sport news Barstool Sports founder Dave Portnoy 'drops $42MILLION on waterfront Nantucket ... trends now

sport news Barstool Sports founder Dave Portnoy 'drops $42MILLION on waterfront Nantucket ... trends now
sport news Barstool Sports founder Dave Portnoy 'drops $42MILLION on waterfront Nantucket ... trends now

sport news Barstool Sports founder Dave Portnoy 'drops $42MILLION on waterfront Nantucket ... trends now

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

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