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  4. [Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity

Kingsway (KFS) CEO Maloney sells 10,000 shares, keeps 1.46M stake

Filing Impact
(High)
Filing Sentiment
(Negative)
Form Type
4

Rhea-AI Filing Summary

KINGSWAY Corp President and CEO John Taylor Maloney reported selling a total of 10,000 shares of common stock in open-market transactions through family trusts. The sales occurred on May 19 and May 20 at prices of about $10.30–$10.43 per share. After these transactions, he continues to hold 1,461,641 shares directly as of May 19, along with additional indirect holdings through trusts, so the sales represent a small portion of his overall position.

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Insider Fitzgerald John Taylor Maloney
Role President and CEO
Sold 10,000 shs ($104K)
Type Security Shares Price Value
Sale Common Stock 5,000 $10.4288 $52K
Sale Common Stock 5,000 $10.3013 $52K
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 29,100 shares (Indirect, Trust-LTF); Common Stock — 1,461,641 shares (Direct, null)
Footnotes (1)
Shares sold May 20 5,000 shares at $10.4288 Open-market sale of common stock via Trust-LTF on May 20, 2026
Shares sold May 19 5,000 shares at $10.3013 Open-market sale of common stock via Trust-GEF on May 19, 2026
Total shares sold 10,000 shares Aggregate open-market sales of Kingsway common stock reported in this Form 4
Direct holdings after transactions 1,461,641 shares Directly owned Kingsway common stock as of May 19, 2026
Indirect holdings after May 20 sale 29,100 shares Common stock held indirectly via Trust-LTF following the May 20, 2026 sale
Indirect holdings after May 19 sale 29,100 shares Common stock held indirectly via Trust-GEF following the May 19, 2026 sale
open-market sale financial
"transaction_action: "open-market sale" for common stock transactions"
An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.
indirect ownership financial
"ownership_type: "indirect" and ownership_code: "I" on sale entries"
Trust-LTF financial
"nature_of_ownership: "Trust-LTF" on the May 20, 2026 sale"
Trust-GEF financial
"nature_of_ownership: "Trust-GEF" on the May 19, 2026 sale"
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED 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).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Fitzgerald John Taylor Maloney
(Last)(First)(Middle)
10 S. RIVERSIDE PLAZA
SUITE 1520
(Street)
CHICAGO ILLINOIS 60606
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
KINGSWAY Corp [ KWY ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
President and CEO
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/19/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
Common Stock05/19/2026S5,000D$10.301329,100ITrust-GEF
Common Stock05/20/2026S5,000D$10.428829,100ITrust-LTF
Common Stock1,461,641D
Common Stock34,100ITrust-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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald05/21/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What did Kingsway (KFS) CEO John Taylor Maloney report in this Form 4?

He reported two open-market sales totaling 10,000 Kingsway common shares through trusts. The transactions were executed on May 19 and May 20, 2026, and are classified as indirect sales by entities identified as family trusts.

How many Kingsway (KFS) shares did the CEO sell and at what prices?

He sold 5,000 shares at $10.3013 per share and another 5,000 shares at $10.4288 per share. Both are recorded as open-market or private sales of Kingsway common stock by trusts associated with him.

What are John Taylor Maloney’s Kingsway (KFS) holdings after these transactions?

After the reported transactions, he directly holds 1,461,641 shares of Kingsway common stock as of May 19, 2026. He also maintains additional indirect holdings through trusts that carried out the 10,000-share aggregate sale.

Were the Kingsway (KFS) CEO’s recent transactions direct or indirect holdings?

The 10,000 shares sold were reported as indirect holdings, with ownership described as trusts labeled LTF and GEF. His large remaining position of 1,461,641 shares is reported as directly owned common stock.

Does this Kingsway (KFS) Form 4 show any option exercises or derivative trades?

No derivative transactions are reported in this Form 4. The filing only lists non-derivative common stock sales and holding entries, with the derivative transaction count and exercise shares both shown as zero.