Debt - Subordinated Borrowing (Table) (Details)	3 Months Ended
	Mar. 31, 2019 USD ($)
Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Principal	$ 15,000,000
Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Principal	17,500,000
Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Principal	20,000,000
Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Principal	15,000,000
Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Principal	10,000,000
Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Principal	$ 13,000,000
LIBOR | Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Annual interest rate	4.00%
LIBOR | Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Annual interest rate	4.10%
LIBOR | Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Annual interest rate	3.95%
LIBOR | Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Annual interest rate	4.20%
LIBOR | Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Annual interest rate	3.85%
LIBOR | Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Annual interest rate	4.00%