Dave Portnoy explains why Barstool was a better partner for Penn than ESPN

When it comes to Penn Entertainment’s breakup with ESPN, Dave Portnoy is feeling bullish.

So much so, that the Davey Day Trader host is making the sportsbook operator his buy of the day.

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

Invest at your own risk. https://t.co/uT6eRlOJQ5

— Dave Portnoy (@stoolpresidente) November 6, 2025

During Thursday’s episode of The Unnamed Show, Portnoy shared his extended reaction to Penn and ESPN mutually agreeing to end their 10-year partnership, which will bring an end to the ESPN Bet sportsbook on Dec. 1. And according to the Barstool Sports founder, the split is a big win for Penn, which will no longer be on the hook for what was originally a 10-year, $1.5 billion deal.

“It just didn’t work. The deal just didn’t work at all,” Portnoy said. “They paid a lot of money to get results — big results from ESPN — and they weren’t even close. I’d argue [Barstool] was more successful when we were pushing and trying than ESPN was. So I think today’s a good day for Penn after a lot of bad days.”

As Dave Portnoy alluded to, he has his own history with Penn, which began branding its mobile product as the Barstool Sportsbook in 2020. But months after purchasing a majority stake in Barstool, Penn sold the sports brand back to Portnoy for $1 in order to enter its agreement with ESPN in August 2023.

After co-host Ryan Whitney theorized Portnoy was the biggest winner in all of this, El Presidente didn’t disagree. Asked for further clarification about why he views Thursday’s news as a positive for Penn, the Boston native pointed to the reality that the gaming operator simply wasn’t getting a return on the investment it had been making with the Worldwide Leader in Sports.

“They were spending $150 million a year with ESPN, burning that money on fire because ESPN wasn’t delivering any results,” he said. “The difference between working with us and ESPN, for the most part, we’re all truly trying to make this thing work. Like, people are overall rooting for Barstool within our company. Like they care about it — for the most part. ESPN, the employees don’t give a f*ck about ESPN… and like, [Pat] McAfee is a needle-mover. There’s no doubt about that. McAfee didn’t promote ESPN [Bet]. If anything, he made fun of it. It didn’t seem like he was incentivized to give a sh*t about it.”

Kirk Minihane, however, also pointed out that his co-host isn’t exactly an independent arbiter here. In addition to his own past dealings with Penn, Portnoy’s personal disdain for all things ESPN has been well documented, as the 48-year-old has been one of the Worldwide Leader’s most vocal critics.

For his part, Dave Portnoy didn’t deny his perspective may have been rooted in some personal bias.

“In terms of the two companies, Penn and ESPN, I despise ESPN,” he said. “I don’t want anything to work out for them.”