Kingsway Corp (KWY) CEO surrenders 30,233 shares to cover tax withholding

Rhea-AI Filing Summary

Kingsway Corp President and CEO John Taylor Maloney reported a tax-related share disposition. On June 15, 2026, he surrendered 30,233 shares of Kingsway common stock at $10.12 per share to cover tax withholding obligations triggered by the vesting of restricted stock.

After this tax-withholding transaction, he directly holds 1,425,641 common shares, which include 300,000 restricted shares granted on March 31, 2021. He also reports indirect ownership of common stock through several family trusts, reflecting additional indirect exposure to Kingsway shares.

Insider Trade Summary

4 transactions reported

Mixed 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	30,233	$10.12	$306K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,425,641 shares (Direct, null); Common Stock — 29,100 shares (Indirect, Trust-GEF)

Footnotes (1)

1. Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement. Includes 300,000 shares of restricted stock granted on March 31, 2021.

Key Figures

Tax-withholding shares: 30,233 shares Tax-withholding price: $10.12 per share Direct holdings after transaction: 1,425,641 shares +1 more

4 metrics

Tax-withholding shares 30,233 shares Shares surrendered to cover tax obligations on vesting

Tax-withholding price $10.12 per share Value used for surrendered common shares

Direct holdings after transaction 1,425,641 shares Common shares directly held after tax-withholding disposition

Restricted stock grant 300,000 shares Restricted stock granted on March 31, 2021, included in holdings

Key Terms

tax withholding obligations, restricted stock, indirect ownership, Form 4

4 terms

tax withholding obligations financial

"surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting"

restricted stock financial

"shares granted under a restricted stock agreement"

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", nature_of_ownership: "Trust-MPF""

Form 4 regulatory

"INSIDER FILING DATA (Form 4)"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

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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		F		30,233(1)	D	$10.12	1,425,641(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. Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement.

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	06/17/2026
	** 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 Corp (KWY) report on June 15, 2026?

Kingsway’s CEO reported surrendering 30,233 common shares at $10.12 each to satisfy tax withholding on vested restricted stock. This Form 4 reflects a compensation-related tax payment, not an open-market purchase or sale of shares.

Was the Kingsway Corp (KWY) CEO’s June 2026 Form 4 an open-market sale?

No. The 30,233 shares were surrendered to cover tax withholding obligations upon restricted stock vesting. This Code F transaction is a tax-withholding disposition, distinct from a discretionary open-market share sale by the insider.

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

Following the tax-withholding disposition, the CEO directly holds 1,425,641 Kingsway common shares. This total includes 300,000 restricted shares granted on March 31, 2021, providing substantial ongoing equity exposure to the company’s stock.

What price was used for the Kingsway Corp (KWY) tax-withholding shares?

The surrendered Kingsway shares for tax withholding were valued at $10.12 per share. This per-share figure applies to the 30,233 common shares used to satisfy the CEO’s tax obligations arising from restricted stock vesting.

What do the family trusts in the Kingsway Corp (KWY) Form 4 represent?

The Form 4 lists indirect ownership of Kingsway common stock through several trusts. Each trust entry reflects holdings attributed to the CEO as indirect ownership, giving him additional exposure beyond his directly held and restricted shares.

What restricted stock grant is referenced in the Kingsway Corp (KWY) Form 4?

The filing notes that the CEO’s direct holdings include 300,000 shares of restricted stock granted on March 31, 2021. These restricted shares form part of his equity compensation and are counted within his 1,425,641 directly held shares.