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Business Segments - Segment Net Operating Income (Details) - USD ($) $ in Millions | 3 Months Ended | 12 Months Ended
--- | --- | ---
Mar. 31, 2020 | Mar. 31, 2019 | Dec. 31, 2019 | Dec. 31, 2018
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | $ 162.9 | $ 98.9 |  |
Income from Continuing Operations | 64.0 | 155.3 |  |
Operating Segments |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | 100.8 | 105.5 |  |
Operating Segments | Specialty Property & Casualty Insurance |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | 60.1 | 79.6 |  |
Operating Segments | Preferred Property & Casualty Insurance |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | 18.4 | 2.8 |  |
Operating Segments | Life & Health Insurance |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | 22.3 | 23.1 |  |
Corporate and Other |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Segment Net Operating Income | 62.1 | (6.6) |  |
Partial Satisfaction of Judgment |  |  | $ 70.6 | $ 0.0
Other |  |  | $ (8.5) | $ (6.6)
Segment Reconciling Items |  |  |  |
Segment Reporting Information [Line Items] |  |  |  |
Change in Fair Value of Equity and Convertible Securities | (93.1) | 50.9 |  |
Net Realized Gains on Sales of Investments | 13.0 | 12.7 |  |
Impairment Losses | (9.5) | (2.8) |  |
Acquisition Related Transaction, Integration and Other Costs | $ (9.3) | $ (4.4) |  |

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