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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($)
$ in Millions
Dec. 31, 2020
Dec. 31, 2019
Income Tax Disclosure [Abstract]    
Share-based payments $ 0.0 $ 0.3
Operating loss carryforwards 119.6 121.5
Insurance reserves: Losses and loss adjustment expenses 7.9 5.0
Accrued expenses 6.4 7.1
Unearned premiums 17.6 15.3
Deferred policy acquisition costs 0.0 0.1
Office properties and equipment 12.7 16.8
Operating lease liability 17.7 21.5
Other temporary differences 2.5 6.1
Total deferred tax assets 184.4 193.7
Less valuation allowance (138.9) (149.2)
Deferred tax assets, net of valuation allowance 45.5 44.5
Unrealized (gains) on investments (2.7) (2.7)
Intangible assets (20.1) (1.6)
Deferred policy acquisition costs (8.4) (16.4)
Operating lease assets (12.3) (19.9)
Other temporary differences (2.0) (3.9)
Total deferred tax (liabilities) (45.5) (44.5)
Deferred Tax Assets, Net $ 0.0 $ 0.0