Subordinated Borrowing (Details)	9 Months Ended
	Sep. 30, 2019 USD ($)
Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Principal	$ 15,000,000
Kingsway CT Statutory Trust I | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.00%
Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Principal	$ 17,500,000
Kingsway CT Statutory Trust II | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.10%
Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Principal	$ 20,000,000
Kingsway CT Statutory Trust III | LIBOR
Debt Instrument [Line Items]
Annual interest rate	3.95%
Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Principal	$ 15,000,000
Kingsway DE Statutory Trust III | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.20%
Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Principal	$ 10,000,000
Kingsway DE Statutory Trust IV | LIBOR
Debt Instrument [Line Items]
Annual interest rate	3.85%
Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Principal	$ 13,000,000
Kingsway DE Statutory Trust VI | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.00%