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Kingsway Corp (KWY) CEO increases stake through share purchase

(Neutral)
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Kingsway Corp President and CEO Fitzgerald John Taylor Maloney purchased 278 shares of Common Stock on July 30, 2026 at $8.98 per share through the company’s Employee Share Purchase Plan. Following this purchase, he directly holds 1,426,414 shares, including 300,000 shares of restricted stock granted March 31, 2021, and also reports indirect holdings of 29,100 shares in each of three trusts.

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Insider Fitzgerald John Taylor Maloney
Role President and CEO
Bought 278 shs ($2K)
Type Security Shares Price Value
Purchase Common Stock F1, F2 278 $8.98 $2K
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 1,426,414 shares (Direct); Common Stock — 29,100 shares (Indirect, Trust-GEF); Common Stock — 29,100 shares (Indirect, Trust-LTF); Common Stock — 29,100 shares (Indirect, Trust-MPF)
Footnotes (2)
  1. F1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.
  2. F2. Includes 300,000 shares of restricted stock granted on March 31, 2021.
Shares purchased 278 shares Common Stock purchased on July 30, 2026 under the ESPP
Purchase price $8.98 per share Price paid for 278 Common Stock shares on July 30, 2026
Direct holdings after purchase 1,426,414 shares Common Stock directly owned by the CEO following the July 30, 2026 transaction
Restricted stock included 300,000 shares Restricted stock granted on March 31, 2021 included in direct holdings
Indirect trust holdings 29,100 shares Common Stock held indirectly through each of three trusts as of July 30, 2026
Employee Share Purchase Plan financial
"acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan"
A program that lets employees buy their employer’s stock, often through regular payroll deductions and sometimes at a discounted price or with matching contributions; think of it as a company-run savings plan that converts part of pay into ownership. It matters to investors because it can increase insider ownership and employee motivation, potentially affecting company performance, and can slightly change share supply when new stock is issued or sold.
restricted stock financial
"Includes 300,000 shares of restricted stock granted on March 31, 2021."
Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.
matching contribution financial
"the company will make a matching contribution equal to 100% of such employee's contribution."
An employer’s matching contribution is when a company adds money to an employee’s retirement or savings account based on the employee’s own contributions, like a store offering to top up a customer’s purchase to reach a discount threshold. It matters to investors because matching increases a firm’s compensation costs and can improve staff retention and morale, which affect productivity, cash flow and long-term liabilities that influence a company’s financial outlook.
adjusted salary financial
"eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period"

AI-generated analysis. How Rhea-AI works. Not financial advice.

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FAQ

What did Kingsway Corp (KWY) CEO purchase in this Form 4 filing?

CEO Fitzgerald John Taylor Maloney acquired 278 shares of Kingsway Corp Common Stock on July 30, 2026 at $8.98 per share. The shares were obtained through the company’s Employee Share Purchase Plan, which buys stock on the open market via a registered broker.

How many Kingsway Corp (KWY) shares does the CEO now hold directly?

After the reported transaction, the CEO directly holds 1,426,414 shares of Kingsway Corp Common Stock. This figure includes 300,000 shares of restricted stock that were granted on March 31, 2021, as disclosed in the filing footnotes.

How does the Kingsway Corp (KWY) Employee Share Purchase Plan work?

Under the ESPP, eligible Kingsway employees may contribute up to 5% of adjusted salary each payroll period. After 12 months of employment, the company makes a 100% matching contribution, and both contributions are used to buy Kingsway Corporation shares on the open market through a stockbroker.

What indirect Kingsway Corp (KWY) holdings are reported for the CEO?

The filing lists indirect ownership of 29,100 shares of Common Stock held through each of three trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF. These trust positions are reported as indirect holdings separate from the CEO’s direct share ownership.

Was the Kingsway Corp (KWY) CEO’s stock purchase under a Rule 10b5-1 plan?

The Form 4’s Rule 10b5-1 checkbox is not marked as affirming use of a trading plan. The narrative footnotes describe acquisition through the Employee Share Purchase Plan but do not state that a Rule 10b5-1 trading plan governed this specific purchase.
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)
07/30/2026
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 Stock07/30/2026P278(1)A$8.981,426,414(2)D
Common Stock29,100ITrust-GEF
Common Stock29,100ITrust-LTF
Common Stock29,100ITrust-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:
1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.
2. Includes 300,000 shares of restricted stock granted on March 31, 2021.
/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald07/31/2026
** 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)