Home Business Barstool Sports founder Dave Portnoy ‘drops $42MILLION on waterfront Nantucket compound featuring a swimming pool and underground tunnel’ … just weeks after announcing layoffs at his website

Barstool Sports founder Dave Portnoy ‘drops $42MILLION on waterfront Nantucket compound featuring a swimming pool and underground tunnel’ … just weeks after announcing layoffs at his website

by Mark Mendoza

Barstool Sports founder, Dave Portnoy, has purchased a waterfront compound on Nantucket Island for a record-breaking $42 million. The compound spans 1.2 acres and includes a main residence, pool, multiple guest quarters, and an underground tunnel connecting a two-bedroom guesthouse to a separate studio. The property overlooks Nantucket Harbor and features luxurious amenities, including an indoor-outdoor shower and foldaway glass doors with harbor views.

Portnoy, who is originally from Swampscott, Massachusetts, is no stranger to Nantucket, as he already owned a $2 million property on the island. However, his recent sale of Barstool Sports to Penn Entertainment for $550 million has allowed him to upgrade to a more lavish compound. Interestingly, Portnoy regained full control of the company in August when he bought it back for just $1. Despite this recent purchase, Portnoy has also announced layoffs at Barstool Sports, citing financial losses.

The Nantucket compound was sold by a pair of trusts and was completed in 2018. The previous owners purchased adjacent land parcels in 2016 and demolished existing structures to create the compound. The high demand and limited availability of properties on Nantucket have driven up prices in recent years, with several sales approaching $40 million. The previous owners decided to sell due to the strong market and premium prices being offered for quality construction.

While Portnoy’s purchase may seem extravagant, it comes at a precarious time for Barstool Sports. Layoffs have already begun, and Portnoy has expressed the need to get the company back to a break-even point. The sale of Barstool Sports back to Portnoy by Penn Entertainment came with certain restrictions and non-compete clauses. If Portnoy were to sell the company again, Penn would have rights to half of the gross proceeds.

Portnoy, who is known for his controversial and provocative content, has built Barstool Sports from a small four-page sports newspaper to a popular and successful website. Initially facing financial difficulties and even filing for bankruptcy, the website gained traction after rebranding as a blog in 2007. Barstool Sports became known for features such as “Local Smokeshow of the Day,” one-bite pizza reviews, and controversial content that often ignited controversies and feuds.

In recent years, Portnoy has expanded into the political realm, endorsing Donald Trump’s presidential campaign and aligning himself with conservative ideals. Despite his success, Portnoy has faced criticism for his unfiltered and often offensive remarks. Nevertheless, his purchase of the Nantucket compound showcases his financial success and his ability to indulge in luxurious properties.

In conclusion, Dave Portnoy’s purchase of a $42 million waterfront compound on Nantucket Island is a testament to his financial success. While facing layoffs at Barstool Sports, Portnoy’s extravagant purchase highlights his ability to splurge on real estate. The high demand and premium prices for Nantucket properties make this a record-breaking sale for the island. Only time will tell how Portnoy’s recent purchase and the future of Barstool Sports will unfold.

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