Barstool Announces Historic Deal with DraftKings

In a dramatic return to the sports betting arena, Barstool Sports, under the leadership of its CEO and founder Dave Portnoy, has inked a groundbreaking multi-year agreement with DraftKings, establishing the latter as the official sports betting partner of Barstool Sports.

This deal, announced in the wake of Super Bowl LVIII, marks a significant chapter in Barstool’s history, symbolizing a full-circle moment for Portnoy and his company.

Dave Portnoy took to social media to express his enthusiasm about the partnership, hinting at the monumental scale of the deal.

dave portnoy

Dave Portnoy

“We are back in the gambling business,” he proclaimed, highlighting the substantial nature of the agreement with DraftKings, which he teased might be one of the biggest in the gambling space to date.

This partnership renewal comes at a pivotal time for Barstool Sports, following a brief separation from the sports betting landscape after PENN Entertainment severed ties with Barstool to forge a new alliance with ESPN, culminating in the launch of ESPN BET.

The separation saw PENN selling Barstool back to Portnoy for a nominal $1, after initially acquiring it for a staggering $550 million, positioning Portnoy as a significant beneficiary of the transaction.

The collaboration between DraftKings and Barstool isn’t their first rodeo; the two powerhouses had previously joined forces in a marketing venture a decade ago. This rekindled partnership is set to debut with an engaging free-to-play contest centered around a free-throw shooting challenge at the Barstool Sports offices, showcasing Barstool employees’ teamwork in pursuit of 41 consecutive free throws.

Portnoy’s announcement, delivered with characteristic flair, underscored the strategic timing of the deal’s unveiling, coming to light mere minutes after the Kansas City Chiefs clinched a 25-22 overtime victory against the San Francisco 49ers in Super Bowl LVIII.

This timing was meticulously planned, adhering to a non-compete clause from Barstool’s previous ownership arrangement with Penn, which precluded any partnership deals until after the Super Bowl.

In a celebratory video, Portnoy, alongside other Barstool personalities, mimicked a classic American Express commercial from “Major League,” illustrating the excitement and theatricality that Barstool brings to its ventures.

“Breaking News: I’m proud to announce that Barstool has signed a multi-year monster deal with DraftKings,” Portnoy declared, emphasizing the rejuvenated partnership’s significance and the anticipation of returning to Barstool’s sports betting roots.

The deal’s announcement not only heralds a new era for Barstool Sports and DraftKings but also signifies a reshuffling of alliances within the dynamic sports betting industry.

As Barstool and DraftKings embark on this revitalized partnership, the landscape of sports betting and online gaming awaits the innovative offerings and immersive experiences that are sure to emerge from this collaboration.

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With a potent blend of lived experience and technical expertise, Stephen Naumov stands as a distinctive voice in Mr. Sweepstakes's content team. Born in the historic city of Sofia, Bulgaria, Stephen studied economics at New Bulgarian University and also enriched his expertise by becoming a software engineer at the renowned Telerik Academy.