On February 11, Barstool Sports founder Dave “El Presidente” Portnoy took to social media to announce a major multi-million-dollar partnership between his company and DraftKings. Portnoy, known for his quirky Twitter bio and ownership of #DDTG Global, confirmed the completion of the multi-year sports betting media partnership that was first reported by Sportico in January.

The agreement was finalized after the Super Bowl, which saw the Kansas City Chiefs triumph over the San Francisco 49ers. This timing was necessary due to a non-compete clause that Barstool Sports had to adhere to following the end of its relationship with PENN Entertainment. PENN had acquired a stake in Barstool in 2020, eventually gaining full control in February 2023 in a deal worth $551 million, with payments made in two installments.

PENN’s decision to give up its Barstool Sportsbook in favor of a new partnership with ESPN paved the way for the completion of the DraftKings partnership. This came after ESPN paid $1.5 billion for the licensing rights to ESPN Bet, leading to Barstool’s elimination from the equation. With the PENN relationship now in the past, Portnoy announced the new partnership with DraftKings, labeling it as a “multi-year monster deal”.

The first event under the new partnership will be a free-throw challenge involving Portnoy, along with other Barstool Sports personalities and DraftKings executives. The goal is to collectively make 41 free throws in a row, which is the National Basketball Association’s record. The live-streamed event will also feature viewer participation, with a set $100,000 prize pool up for grabs for those who answer the most questions correctly based on event outcomes.

In a related development, DraftKings executives Jason Robins, Paul Liberman, and Stanton Dodge sold nearly $78.8 million worth of stock ahead of the company’s fourth quarter and 2023 results.

Overall, the partnership between Barstool Sports and DraftKings represents a significant move in the sports betting and media industries, with the free-throw challenge serving as an early example of the collaborative efforts between the two companies.

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