STOCK TITAN

[Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity

Filing Impact
(Low)
Filing Sentiment
(Neutral)
Form Type
4

John Taylor Maloney, President and CEO and a director of Kingsway Financial Services Inc. (KFS), reported transactions dated 09/26/2025 on a Form 4. The filing shows repeated entries of 14,100-share movements coded J(1) at a price of $14.57 involving transfers between the reporting person’s direct holdings and three trusts (GEF, LTF, MPF). The filing states the reporting person transferred shares to trusts for which he serves as trustee but retained voting and investment power, so his beneficial ownership did not change. The report notes total direct beneficial holdings in the ranges shown: approximately 1,516,645, 1,502,545, and 1,488,445 shares after specific transactions, and discloses inclusion of 400,000 restricted shares granted on 03/31/2021. The Form 4 was signed by an attorney-in-fact, Debra Rouse, on 09/30/2025.

John Taylor Maloney, Presidente e CEO nonché membro del consiglio di Kingsway Financial Services Inc. (KFS), ha riferito operazioni del 26/09/2025 tramite un Modulo 4. Il documento mostra ripetute movimentazioni di 14.100 azioni codificate J(1) al prezzo di $14,57, coinvolgendo trasferimenti tra le partecipazioni dirette del segnalante e tre trust (GEF, LTF, MPF). La comunicazione indica che il segnalante ha trasferito azioni ai trust di cui è trustee ma ha conservato il potere di voto e di investimento, per cui la sua titolarità efficace non è cambiata. Il rapporto annota partecipazioni dirette totali nelle fasce indicate: circa 1.516.645, 1.502.545 e 1.488.445 azioni dopo operazioni specifiche, e segnala l’inclusione di 400.000 azioni vincolate attribuite il 31/03/2021. Il Modulo 4 è stato firmato da un procuratore ad acta, Debra Rouse, il 30/09/2025.

John Taylor Maloney, presidente y director ejecutivo y miembro del consejo de Kingsway Financial Services Inc. (KFS), informó operaciones del 26/09/2025 mediante un Formulario 4. El documento muestra varias entradas de movimientos de 14.100 acciones codificadas como J(1) a un precio de $14,57, involucrando transferencias entre las participaciones directas del informante y tres fideicomisos (GEF, LTF, MPF). La declaración indica que el informante transfirió acciones a fideicomisos de los que actúa como fiduciario pero mantuvo el poder de voto e inversión, por lo que su propiedad beneficiaria no cambió. El informe señala participaciones directas totales en los rangos indicados: aproximadamente 1.516.645, 1.502.545 y 1.488.445 acciones tras operaciones específicas, y divulga la inclusión de 400.000 acciones restringidas otorgadas el 31/03/2021. El Formulario 4 fue firmado por un apoderado, Debra Rouse, el 30/09/2025.

John Taylor Maloney는 Kingsway Financial Services Inc. (KFS)의 사장 겸 CEO이자 이사로, 2025년 9월 26일의 거래를 Form 4에 보고했습니다. 신고인은 14,100주 단위의 반복적 이동을 J(1)로 표시했고 가격은 $14.57이며, 이를 통해 보고자의 직접 보유 주식과 세 개의 신탁(GEF, LTF, MPF) 간의 이전이 이루어졌습니다. 보고서에 따르면 신고인은 신탁의 수탁자로서의 의결권과 투자 권한을 유지했기 때문에 실제 지분은 변하지 않았습니다. 보고서는 구체적 거래 후의 직접 보유 지분이 각각 대략 1,516,645, 1,502,545, 1,488,445주로 나타난다고 명시하고, 2021년 3월 31일에 부여된 400,000주 제한주가 포함되었음을 밝힙니다. Form 4는 2025년 9월 30일 Debra Rouse라는 대리인이 서명했습니다.

John Taylor Maloney, président et directeur général et membre du conseil de Kingsway Financial Services Inc. (KFS), a déclaré des transactions datant du 26/09/2025 sur un formulaire Form 4. Le dossier montre des mouvements répétés de 14 100 actions codés J(1) à un prix de 14,57 $, impliquant des transferts entre les participations directes du déclarant et trois fiducies (GEF, LTF, MPF). Le dépôt indique que la personne déclarante a transféré des actions vers des fiducies dont elle est fiduciaire mais a conservé le pouvoir de vote et d’investissement, de sorte que sa propriété bénéficiaire n’a pas changé. Le rapport note des participations directes totales dans les fourchettes indiquées : environ 1 516 645, 1 502 545, et 1 488 445 actions après des transactions spécifiques, et divulgue l’inclusion de 400 000 actions restreintes attribuées le 31/03/2021. Le Form 4 a été signé par une procuration, Debra Rouse, le 30/09/2025.

John Taylor Maloney, Präsident und Geschäftsführer sowie Direktor der Kingsway Financial Services Inc. (KFS), meldete Transaktionen vom 26.09.2025 über ein Formular 4. Die Einreichung zeigt wiederholte Bewegungen von 14.100 Aktien, codiert mit J(1), zu einem Preis von $14,57, bei Transfers zwischen den direkt gehaltenen Positionen der meldepflichtigen Person und drei Trusts (GEF, LTF, MPF). Die Einreichung besagt, dass die meldende Person Aktien an Trusts übertragen hat, für die sie als Trustee fungiert, aber Stimm- und Anlagemacht behalten hat, sodass sich ihr wirtschaftlicher Besitz nicht geändert hat. Der Bericht vermerkt direkte direkte Beteiligungen in den angegebenen Bereichen: ca. 1.516.645, 1.502.545 und 1.488.445 Aktien nach bestimmten Transaktionen, und macht die Einbeziehung von 400.000 restriktiven Aktien bekannt, die am 31.03.2021 gewährt wurden. Das Formular 4 wurde von einer gesetzlich bevollmächtigten Vertreterin, Debra Rouse, am 30.09.2025 unterschrieben.

جون تايلور مالوني، رئيس مجلس الإدارة والرئيس التنفيذي وعضو مجلس إدارة في Kingsway Financial Services Inc. (KFS)، أبلغ عن معاملات بتاريخ 26/09/2025 على نموذج 4. يظهر التسجيل إدخالات متكررة لحركات 14,100 سهمًا مُرمَّزة بـ J(1) بسعر $14.57 تشارك فيهاTransfers بين الحيازة المباشرة للمبلغ عنه وثلاثة ائتمانات (GEF، LTF، MPF). ينص الإبلاغ على أن الشخص المبلغ له نقل أسهم إلى أمانة يُشرف عليها ك trustee ولكنه احتفظ بحق التصويت والاستثمار، لذا لم يتغير ملكه الفعلي. ي notes المرَاجُ է Direct المؤمنة الإجمالي في النطاقات المذكورة: حوالي 1,516,645، 1,502,545، و1,488,445 سهماً بعد معاملاته المحددة، ويكشف إدراج 400,000 من الأسهم المقيدة الممنوحة في 31/03/2021. تم توقيع النموذج 4 من قبل وكيل قانوني بالإفادة Debra Rouse في 30/09/2025.

John Taylor Maloney,Kingsway Financial Services Inc.(KFS)的主席兼首席执行官及董事,已在 2025-09-26 提交 Form 4 进行披露。 filing 显示多次以 J(1) 编码、价格为 $14.5714,100 股转移,涉及报告人直接持有部分与三个信托(GEF、LTF、MPF)之间的转移。披露表明,报告人将股票转给其担任信托人的信托,但保留投票权和投资权,因此其实际受益所有权未改变。报告还指出直接受益持股大致位于以下区间:约 1,516,6451,502,545、和 1,488,445 股,且披露包含在 2021-03-31 授予的 400,000 股受限股票。 Form 4 于 2025-09-30 由授权代理人 Debra Rouse 签署。

Positive
  • Beneficial ownership unchanged after the reported transfers, indicating no reduction in insider economic or voting exposure
  • Transparent disclosure of trust transfers and retention of voting and investment power
  • 400,000 restricted shares from 03/31/2021 are explicitly disclosed
Negative
  • None.

Insights

TL;DR Insider transferred shares into trusts but retained control; beneficial ownership unchanged, indicating estate/planning reallocation rather than a sale.

The Form 4 records multiple identical J(1)-coded transactions on 09/26/2025 moving 14,100 shares at $14.57 into separate trusts (GEF, LTF, MPF) while the reporting person remains trustee with retained voting and investment power. From an equity-stake perspective, reported direct beneficial totals remain in excess of one million shares across the reported lines, with 400,000 restricted shares noted from a 03/31/2021 grant. These entries are administrative transfers and do not change the economic or voting exposure disclosed on the filing.

TL;DR Transactions appear to be trust transfers with retained control, a routine governance/estate-planning action, not a change in insider intent.

The documentation explicitly states the reporting person retains voting and investment power after transferring shares to trusts for which he serves as trustee. That language is standard when insiders reposition holdings for governance or estate purposes while maintaining control. The signature by an attorney-in-fact and the disclosure of restricted shares from 03/31/2021 are properly noted. No suspension of Section 16 obligations is indicated.

John Taylor Maloney, Presidente e CEO nonché membro del consiglio di Kingsway Financial Services Inc. (KFS), ha riferito operazioni del 26/09/2025 tramite un Modulo 4. Il documento mostra ripetute movimentazioni di 14.100 azioni codificate J(1) al prezzo di $14,57, coinvolgendo trasferimenti tra le partecipazioni dirette del segnalante e tre trust (GEF, LTF, MPF). La comunicazione indica che il segnalante ha trasferito azioni ai trust di cui è trustee ma ha conservato il potere di voto e di investimento, per cui la sua titolarità efficace non è cambiata. Il rapporto annota partecipazioni dirette totali nelle fasce indicate: circa 1.516.645, 1.502.545 e 1.488.445 azioni dopo operazioni specifiche, e segnala l’inclusione di 400.000 azioni vincolate attribuite il 31/03/2021. Il Modulo 4 è stato firmato da un procuratore ad acta, Debra Rouse, il 30/09/2025.

John Taylor Maloney, presidente y director ejecutivo y miembro del consejo de Kingsway Financial Services Inc. (KFS), informó operaciones del 26/09/2025 mediante un Formulario 4. El documento muestra varias entradas de movimientos de 14.100 acciones codificadas como J(1) a un precio de $14,57, involucrando transferencias entre las participaciones directas del informante y tres fideicomisos (GEF, LTF, MPF). La declaración indica que el informante transfirió acciones a fideicomisos de los que actúa como fiduciario pero mantuvo el poder de voto e inversión, por lo que su propiedad beneficiaria no cambió. El informe señala participaciones directas totales en los rangos indicados: aproximadamente 1.516.645, 1.502.545 y 1.488.445 acciones tras operaciones específicas, y divulga la inclusión de 400.000 acciones restringidas otorgadas el 31/03/2021. El Formulario 4 fue firmado por un apoderado, Debra Rouse, el 30/09/2025.

John Taylor Maloney는 Kingsway Financial Services Inc. (KFS)의 사장 겸 CEO이자 이사로, 2025년 9월 26일의 거래를 Form 4에 보고했습니다. 신고인은 14,100주 단위의 반복적 이동을 J(1)로 표시했고 가격은 $14.57이며, 이를 통해 보고자의 직접 보유 주식과 세 개의 신탁(GEF, LTF, MPF) 간의 이전이 이루어졌습니다. 보고서에 따르면 신고인은 신탁의 수탁자로서의 의결권과 투자 권한을 유지했기 때문에 실제 지분은 변하지 않았습니다. 보고서는 구체적 거래 후의 직접 보유 지분이 각각 대략 1,516,645, 1,502,545, 1,488,445주로 나타난다고 명시하고, 2021년 3월 31일에 부여된 400,000주 제한주가 포함되었음을 밝힙니다. Form 4는 2025년 9월 30일 Debra Rouse라는 대리인이 서명했습니다.

John Taylor Maloney, président et directeur général et membre du conseil de Kingsway Financial Services Inc. (KFS), a déclaré des transactions datant du 26/09/2025 sur un formulaire Form 4. Le dossier montre des mouvements répétés de 14 100 actions codés J(1) à un prix de 14,57 $, impliquant des transferts entre les participations directes du déclarant et trois fiducies (GEF, LTF, MPF). Le dépôt indique que la personne déclarante a transféré des actions vers des fiducies dont elle est fiduciaire mais a conservé le pouvoir de vote et d’investissement, de sorte que sa propriété bénéficiaire n’a pas changé. Le rapport note des participations directes totales dans les fourchettes indiquées : environ 1 516 645, 1 502 545, et 1 488 445 actions après des transactions spécifiques, et divulgue l’inclusion de 400 000 actions restreintes attribuées le 31/03/2021. Le Form 4 a été signé par une procuration, Debra Rouse, le 30/09/2025.

John Taylor Maloney, Präsident und Geschäftsführer sowie Direktor der Kingsway Financial Services Inc. (KFS), meldete Transaktionen vom 26.09.2025 über ein Formular 4. Die Einreichung zeigt wiederholte Bewegungen von 14.100 Aktien, codiert mit J(1), zu einem Preis von $14,57, bei Transfers zwischen den direkt gehaltenen Positionen der meldepflichtigen Person und drei Trusts (GEF, LTF, MPF). Die Einreichung besagt, dass die meldende Person Aktien an Trusts übertragen hat, für die sie als Trustee fungiert, aber Stimm- und Anlagemacht behalten hat, sodass sich ihr wirtschaftlicher Besitz nicht geändert hat. Der Bericht vermerkt direkte direkte Beteiligungen in den angegebenen Bereichen: ca. 1.516.645, 1.502.545 und 1.488.445 Aktien nach bestimmten Transaktionen, und macht die Einbeziehung von 400.000 restriktiven Aktien bekannt, die am 31.03.2021 gewährt wurden. Das Formular 4 wurde von einer gesetzlich bevollmächtigten Vertreterin, Debra Rouse, am 30.09.2025 unterschrieben.

SEC Form 4
FORM 4 UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number: 3235-0287
Estimated average burden
hours per response: 0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
1. Name and Address of Reporting Person*
Fitzgerald John Taylor Maloney

(Last) (First) (Middle)
10 S. RIVERSIDE PLAZA
SUITE 1520

(Street)
CHICAGO IL 60606

(City) (State) (Zip)
2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
X Director 10% Owner
X Officer (give title below) Other (specify below)
President and CEO
3. Date of Earliest Transaction (Month/Day/Year)
09/26/2025
4. If Amendment, Date of Original Filed (Month/Day/Year)
6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock 09/26/2025 J(1) 14,100 D $14.57 1,516,645(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 34,100 I Trust-GEF
Common Stock 09/26/2025 J(1) 14,100 D $14.57 1,502,545(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 34,100 I Trust-LTF
Common Stock 09/26/2025 J(1) 14,100 D $14.57 1,488,445(2) D
Common Stock 09/26/2025 J(1) 14,100 A $14.57 34,100 I Trust-MPF
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year) 7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Explanation of Responses:
1. Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.
2. Includes 400,000 shares of restricted stock granted on March 31, 2021.
/s/ Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald 09/30/2025
** Signature of Reporting Person Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transactions did John Taylor Maloney report on Form 4 for KFS?

The filing reports multiple 09/26/2025 J(1)-coded movements of 14,100 shares at $14.57 into trusts (GEF, LTF, MPF).

Did the insider reduce his beneficial ownership in KFS?

No. The filing states the reporting person retained voting and investment power, so beneficial ownership did not change.

How many restricted shares does the filing disclose for John Taylor Maloney?

The Form 4 discloses 400,000 restricted shares granted on 03/31/2021.

Who signed the Form 4 and when was it signed?

The Form 4 was signed by Debra Rouse, attorney-in-fact, on 09/30/2025.

What is the reporting person's role at Kingsway Financial Services (KFS)?

The reporting person is listed as Director and as an Officer with the title President and CEO.
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