January 25, 2024 3 min read


Barstool Sports and DraftKings Set to Forge Strategic Betting Partnership

While the agreement has not yet been officially announced or signed, industry insiders familiar with the matter suggest that the deal is poised to be a game-changer for both companies

Barstool Sports, under the leadership of founder Dave Portnoy, is reportedly in advanced negotiations for a comprehensive sports betting deal with DraftKings

Barstool and DraftKings Forge Unprecedented Marketing Partnership in Secrecy

Unlike previous endeavors, this prospective deal is anticipated to take the form of a traditional marketing partnership. Barstool will play a pivotal role in promoting DraftKings odds, leveraging its extensive reach to refer customers to the renowned sportsbook, reported Sportico. 

The discussions, shrouded in secrecy due to the private nature of the details, are said to revolve around a multiyear contract that could see Barstool pocketing a substantial annual sum in the low eight figures.

However, no agreement can be signed before the Super Bowl, as Barstool faces a lock-up period stemming from its recent separation from Penn Entertainment. The stipulations of the separation, which involved Penn selling Barstool back to Portnoy for a mere dollar, included restrictions on Barstool’s reentry into the betting arena until the conclusion of the current NFL season and playoffs.

Representatives for DraftKings, Barstool, and Penn have yet to officially comment on the ongoing negotiations.

Anticipated Alliance Poised to Shake Up the Sports Betting Landscape

Barstool’s journey into the betting realm is a return to its roots, with the company having originated in 2003 as a betting and fantasy publication distributed by Portnoy. Despite its gambling advice and picks remaining integral to Barstool’s content, the absence of a formal betting sponsor has left the company without a share in the burgeoning sports betting market.

DraftKings, a giant in the online sports betting industry, has been keen on establishing strategic partnerships with media companies to enhance its brand recognition and attract a broader customer base. The company’s notable moves include the acquisition of Vegas Stats & Information Network (VSiN) and partnerships with prominent sports podcasts.

This potential collaboration between Barstool and DraftKings follows Barstool’s tumultuous relationship with Penn Entertainment, which initially acquired a significant stake in Barstool for $163 million in 2020 and eventually offloaded the media company back to Portnoy for $1 after a failed attempt to create a sustainable betting app. 

Portnoy clarified that Penn encountered difficulties in fully leveraging the brand due to compliance-related obstacles. Among these challenges, Portnoy highlighted issues with gambling regulators, major media corporations, and fluctuations in the stock market affecting both Penn and Barstool Sports.The pending deal between Barstool and DraftKings is creating waves in the market, with DraftKings’ stock rallying to its highest levels since late 2021. Investors are closely watching this space, anticipating a breakthrough that could reshape the dynamics of the sports betting industry.


Silvia has dabbled in all sorts of writing – from content writing for social media to movie scripts. She has a Bachelor's in Screenwriting and experience in marketing and producing documentary films. With her background as a customer support agent within the gambling industry, she brings valuable insight to the Gambling News writers’ team.

Leave a Reply

Your email address will not be published. Required fields are marked *