John Taylor Maloney Fitzgerald, who serves as President and Chief Executive Officer of Kingsway Financial Services Inc., bought 183 shares of the company's common stock on February 2, 2026, at a per-share price of $13.69, for a total cash outlay of $2,505.
The purchase was executed through the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which permits eligible employees to contribute up to 5% of adjusted salary each payroll period. Under the ESPP terms cited, Kingsway matches 100% of contributions for employees with at least 12 months of service, and contributed funds are used to acquire Kingsway Financial Services shares on the open market.
Following this transaction, Fitzgerald's direct ownership in the company stands at 1,460,086 shares. That total includes 400,000 shares of restricted stock that were granted on March 31, 2021. In addition to his direct holdings, he also holds indirect stakes through three trusts - GEF, LTF, and MPF - each of which owns 34,100 shares.
The insider purchase comes against a backdrop of notable share price performance and mixed underlying fundamentals. Kingsway's stock has returned approximately 70% over the past 12 months, and at the time of the purchase the shares were trading near $13.61. However, InvestingPro data indicates the company was not profitable over the trailing twelve months, recording a diluted earnings per share of -$0.44.
Valuation metrics cited by InvestingPro show a market capitalization of $394 million and a Price/Book ratio of 23.7. That Price/Book figure leads InvestingPro analysts to conclude the stock appears overvalued despite a strong five-year performance record, according to the data noted.
On the operating front, Kingsway Financial Services reported consolidated revenue of $37.2 million for the third quarter of 2025, a 37% increase compared with the same quarter a year earlier. The company attributed the revenue expansion to a combination of acquisition activity and organic growth. Although aftermarket trading experienced a modest decline, the reported financial results were presented as evidence of an effective market strategy and improved revenue generation.
This insider acquisition is relatively small in dollar terms compared with Fitzgerald's aggregate ownership and the company's market capitalization. The ESPP mechanism that facilitated the buy is designed to encourage employee ownership by permitting salary-directed contributions and employer matching for qualifying employees.
Investors seeking further analysis can find a dedicated Pro Research Report for KFS through an InvestingPro subscription, as noted in the InvestingPro material referenced. That reporting and the valuation metrics underline the contrast between recent top-line momentum and the absence of trailing twelve-month profitability.
Market context - The transaction highlights a common dynamic in corporate ownership where insider purchases occur alongside both strong revenue growth and stretched valuation measures. The facts recorded here reflect the exact size of Fitzgerald's recent purchase, the ESPP mechanics, current ownership totals including restricted shares and trust holdings, recent revenue performance, and InvestingPro's trailing profitability and valuation observations.