PENN CEO And Director Buy Up Shares After Price Drop

Recent developments at Penn Entertainment have drawn significant attention as CEO Jay Snowden and Director David Handler made noteworthy investments in the company, purchasing a combined total of 44,000 shares following a notable decline in share prices. This downturn was precipitated by a critical report from investor HG Vora, highlighting performance issues under Snowden’s leadership.

In a strategic move, Snowden acquired 34,000 shares at an average price of $14.699, totaling approximately $499,766. With this purchase, he now holds over a million shares in the company, which experienced a slight rebound post-investment, reaching prices above $15. As of May 28, shares are trading at approximately $15.38.

In addition, Handler purchased 10,000 shares at $14.83 each, amounting to over $148,000. He possesses 322,941 shares directly and an additional 20,000 indirectly via a foundation.

Penn’s Stock Performance: A Steep Decline

Penn Entertainment’s stock has faced tumultuous challenges recently, particularly after the release of HG Vora’s 116-page report titled “Genuine Change is Needed at PENN.” The document emphasized a series of miscalculations that have contributed to a steep decline in share value over the years.

Initially priced at $0.50 per share in 2000, PENN’s stock saw a remarkable uptick until 2019, yielding staggering returns for investors such as Vora—an impressive 4926%. However, following Snowden’s ascension to CEO in 2020, this trend reversed, resulting in a staggering 37% loss for investors.

At its peak, PENN’s stock reached $130.47 in February 2021; however, it has since experienced a consistent downward trajectory. Analysts have expressed concerns regarding the stock’s overvaluation relative to its fundamentals, particularly considering the digital division’s sluggish performance. Currently, at $15.38, the share price illustrates a significant 26% decrease compared to the same time last year.

Navigating Sports Betting Challenges

The report also criticized PENN’s sports betting segment, particularly its hefty investment of $550 million in Barstool Sports over two phases. The company encountered substantial hurdles in obtaining necessary gambling licenses tied to the brand’s controversial reputation. Ultimately, PENN sold Barstool back to founder Dave Portnoy for a symbolic $1 in 2023.

Portnoy reflected on the challenges, stating, “We got denied gambling licenses because of me; you name it. So the regulated industry is probably not the best place for Barstool Sports and the type of content we create.” Despite facing multiple allegations of misconduct in recent years, he has yet to face legal consequences.

In light of the sale, Snowden acknowledged, “Barstool is a great media company, but not the right fit for our long-term sports betting strategy in a regulated market.” Coinciding with this transition, PENN unveiled a landmark 10-year, $2 billion partnership with ESPN, launching “ESPN Bet” as its newly branded sportsbook.

ESPN Bet: A Path to Profitability?

Since its launch in 2023, PENN’s interactive division—which includes ESPN Bet, theScore Bet, and Hollywood Casino—reported substantial revenue growth, generating $960 million in 2024, up from $719 million in 2023. However, this growth has been accompanied by increasing annual losses, rising from $403 million in 2023 to nearly $500 million in 2024.

While revenue has seen improvements, with the interactive segment reporting $162 million in Q1 2025 (up from $151 million in Q1 2024), the losses narrowed significantly to $89 million, down from $196 million the previous quarter—indicating a cautious move toward profitability.

As of early 2025, ESPN Bet claims approximately 2–4% of the U.S. online sports betting market share. PENN previously aimed for a 20% market share by 2027, but current trends suggest that achieving this goal may prove to be a formidable challenge.

To address these ongoing issues, PENN recently restructured its board of directors. However, investor HG Vora continues to advocate for additional leadership changes, emphasizing the need for a renewed strategy to steer the company back to profitability.