James Chanos (Still) Selling Triplex Penthouse Atop the Manhattan Mansion Worchestershire Sauce Built

In 1901, Stuart Duncan, heir to a 19th-century fortune derived from the importation of Lea & Perrins Worchestershire Sauce to America, purchased two 25-foot-wide vacant parcels on East 75th Street, just 115 feet off New York’s tony Fifth Avenue.

The condiment heir commissioned high-society architect C.P.H. Gilbert to build him an impressive private home on the two lots, which was completed in 1904. The results were undeniably spectacular. Standing six floors behind a wrought-iron fence atop a rusticated base, the limestone mansion sported two-foot-thick walls for soundproofing, a bronze-railed marble staircase, and rooms paneled in exotic woods. Other lavish amenities included a 50-foot ballroom with a 20-foot ceiling and on the top floor, a squash court complete with a spectator’s gallery.

Duncan and his wife were prominent members of society and, as such, entertained all manner of Carnegies, Astors, Phippses and Dodges during their residency. They sold the house in 1920 for $750,000, an amount equivalent to about $12 million today, to fabulously rich silver scion Clarence Hungerford Mackay, whose father was one of the folks who discovered Nevada’s Comstock Lode in 1876. A divorcée with three daughters, one of whom married Irving Berlin in 1926, Mackay also entertained the beau monde; in 1927 he hosted a gala dinner in honor of Charles Lindbergh, who had just returned to New York from his record-setting nonstop solo flight from Long Island to Paris.

By the mid 1940s, the mansion had been acquired by a real estate investment concern and carved up in almost two dozen small rental apartments, with one to three rooms apiece. Then, in 2005, the mansion-cum-apartment-house was converted to condos and once again reconfigured, but this time with just seven apartments ranging in size from a picayune street-level studio to a mansion-sized triplex penthouse. Though one of the smaller units occasionally pops 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 last year for almost $19 million, it’s rare for one of the boutique building’s apartments to change hands. Prior to the Segalot sale, the most recent recorded sale was in 2011, when a duplexed one-bedroom went for nearly $2.7 million.

One of the building’s long-time residents, short-selling investor James Chanos, 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. The 60-something-year-old investment manager’s decades of predictive market savvy and well-timed short selling have earned him a slew of sobriquets such as “Darth Vadar of Wall Street,” the “Catastrophe Capitalist” and the “LeBron James of Short Selling.” He is probably best known for correctly predicting the downfall and shorting the stock of the now defunct energy firm Enron, for which he reportedly hauled in half a billion bucks. More recently, among other prognostications, Chanos predicted the collapse of the cryptocurrency market and that Tesla’s profit margins will fall, which would, of course, make the value of his short position in the popular but expensively niche car company soar.

However, and though he’s unlikely to have to sell it short, he’s not likely to make much, if anything, on the sale of his penthouse when carrying costs, improvement expenses and real estate fees are factored in; he bought the place 2008 for $20.365 million and, after first giving it a go in 2019 at $34 million, now has on the market at $23.5 million.

Next door to the equally extravagant townhouse used as the exterior of the Sheffield family home on the 1990s sitcom “The Nanny,” the 50-foot-wide mansion’s exterior looks as gracious as it did when it was built 120 years ago. However, much of the building’s fantastical interior detailing and frippery was removed during one or another of its conversions. Indeed, the Chanos penthouse, with four bedrooms and three bathrooms, plus a pair of powder rooms, bears few reminders of the past and instead presents a light-filled multi-level contemporary space that’s perfect for the large gatherings, both inside and out, along with the display of a small museum’s worth of artworks.

The triplex’s middle, main floor comprises the entrance gallery, a 1,200-square-foot great room that stretches to almost sixty feet long with a wood burning fireplace (it may very well be where Duncan’s squash court was once-upon-a-time located), and a much more cozily proportioned and elegantly paneled den. Also on this floor is the sleek galley kitchen that’s complete with walk-in wine cellar and a breakfast area that opens to a pergola-shaded dining terrace with a stainless-steel outdoor kitchen and grill.

Bedrooms are all on the lower level, including the super-sized main suite, while the uppermost floor is devoted to leisure and entertainment. A spacious screening room seats a dozen, while an adjoining bar, big enough to accommodate a pool table, spills out to one of the penthouse’s six terraces, two of which are conveniently connected by an exterior stair. There’s even a building-framed view of Central Park from the upper terraces.

Available through Richard Steinberg, principal of the Richard Steinberg Team at Compass, who declined to comment, annual taxes run just over $80,000 a year and condo fees, which cover security and doorman services among other things, tally up to almost $144,000.

Tax records indicate Chanos has owned a nearly 5,000-square-foot Miami Beach condo for about 20 years but in 2021, after three decades of ownership, he off-loaded his oceanfront estate along one of the finest streets in all of the Hamptons in an off-market deal valued at almost $60 million.