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Business Segments - Segment Net Income (Details) - USD ($) $ in Millions | 12 Months Ended
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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)

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