PENN CEO Jay Snowden Buys Over $496,000 in Company Stock

Author: Mateusz Mazur

Date: 11.11.2025

Jay Snowden, Chief Executive Officer of PENN Entertainment, executed a substantial purchase of his company’s stock, acquiring 34,700 shares for a total of $$496,938.70. The purchase was made on Friday at an average price of $$14.32 per share.

This major insider investment is typically viewed by the market as a strong signal of confidence in the company’s future outlook. The timing follows a significant drop in PENN’s stock price after the announcement of its third-quarter financial results.

Stock Movement and Analyst Confidence

The CEO’s move, combined with positive analyst coverage, sparked a rally in PENN’s share price. Following the news, PENN Entertainment shares (NASDAQ: PENN) closed the trading session at $$15.60, a  increase compared to the previous Friday’s close.

The increase came after the stock had fallen by on Thursday. This decline was triggered by the company’s Q3 2025 earnings report and the news of the early termination of its -year exclusive partnership with ESPN Bet.

The rally was supported by Stifel analyst Jeffrey Stantial, who upgraded PENN’s rating from “hold” to “buy,” with a price target increase to .

Stantial noted that the decision to end the ESPN Bet partnership removed an “overhang”from the stock, providing a future “tailwind” for the company. The shares had traded nearly lower than their opening price at the start of the year prior to the rally.

Strategic Shift Follows Digital Challenges

Snowden’s tenure, which began in January , has been defined by severe financial difficulties in the digital sector. PENN reported a substantial net loss of million in Q3 , primarily due to million in asset impairment losses booked entirely in the Interactive segment.

While the core retail casino business remained stable, generating billion in revenue, the Interactive segment showed an Adjusted EBITDA loss of million.

The company has spent billions on two major digital transactions that ultimately brought in less than million digital customers. The acquisition of Barstool Sports was widely deemed a failure; PENN paid million for the entire company only to sell it back to founder Dave Portnoy for .

Following the costly digital missteps, PENN is implementing a radical digital reorientation called “iCasino forward.”

New Focus on Online Casino and Omnichannel Advantage

The decision to mutually end the ESPN Bet partnership, effective December 1, 2025, allows PENN to shift its strategy. The company will discontinue its million annual cash payments and warrant commitments to ESPN.

The new focus will be on the high-margin iCasino business and Canadian operations. The North American iCasino segment achieved its highest quarterly gaming revenue ever in Q3, growing by nearly year-over-year.

The US online sports betting (OSB) offering will be rebranded as theScore Bet®, functioning mainly as an acquisition tool to direct customers toward the Hollywood-branded iCasino where legal. This aims to replace fixed media spending with more effective, performance-based marketing.

The strategy seeks to leverage the company’s omnichannel advantage. The digital business will connect deeply with the PENN Play™ loyalty program, which has a million members. Customers who use both retail and digital channels historically generate six times higher value and show three times better retention than single-channel users.