Dave Portnoy might be what’s considered nouveau riche, but he has old money taste when it comes to property. In fact, the media disrupter has just bought a USD$42 million (AU$67 million) home in Nantucket that looks straight out of an episode of Succession. And while the Barstool Sports founder might not have the bank balance of a Kendall Roy, the off-market deal not only set a record for the island but also hurdled records across Portnoy’s native Massachusetts.
MORE: A Look at Atlassian Co-Founder Scott Farquhar’s $130 Million Point Piper Icon
This prime piece of real estate is nestled in the exclusive Monomoy area, sprawling across 1.2 acres with stunning views of the Nantucket Harbour. According to The Wall Street Journal, the sellers purchased adjacent parcels for a combined USD$13.3 million in 2016 before turning both homes into the giant compound that now lives on the island.
The luxurious estate is a young mogul’s dream, boasting a main residence, a resort-style pool area, separate guest house. All designed by renowned architecture firm Workshop/APD, the main house features four bedrooms, with the primary suite equipped with an indoor/outdoor shower and foldaway glass doors that open up to views of the harbour.
Behind the main residence lives a two-bedroom guesthouse and a separate studio that is connected by an underground tunnel. The secret tunnel is reminiscent of something out of a spy-thriller, which will surely get his frat-bro friends wet when they come for a sleepover. Enhancing the price tag with his personal touch, the new owner also included an extra USD$2 million (AU$3 million) worth of boujee furnishings and other items.
Portnoy’s rise to fame and fortune is nothing short of incredible. From humble beginnings, the now 46-year-old founded his gambling newspaper in Boston in 2003. Since then, His Barstool Sports brand has gone on to become a media giant across the globe, boasting some of the most popular podcasts and content on the internet.
In early 2020, Portnoy made headlines by selling Barstool to the casino operator Penn Entertainment for a staggering USD$550 million (AU$871 million). However, an unexpected turn of events occurred in August when he managed to buy it back for a mere $1. How did this happen, you ask?
Well, Penn Entertainment found a new partner in the form of ESPN. ESPN had long desired to enter the sports betting industry but was hesitant to directly operate a sportsbook due to concerns about potential conflicts of interest within its editorial content.
Seizing this opportunity, Penn Entertainment struck a deal with ESPN. As a result, they decided to sell Barstool back to its original founder, thus completing a remarkable outcome for Portnoy. Taking back control of his company with the added mountain of money, expect to see the media personality snatch up more elite cribs in the future.
Join Our Exclusive Community!
Keep up with the latest trends, best stories, and crucial updates from Man of Many direct to your inbox.
