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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($)
$ in Millions
Dec. 31, 2021
Dec. 31, 2020
Income Tax Disclosure [Abstract]    
Operating loss carryforwards $ 170.2 $ 147.8
Insurance reserves: Losses and loss adjustment expenses 16.7 12.2
Accrued expenses 4.6 6.4
Foreign tax credit carryforwards 20.2 16.7
Unearned premiums 28.3 24.5
Office properties and equipment 15.1 12.7
Operating lease liability 19.2 17.9
Other temporary differences 3.2 2.5
Total deferred tax assets 277.5 240.7
Less valuation allowance (225.9) (187.1)
Deferred tax assets, net of valuation allowance 51.6 53.6
Unrealized (gains) on investments (2.5) (8.4)
Intangible assets (2.8) (2.7)
Deferred policy acquisition costs (28.6) (33.3)
Operating lease assets (10.6) (12.5)
Deferred Tax Liabilities, GAAP differences 8.3 0.0
Other temporary differences (1.6) (1.9)
Total deferred tax (liabilities) (54.4) (58.8)
Deferred tax liabilities, net $ (2.8) $ (5.2)