Insider Buying Wave Signals Renewed Confidence at Chicago Atlantic

Chicago Atlantic Real Estate Finance Inc (REFI:US), a commercial mortgage REIT, operates in a space few lenders touch. The company focuses on originating and investing in senior secured loans to state-licensed operators in the cannabis industry and other underserved sectors. That specialization gives REFI an edge in yield generation, but it also exposes it to higher regulatory and credit risks than traditional REIT peers. As of mid-October 2025, the firm has a market capitalization of roughly $270 million.

A Wave of Insider Buying

From October 1 through October 16, Chicago Atlantic insiders collectively purchased more than 50,000 shares on the open market, an unusually dense period of buying across the company’s leadership team.

Executive Chairman John Mazarakis led the charge, buying 7,500 shares on October 1 and another 8,000 shares on October 16 at prices around $12.40 to $12.75, investing roughly $195,000 of his own capital. Director Jason D. Papastavrou followed with two separate buys totaling 18,000 shares at prices just below $12.70, committing over $225,000.

Co-CEO Peter Sack and Chief Operating Officer David Kite also joined in with hefty purchases. Interestingly, during this period, every single one of these transactions was a purchase, with no insider sales reported. The timing and concentration of these trades mark what analysts often call a “cluster buy”, a signal that carries more weight than isolated insider activity.

Why This Cluster Matters

When several insiders buy simultaneously, especially those deeply involved in the company’s operations, it often reflects a shared belief that the stock is undervalued. In Chicago Atlantic’s case, these purchases came just as the shares approached their 52-week lows, suggesting executives view current prices as an attractive entry point.

The pattern is also notable because of who’s buying. Mazarakis and Papastavrou are among the company’s largest shareholders, already holding meaningful stakes. Their willingness to commit additional personal funds implies conviction in the business’s outlook. Sack’s and Kite’s purchases further strengthen the message from inside the C-suite, that leadership is aligned with shareholders and confident about future earnings and dividend stability.

Market Context and Financial Backdrop

Chicago Atlantic continues to pay one of the highest dividends among mortgage REITs, offering a yield that stands out even in a high-rate environment. The company’s most recent quarterly dividend of $0.47 per share reflects steady distributable earnings and a commitment to returning value despite modest near-term headwinds.

The company operates at the crossroads of two trends: restrictive credit conditions and gradual normalization in cannabis financing. Any easing in banking access could expand lending opportunities and reduce risk spreads, a potential dual benefit.

Insiders at Chicago Atlantic are clearly sending a message. The Executive Chairman, Co-CEO, COO, and directors bought shares within days of one another, a show of real conviction, not casual optimism. For a REIT trading near its lows and yielding in the double digits, such insider alignment signals strong confidence in Chicago Atlantic’s long-term value.