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Business Segments - Earned Premiums by Product Line (Details) - USD ($) $ in Millions | 3 Months Ended
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Mar. 31, 2019 | Mar. 31, 2018
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | $ 1,074.8 | $ 609.8
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] | Preferred Automobile [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 115.4 | 104.9
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] | Homeowners [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums |  | 61.8
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 185.6 | 176.8
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] | Homeowners [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 60.3 |
Operating Segments [Member] | Preferred Property & Casualty Insurance [Member] | Other Personal Property and Casualty Insurance [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 9.9 | 10.1
Operating Segments [Member] | Specialty Property & Casualty Insurance [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 729.3 |
Operating Segments [Member] | Specialty Property & Casualty Insurance [Member] | Specialty Automobile [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 669.6 | 266.2
Operating Segments [Member] | Specialty Property & Casualty Insurance [Member] | Commercial Automobile [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 59.7 | 12.2
Operating Segments [Member] | Life and Health Insurance [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 159.9 | 154.6
Operating Segments [Member] | Life and Health Insurance [Member] | Life [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 95.8 | 93.7
Operating Segments [Member] | Life and Health Insurance [Member] | Accidental and Health [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | 46.9 | 43.3
Operating Segments [Member] | Life and Health Insurance [Member] | Property [Member] |  |
Entity-Wide Information, Revenue from External Customer [Line Items] |  |
Total Earned Premiums | $ 17.2 | $ 17.6

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- Definition Amount, after premiums ceded to other entities and premiums assumed by the entity, of premiums earned. + References Reference 1: http://www.xbrl.org/2003/role/disclosureRef -Publisher FASB -Name Accounting Standards Codification -Topic 944 -SubTopic 220 -Section S99 -Paragraph 1 -Subparagraph (SX 210.7-04(1)) -URI http://asc.fasb.org/extlink&oid=114873790&loc=SL114874131-224263 Reference 2: http://www.xbrl.org/2003/role/disclosureRef -Publisher FASB -Name Accounting Standards Codification -Topic 944 -SubTopic 235 -Section S99 -Paragraph 2 -Subparagraph (SX 210.12-17(Column E)) -URI http://asc.fasb.org/extlink&oid=34713774&loc=d3e574992-122915 Reference 3: http://www.xbrl.org/2003/role/disclosureRef -Publisher FASB -Name Accounting Standards Codification -Topic 942 -SubTopic 220 -Section S99 -Paragraph 1 -Subparagraph (SX 210.9-04(13)(c)) -URI http://asc.fasb.org/extlink&oid=114873765&loc=SL114874048-224260 Reference 4: http://www.xbrl.org/2003/role/disclosureRef -Publisher FASB -Name Accounting Standards Codification -Topic 944 -SubTopic 605 -Section 50 -Paragraph 1 -Subparagraph (c)(3) -URI http://asc.fasb.org/extlink&oid=6486672&loc=d3e27261-158547 + Details
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