The “Worldwide Leader in Sports” is getting into the gambling business with ESPN BET. However, in some corners of the sports world, the bigger news related to this deal is that this partnership between ESPN and PENN Entertainment means that the controversial Dave Portnoy just got ownership of Barstool Sports back for next to nothing.

On Tuesday, ESPN PR announced that the company “has entered an agreement with [PENN Entertainment] to launch ESPN BET, a branded sportsbook in the U.S. ESPN BET will be available for fans this fall.”

The biggest roadblock to making this landmark deal happen was that PENN Entertainment acquired a 36% stake in another sports media company, Barstool Sports, in February 2020, and in 2023, the company bought the remaining interest for approximately $388 million.

To get over this hurdle and complete the blockbuster deal with America’s biggest sports cable network, PENN had to divest its interest in Barstool, and the company’s founder and president, Dave Portnoy, was more than happy to swoop in and help out.

According to reports in the Wall Street Journal, the sale of Barstool back to Portnoy involved the founder “buying” all the company’s common stock shares for “certain non-compete and other restrictive covenants” plus the “right to 50% of the gross proceeds received by Portnoy in any subsequent sale.”

After the news broke, Portnoy did an “emergency press conference” stating that he would never sell Barstool Sports again.

For ESPN, this is one of the biggest and boldest moves in company history, alongside the ESPN+ streaming platform, their mobile phone venture, and the ESPN Zone restaurant chain. As many longtime “Worldwide Leader” watchers know, these massive moves into areas other than sports coverage have had mixed results (at best) for the company.