Barstool Sports founder Dave Portnoy has reportedly splurged $42 million on a waterfront Nantucket compound just weeks after announcing layoffs for the controversial website.

The price tag is a record for the island off the coast of Massachusetts, breaking a $38.1 million mark set back in June, according to reporting by The Wall Street Journal.

The compound spans 1.2 acres on Nantucket Harbor and includes $2 million worth of furniture, people familiar with the deal told WSJ.com. Best of all, the compound features an underground tunnel connecting a two-bedroom guesthouse to a separate studio, as well as a pool. 

A native of Swampscott, Massachusetts, Portnoy previously purchased a $2 million property on the island, but has since banked considerably more money thanks to his $550 million sale of Barstool Sports to gaming conglomerate, Penn Entertainment.

However, the 46-year-old regained full control of the company in August when he bought it back for just $1, according to a security filing. Since then, Portnoy has announced layoffs at Barstool Sports, saying that the company is ‘losing a lot.’

Barstool Sports founder Dave Portnoy has reportedly splurged $42 million on a waterfront Nantucket compound (pictured)

Barstool Sports founder Dave Portnoy has reportedly splurged $42 million on a waterfront Nantucket compound (pictured)

Portnoy's new property overlooks Nantucket Harbor

Barstool Sports Founder Dave Portnoy (pictured, right, with his his girlfriend, Silvana Mojica) already owned a $2 million property on Nantucket, but has reportedly splurged $42 million on his new compound

Barstool Sports Founder Dave Portnoy (pictured, right, with his his girlfriend, Silvana Mojica) already owned a $2 million property on Nantucket, but has reportedly splurged $42 million on his new compound (pictured left)

The property includes a main residence, pool, and multiple guest quarters, according to reporting by the Wall Street Journal

The property includes a main residence, pool, and multiple guest quarters, according to reporting by the Wall Street Journal

The seller is identified by the WSJ as a pair of trusts — MAK Daddy Trust and MAK Shack Trust — and was sold by Shellie Dunlap of Lee Real Estate.

The home, which is located on the Monomoy area of the island, was completed in 2018. The previous owners added adjacent parcels of land in 2016 at a cost of $13.3 million and subsequently demolished a pair of existing structures to complete the compound.

The main house, designed by Andrew Kotchen of Workshop/APD, includes four bedrooms, one of which has an indoor-outdoor shower as well as foldaway glass doors that look out onto the harbor.

Prices for Nantucket mansions have recently spiked due to high demand and limited availability, the WSJ reports.

In recent years, there have been multiple sales approaching $40 million.

It was due to the strong market that the previous owners decided to sell, according to Dunlap.

‘They saw the strength of the market and the moment in time we’re in,’ Dunlap told WSJ.com.’When there’s quality construction and a buyer can literally walk right in…they’re willing to pay a premium.’

Pictured: The kitchen in the main residence of Dave Portnoy's new $42 million compound overlooking Nantucket Harbor

Pictured: The kitchen in the main residence of Dave Portnoy’s new $42 million compound overlooking Nantucket Harbor 

The main house, designed by Andrew Kotchen of Workshop/APD, includes four bedrooms, one of which has an indoor-outdoor shower as well as foldaway glass doors that look out onto the harbor

The main house, designed by Andrew Kotchen of Workshop/APD, includes four bedrooms, one of which has an indoor-outdoor shower as well as foldaway glass doors that look out onto the harbor

The purchase comes at a precarious time for Barstool Sports.

‘I’ve been very clear,’ Portnoy said in August while announcing layoffs. ‘Anybody that’s paid attention, we are going to have layoffs and cuts, and they’ve started and it sucks.

‘And people who know me from the beginning, I hate firing people. You can be incompetent, not work and I generally don’t fire because I hate it so much. It’s the worst thing to f*****g do.

‘Having said that, we’re in a position it’s a no-brainer. It’s not like I have that moral – well you can’t do it because nobody will have jobs. We’ll all not have jobs. So we have to get back to a break-even thing. We’re losing a lot and it sucks.’

On its surface, Penn’s decision to sell the website back to Portnoy looked like a major win for Barstool’s El Presidente. He got his company back and didn’t have to pay for the privilege.

What’s more, he reversed some of Penn’s most unpopular decisions, such as the firing blogger and podcast host Ben Mintz (a.k.a. Mintzy), who was let go for saying the N-word while reading rap lyrics during a broadcast.

Dave Portnoy wears a shirt mocking Roger Goodell during a 2017 appearance on NBC

Dave Portnoy wears a shirt mocking Roger Goodell during a 2017 appearance on NBC 

Portnoy clashed with Penn executives over several issues, including Ben Mintz's firing in May

Portnoy clashed with Penn executives over several issues, including Ben Mintz’s firing in May

But the deal had some strings attached. The sale of all of Barstool’s stock to Portnoy for $1 came ‘in exchange for certain non-compete and other restrictive covenants,’ which is significant for a website that has traditionally relied on gambling-related advertising. Furthermore, if Portnoy ever tries to sell Barstool again, Penn has rights to half the gross proceeds.

Although he’s normally quick to declare himself the winner in any situation, Portnoy might be a bit humbled by his experience with Penn. After years of taunting traditional sports media with his successful genre of puerile, sexualized content, Portnoy is now in the business of rebuilding his ‘pirate ship,’ as he calls it.

A native of Swampscott on the North Shore of Massachusetts, Portnoy was a high school classmate of future ESPN college football analyst Todd McShay (the two actually share a birthday). The dedicated Patriots fan would go on to enroll at the University of Michigan and studied in Ann Arbor during Tom Brady’s playing days with the Wolverines.

Portnoy found himself back in the Boston area after graduating with a degree in education, spending a few years working for an IT market research firm before launching a four-page sports newspaper in 2003.

That paper was the first iteration of Barstool Sports and, much like its successor website, lured teenage boys and young men with photos of bikini-clad women and frequent attacks on political correctness.

It was hardly an immediate success, and Portnoy filed for bankruptcy protection in 2004 as he faced around $90,000 in debt and back taxes, including $30,000 in gambling losses, The New York Times reported in 2022.

But things began to change after Barstool morphed into a blog in 2007. Soon the website was cashing in with daily features such as ‘Local Smokeshow of the Day,’ featuring photos of attractive women, one-bite pizza reviews, and ‘Guess That Ass,’ which is more or less what it sounds like.

Meanwhile, Portnoy was cultivating his ‘El Presidente’ identity by unapologetically weighing into controversies and igniting some of his own.

Like Mintz, Portnoy also said the N-word on air, for which he later apologized, and was banned from Boston sports radio station WEEI after posting a naked photograph of Brady’s 20-month-old son.

‘We don’t back down from controversy – we fan the fires,’ Portnoy told NBC in 2013. ‘People think we go out of our way to create it, but we don’t. We’re not trying to gain new readers by being crazy-outrageous. Our readers get what we do, and I don’t think about what it’s going to look like to the outside world. I don’t really care.’

Portnoy takes particular pleasure in attacking commissioner Roger Goodell over the league’s ‘Deflategate’ scandal, in which it penalized Brady for allegedly deflating footballs in violation of NFL rules. Academics have insisted that the NFL failed to prove its case against Brady, who may have actually been exonerated by the league’s data, and Portnoy has never forgiven Goodell for Brady’s four-game ban.

As a result, Portnoy and three other Barstool employees staged a protest at the NFL’s Manhattan headquarters in 2015, handcuffing themselves to 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 tips and gambling predictions, but with the emergence of Donald Trump as a viable presidential candidate, Portnoy started to ingratiate himself to conservatives.

‘I am 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 it. I hope he stays in the race and I hope he wins. Why? Because I love the fact that he is making other politicians squirm. I love the fact he says s*** nobody else will say, regardless of how ridiculous it is.’

Barstool Sports was lending its name to casino chain, but that signage will soon be replaced

Barstool Sports was lending its name to casino chain, but that signage will soon be replaced  

In the coming years, Portnoy would become a regular guest on Tucker Carlson’s Fox News program, where he often defended himself against a growing number of scandals.

Portnoy was subject to a 2019 National Labor Relations Board investigation over Twitter posts claiming that he threatened to fire workers if they unionized. He ultimately reached an informal settlement with the Board, but suffered no 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 Business Insider expose, alleging that he had violent and aggressive sexual encounters with women, some of whom he filmed without their consent. Portnoy has denied the claims, insisting the article was a ‘hit piece.’

Portnoy later sued Insider, claiming its reporting was ‘false and defamatory,’ but the lawsuit was ultimately dismissed.

Due to the scandal, Penn Chief Executive Officer Jay Snowden felt compelled to quell shareholders’ fears during an earnings call in February of 2022. Snowden told his audience to ‘give this time to play out’ according to Bloomberg.

‘There undoubtedly will be more to come in the coming days, just as what transpired three months ago,’ Snowden said, as quoted by Bloomberg.

Soon thereafter, a second Business Insider article was published that included new allegations that he filmed himself having intercourse with women who were unaware that they were being recorded.

David Portnoy, founder of Barstool Sports, speaks during a radio broadcast in 2020

David Portnoy, founder of Barstool Sports, speaks during a radio broadcast in 2020

The incident foreshadowed Portnoy and Barstool’s growing issues with Penn, which was concerned how the news would impact its share price and standing with regulators.

Those fears appear to have led Penn to divest from Barstool altogether, particularly after the Ohio Casino Control Commission (OCCC) fined Penn $250,000 and over a Barstool event at the University of Toledo in December of 2022. The event violated two state gaming regulations barring sportsbooks from advertising sports betting to college students and to minors.

‘Penn Entertainment and Barstool Sports have gone our separate ways,’ Portnoy said in a video posted. ‘So that is 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, two steps back,’ Portnoy continued. ‘We got denied licenses because of me. You name it. So the regulated industry probably not the best place for Barstool Sports and the type of content we make.’

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Post source: Daily mail

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