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The $2,000 an-Hour Woman

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Jason Itzler at Rikers Island.  

Natalia looked up at Jason, makeup streaming from her face.

“It’s great, isn’t it?” Jason enthused. “A brilliant idea.”

“Yeah,” Natalia said wearily. “Great, in theory.” Almost everything Jason Itzler said was great, in theory.

They call it the oldest profession, and maybe it is. The prostitute has always been part of the New York underworld. According to Timothy J. Gilfoyle’s City of Eros, in 1776, Lieutenant Isaac Bangs of the Continental Army complained that half his troops were spending more time in lower-Manhattan houses of ill repute than fighting the British. In the nineteenth century, lower Broadway had become, in the words of Walt Whitman, a “noctivagous strumpetocracy,” filled with “tawdry, foul-tongued and harsh-voiced harlots.”

By the eighties, the image of the New York prostitute encompassed both the call-girl minions of Sydney Biddle Barrows, the famous Mayflower Madam, and the hot-pants-clad hooker trying to keep warm beside a burning 55-gallon drum outside the Bronx’s Hunts Point Market. On Eighth Avenue’s so-called Minnesota Strip were the runaways in the wan-eyed Jodie Foster–in–Taxi Driver mode. The nineties brought the “Natasha Trade,” an influx of immigrant Russian girls and their ex-Soviet handlers who locked the women up in Brighton Beach apartments and drove them, fifteen at a time, in Ford Econoline vans to strip joints on Queens Boulevard.

The Internet would reconfigure all that. Today, with highly ad hoc estimates of the New York “sex worker” population hovering, depending on whom you ask, anywhere from 5,000 to 25,000, horny men looking for a more convivial lunch hour don’t have to cruise midtown bars or call a number scribbled on a piece of paper. All that’s needed is a high-speed connection to any of the many “escort malls,” such as the highly clickable CityVibe or Eros.

The typical site includes a photo or two, a sparse bio, a schedule of when the escort is available, and a price (“donation”) list. There is also the standard disclaimer, detailing how any money exchanged “is simply for time only and companionship” and that anything else “is a matter of personal preference between two or more consenting adults.” For, as everyone in the escort business is quick to say, selling “companionship” is not against the law.

The system is not without its bugs. The most common question: “Is she the girl in the picture?” Says a longtime booker, “About two-thirds of the time, when a guy calls up asking for a girl they’ve seen on the site, she doesn’t work for us, quit six months ago, or we Photoshopped her picture from the Victoria’s Secret catalogue.

“The place was full of naked women and underwear. On the couch is Jason, a phone in either ear, the other one ringing on the coffee table.”

“If they ask for Nicolette, I take out the three-by-five card with NICOLETTE written on top. It lists the contacts of girls who kind of look like the fake Nicolette. What blows my mind is the stupid bastards spend hours searching the sites looking for their super-fantasy, are willing to shell out $700 an hour, and then when someone else knocks on the hotel-room door, they go, ‘Oh, whatever.’ They can still go back to Indianapolis, show the girl in the picture to their buddies, and say, ‘See her? Like, awesome, dude!’ ”

It was this kind of slipshod, postmodern fakery that Jason Itzler says he started NY Confidential to wipe out. At NY Confidential, you always got the girl in the picture.

“That’s because we were the best,” says Itzler. “At NY Confidential, I told my girls that the pressure is on them because we have to provide the clients with the greatest single experience ever, a Kodak moment to treasure for the rest of their lives. Spreading happiness, positive energy, and love, that’s what being the best means to me. Call me a dreamer, but that’s the NY Confidential credo.”

Such commentary is typical of Jason, who, in the spirit of all great salesmen, actually believes much of it.

Not yet 40, Jason Itzler has a story that is already a mini-epic of Jewish-American class longing, a psycho-socio-sexual drama crammed with equal parts genius (occasionally vicious) boychick hustle, heartfelt neo-hippie idealism, and dead-set will to self-destruction. Born Jason Sylk, only son of the short-lived marriage between his revered mother, Ronnie Lubell, and his “sperm dad,” Leonard Sylk, heir to the Sun Ray drugstore fortune built up by Harry Sylk, who once owned a piece of the Philadelphia Eagles, Jason spent his early years as one of very few Jewish kids on Philly’s Waspy Main Line. If he’d stayed a Sylk, says Jason, “I would have been the greatest Richie Rich, because Lenny Sylk is the biggest thing in the Jewish community. He’s got a trust that gives money to stuff like the ballet, a house with an eighteen-car garage, and a helicopter landing pad. Golda Meir used to stay with us when she was in town.”


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