The Founder of Barstool Sports is Betting $1 Million on a College Football Game - Here's Why

Dave Portnoy, the irreverent and entrepreneurial mind behind Barstool Sports, recently made headlines by placing a hefty $1 million bet on Michigan. However, this wager is just one in the saga of Portnoy's audacious financial moves this year. 

Most notably in what is considered to be Portnoy's savvy moves, he managed to buy back Barstool Sports for a mere $1, a move that stunned the business world. Here are some of his most shocking money moves yet.

Portnoy's $1 million bet on Michigan

Let's start with the most recent headline-grabbing move — Portnoy's $1 million bet on Michigan. Known for his adventurous spirit, Portnoy is no stranger to placing high-stakes bets, but this one caught the attention of many. Betting on sports has become a trademark for Portnoy, aligning with Barstool Sports' foray into the sports gambling space. 

Surely there will be many waiting for the outcome of this bet, as many think the game is too close to call for that kind of wager. The college football world has been debating whether Alabama, seeded fourth to Michigan's #1 overall seed, deserved to make it into the playoff over an undefeated Florida State team that lost their quarterback to an injury. 

While Portnoy clearly took sides in the argument stating, with his money, that Michigan would blow out the possibly undeserving team, is it a crazy bet? Only time will tell for sure but for someone who is reportedly worth more than $100 million, it might not matter all that much, especially if it drums up attention to Barstool. If Michigan loses and Barstool doesn't benefit then the entrepreneur might want to learn how to stop throwing money away.

The $1 Barstool buyback

In a move that left many scratching their heads, Portnoy orchestrated a deal to buy back Barstool Sports from its parent company, Penn Entertainment, for the symbolic sum of $1. This transaction came after Penn Entertainment gained full control of Barstool earlier in the year, completing a deal worth $551 million. The sale raised eyebrows, especially considering that Penn Entertainment expects to incur losses between $800 million to $850 million.

If Portnoy decides to sell Barstool again, Penn Entertainment has secured the right to receive 50% of the gross proceeds. However, in a video announcing the deal, Portnoy asserted that he has no intentions of parting with Barstool Sports again. The reasons behind this peculiar transaction lie in the challenges Barstool faced while operating in the highly regulated gambling space.

Portnoy cited the difficulty of navigating the regulated industry, stating, "Every time we did something, it was one step forward, two steps back. We got denied licenses because of me. You name it. So the regulated industry is probably not the best place for Barstool Sports and the type of content we make." This buyback allows Barstool to return to its roots, or as Portnoy puts it, "back to the pirate ship."

Abandoning Barstool's $2 Billion ESPN rebranding

Prior to this buyback, Penn Entertainment had inked a $2 billion deal with ESPN, intending to rebrand Barstool Sportsbook as ESPN Bet. This strategic move aimed to leverage Barstool's popularity in the sports gambling arena while repositioning it under the ESPN umbrella. However, Portnoy's decision to reclaim Barstool signaled a departure from this planned rebranding, providing an unexpected twist to the narrative.

Portnoy's other unconventional business moves

Dave Portnoy's financial journey is a rollercoaster of unconventional decisions and risks. From founding Barstool Sports as a print sports publication in 2003 to turning it into a digital sports media empire, Portnoy has consistently defied norms. The initial sale of Barstool to Penn Entertainment in 2020 for $551 million was already a lucrative move for Portnoy. However, the audacity to buy it back for a nominal sum of $1 showcases his fearless approach to business.

Portnoy's net worth reflects the success and financial gains he has reaped from his ventures. The controversies surrounding Portnoy, including criticism for comments and accusations of alleged violent encounters, add a layer of complexity to his public persona. One thing is for sure though, he knows how to garner attention.

Bottom line

Dave Portnoy's $1 million bet on Michigan is just the latest chapter in a year marked by bold money moves. From the symbolic $1 buyback of Barstool Sports to the planned ESPN rebranding, Portnoy's unconventional business decisions continue to captivate and confound. Whether he's making headlines for his bets, buybacks, or controversies, one thing is certain — Dave Portnoy remains a maverick in the business world, navigating uncharted waters and rewriting the rules of the game.