[Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Kingsway Financial Services President and CEO John Taylor Maloney bought 230 shares of Common Stock on May 15, 2026 at $10.85 per share through the company’s employee share purchase plan. This increased his direct holdings to 1,461,641 shares, alongside indirect holdings of 34,100 shares in each of three trusts, including 400,000 restricted shares granted on March 31, 2021.
Positive
- None.
Negative
- None.
Insider Trade Summary
Net Buyer: 230 shares ($2,496)
Net Buy
4 txns
Insider
Fitzgerald John Taylor Maloney
Role
President and CEO
Bought
230 shs ($2K)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Purchase | Common Stock | 230 | $10.85 | $2K |
| holding | Common Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
| holding | Common Stock | -- | -- | -- |
Holdings After Transaction:
Common Stock — 1,461,641 shares (Direct, null);
Common Stock — 34,100 shares (Indirect, Trust-GEF)
Footnotes (1)
- The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker. Includes 400,000 shares of restricted stock granted on March 31, 2021.
Key Figures
Shares purchased: 230 shares
Purchase price: $10.85 per share
Direct holdings after transaction: 1,461,641 shares
+2 more
5 metrics
Shares purchased
230 shares
Common Stock bought on May 15, 2026
Purchase price
$10.85 per share
Employee Share Purchase Plan acquisition
Direct holdings after transaction
1,461,641 shares
Common Stock held directly after May 15, 2026 trade
Indirect trust holdings
34,100 shares each
Common Stock in Trust-MPF, Trust-LTF, Trust-GEF
Restricted stock grant
400,000 shares
Restricted stock granted March 31, 2021
Key Terms
Employee Share Purchase Plan, restricted stock, open-market purchase, indirect ownership, +1 more
5 terms
restricted stock financial
"Includes 400,000 shares of restricted stock granted on March 31, 2021."
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.
open-market purchase financial
"Purchase in open market or private transaction"
An open-market purchase is when an investor or a company buys shares on a public stock exchange at the going market price, rather than through a private deal. It matters to investors because these purchases change how many shares are available, can push the stock price up or signal confidence from large buyers, and often affect per-share metrics like earnings—think of it like someone buying lots of apples off a grocery shelf, reducing supply and potentially raising the price.
indirect ownership financial
"direct_or_indirect: "I", nature_of_ownership: "Trust-MPF""
matching contribution financial
"the company will make a matching contribution equal to 100% of such employee's contribution"
An employer’s matching contribution is when a company adds money to an employee’s retirement or savings account based on the employee’s own contributions, like a store offering to top up a customer’s purchase to reach a discount threshold. It matters to investors because matching increases a firm’s compensation costs and can improve staff retention and morale, which affect productivity, cash flow and long-term liabilities that influence a company’s financial outlook.
