Dave Portnoy: History & Net Worth

Dave Portnoy is the charismatic genius behind Barstool Sports. An extremely outspoken individual who doesn’t sugarcoat how he feels. He is self-described as having “f*ck you money.” But how much is Dave Portnoy worth?

His infamous buyback of Barstool Sports for a mere $1—a company he previously sold to Penn Entertainment for $551 million—will certainly go down in history as one of the most epic business deals of our generation.

Penn Entertainment, a sports betting platform based in Pennsylvania, struggled to gain regulatory approval and licensing for Barstool Sports. Portnoy stated in a video that, “Every time we did something, it was one step forward, two steps back. We got denied licenses because of me. You name it.”

In 2020, Penn Entertainment originally purchased a 36% share in Barstool Sports for $163 million. That gave it a valuation of $452.77 million. In February of 2023, Penn paid an additional $388 million for the remaining shares for a total sum of $551 million to Portnoy.

Dave Portnoy History

Portnoy grew up in Massachusetts. His dad was a lawyer and his mom was a high school teacher. Portnoy attended the University of Michigan and received a degree in education. While at the University, Dave founded a site called thegamblingman.com. This is where he put out all his favorite picks in sports. While it is no longer operational, this was the start of Portnoy’s foray into sports media.

A few years later, in 2004, Portnoy launched Barstool Sports. Originally, this was a four-page newspaper that he handed out on the street corners and subway stations in Boston. Originally, all the content in the paper was written by Portnoy. However, he started bringing on freelance writers such as ESPN’s Todd McShay, one of his classmates at the University of Michigan.

Initially, the paper didn’t receive much traction. But the appeal to the younger generation and the middle finger to political correctness resonated with many young adults at the time. It wasn’t until a short time later when Portnoy began placing pictures of women in bikinis on the front of the paper that the Barstool Sports “newsletter” started taking off.

In 2007, Barstool Sports transitioned to a blog and Portnoy began sealing his reputation as a brandish, outspoken “El Presidente.” Barstool Sports blog attracted many advertisers in the sports betting arena. This included the illegally operating, Party Poker website, but also many others. Barstool Sports quickly grew as a Sports Media Company.

Acquisition by Chernin Group

In 2016, before the Penn acquisition, Portnoy sold a 51% stake in Barstool Sports for $163 million to investor, Peter Chernin of The Chernin Group (TCG). The Chernin Group is a stakeholder in numerous companies such as Doug Demuro’s Cars & Bids, Funko, and Pandora, and was a former stakeholder in Twitter (prior to the acquisition of Musk), along with many others.

That $163 million placed an overall valuation on Barstool Sports at $320 million. Meaning, the Penn acquisition of $551 million gave Portnoy $270 million in free cash before taxes. Combining the $270 million with the $163 million he received initially would total $433 million before taxes.

However, 6 months after the Penn acquisition, Portnoy purchased the company back for $1. That gives him 100% control over the company he sold twice, with the most recent valuation of $551 million. The only caveat is that if Barstool Sports is ever sold he agrees to pay Penn Entertainment 50% of the proceeds. But Portnoy stated in a video that he will never sell Barstool Sports again.

One Bite Everyone Knows The Rules

In 2017, off the heels of his breakup with his wife and a major cash injection from Peter Chernin’s TCG, Portnoy had the goal of rating every single pizza shop in Manhattan from 0 to 10 based on a slice of pizza. His video series, which he starts off by always saying “One bite, everyone knows the rules” is a viral smash hit today. Portnoy is known for his infamous ratings that often never make it above a 9 out of 10.

Portnoy uses multiple factors in his decision. He favors crispy pizza with solid undercarriage and tends to dislike sloppy or soft pizza slices. His pizza ratings often drive droves of Barstool Sports fans who flock to the pizza shops he gives anything above a 9 out of 10. To date, he has given one pizzeria a perfect 10. You can see a list of all the scores ranked here.

He has also given several 0 out of 10 scores. Portnoy was widely criticized when he got into an altercation with Charlie Redd, the owner of Dragon’s Pizzeria in Sommerville, Massachusets. In 2020, Portnoy donated $500,000 to struggling pizzerias in the wake of the pandemic and also raised over $39 million for pizza shops on the brink of failure through his platform.

Where Does Dave Portnoy Live?

Dave Portnoy lives in Miami, Florida. He purchased 5811 Bayshore Drive in Miami for nearly $14 million in 2021. In 2023, Portnoy purchased a $42 million “vacation home” in Nantucket. Florida has no state tax so the move was likely a strategic one, and well played because in 2023 he saved tens of millions of dollars by calling Florida his home state in the wake of the Penn deal.

Portnoy has always had a fascination with Nantucket, a tiny island in Massachusetts. The island is located roughly 30 miles just south of Cape Cod and features some of the most expensive real estate in the Northeast.

Nantucket Island is often called the “Billionaire’s Island” and Portnoy recently stated on X that “Nantucket has always been my favorite place on earth. The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home.”

How Much Money Does Dave Portnoy Have?

Dave Portnoy has a lot of money. In 2019 he claimed his net worth was $100 million. Considering he sold a 51% stake in Barstool Sports for $163 million in 2016, after taxes and investments, those numbers certainly add up. However, Portnoy’s divorce in 2017 from Renee Portnoy means he likely gave up half of those funds.

When you add it all up, combined with his recent re-acquisition of Barstool Sports, investments, and real estate portfolio, Portnoy has an estimated net worth of $838 million on paper. That is a wild sum of money. That just goes to show you what you can achieve when you follow your passions in life. Portnoy’s appeal certainly comes from his do-not-care-what-you-think personality.

He is an authentic and charismatic figure who is one of the most loyal individuals. Once you’re inside Portnoy’s circle, he will do whatever he can to take care of you.