<SEC-DOCUMENT>0001104659-24-121503.txt : 20241121
<SEC-HEADER>0001104659-24-121503.hdr.sgml : 20241121
<ACCEPTANCE-DATETIME>20241121160122
ACCESSION NUMBER:		0001104659-24-121503
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20241119
FILED AS OF DATE:		20241121
DATE AS OF CHANGE:		20241121

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			STILWELL ASSOCIATES L P
		CENTRAL INDEX KEY:			0000913960
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484174

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		212-269-5800

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Value LLC
		CENTRAL INDEX KEY:			0001397076
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484175

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		2122695800

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			STILWELL JOSEPH
		CENTRAL INDEX KEY:			0001113303
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484176

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Activist Investments, L.P.
		CENTRAL INDEX KEY:			0001573720
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484178

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		212-269-5800

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Value Partners VII, L.P.
		CENTRAL INDEX KEY:			0001555931
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484177

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		212-269-5800

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY, 12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Stilwell Activist Fund, L.P.
		CENTRAL INDEX KEY:			0001564452
		ORGANIZATION NAME:           	
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		241484173

	BUSINESS ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006
		BUSINESS PHONE:		212-269-5800

	MAIL ADDRESS:	
		STREET 1:		111 BROADWAY
		STREET 2:		12TH FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10006

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			KINGSWAY FINANCIAL SERVICES INC
		CENTRAL INDEX KEY:			0001072627
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		ORGANIZATION NAME:           	02 Finance
		IRS NUMBER:				999999999
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
		BUSINESS PHONE:		(312) 766-2144

	MAIL ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
</SEC-HEADER>
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<SEQUENCE>1
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    <periodOfReport>2024-11-19</periodOfReport>

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        <issuerCik>0001072627</issuerCik>
        <issuerName>KINGSWAY FINANCIAL SERVICES INC</issuerName>
        <issuerTradingSymbol>KFS</issuerTradingSymbol>
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            <rptOwnerCik>0001113303</rptOwnerCik>
            <rptOwnerName>STILWELL JOSEPH</rptOwnerName>
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            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>SAN JUAN</rptOwnerCity>
            <rptOwnerState>PR</rptOwnerState>
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            <rptOwnerStateDescription>PUERTO RICO</rptOwnerStateDescription>
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    <reportingOwner>
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            <rptOwnerCik>0001397076</rptOwnerCik>
            <rptOwnerName>Stilwell Value LLC</rptOwnerName>
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        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
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    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0000913960</rptOwnerCik>
            <rptOwnerName>STILWELL ASSOCIATES L P</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
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    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001564452</rptOwnerCik>
            <rptOwnerName>Stilwell Activist Fund, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
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        </reportingOwnerRelationship>
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    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001573720</rptOwnerCik>
            <rptOwnerName>Stilwell Activist Investments, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
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        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001555931</rptOwnerCik>
            <rptOwnerName>Stilwell Value Partners VII, L.P.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>111 BROADWAY, 12TH FLOOR</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>NEW YORK</rptOwnerCity>
            <rptOwnerState>NY</rptOwnerState>
            <rptOwnerZipCode>10006</rptOwnerZipCode>
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    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>162500</value>
                    <footnoteId id="F1"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2024-11-19</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F2"/>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>22387</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>8.7808</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>4830925</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F3"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2024-11-19</value>
            </transactionDate>
            <deemedExecutionDate></deemedExecutionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
                <footnoteId id="F2"/>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>2613</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>8.7808</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>636159</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F4"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>918786</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F5"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>904657</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>See footnote</value>
                    <footnoteId id="F6"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">These are shares owned directly by Joseph Stilwell.</footnote>
        <footnote id="F2">This Form 4 reports the following sales: on November 19, 2024: (a) Stilwell Activist Investments, L.P. (&quot;SAI&quot;) sold 22,387 shares at $8.7808; and (b) Stilwell Activist Fund, L.P. (&quot;SAF&quot;) sold 2,613 shares at $8.7808.</footnote>
        <footnote id="F3">These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC (&quot;Value&quot;), 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.</footnote>
        <footnote id="F4">These are shares owned directly by 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.</footnote>
        <footnote id="F5">These are shares owned directly by Stilwell Value Partners VII, L.P. (&quot;SVP VII&quot;) and indirectly by Joseph Stilwell in his capacity as the managing member and owner of 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.</footnote>
        <footnote id="F6">These are shares owned directly by Stilwell Associates, L.P. (&quot;Associates&quot;) 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.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P.</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P.</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P.</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P.</signatureName>
        <signatureDate>2024-11-21</signatureDate>
    </ownerSignature>
</ownershipDocument>
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</SEC-DOCUMENT>
