February 12, 2024 3 min read


DraftKings and Barstool Sports Ink Multi-Year Landmark Deal

Barstool Sports founder Dave Portnoy has confirmed a multi-year sports betting media agreement between DraftKings and Barstool Sports

On February 11, the “inventor” of Barstool Sports, Dave “El Presidente” Portnoy, used his social media to make the big announcement regarding the new multi-million-dollar partnership that his company and DraftKings have agreed upon.  

Portnoy, who is also the owner of #DDTG Global and a “Brick Watch Man” and “2-time bee sting survivor” as he describes himself on his X (former Twitter) account, officially confirmed that the two companies have completed the multi-year sports betting media partnership, a deal that was initially reported by Sportico in January

His X message said “We’re back to our roots. DK is once again the exclusive sports betting partner of Barstool Sports. The more things change, the more they stay the same.”

The Partnership, Completed at the End of the Super Bowl

The agreement could only be completed after the Super Bowl came to an end, with the Kansas City Chiefs edging the San Francisco 49ers

The reason was a non-compete clause that Barstool Sports had to respect. The clause referred to the closing of the company’s relationship with PENN Entertainment after the operator decided to give up on its Barstool Sportsbook in favor of a new partnership with ESPN.

PENN paid $1.5 billion to obtain the licensing rights for ESPN Bet

In August 2023, the most innovative provider of gaming entertainment in North America sold 100% of outstanding Barstool Sports shares to Portnoy after inking an agreement with ESPN to rebrand their current sportsbook while eliminating Barstool from the equation. 

Originally, PENN acquired a stake in Barstool in 2020, gaining complete control in February 2023 in a deal valued at $551 million that was paid over two tranches.

First on the List, a Free-Throw Challenge

The “multi-year monster deal with DraftKings,” as Portnoy called it, will first lead to the latter along with various other Barstool Sports personalities including Dave, Big Cat, Hank, Jersey Jerry, Steven Cheah, Rico Bo$co, Mark Titus, Brandon Walker, Big T, Kirk, and other Bullpen members from participating in a free-throw challenge.

The goal of the event has been set to 41 made free throws in a row, which is the National Basketball Association’s Record for most free throws in a row. 

The event will be commented on by PFT commenter Nick Turani and KB. During each new round, Portnoy and Dan will pick five participants to join them as a team and try to reach the 41 throws in a row. 

Each team member must complete at least two free throws and up to 10 free throws. Portnoy will need to hit the 15th, 30th, and 41st free throws. 

The group will start with 75 mulligans. Once all are used, the group will only receive one extra mulligan every three rounds.  

The challenge will be streamed live and incorporate a series of questions that viewers will need to answer based on what they think will happen during the stream.

Those viewers who answer the most questions correctly win a share of the set $100,000 prize pool.

Elsewhere, DraftKings executives Jason Robins, Paul Liberman, and Stanton Dodge sold close to $78.8 million worth of stock before the release of the company’s fourth quarter and 2023 results. 

After finishing her master's in publishing and writing, Melanie began her career as an online editor for a large gaming blog and has now transitioned over towards the iGaming industry. She helps to ensure that our news pieces are written to the highest standard possible under the guidance of senior management.

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