Barstool Sports Founder Dave Portnoy Now Owns $100 Million Worth Of Real Estate Thanks To Latest $28 Million Florida Mansion Purchase

I heard about Dave Portnoy's latest $28 million mansion purchase in a group chat. The guy who shared the news also posed: "I can't figure out if I love or hate this guy." The other half-dozen guys on the chain, including myself, quickly replied, "Love him."

Here's why I am a fan of Dave. First off, I do not care about sports. I don't care which team he's choosing to bet for or against this week. I don't care what Dave thinks of NFL Commissioner Roger Goodell. I love Dave's professional business story.

For those who are not aware, Dave founded Barstool Sports back in 2003 originally AS A PRINT PUBLICATION! The paper offered fantasy sports predictions, gaming ads, and sports coverage. The website wasn't launched until 2007. Over the next ten years, Barstool would grow into an unlikely sports media powerhouse.

In 2016, Dave first sold a majority stake in Barstool Sports to The Chernin Group. In January 2020, Penn Gaming acquired a 36% stake from the founders for $163 million. This purchase came with an option to buy the entire company at a future date. In August 2022, Penn Gaming exercised that option to buy Barstool outright at a valuation of $390 million.

In a surprise twist, on August 8, 2023, it was revealed that Penn divested its stake in Barstool as part of a separate licensing deal it had signed with ESPN. As a result, Penn agreed to sell Barstool back to Dave for $1.00.

To recap – From start to finish, over all transactions, Penn Gaming paid $550 million to buy Barstool. Then just 12 months after securing its largest and most valuable stake, Penn sold it all back to Portnoy for a buck. Dave has since vowed never to give up control again.

Over the course of each of these transactions, Dave got very wealthy. By our estimate, the original Pen Gaming deal in 2020 pushed his net worth to $100 million for the first time. Based on the latter transactions and today's estimated value of Barstool, we currently peg Dave Portnoy's net worth at $250 million. Oh. And that $250 million includes a really impressive real estate portfolio.

$97 Million Real Estate Portfolio

In 2015, Dave made his first major real estate purchase when he bought a waterfront home in Nantucket for about $2 million. In 2023, he shattered a Massachusetts sales record by paying $42 million for a six-bedroom, 8,600-square-foot compound in Nantucket's Monomoy area.

In 2021, Portnoy paid just under $14 million for a nine-bedroom, 1930s-era mansion in Miami's Morningside neighborhood, setting a record for the area. The bayfront property features 150 feet of waterfront, a pool, cabana, and guesthouse. After purchasing this mansion, he embarked on extensive renovations. Unfortunately, as he has made clear over social media, the project became notorious for delays and a mold problem that was reportedly so bad that he threatened to take legal action against his contractor.

In 2021, he also bought a newly built home in the Hamptons hamlet of Montauk, paying around $9.75 million in an off-market deal.

In 2023, Portnoy bought a $1.4 million home in Saratoga Springs, New York, overlooking the Oklahoma Training Track. A lifelong racing fan and thoroughbred owner, he replaced the existing 1960s structure with a new two-story home featuring a large patio and direct track views.

And then there's his most recent transaction, which literally closed on the Multiple Listing Service today. It was just revealed, as first noted by the Wall Street Journal, that Dave has paid yet another record-setting (for the area) $27.75 million for a 1.65-acre island compound located in Islamorada, Florida. The compound includes a 7,600-square-foot main house, a 2,700-square-foot guesthouse, two pools, a private dock, and an outdoor pizza oven — a quirky but fitting touch for the man behind the "One Bite Pizza Reviews."

Assuming he still owns his first Nantucket house, and he does appear to still own every other property mentioned above, in the last decade, Dave has spent $96.9 million on real estate. And you know what, I think he's earned it! Here is a video tour of his latest Florida island compound purchase:

Whether you love or hate him, you have to admit, who else in history has turned pizza reviews and sports banter into a quarter-billion-dollar net worth with a $100 million real estate empire?