PENN and Barstool’s Nixed Sports Betting Deal Still Under Watch

James Bisson - Head of Content, Betting
James Bisson • Head of Content, Betting 16+ years betting experience
Updated: Oct 3, 2023 , 05:05 PM ET • 4 min read

PENN Entertainment — the part-owner of ESPN Bet — is facing scrutiny by the Massachusetts Gaming Commission over its previous relationship with Barstool Sports.

Barstool Sportsbook
Photo By - USA TODAY Sports

A legal sports betting operator is continuing to address a previous partnership.

PENN Entertainment — the part-owner of ESPN Bet — is facing scrutiny by the Massachusetts Gaming Commission over its previous relationship with Barstool Sports. In 2020, PENN purchased a 36% stake in the media company for $163 million. That same year, the two entities launched Barstool Sportsbook. Penn would acquire the remaining 64% of Barstool in February 2023 for $388 million. Six months later, PENN agreed to a long-term deal with ESPN to launch online betting sites across the United States through a rebrand of Barstool Sportsbook.

As a result of PENN’s new deal, the company’s previous partnership with Barstool has been under a microscope. An IEB report revealed that in order for Barstool and PENN to be awarded an online wagering license the companies were required to have no one under the age of 21 attend Barstool College Football shows — a live weekly program that broadcasts on YouTube.

PENN was fined $250,000 in 2022 following a college football show. The then-Barstool owner was fined for targeting underage bettors because the show was held at the University of Toledo.

Questioning management

Barstool’s leadership was also a focal point of the report. Barstool founder Dave Portnoy, who bought back the company for $1 in August, was included due to his relinquishing of a leadership role under PENN ownership. Portnoy’s role came into question after he made public comments on social media regarding the salary negotiations and firing of several Barstool employees.

The IEB would inquire with PENN regarding Portnoy’s leadership and management roles. PENN would vow that under its ownership of Barstool Portnoy lacked any leadership responsibilities.

Despite the looming end of its sportsbook, Barstool holds a non-gaming vendor registration with the MGC. The company is also still licensed in seven jurisdictions, including Massachusetts.

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Financial results

PENN generated $1.67 billion in revenue in Q2 2023 — a 2.9% increase year-over-year. The company reported a net income of $78.1 million during the quarter, up from $28.1 million in Q2 2022. PENN’s adjusted EBITDA reached $330.4 million in Q2 2023 — down 30.7% from Q2 2022.

The results were attributed to expansion and growth in the company’s interactive segment, which includes online sports betting operations. PENN’s interactive segment generated $88.5 million in revenue in Q2 2023 compared to $55.4 million for the same period last year.

PENN will continue to maintain sports betting operations in Ontario under theScore Bet. The media and gaming company was acquired by PENN in 2021 in a deal valued at $2 billion.

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James Bisson
Head of Content, Betting

James Bisson is the Editor-in-Chief at Covers. He has been a writer, reporter and editor for more than 20 years, including a nine-year stint with The Canadian Press and more than five years at theScore. He has covered dozens of marquee events including the 2010 Winter Olympics, the 2006 Stanley Cup final and Wrestlemania 23, and his work has appeared in more than 200 publications, including the Los Angeles Times, the Guardian, Yahoo! Sports, the Toronto Star and The Globe and Mail.

His book, “100 Greatest Canadian Sports Moments”, was a hardcover best-seller in Canada in 2008 and earned him appearances on CBC Radio and Canada AM. He has written more than 50 sportsbook reviews, more than 200 industry news articles, and dozens of other sportsbook-related content articles.

A graduate of the broadcast journalism program at Ryerson University (now Toronto Metropolitan University), James has been an avid bettor since the early 2000s, and cites bet365 as his favorite sports betting site due to its superior functionality and quick payouts. His biggest professional highlight: Covering Canada's first Olympic gold medal on home soil – and interviewing Bret Hart. Twice.

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