Barstool Sports, DraftKings Eye Lucrative Betting Partnership

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Barstool Sports is once again edging towards the high stakes table of sports betting partnerships, as it enters advanced negotiations with DraftKings, a leader in the digital sports entertainment and gaming industry. If the deal materializes, Barstool, under the guidance of its founder David Portnoy, will be thrust back into the limelight of sports wagering following its recent split from Penn Entertainment.

This prospective collaboration is set to be a “more traditional marketing partnership,” with Barstool Sports leveraging its influential platform to broadcast DraftKings’ odds and direct its substantial audience towards the betting operator’s services. Acknowledging that the fine print is yet to be penned, insiders reveal that if such an agreement was to be sealed, it could prove lucrative for Barstool, possibly surpassing the $10 million mark on an annual basis.


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Although still navigating through the sports gambling conversations, Barstool hasn’t secured a similar marketing deal since Portnoy reacquired the company last August, snapping it back from Penn’s hands for the nominal sum of $1. This came after Penn had shelled out an enormous $551 million to initially acquire Barstool, only to later endure a staggering $850 million write-down post-divestment.

A clause inked during the dissolution of Barstool’s tenure with Penn indicated that if Portnoy chose to sell the media enterprise to another gambling firm, Penn would be entitled to half of the financial gains. As of now, it isn’t a sale that’s on the table, but rather, a strategic marketing move with DraftKings—potentially exploiting a loophole in the noncompete duration specified by Penn.

Those watching the calendar were quick to note that any development between Barstool and DraftKings would only surface post-current NFL season, adhering to a term of the separation agreement with Penn that restricts Barstool from wagering ventures until after the Super Bowl. And yet, the significance of sports betting to Barstool’s content portfolio suggests it’s not a matter of if but when it will revisit such a partnership.

The ties between Barstool Sports and DraftKings have roots that run deep and mutual, with both organizations springing from Bostonian soil. Moreover, DraftKings has demonstrated a deft hand in media collaborations, previously acquiring the Vegas Stats & Information Network (VSiN) and clinching a content distribution deal with Meadowlark Media.

The contemplated union of these two powerhouses comes at a time when DraftKings itself has gained an edge, with some observing that the Penn-ESPN alliance has relieved DraftKings of a costly sports network relationship. It paints the picture of a strategic repositioning that might just herald a reshuffling of the deck in the sports betting ecosystem.


As we circle back to the essence of betting and gaming, it becomes clear that the navigation of this landscape is of significant interest to many enthusiasts. With the potential re-entry of Barstool Sports into the realm of gambling through a DraftKings partnership, it’s opportune to consider where one might engage in such activities online.

Balancing the thrill of the game with the safety of responsible play, we have curated a list of the top online casinos for this month. Whether you’re a seasoned bettor or new to the scene, exploring these [top online casinos in Canada offers a comprehensive experience from the comfort of your home. At West Island Blog, we pride ourselves on guiding our readers through an ever-expanding digital casino floor, ensuring you’re always at the forefront of the best betting avenues available.