What Happened?

Shares of casino, sports betting and entertainment operator PENN Entertainment (NASDAQ: PENN) jumped 8.2% in the afternoon session after an analyst upgrade from Stifel and a significant stock purchase by the company's CEO, Jay Snowden. 

The move followed an upgrade from Stifel analyst Jeffrey Stantial, who raised the rating on the stock to “buy” from “hold” and increased the price target to $21. Stantial noted that PENN's decision to end its sports betting partnership with ESPN early removed an “overhang” from the stock and would provide a tailwind for the company moving forward. The companies mutually agreed to end their partnership, with PENN planning to rebrand its U.S. online sports betting offering. Adding to the positive sentiment, CEO Jay Snowden bought 34,700 shares for a total of $496,938. Such a large purchase by a top executive was often viewed by investors as a strong signal of confidence in the company's future prospects.

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What Is The Market Telling Us

PENN Entertainment’s shares are very volatile and have had 22 moves greater than 5% over the last year. In that context, today’s move indicates the market considers this news meaningful but not something that would fundamentally change its perception of the business.

The previous big move we wrote about was 21 days ago when the stock gained 3.9% on the news that investor optimism grew ahead of its third-quarter 2025 earnings report, fueled by expectations of significant profit growth. The company's earnings for the quarter were expected to increase by 58.3%. Adding to the positive outlook, PENN Entertainment had a history of surpassing earnings expectations, having reported better-than-expected results in three of the four previous quarters. Furthermore, JMP Securities maintained its Market Outperform rating on the stock, reflecting continued positive sentiment within the online gaming and entertainment industry.

PENN Entertainment is down 18.1% since the beginning of the year, and at $15.75 per share, it is trading 30.7% below its 52-week high of $22.73 from February 2025. Investors who bought $1,000 worth of PENN Entertainment’s shares 5 years ago would now be looking at an investment worth $246.56.

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