By Alex Raskin Sports News Editor for Dailymail.com 00:34 September 30, 2023, updated 01:37 September 30, 2023
- Dave Portnoy of Barstool Sports has reportedly spent $42 million on a waterfront property in Nantucket
- Portnoy, 46, recently announced layoffs at the controversial sports and culture website
- DailyMail.com provides the latest international sports news
Barstool Sports founder Dave Portnoy has reportedly spent $42 million on a waterfront property in Nantucket just weeks after announcing layoffs for the controversial site.
According to a Wall Street Journal report, the price is a record for the island off the coast of Massachusetts, surpassing the $38.1 million mark set in June.
The site spans 1.2 acres along Nantucket Harbor and includes $2 million worth of furniture, people familiar with the deal told WSJ.com. Best of all, the site features an underground tunnel connecting a two-bedroom guesthouse with a separate studio, as well as a pool.
A native of Swampscott, Massachusetts, Portnoy previously purchased a $2 million estate on the island, but has raised significantly more money thanks to his $550 million sale of Barstool Sports to gaming conglomerate Penn Entertainment.
However, according to a security filing, the 46-year-old regained full control of the company in August when he bought it back for just $1. Since then, Portnoy has announced layoffs at Barstool Sports, saying the company is “losing a lot.”
Barstool Sports founder Dave Portnoy reportedly spent $42 million on a waterfront property in Nantucket (pictured). Portnoy’s new property overlooks Nantucket Harbor. Barstool Sports founder Dave Portnoy (pictured right, with his girlfriend Silvana Mojica) already owned a $2 million estate in Nantucket, but has reportedly spent $42 million on his new estate. The property includes a primary residence, a pool and several guest quarters, according to a Wall Street Journal report
The seller is identified by the WSJ as two trusts – MAK Daddy Trust and MAK Shack Trust – and was sold by Shellie Dunlap of Lee Real Estate.
The house, located in the Monomoy area of the island, was completed in 2018. The previous owners added adjacent properties for $13.3 million in 2016 and then demolished two existing buildings to complete the site.
Designed by Andrew Kotchen of Workshop/APD, the main house has four bedrooms, one of which has an indoor-outdoor shower and retractable glass doors overlooking the harbor.
Nantucket villa prices have recently skyrocketed due to high demand and limited availability, the WSJ reports.
There have been several sales approaching $40 million in recent years.
According to Dunlap, the previous owners decided to sell due to the strong market.
“They recognized the strength of the market and the moment we are in,” Dunlap told WSJ.com. “If there’s high-quality construction and a buyer can literally jump right in, they’re willing to pay a premium.”
Pictured: The kitchen in the primary residence of Dave Portnoy’s new $42 million estate overlooking Nantucket Harbor. Designed by Andrew Kotchen of Workshop/APD, the main house has four bedrooms, one of which has an indoor-outdoor shower and folding glass doors that overlook the harbor
The purchase comes at a precarious time for Barstool Sports.
“I made myself very clear,” Portnoy said in August when he announced layoffs. “Anyone who’s been paying attention, we’re going to have layoffs and cutbacks, and they started it, and it sucks.”
“And people who have known me since the beginning, I hate firing people.” You can be incompetent, not working and I generally don’t fire because I hate it so much. It’s the worst thing you can do.
“Nevertheless, we are in a position where it is a matter of course. It’s not that I have these morals – well, you can’t do it because no one will have a job. We won’t all have jobs. So we need to get back to a break-even value. We’re losing a lot and it sucks.’
On the surface, Penn’s decision to sell the site back to Portnoy looked like a big win for Barstool’s El Presidente. He got his company back and didn’t have to pay for the privilege.
He also reversed some of Penn’s most unpopular decisions, such as the firing of blogger and podcast host Ben Mintz (aka Mintzy), who was fired for saying the N-word while reading rap lyrics during a broadcast.
Dave Portnoy wears a t-shirt mocking Roger Goodell during an appearance on NBC in 2017. Portnoy clashed with Penn executives over several issues, including the firing of Ben Mintz in May
But the deal was subject to certain conditions. The sale of all shares of Barstool to Portnoy for $1 was “in exchange for certain non-compete and other restrictive covenants,” which is significant for a site that has traditionally relied on gambling-related advertising. Additionally, if Portnoy ever attempts to sell Barstool again, Penn will be entitled to half of the gross proceeds.
Although he’s usually quick to declare himself the winner in any situation, Portnoy might be a little humbled by his experience with Penn. After years of mocking traditional sports media with his successful genre of childish, sexualized content, Portnoy is now busy rebuilding his “pirate ship,” as he calls it.
A native of Swampscott on the north coast of Massachusetts, Portnoy was a high school classmate of future ESPN college football analyst Todd McShay (the two actually share the same birthday). The dedicated Patriots fan later enrolled at the University of Michigan and studied in Ann Arbor while Tom Brady was a player for the Wolverines.
Portnoy returned to the Boston area after earning a degree in education and worked for an IT market research company for several years before launching a four-page sports newspaper in 2003.
This newspaper was the first edition of Barstool Sports and, like its successor website, attracted teenagers and young men with photos of women in bikinis and frequent attacks on political correctness.
It was hardly an immediate success, and Portnoy filed for bankruptcy protection in 2004, facing around $90,000 in debts and back taxes, including $30,000 in gambling losses, the New York Times reported in 2022.
But things started to change after Barstool morphed into a blog in 2007. Soon the site was benefiting from daily features such as “Local Smokeshow of the Day,” featuring photos of attractive women, One Bite Pizza reviews, and “Guess That Ass.” ‘ and that’s more or less what it sounds like.
Meanwhile, Portnoy cultivated his “El Presidente” identity by unapologetically engaging in controversy and sparking some of his own.
Like Mintz, Portnoy said the N-word on air, for which he later apologized, and was banned from Boston sports radio station WEEI after posting a nude photo of Brady’s 20-month-old son.
“We don’t shy away from controversy — we stoke the fire,” Portnoy told NBC in 2013. “People think we’re doing everything we can to make it, but we’re not.” We’re not trying to get new readers by being crazy and outrageous. Our readers understand what we do, and I don’t think about how it will look to the outside world. I don’t really care.’
Portnoy is particularly pleased to attack commissioner Roger Goodell over the league’s “Deflategate” scandal, in which Brady was punished for allegedly deflating footballs in violation of NFL rules. Scholars have insisted that the NFL failed to prove its case against Brady, who may actually have been exonerated by the league’s data, and Portnoy has never forgiven Goodell for Brady’s four-game suspension.
Portnoy and three other Barstool employees then protested at NFL headquarters in Manhattan in 2015 and handcuffed each other in the lobby. Four years later, Portnoy was briefly arrested after creating fake press credentials to gain access to Super Bowl LIII in Atlanta.
It was around this time that Portnoy became increasingly political. He had always been outspoken about his stock picks and gambling predictions, but when Donald Trump emerged as a possible presidential candidate, Portnoy began ingratiating himself with conservatives.
“I’m voting for Donald Trump,” Portnoy wrote on his blog in 2015. “I don’t care if he’s a joke.” I don’t care if he’s racist. I don’t care if he’s sexist. I don’t care about any of that. I hope he stays in the race and I hope he wins. Why? Because I love the fact that he makes other politicians squirm. “I love the fact that he says shit that no one else will say, no matter how ridiculous it is.”
Barstool Sports lent its name to the casino chain, but that signage will soon be replaced
In the coming years, Portnoy became a regular guest on Tucker Carlson’s Fox News show, where he often defended himself against a growing number of scandals.
Portnoy was the subject of a National Labor Relations Board investigation in 2019 over Twitter posts that claimed he threatened to fire workers if they unionized. He eventually reached an informal agreement with the board, but did not face a significant financial penalty.
Then, after his infamous decision to sell Barstool Sports to Penn in 2020, Portnoy was accused of sexual misconduct in a 2021 expose by Business Insider. Portnoy has denied the claims and insisted the article was a “hit piece”.
Portnoy later sued Insider, claiming the reporting was “false and defamatory,” but the lawsuit was ultimately dismissed.
The scandal forced Penn CEO Jay Snowden to allay shareholder fears during a February 2022 earnings call. According to Bloomberg, Snowden told his listeners to “take this time to make this happen.”
“There is no doubt that more will happen in the coming days, just as it did three months ago,” Snowden said, quoted by Bloomberg.
Soon after, a second Business Insider article was published containing new claims that he had filmed himself having sex with women who did not know they were being recorded.
David Portnoy, founder of Barstool Sports, speaks during a radio show in 2020
The incident was a harbinger of Portnoy and Barstool’s growing problems with Penn, which was concerned about how the news would affect the company’s stock price and reputation with regulators.
These fears appear to have led Penn to divest itself from Barstool entirely, particularly after the Ohio Casino Control Commission (OCCC) fined Penn $250,000 over a Barstool event at the University of Toledo in December 2022 . The event violated two state gambling regulations that bar sports betting from promoting sports betting to students and minors.
“Penn Entertainment and Barstool Sports have gone their separate ways,” Portnoy said in a released video. “That’s right, for the first time in a decade I own 100 percent of Barstool Sports.”
“Every time we did something, it was one step forward and two steps back,” Portnoy continued. “We were denied a license because of me.” You name it. Therefore, the regulated industry is probably not the best place for Barstool Sports and the type of content we create.”