Kingsway CEO adds shares through ESPP purchase

Rhea-AI Filing Summary

Kingsway Corp President and CEO Fitzgerald John Taylor Maloney acquired 256 common shares on 2026-07-15 at $9.76 per share through the company’s Employee Share Purchase Plan, bringing his direct holdings to 1,426,136 shares, including 300,000 shares of restricted stock. He also reports indirect ownership of 29,100 shares in each of three family trusts.

Insider Trade Summary

Net Buyer: 256 shares

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 256 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock F1, F2	256	$9.76	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,426,136 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.

Key Figures

Shares Purchased: 256 shares Purchase Price: $9.76 per share Direct Holdings After: 1,426,136 shares +4 more

7 metrics

Shares Purchased 256 shares Common Stock acquired on 2026-07-15 in open-market ESPP transaction

Purchase Price $9.76 per share Price paid for the 256 common shares under the ESPP

Direct Holdings After 1,426,136 shares Total direct Kingsway Corp common shares held by CEO after transaction

Restricted Stock Included 300,000 shares Portion of direct holdings consisting of restricted stock granted March 31, 2021

Trust Holdings Per Trust 29,100 shares Indirect common stock holdings reported in each of Trust-MPF, Trust-LTF, and Trust-GEF

ESPP Salary Contribution Limit 5% of adjusted salary Maximum employee contribution rate under the Kingsway America Inc. ESPP

ESPP Company Match 100% of employee contribution Company matching contribution level under the ESPP

Key Terms

Employee Share Purchase Plan, restricted stock, indirect ownership

3 terms

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.

indirect ownership financial

"indirect ownership of 29,100 shares in each of three family trusts"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Kingsway Corp (KWY) report for its CEO?

Kingsway Corp’s President and CEO Fitzgerald John Taylor Maloney acquired 256 common shares on 2026-07-15 at $9.76 per share. The purchase was made through the company’s Employee Share Purchase Plan rather than a discretionary open-market trade.

How many Kingsway Corp (KWY) shares does the CEO hold after this Form 4?

After the reported transaction, CEO Fitzgerald John Taylor Maloney directly holds 1,426,136 Kingsway Corp common shares. This direct position includes 300,000 shares of restricted stock granted on March 31, 2021, as disclosed in the footnotes.

At what price were the new Kingsway Corp (KWY) shares acquired by the CEO?

The CEO’s new Kingsway Corp shares were acquired at $9.76 per share. The shares were purchased under the company’s Employee Share Purchase Plan, with the plan administrator buying them on the open market through a registered stockbroker.

What is the role of the Employee Share Purchase Plan in the Kingsway Corp (KWY) Form 4?

The filing states the shares were acquired under Kingsway America Inc.’s Employee Share Purchase Plan (ESPP). Eligible employees may contribute up to 5% of adjusted salary, and the company provides a 100% matching contribution used to buy shares on the open market.

What indirect Kingsway Corp (KWY) holdings does the CEO report in this Form 4?

In addition to direct holdings, the CEO reports indirect ownership of 29,100 Kingsway Corp common shares in each of three family trusts labeled Trust-MPF, Trust-LTF, and Trust-GEF. These entries reflect trust-held positions rather than personally registered shares.

Does the Kingsway Corp (KWY) Form 4 indicate any insider share sales by the CEO?

No insider sales are reported for the CEO in this Form 4. The structured summary shows one open-market purchase of 256 shares and no sale, gift, or tax-withholding transactions during the reported period.

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

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Accepted by SEC EDGAR 07/16/2026 - 04:43 PM EDT Learn about SEC filing dates

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).

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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
07/15/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form 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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	07/15/2026		P		256(1)	A	$9.76	1,426,136(2)	D
Common Stock								29,100	I	Trust-GEF
Common Stock								29,100	I	Trust-LTF
Common Stock								29,100	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. 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 Fitzgerald	07/16/2026
	** 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.
* Form 4: SEC 1474 (03-26)