Not everyone sees the failed partnership with ESPN as a bad thing for casino and gaming operator PENN Entertainment.
Key Takeaways
- Barstool owner Dave Portnoy worked with PENN during the operator’s first run at a U.S. sportsbook.
- Portnoy believes ESPN didn’t promote PENN’s sports betting platform well.
- The Barstool founder sees better days ahead for PENN.
A man who used to be in business with PENN saw Thursday’s termination of the ESPN-branded sports betting platform deal as a “good day” for the gaming company.
“I think the bad day happened long before today,” Barstool Sports founder and owner Dave Portnoy said on "The Unnamed Show" podcast Thursday. “The deal just didn’t work at all. They paid a lot of money to get big results from ESPN, and they weren’t even close.
“I think today is a good day for PENN after a lot of bad days.”
PENN undervalued?
Portnoy partnered with PENN in early 2020 to have the gaming operator use the Barstool brand to launch its first U.S. online sportsbook. PENN ended that agreement when a chance to rebrand with the World Wide Leader in Sports came about in 2023, creating ESPN BET as the company's new platform.
However, a 10-year. $2-billion deal officially fell apart Thursday, with the two sides opting out after just two years. Portnoy said he believes PENN is due for a rebound.
“I think the stock is undervalued by a mile right now,” he said. “I just bought it. I thought it would go up once they got out of this deal.”
PENN’s stock was down over 8% as of Thursday afternoon.
I am buying $penn today. I think them unburdening themselves from ESPN is a great move. It’s my buy of the day on #ddtg
— Dave Portnoy (@stoolpresidente) November 6, 2025
Invest at your own risk. https://t.co/uT6eRlOJQ5
Reading tea leaves
Portnoy said the dissolving of the PENN-ESPN deal was “not surprising,” and that the “tea leaves were there.” He believes PENN now feels “unburdened” by an expensive contract that frees up a lot of cash for an operator that’s struggled to reach 5% of the market share.
“They were spending $150 million a year with ESPN, burning that money on fire because ESPN wasn’t delivering any results,” Portnoy said.
One reason the Barstool owner, who bought his company back from PENN in 2023 for $1, believes the marriage with ESPN didn’t work is because the personalities of the sports media company, “for the most part,” didn’t have a real interest in promoting the ESPN BET product.
“You pay all this money to a faceless brand and nobody really cares,” Portnoy said. “I’d argue that (Barstool was) more successful when we were pushing and trying than ESPN was.”
PENN is taking its theScore brand that it owns and operates in Ontario and will use it as its U.S. platform. ESPN announced a new sports betting partner deal with DraftKings, which also has a partnership with Barstool, right after the PENN termination agreement was announced.
“I don’t know if I would’ve done it if I were DraftKings,” Portnoy said about the deal. “I hope they made the right move. We obviously work with them. I own a ton of DraftKings stock.”
Competitive battle
Portnoy, who admitted he “despises” ESPN, thinks DraftKings linked up with the sports media company to help get an edge on FanDuel, which he believes might’ve taken a deal with the sports media company had DraftKings not.
Portnoy added it could hurt DraftKings in its competitive battle. FanDuel is the top market-share leader in sports betting and iGaming in the U.S., while DraftKings is a close second.
Portnoy said if Barstool Sportsbook had not had licensing issues in New York, it could’ve been a “legitimate competitor” to DraftKings and FanDuel in the U.S.’s most lucrative market.
“If we could’ve gotten around the regulatory issue - big if, we didn’t - we could’ve promoted a lot better than ESPN,” he said. “And we would've.”
