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Reserves for Unpaid Losses and Loss Adjustment Expenses (Average Annual Percentage Payout of Incurred Claims) (Details)
Dec. 31, 2019
Commercial Auto business units [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 14.50%
Average annual percentage payout of incurred claims, year two 25.60%
Average annual percentage payout of incurred claims, year three 26.30%
Average annual percentage payout of incurred claims, year four 16.30%
Average annual percentage payout of incurred claims, year five 10.00%
Average annual percentage payout of incurred claims, year six 3.60%
Average annual percentage payout of incurred claims, year seven 2.60%
Average annual percentage payout of incurred claims, year eight 0.10%
Average annual percentage payout of incurred claims, year ten 1.00%
E&S Casualty business unit [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 12.40%
Average annual percentage payout of incurred claims, year two 15.80%
Average annual percentage payout of incurred claims, year three 19.90%
Average annual percentage payout of incurred claims, year four 21.30%
Average annual percentage payout of incurred claims, year five 14.30%
Average annual percentage payout of incurred claims, year six 4.70%
Average annual percentage payout of incurred claims, year seven 2.20%
Average annual percentage payout of incurred claims, year eight 7.60%
Average annual percentage payout of incurred claims, year nine 0.80%
Average annual percentage payout of incurred claims, year ten 1.00%
Commercial Accounts business unit [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 36.80%
Average annual percentage payout of incurred claims, year two 16.80%
Average annual percentage payout of incurred claims, year three 5.80%
Average annual percentage payout of incurred claims, year four 6.30%
Average annual percentage payout of incurred claims, year five 5.80%
Average annual percentage payout of incurred claims, year six 7.00%
Average annual percentage payout of incurred claims, year seven 5.70%
Average annual percentage payout of incurred claims, year eight 2.80%
Average annual percentage payout of incurred claims, year nine 6.90%
Average annual percentage payout of incurred claims, year ten 6.10%
Aviation [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 63.50%
Average annual percentage payout of incurred claims, year two 22.70%
Average annual percentage payout of incurred claims, year three 6.20%
Average annual percentage payout of incurred claims, year four 3.30%
Average annual percentage payout of incurred claims, year five 2.80%
Average annual percentage payout of incurred claims, year six 1.50%
Average annual percentage payout of incurred claims, year seven 0.50%
Average annual percentage payout of incurred claims, year eight 1.60%
Average annual percentage payout of incurred claims, year nine 0.10%
Average annual percentage payout of incurred claims, year ten (2.20%)
Runoff [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 31.90%
Average annual percentage payout of incurred claims, year two 37.80%
Average annual percentage payout of incurred claims, year three 17.60%
Average annual percentage payout of incurred claims, year four 6.90%
Average annual percentage payout of incurred claims, year five 4.20%
Average annual percentage payout of incurred claims, year six 1.40%
Average annual percentage payout of incurred claims, year seven 1.50%
Average annual percentage payout of incurred claims, year eight (1.30%)
Specialty Programs Business Unit [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 73.20%
Average annual percentage payout of incurred claims, year two 20.30%
Average annual percentage payout of incurred claims, year three 6.50%
Personal Segment [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 56.00%
Average annual percentage payout of incurred claims, year two 28.80%
Average annual percentage payout of incurred claims, year three 8.90%
Average annual percentage payout of incurred claims, year four 4.70%
Average annual percentage payout of incurred claims, year five 0.90%
Average annual percentage payout of incurred claims, year six 0.30%
Average annual percentage payout of incurred claims, year seven 0.10%
Average annual percentage payout of incurred claims, year eight 0.20%
Average annual percentage payout of incurred claims, year nine 0.10%
Property [Member]  
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense [Line Items]  
Average annual percentage payout of incurred claims, year one 77.20%
Average annual percentage payout of incurred claims, year two 15.80%
Average annual percentage payout of incurred claims, year three 1.70%
Average annual percentage payout of incurred claims, year four 0.50%
Average annual percentage payout of incurred claims, year five 3.60%
Average annual percentage payout of incurred claims, year six 1.20%