Ashley Dupre's 'Uncle Jim' Buying East 75th Triplex Penthouse

If the economy plunges further, if the recession becomes a depression, if there’s blood on the streets and panic in the air, short sellers, the investors who make money by betting that stocks will fall, will be seen as an evil coterie of cackling villains that profited from downturns they may have encouraged.

More than John Paulson (who made $3.7 billion last year by betting against subprime mortgages) or David Einhorn (who may be helping Lehman Brothers go the way of Bear Stearns), James S. Chanos, the president and founder of a hedge-fund group called Kynikos (from “cynic” in Greek), may be the best short seller of them all. He’s at least one of the most lauded, considering that he started shorting Enron in November 2000, practically a year before the rest of the world, which Barron’s called “the market call of the decade, if not the past 50 years.”

Now he has a five-bedroom, 14-room triplex penthouse overlooking Central Park to reward his hard work. According to a source in the building, Mr. Chanos is in contract to buy the penthouse at the iron-fenced mansion 3 East 75th Street, listed for $24,850,000 by Paula Del Nunzio, who would not comment.

The triplex, one of seven units carved out of the 50-foot-wide Beaux-Arts mansion when it was converted into condominiums, is the kind of place with a fireplace in the master bedroom and one in the master bathroom, too. According to the listing, there’s 7,800 square feet of interior space and 3,600 square feet outdoors, spread over spaces like that master suite’s rear terrace and a high-walled front terrace.

The Post reported that Robert De Niro “came this close” to buying the penthouse. In a separate story, that paper also pointed out that Mr. Chanos knows Ashley Dupré, the prostitute that felled Eliot Spitzer. He reportedly introduced her to guests at his clambake on the East End last summer as a house-sitter. She called him Uncle Jim.

While “everyone was out on the beach partying, she was in the kitchen helping … with the dishes,” the short seller told the paper. “She’s got her heart in the right place, but maybe not her head.” Ashley Dupre's 'Uncle Jim' Buying East 75th Triplex Penthouse