Interesting turn of events

Just five months after PENN Entertainment sold Barstool Sports back to its founder Dave Portnoy, the sports entertainment brand is reportedly close to agreeing to a marketing deal with DraftKings.

PENN operated Barstool-branded sportsbooks for a few years before deciding to take a different approach. It is now running ESPN Bet after entering a ten-year deal with the media giant for about $2bn. This led to Portnoy buying back his old company for just $1, having sold it for a total of $551m.

DraftKings paying a low eight-figure sum annually

Sportico reported on Wednesday that advanced talks are underway that would see DraftKings pay a low eight-figure sum annually to Barstool in return for showcasing the operator’s odds on its content, as well as directing people to the sportsbook.

Getting back in the game

PENN put a short-term non-compete clause in the contract when selling Barstool, which means Barstool cannot step back into the sports betting space until the NFL season comes to a close next month. PENN will also receive half of the gross proceeds of any future sale of Barstool.

Portnoy didn’t waste much time making big changes at Barstool after resuming control. He cut its 430-person staff by 25% a few weeks after re-joining and CEO Erika Ayers resigned a few weeks ago.

History of similar partnerships

Barstool has embraced gambling all the way back to its beginning days in 2003 when Portnoy started a free weekly fantasy sports and betting newsletter. It has previously partnered with other sportsbook operators.

Numerous sportsbook operators have entered deals with similar types of media companies to try to leverage their audiences. DraftKings already has partnerships with various sports-related podcasts and purchased the gambling media firm Vegas Stats & Information Network (VSiN) in 2021. It previously had an arrangement with ESPN before PENN and the media giant got together.