Barstool Sports Eyes DraftKings Betting Deal Amidst Industry Shuffle

Barstool Sports in Talks with DraftKings for a Lucrative Betting Deal

In a significant development within the sports betting industry, Barstool Sports is currently in discussions with DraftKings to forge a partnership potentially valued in the low eight figures annually. This comes after Dave Portnoy, the company's founder, has taken back control of Barstool Sports in a remarkable turn of events.

Barstool's Lock-Up Arrangement Postpones Deals

Despite the buzz surrounding this potential alliance, Barstool Sports must navigate a lock-up arrangement that prevents them from finalizing any betting deals until the conclusion of the Super Bowl. This stipulation puts a temporary hold on their ambitions to re-enter the sports betting market immediately.

Penn Entertainment Divests from Barstool

The backdrop to these negotiations is Penn Entertainment's decision to sell its stake in Barstool back to Portnoy for the nominal fee of $1. Penn had previously invested heavily in Barstool, initially acquiring 36% of the company for $163 million before purchasing the remaining 64% for an additional $388 million. However, the strategy to leverage Barstool's brand to boost their own sportsbook fell short of expectations, prompting Penn to part ways with Barstool and subsequently take an $850 million write-off from the acquisition.

New Horizons: ESPN Bet Emerges

Following the divestiture, Penn has not exited the betting scene but instead formed a new partnership with ESPN to create ESPN Bet. This strategic move came after Penn recognized that their collaboration with Barstool did not yield the anticipated results.

Financial Stakes and Future Sales

The financial intricacies of the deal between Portnoy and Penn include a clause where if Portnoy decides to sell Barstool in the future, Penn will be entitled to half of the gross proceeds. This agreement signifies Penn's continued vested interest in Barstool's financial trajectory even after stepping away from direct ownership.

Barstool's Betting Industry Ban

Currently, Barstool is barred from directly participating in the betting industry until the current NFL season is over. This restriction is part of the lock-up terms, yet it does not deter Barstool's intention to make a strong comeback in the sports betting space once the season concludes.

DraftKings Slows Down Marketing Investment

DraftKings, a leading contender in the sports betting market, has significantly invested in sales and marketing, with expenditures reaching $1.19 billion in fiscal 2022. Notably, this marks the first time in over three years that DraftKings has reduced its marketing spend. The reduction coincides with DraftKings ending its marketing partnership with ESPN, which has since allied with Penn for ESPN Bet.

Barstool's Continued Influence in Gambling

Despite the ongoing negotiations and restrictions, Barstool continues to exert influence in the gambling world by offering advice and picks to its audience. Their plan to expand their presence through strategic partnerships is clear, as they aim to re-establish themselves as a formidable entity in sports betting.

Portnoy's Vision for Barstool's Betting Future

Dave Portnoy remains optimistic about Barstool's role and future in sports betting, stating, "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." His comment reflects both the historical significance of betting to Barstool's brand and the forward-looking ambition to regain prominence in the industry. As negotiations between Barstool Sports and DraftKings continue, the sports media landscape watches with keen interest. The outcome could shape the dynamics of sports betting partnerships for years to come, with Barstool poised to make a notable impact once again.