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Business Segments - Segment Net Income (Details) - USD ($) $ in Millions | 12 Months Ended
--- | ---
Dec. 31, 2018 | Dec. 31, 2017 | Dec. 31, 2016
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | $ 258.4 | $ 92.5 | $ 12.4
Change in Fair Value of Equity and Convertible Securities | (50.8) | 0.0 | 0.0
Partial Satisfaction of Judgment | 28.2 | 0.0 | 0.0
Income (Loss) from Continuing Operations | 188.4 | 119.9 | 12.7
Operating Segments [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | 233.0 | 102.8 | 32.1
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | 25.7 | (45.4) | 15.6
Operating Segments [Member] | Specialty Property & Casualty Insurance [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Operating Income (Loss), Net of Tax | 115.8 | 56.3 | (14.5)
Operating Segments [Member] | Life and Health Insurance [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | 91.5 | 91.9 | 31.0
Corporate, Non-Segment [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | 25.4 | (10.3) | (19.7)
Tax Cuts and Jobs Act of 2017, Incomplete Accounting, Provisional Income Tax Expense (Benefit) | 26.4 | 7.4 | 0.0
Segment Reconciling Items [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Realized Gains on Sales of Investments | 20.9 | 36.7 | 21.5
Net Impairment Losses Recognized in Earnings | 3.6 | 9.3 | 21.2
Loss from Early Extinguishment of Debt | 36.5 | 0.0 | 0.0
Excluding amounts attributable to Tax Law Changes [Member] | Corporate, Non-Segment [Member] |  |  |
Segment Reporting Information [Line Items] |  |  |
Net Operating Income | $ (29.2) | $ (17.7) | $ (19.7)

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