Two 25-foot-wide parcels on East 75th Street were purchased by Stuart Duncan in 1901, heir to a 19th-century fortune derived from the importation of Lea & Perrins Worchestershire Sauce to America.

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In 1904, the condiment heir commissioned high-society architect C.P.H. Gilbert to design and build an impressive private residence. Undoubtedly, the results were spectacular. Its walls were two feet thick, its marble staircase was bronze-railed, and it had rooms lined with exotic woods. The limestone mansion stood six stories high behind a wrought-iron fence on a rusticated base. Among the lavish amenities were a 50-foot ballroom, a squash court, and a spectator's gallery on the top floor.

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They entertained Carnegies, Astors, Phippses and Dodges during their residency as prominent members of society. Clarence Hungerford Mackay, whose father was one of the people who discovered Nevada's Comstock Lode in 1876, bought the house for $750,000 in 1920, an amount equivalent to about $12 million today. Mackay was a divorcee with three daughters, one of whom married Irving Berlin in 1926, and he also entertained the affluent; he hosted a gala dinner for Charles Lindbergh in 1927, after he returned from his record-breaking nonstop solo flight from Long Island to Paris.

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According to Rich Report, as early as the 1940s, a real estate investment company acquired the mansion and divided it into almost two dozen one- to three-bedroom apartments. Eventually, the mansion-turned-apartment-house was converted to condos and reconfigured again, this time with just seven apartments, ranging in size from a street-level studio to a triplex penthouse. One of the smaller units occasionally shows up as a rental - most recently, in 2020, the aforementioned street-level studio was available at $3,750 per month — and French art dealer Philippe Segalot sold his sprawling duplex for almost $19 million last year, but renting one of the boutique building's apartments is rare. In 2011, a duplexed one-bedroom went for nearly $2.7 million, the most recent sale prior to the Segalot sale.

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James Chanos, who has lived in the building for more than a decade, would certainly like to add his one-of-a-kind penthouse to the short list of recent sales at what is still known as The Stuart Duncan House. It has been his decades of market prediction and well-timed short selling that have earned him a variety of sobriquets, such as "Darth Vadar of Wall Street," "Catastrophe Capitalist," and "LeBron James of Short Selling." The most famous thing about him is that he correctly predicted Enron's downfall and shorted the company's stock, earning him a profit of half a billion dollars. As part of his prognostications, Chanos recently predicted the collapse of cryptocurrency markets and Tesla's profit margins would fall, which would make his short positions in the popular, but expensive, niche car company extremely valuable.

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When carrying costs, improvement expenses, and real estate fees are factored in, he won't make much, if any, on the sale of his penthouse, even if he doesn't have to sell it short; he bought it in 2008 for $20.365 million and, after first selling it for $34 million in 2019, is now selling it for $23.5 million; he bought it for $20.365 million in 2008.

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The 50-foot-wide mansion's exterior still looks as elegant as it did when it was built 120 years ago, next to the equally extravagant townhouse used for the Sheffield family home on the 1990s sitcom "The Nanny." One or more of the building's conversions, however, removed most of its fantastical interior details and frippery. A light-filled multi-level contemporary space with four bedrooms, three bathrooms, and a pair of powder rooms, the Chanos penthouse bears very few traces of the past, presenting a space that is perfect for large gatherings, both indoors and outdoors, as well as displaying a small museum's worth of artwork.

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A 1,200-square-foot main floor of the triplex houses the entrance gallery, a great room almost sixty feet long with a wood burning fireplace (this may have been Duncan's squash court at one time), and a den that is much more spacious and elegantly paneled. The sleek galley kitchen features a walk-in wine cellar and a breakfast area that opens to an outdoor kitchen and grill under a pergola on this floor.

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The bedrooms are all located on the lower level, including the super-sized master suite, while the uppermost floor is dedicated to leisure and entertainment. There are six terraces in the penthouse, two of which are connected by an exterior stairway, plus a spacious screening room that seats twelve, and an adjacent bar with a pool table. The upper terraces even offer a view of Central Park framed by the building.

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There are just over $80,000 in annual taxes and almost $144,000 in condo fees, which cover security and doorman services.

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His Miami Beach condo, which is nearly 5,000 square feet, has been owned by Chanos for about 20 years, but after three decades of ownership, he sold it off-market for almost $60 million in 2021, after three decades of ownership.

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