Joseph Stilwell - Dec 29, 2022 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: Director, 10%+ Owner
Signature: /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell
Stock symbol: KFS
Transactions as of: Dec 29, 2022
Transactions value $: -$53,321
Form type: 4
Date filed: 1/3/2023, 03:54 PM
Previous filing: Aug 30, 2022
Next filing: Jan 5, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	KFS	Common Stock	Sale	-$42.3K	-5.28K	-0.55%	$8.02	955K	Dec 29, 2022	See footnote	F2, F3
transaction	KFS	Common Stock	Sale	-$11K	-1.38K	-0.14%	$8.00	954K	Dec 30, 2022	See footnote	F2, F3
holding	KFS	Common Stock						163K	Dec 29, 2022	Direct	F1
holding	KFS	Common Stock						5.05M	Dec 29, 2022	See footnote	F4
holding	KFS	Common Stock						665K	Dec 29, 2022	See footnote	F5
holding	KFS	Common Stock						939K	Dec 29, 2022	See footnote	F6

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	KFS	Series B Warrant	Sale	$0	-708K	-100%	$0.00^*	0	Dec 29, 2022	Common Stock	708K	$5.00	See footnote	F7

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	These are shares owned directly by Joseph Stilwell.
F2	This Form 4 reports the following sales: on December 29, 2022 Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,275 shares at $8.023 and on December 30, 2022 SVP VII sold 1,375 shares at $8.00.
F3	These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F4	These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F5	These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F6	These are shares owned directly by Stilwell Associates L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F7	Prior to the sale of all Series B Warrants, SAI directly owned 478,582 Series B Warrants, SAF directly owned 48,004 Series B Warrants, Joseph Stilwell directly owned 31,250 Series B Warrants and Associates directly owned 150,511 Series B Warrants. Joseph Stilwell disclaims beneficial ownership of all warrants reported as owned indirectly except to the extent of his pecuniary interest therein.