Larry G. Swets, Jr. - Press Release

TORONTO, April 6, 2015 /CNW/ - On March 28, 2014, Larry G. Swets, Jr., President, Chief Executive Officer and a Director of Kingsway Financial Services Inc. (the Company), was granted (i) 1,382,665 restricted common shares of the Company (the Restricted Common Shares); and (ii) 400,000 options to acquire common shares of the Company (the Stock Options), pursuant to grants made to certain participants of the Company's 2013 Equity Incentive Plan dated December 4, 2013, as amended (the Plan) that was approved at the meeting of shareholders of the Company held on June 4, 2013. Pursuant to the terms of the Plan, Mr. Swets may not vote the Restricted Common Shares until the vesting date (being the tenth anniversary of the date of grant provided that Mr. Swets remains in continuous employment with the Company through such anniversary).

As a result of the grant of Restricted Common Shares, Mr. Swets owned, directly or indirectly, an aggregate of 1,859,144 common shares of the Company on March 28, 2014, representing approximately 10.1% of the issued and outstanding common shares of the Company on such date. Assuming the exercise of the Stock Options in full (and assuming no other outstanding stock options of the Company were exercised), Mr. Swets owned, directly or indirectly, 2,259,144 common shares of the Company on March 28, 2014, representing approximately 12.0% of the issued and outstanding common shares of the Company on such date.

Between March 28, 2014 and the date hereof: (i) an aggregate of 7,036 common shares of the Company were purchased for the benefit of Mr. Swets pursuant to the Company's Employee Share Purchase Plan dated January 9, 2014, as amended, at the market prices on the New York Stock Exchange at the time of such acquisitions; and (ii) an aggregate of 182,536 common shares of the Company were issued to Mr. Swets upon the exercise of his Series A Warrants at a price of US$4.50 per common share as a result of such warrants becoming exercisable due to the Company's notice of redemption of the Series A Warrants dated August 18, 2014.

As of the date hereof, Mr. Swets owns, directly or indirectly, 2,048,716 common shares of the Company (including the Restricted Common Shares), representing approximately 9.4% of the issued and outstanding common shares of the Company. Assuming the exercise of the Stock Options in full (and assuming no other outstanding stock options in the Company are exercised), Mr. Swets owns, directly or indirectly, 2,448,716 common shares of the Company, representing approximately 11.1% of the issued and outstanding common shares of the Company as of the date hereof.

The Restricted Common Shares and Stock Options were granted to Mr. Swets by the board of directors of the Company pursuant to the terms of the Plan. Subject to compliance with applicable securities laws, Mr. Swets may purchase or sell securities of the Company in the future depending on price, availability, general market conditions and other factors material to his investment decisions.

SOURCE Larry G. Swets, Jr.

For further information: To obtain a copy of this report, please contact Ann Brooks, Vice President & General Counsel, 1-847-871-6408; Larry G. Swets, Jr., 150 Pierce Road, 6th Floor, Itasca, Illinois 60143, United States

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