Kingsway CEO buys 254 shares at $9.82 via plan

Kingsway’s CEO increased his direct share ownership via the employee share purchase plan in a small open‑market transaction.

Available on EDGAR 09/16/2026 - 06:11 PM EDT Accepted by SEC EDGAR 09/16/2026 - 06:10 PM EDT Learn about SEC filing dates

Rhea-AI Filing Summary

KINGSWAY Corp (KWY) reported that President and CEO, and director, John Taylor Maloney purchased 254 shares of Common Stock on September 15, 2026 at $9.82 per share through the company’s Employee Share Purchase Plan. Following this, he directly holds 1,427,161 shares, including 300,000 restricted shares, plus additional indirect holdings through family trusts. No Rule 10b5-1 trading plan is reported.

Insider Trade Summary

Net Buyer: 254 shares

Net Buy 1 txn

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 254 shs ($2K)

Increase in Position 0.02%

Type	Security	Shares	Price	Value
Purchase	Common Stock F1, F2	254	$9.82	$2K
Holding	Common Stock	--	--	--
Holding	Common Stock	--	--	--
Holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,427,161 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)

Holdings Before and After: Common Stock, 1,426,907 to 1,427,161 shares (Direct)

Other Insiders: 2 other insiders reported open-market purchases of this stock in the 30 days up to this filing.

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: 254 shares Purchase price per share: $9.82 per share Direct holdings after transaction: 1,427,161 shares +3 more

6 metrics

Shares purchased 254 shares Common Stock bought by the CEO on September 15, 2026

Purchase price per share $9.82 per share Price paid for the 254-share purchase

Direct holdings after transaction 1,427,161 shares CEO’s direct Common Stock ownership after the purchase

Included restricted stock 300,000 shares Restricted stock granted on March 31, 2021, included in direct holdings

Indirect trust holdings per trust 29,100 shares Indirect holdings reported in each of Trust-GEF, Trust-LTF, and Trust-MPF

Net insider share change 254 shares Net buy across all reported transactions in this Form 4

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 holdings reported in Trust-GEF, Trust-LTF and Trust-MPF"

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 reported that President and CEO John Taylor Maloney purchased 254 shares of Common Stock on September 15, 2026 at $9.82 per share, acquired through participation in the company’s Employee Share Purchase Plan.

How many KINGSWAY Corp (KWY) shares does the CEO own after this Form 4?

After the reported purchase, John Taylor Maloney directly holds 1,427,161 shares of KINGSWAY Corp Common Stock, which includes 300,000 shares of restricted stock granted on March 31, 2021, plus additional indirect holdings through several family trusts.

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

No. The filing indicates no Rule 10b5-1 trading plan applies to this transaction. The 254 shares were acquired through the Employee Share Purchase Plan, where shares are bought on the open market by the plan administrator.

What is the Employee Share Purchase Plan mentioned in the KWY Form 4?

The filing describes the ESPP as allowing eligible employees to contribute up to 5% of adjusted salary, with Kingsway America Inc. matching 100% of contributions after 12 months’ employment. Combined contributions are used to buy KINGSWAY Corp shares on the open market.

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

The Form 4 lists indirect ownership of 29,100 shares of Common Stock in each of three trusts labeled Trust-GEF, Trust-LTF, and Trust-MPF, reported as indirect holdings separate from the CEO’s directly owned shares.

How many insider buy transactions does this KINGSWAY Corp (KWY) Form 4 report?

The transaction summary shows one purchase transaction totaling 254 shares and no sales, for a net buy of 254 shares of KINGSWAY Corp Common Stock on September 15, 2026.

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

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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)
09/15/2026

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	09/15/2026		P		254(1)	A	$9.82	1,427,161(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	09/16/2026
	** 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)