Kingsway (KWY) CEO adds 240 shares through employee purchase plan

Rhea-AI Filing Summary

KINGSWAY Corp President and CEO John Taylor Maloney increased his stake through the company’s employee share purchase plan. He bought 240 shares of Common Stock at $10.43 per share in an open-market purchase, bringing his directly held position to 1,455,874 shares, including 400,000 shares of restricted stock granted on March 31, 2021. He also has indirect ownership of 29,100 shares in each of three personal trusts.

Insider Trade Summary

Net Buyer: 240 shares ($2,503)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 240 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	240	$10.43	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,455,874 shares (Direct, null); Common Stock — 29,100 shares (Indirect, Trust-GEF)

Footnotes (1)

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. Includes 400,000 shares of restricted stock granted on March 31, 2021.

Key Figures

Shares purchased: 240 shares Purchase price: $10.43 per share Direct holdings after transaction: 1,455,874 shares +4 more

7 metrics

Shares purchased 240 shares Open-market purchase under employee share purchase plan

Purchase price $10.43 per share Price for 240 Common Stock shares

Direct holdings after transaction 1,455,874 shares Common Stock held directly by CEO after purchase

Restricted stock included 400,000 shares Restricted stock granted on March 31, 2021

Trust-MPF holdings 29,100 shares Indirect Common Stock ownership via Trust-MPF

Trust-LTF holdings 29,100 shares Indirect Common Stock ownership via Trust-LTF

Trust-GEF holdings 29,100 shares Indirect Common Stock ownership via Trust-GEF

Key Terms

Employee Share Purchase Plan, restricted stock, indirect ownership, open-market purchase

4 terms

Employee Share Purchase Plan financial

"The shares of Common Stock were 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 400,000 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

"direct_or_indirect: "I" with nature_of_ownership identified as Trust-MPF, Trust-LTF, and Trust-GEF"

open-market purchase financial

"transaction_action: "open-market purchase" with transaction_code "P""

An open-market purchase is when an investor or a company buys shares on a public stock exchange at the going market price, rather than through a private deal. It matters to investors because these purchases change how many shares are available, can push the stock price up or signal confidence from large buyers, and often affect per-share metrics like earnings—think of it like someone buying lots of apples off a grocery shelf, reducing supply and potentially raising the price.

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Form 4 Insider Transactions: What Each Field Means →

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)
06/15/2026

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	06/15/2026		P		240(1)	A	$10.43	1,455,874(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 400,000 shares of restricted stock granted on March 31, 2021.

	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	06/15/2026
	** 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)

FAQ

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

KINGSWAY reported that President and CEO John Taylor Maloney bought 240 Common Stock shares at $10.43 each. The shares were acquired through the company’s employee share purchase plan, adding to his existing direct and indirect ownership stakes.

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

After the transaction, John Taylor Maloney directly holds 1,455,874 KINGSWAY Common Stock shares. This total includes 400,000 restricted shares granted on March 31, 2021, plus additional indirect holdings through three personal trusts.

At what price did the KINGSWAY (KWY) CEO buy new shares?

John Taylor Maloney purchased 240 KINGSWAY Common Stock shares at $10.43 per share. The filing notes this open-market purchase was executed under the company’s employee share purchase plan, which uses employee and company contributions to buy shares.

What is the Kingsway America Inc. Employee Share Purchase Plan mentioned for KWY?

The employee share purchase plan allows eligible Kingsway America employees to contribute up to 5% of adjusted salary. After 12 months’ employment, the company matches 100% of contributions, and combined funds are used to buy KINGSWAY shares on the open market.

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

The Form 4 lists indirect ownership of 29,100 KINGSWAY Common Stock shares in each of three trusts labeled Trust-MPF, Trust-LTF, and Trust-GEF. These entries are reported as indirect holdings separate from his primary direct share position.

How many restricted KINGSWAY (KWY) shares are included in the CEO’s holdings?

The filing specifies that the CEO’s direct holdings include 400,000 restricted KINGSWAY Common Stock shares. These restricted shares were originally granted on March 31, 2021, and form part of his total reported direct ownership of 1,455,874 shares.