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Segments Segment Net Income Before Income Taxes (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2021
Dec. 31, 2020
Dec. 31, 2019
Segment Reporting, Reconciling Item for Operating Profit (Loss) from Segment to Consolidated [Line Items]      
Gross premiums written $ 589.7 $ 580.1 $ 696.9
Premiums Written, Net 583.1 574.9 691.5
Net premiums earned 574.4 615.3 695.8
Net investment income 72.7 76.3 88.1
Net realized and unrealized gains on investments 54.6 19.0 51.1
Other income 1.4 0.8 0.9
Total revenues 703.1 711.4 835.9
Losses and loss adjustment expenses 315.2 302.4 365.9
Commission expense 76.1 78.8 88.1
Underwriting and general and administrative expenses 160.2 181.3 187.5
Interest and financing expenses 0.5 0.4 0.6
Other Expenses 4.1 0.8 0.0
Total expenses 556.1 563.7 642.1
Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest 147.0 147.7 193.8
Employers Segment [Member]      
Segment Reporting, Reconciling Item for Operating Profit (Loss) from Segment to Consolidated [Line Items]      
Gross premiums written 588.2 579.8 696.8
Premiums Written, Net 581.6 574.6 691.4
Net premiums earned 573.7 615.1 695.8
Net investment income 69.3 72.1 84.1
Net realized and unrealized gains on investments 54.5 20.9 47.7
Other income 1.4 0.8 0.9
Total revenues 698.9 708.9 828.5
Losses and loss adjustment expenses 326.2 314.2 378.6
Commission expense 76.1 78.8 88.1
Underwriting and general and administrative expenses 131.2 151.1 153.2
Interest and financing expenses 0.0 0.1 0.6
Other Expenses 4.1 0.7  
Total expenses 537.6 544.9 620.5
Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest 161.3 164.0 208.0
Cerity Segment [Member]      
Segment Reporting, Reconciling Item for Operating Profit (Loss) from Segment to Consolidated [Line Items]      
Gross premiums written 1.5 0.3 0.1
Premiums Written, Net 1.5 0.3 0.1
Net premiums earned 0.7 0.2 0.0
Net investment income 2.8 3.1 0.3
Net realized and unrealized gains on investments 0.3 0.0 0.1
Other income 0.0 0.0 0.0
Total revenues 3.8 3.3 0.4
Losses and loss adjustment expenses 0.5 0.1 0.0
Commission expense 0.0 0.0 0.0
Underwriting and general and administrative expenses 12.9 16.6 16.0
Interest and financing expenses 0.0 0.0 0.0
Other Expenses 0.0 0.1  
Total expenses 13.4 16.8 16.0
Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest (9.6) (13.5) (15.6)
Corporate Segment [Member]      
Segment Reporting, Reconciling Item for Operating Profit (Loss) from Segment to Consolidated [Line Items]      
Gross premiums written 0.0 0.0 0.0
Premiums Written, Net 0.0 0.0 0.0
Net premiums earned 0.0 0.0 0.0
Net investment income 0.6 1.1 3.7
Net realized and unrealized gains on investments (0.2) (1.9) 3.3
Other income 0.0 0.0 0.0
Total revenues 0.4 (0.8) 7.0
Losses and loss adjustment expenses (11.5) (11.9) (12.7)
Commission expense 0.0 0.0 0.0
Underwriting and general and administrative expenses 16.1 13.6 18.3
Interest and financing expenses 0.5 0.3 0.0
Other Expenses 0.0 0.0  
Total expenses 5.1 2.0 5.6
Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest $ (4.7) $ (2.8) $ 1.4