Business Segments - Segment Operating Profit (Details) - USD ($) $ in Millions	3 Months Ended	9 Months Ended
Sep. 30, 2022	Sep. 30, 2021	Sep. 30, 2022	Sep. 30, 2021
Segment Reporting Information [Line Items]
Operating Income (Loss)	$ (45.3)	$ (130.6)	$ (181.2)	$ (190.8)
Corporate and Other Operating Income (Loss) From:
Income (Loss) from Change in Fair Value of Equity and Convertible Securities	(11.2)	(0.6)	(79.9)	92.4
Debt and Equity Securities, Realized Gain (Loss)			0.4	43.1
Impairment Losses	8.3	0.6	22.1	7.8
Loss from Early Extinguishment of Debt	0.0	0.0	(3.7)	0.0
Income (Loss) before Income Taxes	(89.6)	(129.8)	(313.8)	(97.9)
Operating Segments
Segment Reporting Information [Line Items]
Operating Income (Loss)	(28.7)	(115.1)	(149.0)	(150.0)
Operating Segments \| Specialty Property & Casualty Insurance
Segment Reporting Information [Line Items]
Operating Income (Loss)	(39.2)	(91.8)	(150.4)	(128.7)
Operating Segments \| Preferred Property & Casualty Insurance
Segment Reporting Information [Line Items]
Operating Income (Loss)	(3.3)	(17.4)	(34.4)	(27.8)
Operating Segments \| Life & Health Insurance
Segment Reporting Information [Line Items]
Operating Income (Loss)	13.8	(5.9)	35.8	6.5
Corporate and Other
Segment Reporting Information [Line Items]
Operating Income (Loss)	(16.6)	(15.5)	(32.2)	(40.8)
Corporate and Other Operating Income (Loss) From:
Other	(16.6)	(15.5)	(32.2)	(40.8)
Segment Reconciling Items
Corporate and Other Operating Income (Loss) From:
Income (Loss) from Change in Fair Value of Equity and Convertible Securities	(11.2)	(0.6)	(79.9)	92.4
Debt and Equity Securities, Realized Gain (Loss)	(12.1)	10.1	0.4	43.1
Impairment Losses	8.3	0.6	22.1	7.8
Acquisition and Disposition Related Transaction, Integration, Restructuring and Other Costs	(12.7)	(8.1)	(27.3)	(34.8)
Loss from Early Extinguishment of Debt	$ 0.0	$ 0.0	$ (2.9)	$ 0.0

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