STILWELL JOSEPH

PrivateCIK: 1113303

Location

NEW YORK, NY

STILWELL JOSEPH reported 4 transactions at KINGSWAY CORP

Review the transaction codes below to understand the nature of each event.

STILWELL JOSEPH

Filed: 12/19/2025ACC: 0001104659-25-123371

InsiderSTILWELL JOSEPHCIK 1113303

→

IssuerKINGSWAY CORPCIK 1072627

Director10% Owner

Since Sep 2018

-3.50M

Net shares

Net seller

$14.44M

Total sold

0

Open market trades

0B · 0S

8

Total transactions

3.50M disposed

Non-Derivative Transactions4

Common Stock

Indirect

X · X

Shares

−215.48K

Price / share

$8.25

Trade value

$1.78M

% of position

40.3%

12/17/2025

534.71K→319.23K

Common Stock

Indirect

X · X

Shares

−1.30M

Price / share

$8.25

Trade value

$10.69M

% of position

36.5%

12/17/2025

3.55M→2.25M

Common Stock

Indirect

X · X

Shares

−20.27K

Price / share

$8.25

Trade value

$167.23K

% of position

4.4%

12/17/2025

457.18K→436.91K

Common Stock

Indirect

X · X

Shares

−218.84K

Price / share

$8.25

Trade value

$1.81M

% of position

37.1%

12/17/2025

590.41K→371.57K

Total

Net shares

−1.75M

Net value

-$14.44M

Security	Date	Type	Shares	Price / Share	Trade Value	% of Position	Held Before	Held After
Common Stock Indirect	12/17/2025	X · X	−215.48K	$8.25	$1.78M	40.3%	534.71K	319.23K
Common Stock Indirect	12/17/2025	X · X	−1.30M	$8.25	$10.69M	36.5%	3.55M	2.25M
Common Stock Indirect	12/17/2025	X · X	−20.27K	$8.25	$167.23K	4.4%	457.18K	436.91K
Common Stock Indirect	12/17/2025	X · X	−218.84K	$8.25	$1.81M	37.1%	590.41K	371.57K
Total			−1.75M		-$14.44M

Derivative Transactions4

Stock Option (obligation to sell)

Indirect

X · X

Converts to

Common Stock

215.48K shares

Shares

−215.48K

Strike price

8.25

Held after

0.00

Exercisable

—

12/17/2025

Stock Option (obligation to sell)

Indirect

X · X

Converts to

Common Stock

1.30M shares

Shares

−1.30M

Strike price

8.25

Held after

0.00

Exercisable

—

12/17/2025

Stock Option (obligation to sell)

Indirect

X · X

Converts to

Common Stock

20.27K shares

Shares

−20.27K

Strike price

8.25

Held after

0.00

Exercisable

—

12/17/2025

Stock Option (obligation to sell)

Indirect

X · X

Converts to

Common Stock

218.84K shares

Shares

−218.84K

Strike price

8.25

Held after

0.00

Exercisable

—

12/17/2025

Security	Converts To	Date	Type	Shares	Strike Price	Exercisable	Held After
Stock Option (obligation to sell) Indirect	Common Stock215.48K shares	12/17/2025	X · X	−215.48K	8.25	—	0.00
Stock Option (obligation to sell) Indirect	Common Stock1.30M shares	12/17/2025	X · X	−1.30M	8.25	—	0.00
Stock Option (obligation to sell) Indirect	Common Stock20.27K shares	12/17/2025	X · X	−20.27K	8.25	—	0.00
Stock Option (obligation to sell) Indirect	Common Stock218.84K shares	12/17/2025	X · X	−218.84K	8.25	—	0.00

Non-Derivative Holdings (Post-Transaction)1

Common Stock

Direct

Shares owned162.50K

Total

162.50K direct162.50K

Security Title	Shares Owned	Ownership Type
Common Stock	162.50K	Direct
Total	162.50K	162.50K direct

Derivative Holdings (Post-Transaction)3

Class C Preferred Stock

Indirect

Underlying security

Common Stock

Underlying shares

88.42K

Shares owned

33.60K

Exercise price

9.5

Expiration

—

Exercise window

—

Class D Preferred Stock

Indirect

Underlying security

Common Stock

Underlying shares

52.63K

Shares owned

20K

Exercise price

9.5

Expiration

—

Exercise window

—

Class C Preferred Stock

Indirect

Underlying security

Common Stock

Underlying shares

16.84K

Shares owned

6.40K

Exercise price

9.5

Expiration

—

Exercise window

—

Total

Underlying

157.89K

Owned

60K

Security	Underlying	Exercise Price	Exercise Window	Expiration	Underlying Shares	Shares Owned
Class C Preferred Stock Indirect	Common Stock	9.5	—	—	88.42K	33.60K
Class D Preferred Stock Indirect	Common Stock	9.5	—	—	52.63K	20K
Class C Preferred Stock Indirect	Common Stock	9.5	—	—	16.84K	6.40K
Total					157.89K	60K

STILWELL JOSEPH — Insider Transaction (Form 4) Filed Dec 19, 2025 | Finecho