
Net Realized Gains on Sales of Investments 51.2 30.1 33.1
Impairment Losses (8.7) (15.4) (10.9)
Acquisition Related Transaction, Integration and Other Costs $ (34.7) $ (50.0) $ (14.5)