Penn Entertainment CEO Purchases $500K in Casino Shares.


Published on: November 12, 2025, 11:13 AM.

Updated on: November 12, 2025, 11:39 AM.

  • Penn CEO Jay Snowden acquires stock after earnings decline
  • He added 34,700 shares, increasing his total holdings to over 1.11 million
  • Shareholders express concerns regarding stock performance under his management

Penn Entertainment (NASDAQ: PENN) CEO Jay Snowden seized the opportunity presented by a post-earnings dip in the casino stock to expand his shareholding.

Penn Entertainment
Jay Snowden, CEO of Penn Entertainment, recently invested $500K in the casino stock. (Image: Bloomberg)

A new Form 4 filing with the Securities and Exchange Commission (SEC) reveals that the CEO acquired 34,700 shares of the regional casino for around $500K on November 7, shortly after Penn released its third-quarter results. During this report, the company announced the end of its partnership with ESPN regarding the ESPN Bet.

Snowden paid an average of $14.32 per share for this latest acquisition, bringing his total ownership in Penn’s stock to over 1.11 million. His timing appears to be strategic, as the gaming stock is currently trading at approximately $15.40. This marks his first reported purchase of Penn shares in 13 months.

Snowden’s recent stock purchase could signify his confidence in the company’s digital gaming strategy and its network of regional casinos, though the CEO’s office has not made an official statement regarding this. Typically, corporate insiders acquire shares when they perceive them as undervalued and expect future appreciation.

Investor Concerns Regarding Snowden’s Tenure

On a positive note, Snowden is purchasing Penn stock at a time when other gaming executives are hesitant to buy into their own companies, especially amid notable insider sales at competing firms. Nonetheless, investors have voiced critiques of Snowden’s performance as CEO.

Since Snowden took over as CEO at the beginning of 2020, Penn’s stock has plummeted nearly 76%, significantly underperforming compared to rival Boyd Gaming (NYSE: BYD), which has surged 143% during the same timeframe. Penn’s stock has also trailed behind specialized sports betting companies and broader gaming market indicators, which overall have not delivered impressive returns.

Penn’s declining stock price under Snowden has led to discontent among major shareholders, prompting criticism of the board’s decision to indulge the CEO’s online sports betting initiatives while compensating him generously during a time of stock decline.

Last year, the Donerail Group urged Penn to explore self-sale options, while earlier this year, hedge fund HG Vora initiated a proxy battle to appoint three members to the company board, successfully securing two of those positions.

Ending ESPN Bet May Prove Beneficial

With the cessation of the ESPN Bet partnership, Wall Street analysts believe a significant burden has been lifted from Penn’s investment narrative. This development could allow the operator to concentrate on its iGaming and regional casino ventures.

In a recent analysis, Macquarie analyst Chad Beynon described the termination of the partnership as a positive shift, rating Penn as “outperform.” He stated that this move “mitigates the risk surrounding the Penn value proposition.”

“We maintain our Outperform rating based on potential value if PENN can effectively execute its strategy, although we recognize the tight margin for error. Given its history of resilience during recessions, PENN is favorably positioned, and we believe the investment thesis will depend on online momentum in the US and Canada,” he concluded.



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