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Income Taxes - Tax Effects of Deferred Tax Assets and Deferred Tax Liabilities (Details) - USD ($)
$ in Millions
Dec. 31, 2019
Dec. 31, 2018
Income Tax Disclosure [Abstract]    
Share-based payments $ 0.3 $ 2.2
Operating loss carryforwards 121.5 126.4
Net loss reserves and loss adjustment expenses 5.0 5.0
Unrealized losses on investments 0.0 0.8
Accrued expenses 7.1 7.9
Foreign tax credit carryforwards 0.0 3.8
Unearned premiums 15.3 15.5
Deferred policy acquisition costs 0.1 0.0
Office properties and equipment 16.8 11.1
Operating lease liability 21.5 3.3
Other temporary differences 6.1 0.0
Total gross deferred tax assets 193.7 176.0
Less valuation allowance (149.2) (111.9)
Net deferred tax assets 44.5 64.1
Equalization provision reserves 0.0 0.0
Unrealized (gains) on investments (2.7) 0.0
Intangible assets (1.6) (2.5)
Deferred policy acquisition costs (16.4) (18.5)
Quota share losses 0.0 (0.6)
Loss portfolio transfer costs 0.0 (6.1)
Operating lease assets (19.9) 0.0
Other temporary differences (3.9) (1.0)
Total gross deferred tax (liabilities) (44.5) (28.7)
Deferred Tax Assets, Net $ 0.0 $ 35.4