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Business Segments - Segment Operating Profit (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	$ (369.8)	$ 546.8	$ 518.8
Income (Loss) from Change in Fair Value of Equity and Convertible Securities	114.6	72.1	138.9
Net Realized Gains on the Sales of Investments	64.8	38.1	41.9
Net Impairment Losses Recognized in Earnings	(11.0)	(19.5)	(13.8)
Pension Obligation Settlement Costs		64.1
Loss from Early Extinguishment of Debt	0.0	0.0	(5.8)
Income (Loss) before Income Taxes	(245.3)	510.1	661.6
Operating Segments
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	(321.4)	493.9	530.1
Operating Segments | Specialty Property & Casualty Insurance
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	(292.1)	420.9	355.9
Operating Segments | Preferred Property & Casualty Insurance
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	(39.8)	1.8	52.3
Operating Segments | Life & Health Insurance
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	10.5	71.2	121.9
Corporate, Non-Segment
Segment Reporting Information [Line Items]
Segment Operating Profit (Loss)	(48.4)	52.9	(11.3)
Partial Satisfaction of Judgment	0.0	89.4	20.1
Other	(48.4)	(36.5)	(31.4)
Segment Reconciling Items
Segment Reporting Information [Line Items]
Income (Loss) from Change in Fair Value of Equity and Convertible Securities	114.6	72.1	138.9
Net Realized Gains on the Sales of Investments	64.8	38.1	41.9
Net Impairment Losses Recognized in Earnings	(11.0)	(19.5)	(13.8)
Acquisition Related Transaction, Integration and Other Costs	(43.9)	(63.3)	(18.4)
Pension Obligation Settlement Costs	$ 0.0	$ (64.1)	$ 0.0

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