Barstool Sports Eyes DraftKings Deal Amid Betting Market Changes

Barstool Sports Enters Negotiations with DraftKings

In a significant development within the sports betting industry, Barstool Sports has initiated discussions for a potentially lucrative partnership with DraftKings. The move comes after Dave Portnoy, the company's founder, regained control of the popular sports and pop culture blog.

Deal Details and Financial Implications

Sources close to the matter suggest that if the negotiations are successful, the partnership could yield low eight figures annually for Barstool. However, any formal agreement will have to wait until the conclusion of the Super Bowl due to an existing lock-up arrangement.

Penn Entertainment Divests from Barstool

The backdrop to these negotiations is Penn Entertainment's decision to sell their stake in Barstool back to Portnoy for a nominal fee of $1. This transaction marks a sharp turn from Penn's initial investment strategy, where they acquired 36% of Barstool for $163 million, followed by the remaining 64% for an additional $388 million. Despite their efforts, Penn's strategy to leverage Barstool's brand to bolster their own sportsbook offerings did not meet expectations. Consequently, Penn has since partnered with ESPN to create a new venture, ESPN Bet, and took an $850 million write-off from the original Barstool acquisition.

Future Sale Provisions

A clause in the agreement stipulates that should Portnoy decide to sell Barstool, Penn would receive half of the gross proceeds from the sale, safeguarding their financial interests to some extent.

Barstool's Betting Industry Aspirations

Barstool remains a key player in the gambling advice arena and is barred from entering the betting market only until the current NFL season ends. With a clear intent to re-enter the sports betting market, Barstool is positioning itself to capitalize on future opportunities in this space.

DraftKings Scaling Back Marketing Investments

DraftKings, meanwhile, has been adjusting its marketing strategies. After investing $1.19 billion in sales and marketing during fiscal 2022, the company saw a decrease in such expenditures for the first time in over three years. This scaling back coincided with the termination of DraftKings' marketing partnership with ESPN, which pivoted to collaborate with Penn on ESPN Bet.

Barstool's Ongoing Influence and Future Plans

Despite the shifting landscape, Barstool continues to influence the betting community by providing gambling advice and picks. The quote from an unnamed source at Barstool underscores the brand's commitment to sports betting: "I would still argue that [sports betting] is a huge part of what we do today. Our crew bets obsessively on games, we always have... But I think you'll see, into next year, that we start to establish ourselves back in that space." This statement reflects Barstool's ambition to not only maintain its presence but also to expand its footprint through strategic partnerships in the betting industry.

Conclusion

The unfolding scenario presents a fascinating chapter in the sports betting narrative. Barstool Sports' pivot back towards its roots in sports betting, coupled with its potential alliance with DraftKings, signals a robust attempt to reclaim a dominant position in the market. At the same time, Penn Entertainment's shift in strategy and partnership with ESPN indicates a dynamic and evolving sector where media and betting continue to converge in innovative ways. As the industry watches closely, the outcomes of these negotiations and partnerships will undoubtedly shape the future of sports betting.