Barstool close to bet deal with DraftKings

Barstool is on the verge of a new betting partner.

Dave Portnoy’s Barstool Sports is in advanced talks to work with DraftKings Sportsbook in a marketing capacity, according to Sportico, a stunning development in the sports betting industry.

The deal, which reports suggest has not yet been announced or signed due to Barstool’s previous contract restrictions with PENN Entertainment, would pay Barstool in the low eight figures per year to host DraftKings odds while also sending customers to the platform.

Barstool will not be lending its name to DraftKings.

PENN bought Barstool from Portnoy and his investors for $388 million, a sale completed in February 2023.

The partnership was a failure, though, as PENN gave Portnoy the company back for $1, eating the $388 million purchase price as a loss before turning around and shoveling out $1.5 billion over 10 years to ESPN for its name.

PENN did report a $850 million write-off as a result of the failed Barstool acquisition.

DraftKings will look to make use of Portnoy and Barstool’s other talent, such as Dan “Big Cat” Katz, Frank The Tank and others across their podcast network.

This deal rivals what other media companies achieved through a betting partnership, as Dan Le Batard’s Meadowlark Media snagged a clean $50 million from DraftKings over three years, while FanDuel and The Ringer extended a deal that founder Bill Simmons called a “significant investment.”

Upon completion of the deal, Portnoy would be reunited with ex-talent Jared Carrabis, who departed from Barstool for DraftKings in 2022.

If at any point Barstool were to be bought out, PENN would get 50 percent of the sale price as a sort of schmuck-insurance stipulation that the gambling giant implemented when they gave the company back to Portnoy for $1.