DEBT - Subordinated Borrowing (Details) $ in Thousands	3 Months Ended
	Mar. 31, 2020 USD ($)
Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Principal	$ 15,000
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
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
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
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
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
Kingsway DE Statutory Trust VI | LIBOR
Debt Instrument [Line Items]
Annual interest rate	4.00%