Form 4: KFS Director Sells 500,000 Shares via Option Exercise

Kingsway Financial Services Director Gregory Paul Hannon, through Oakmont Capital Inc., disposed of 500,000 common shares at $8.25 per share via an option exercise.

Summary

• Gregory Paul Hannon, a Director of Kingsway Financial Services Inc. (KFS), through Oakmont Capital Inc., disposed of 500,000 shares of KFS common stock.
• The shares were sold at an exercise price of $8.25 per share, totaling $4,125,000.
• This transaction occurred on December 17, 2025, following an amendment to an Option Agreement originally entered into on March 31, 2025, with David Capital Partners Special Situation Fund, LP (DCPSS).
• The amendment, made on December 17, 2025, allowed the option to be exercised at any time prior to its expiration on December 29, 2025.
• Following this transaction, Hannon's indirect beneficial ownership of common stock through Oakmont Capital Inc. is 1,987,830 shares.
• Additional indirect common stock ownership includes 29,500 shares via a Retirement Plan, 13,750 shares by a Spouse, and 4,500 shares by a Trust.
• Hannon also indirectly beneficially owns 80,000 shares of Class B Preferred Stock and 40,000 shares of Class C Preferred Stock through Oakmont Capital Inc., convertible into 210,526.4 and 105,263.2 common shares, respectively.

Sentiment

Score: 5

Explanation: A director's sale of shares via a pre-existing option agreement is a routine insider transaction and does not inherently indicate positive or negative sentiment about the company's future performance.

Future Outlook

The filing does not contain any forward-looking statements or guidance regarding the company's future performance.

Industry Context

This is an insider transaction report and does not provide information directly related to broader industry trends or competitors.

Related Party Transactions

• The transaction involves Oakmont Capital Inc., an entity through which Gregory Paul Hannon (the reporting person and a Director) holds beneficial ownership, granting an option to David Capital Partners Special Situation Fund, LP.

Stakeholder Impact

• Shareholders may note a director's significant share disposition, which could be interpreted in various ways depending on the broader market context and company performance.

Key Dates

Recommendation

The filing reports a director's sale of shares through a pre-existing option agreement. While a significant disposition, it is often a planned liquidity event rather than a direct signal of company performance. Investors should consider this transaction in the broader context of the company's fundamentals and market conditions.

Keywords

Kingsway Financial Services, KFS, Gregory Paul Hannon, Oakmont Capital Inc., SEC Form 4, Insider Transaction, Stock Option, Share Sale, Director Transaction, Beneficial Ownership