American Gangster

by Mark Jacobson

  By the 1970s and 80’s, 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 fifty-five-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 five thousand to twenty-five thousand, 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.

  “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 superfantasy, 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 forty, Jason Itzler has a story that is already a mini-epic of Jewish-American class longing, a psychosociosexual 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.”

  After his parents’ divorce, Jason moved to New York with his mother, whom he describes as “the hottest mom in the world. She had this Mafia princess–Holly Golightly thing about her. Her vanity license plate was TIFF. My mother being beautiful made me into who I am today, because when you grow up around a beautiful woman, you always want to be surrounded by beautiful women.”

  Also a big influence was his mom’s father, the semi-legendary Nathan Lubell, “the biggest bookmaker in the garment industry, a gangster wizard,” says Jason. “He owned a lot of hat stores, a bunch of the amusement park in Coney Island, and was hooked up with Meyer Lansky in Las Vegas hotels. I used to love it when he took me to the Friars Club, where he was a king. Even as a kid, I could feel the action.”

  With his mom remarried, to Ron Itzler, then a lawyer in the firm of Fischbein, Badillo (as in Herman), Wagner, and Itzler, the family lived in the Jersey suburbs. Displaying his compulsive intelligence by setting the all-time record on the early-generation video game Scramble, Jason, “pretty much obsessed with sex from the start,” wrote letters to Mad magazine suggesting they put out a flexi-record of “teenage girls having orgasms.” Summers were spent in the Catskills, where as a cabana boy at the Concord Hotel he befriended people like Jason Binn, now the playboy publisher of the Hamptons and Los Angeles Confidential magazines, a name Itzler paid homage to with his NY Confidential.

  Itzler remembers, “At the Concord, when Jason Binn said he was the son of a billionaire, and my stepfather told me, yeah, he was, I got light-headed.”

  In the late eighties, after getting through George Washington University, even though he was “mostly running wet-T-shirt contests,” Itzler entered Nova Southeastern University, a bottom-tier law school in Fort Lauderdale, Florida, where he embarked on what he calls “my first great chapter” as “the twenty-two-year-old phone-sex king of South Beach.” Advertising a “Free Live Call” (after which a $4.98-a-minute charge set in), Itzler’s company was doing $600,000 a month, hitting a million and a half within a year.

  “I had so much money,” Jason recalls, “I bought an Aston Martin Virage, three hundred feet of oceanfront property. Like a moron, I spent half a million decorating a one-bedroom apartment.”

  Alas, it would all soon come tumbling down, owing to what Jason now calls a “kind of oversight,” which left him owing $4.5 million at 36 percent interest. Forced to declare bankruptcy in 1997, he lost everything, including his visionary acquisition of one of the fledgling Internet’s most valuable URLs: pussy.com.

  The demise of Itzler’s phone-sex company set a pattern that would be repeated in 2000 with his next big act, the SoHo Models fiasco. With typical overreach, Jason rented an eight-thousand-square-foot space at the corner of Canal and Broadway and declared himself the new Johnny Casablancas. Unfortunately for the young models hoping to find their faces on the cover of Vogue, the true business of SoHo Models was to supply Webcam porn. For a fee, the voyeur would type in “take off blouse … insert dildo.” Squabbling among gray-market partners soon ensued. Within months, Jason found himself dangling over the side of the Canal Street building, held by the ankles by a guy named Mikey P.

  Jason says he would have gotten through these setbacks more easily if his mother were still alive, but Ronnie Itzler died of cancer in 1994, “after which I went kind of a little nuts.” Following the collapse of the phone-sex firm, he twice attempted suicide, once running himself through with a steak knife and on another occasion drinking “a milk shake” he claims contained “75 Valium, 75 Klonopin, and a couple bottles of Scotch.” Much to his surprise, he survived both times.

  Desperate for money after the SoHo Models disaster, Itzler decided his best option was to go to Amsterdam to buy four thousand tabs of Ecstasy. “In retrospect, it was a totally retarded idea,” says Jason, who would leave Newark airport in handcuffs. He was sentenced to five years in the Jersey pen. The fact that his grandfather, whom he’d idolized as a gangster, stopped talking to him when he got locked up “was hard to take.”

  “Jail is terrible, really boring,” says Jason. “But it does give you plenty of time to plan your next move.”

  On parole after servi
ng seventeen months of his smuggling sentence, living in a funky third-floor walk-up in Hoboken per the terms of his release, Jason started NY Confidential (he would remain on parole his entire pimp career) in late 2003. Business was spotty at first but picked up dramatically in early 2004, when Natalia walked into the company’s place at Fifty-fourth Street and Sixth Avenue, an office previously occupied by the magician David Blaine.

  “It was my birthday,” Natalia remembers. “I’d just been cast as Ingrid Superstar in this play, Andy & Edie, written by soon-to-be famous sex criminal, Peter Braunstein. “I wanted to be Edie,” Natalia relates, “but Misha Sedgwick, Edie’s niece, also wanted it, so forget that. I was eating in a restaurant with Peter Beard, the photographer. I was a kind of party girl for a while. I met Peter one night, and we hit it off. He said I should meet this guy Jason.”

  Beard, a nocturnal bon vivant known for his “discovery” of exotic models like Iman, and who had been associated with Jason during the SoHo Models episode, warned Natalia off Itzler’s new venture. Eventually, however, Natalia decided to give Jason a call. “Being an escort never crossed my mind. It wasn’t something girls like me did. I was an actress. From a very nice home. But I was involved in an abusive relationship, with this Wall Street guy,” she says. “In the beginning, all I wanted was enough money to move out.”

  Jason says, “When Natalia came over with Peter, I said, Wow, she’s so hot. She has one of the all-time great tushes. But there was this other girl there, too. Samantha. When she took off her shirt, she had these amazing breasts. So it was Natalia’s butt against Samantha’s boobies. I went with the tits. But when Natalia came back from making a movie, she moved in with us. Samantha could tell I was kind of more into Natalia. So we became boyfriend and girlfriend.”

  At the time, Jason’s top girl was Cheryl, a striking blond ballroom dancer from Seattle who says she got into the business to buy her own horse. “I did NY Confidential’s first date,” Cheryl recalls. “I had on my little black dress and was shaking like a leaf. Jason was nervous, too. He said, ‘Just go up there and take your clothes off.’ I told him, ‘No, you’ve got to make it romantic. Special.’”

  It was Cheryl who came up with the mantra Jason would later instruct all the NY Confidential girls to repeat, “three times,” before entering a hotel room to see a client: “This is my boyfriend of six months, the man I love, I haven’t seen him for three weeks…. This is my boyfriend of six months, the man I love.”

  “That’s the essence of the true GFE, the Girlfriend Experience,” says Jason. As opposed to the traditional “no kissing on the mouth” style, the GFE offers a warmer, fuzzier time. For Jason, who says he never hired anyone who’d worked as an escort before, the GFE concept was an epiphany. “Men see escorts because they want to feel happier. Yet most walk away feeling worse than they did before. They feel dirty, full of self-hatred. Buyer’s remorse big-time. GFE is about true passion, something genuine. A facsimile of love. I told guys this was a quick vacation, an investment in the future. When they got back to their desks, they’d tear the market a new asshole, make back the money they spent at NY Confidential in an hour.

  “What we’re selling is rocket fuel, rocket fuel for winners.”

  Jason decided Natalia would become his great creation, the Ultimate GFE. It mattered little that Natalia, for all her French-Scottish sultriness, might strike some as a tad on the skinny side. Brown-eyed, dark-haired, olive-skinned, not to mention lactose-intolerant, she didn’t fit the usual description of a big ticket in an industry filled with PSE (Porn-Star Experience) babes with store-bought bazangas out to here. Jason took this as a challenge. If he was into Natalia, he’d make sure everyone else was, too. It was a simple matter of harnessing the available technology.

  The main vehicle was the aforementioned TheEroticReview.com, “the Consumer Reports of the escort industry,” according to the site’s founder and owner, the L.A.-based Dave Elms, a.k.a. Dave@TER. “The most important thing was to break Natalia out big,” Jason says. “To get the ball rolling with a number of fabulous reviews, I sent her to some friends, to sort of grease the wheel. I knew those 10/10s would keep coming, because no man wants to admit he got less. They’re brainwashed that way.”

  If any hobbyist had the temerity to hand out a paltry 8/8, or even a 9/10, he would be contacted. “Don’t break my girl’s streak, this is history in the making,” Jason cajoled, offering to throw in a couple hours of free time to get the customer to do a little recalculating. If that didn’t work, good reviews could be ensured by the $5,000 everyone working at NY Confidential (except Jason) swears was FedExed to Dave@TER on the fifteenth of every month. Dave, who says he “would not argue with that” when asked if he is the single most important person in the escort business, vehemently denies any payoffs, from NY Confidential or anyone else.

  With her 10/10s piling up, Natalia’s hourly rate jumped from $800 to $1,200 with a two-hour minimum. (The split: 45 percent for the escort, 45 percent for the agency, 10 percent for the booker.) If clients haggled, they would be told to call back when they were “more successful.” Jason says, “I always ask prospective clients to give me strong points about themselves, where they went to school, if they’re good-looking. It established rapport but also put them on the defensive, let them know that I was interviewing them, to see if they were good enough to go out with our girls.”

  Jason’s hyping sometimes was faintly embarrassing. “Jason would be saying, ‘Natalia is the greatest escort in the history of the world, as good as Cleopatra or Joan of Arc,’” says Natalia, “and I’d be like, ‘Jason! Joan of Arc was not an escort, she was a religious martyr.’ Then he’d be saying I was the greatest escort since Mary Magdalene.”

  But all the hype in the world (an Asian toy manufacturer wanted to mass-produce Barbie-style Natalia dolls, complete with tiny lingerie) wouldn’t have helped if Natalia, who never imagined she’d wind up staying in “every expensive hotel in New York,” hadn’t turned out to be a natural.

  “I’m a little moneymaking machine, that’s what I am,” she says as she takes a languorous drag of her Marlboro while stretching out on her apartment couch in a shiny pink satin corset, Marlene Dietrich style. Then she cracks up, because “you know, the whole thing is so ridiculous sometimes.”

  People wonder what it is about Natalia that made her the Perfect 10. “From the start, you know this is going to be fun,” says one client. “It is like having sex in a tree house.” Says another, “Nat isn’t this all-knowing geisha thing. But in a way, it’s deeper, because she gets to a place inside where you used to be free.” And another: “When you’re with her, there’s none of that feeling that ‘this is costing as much as a first-class ticket to London and the chick is in the bathroom half the time and couldn’t care less.’ From the first minute Natalia comes in and bats those brown eyes you know this is a nonstop this-is-all-about-you experience.”

  Suffice it to say, it’s in the pheromones. According to Natalia, she’s always gotten along with men. “Jason understood who I was,” she says. “Yes, he sold the shit out of me, but he sold me as myself, someone anyone can be comfortable with, someone who really likes sex. Because the truth is, I do. I loved my job, totally.”

  It is another old story, along with the heart of gold, that many “providers” actually like what they do. But even if she professes to be “horrified” by stories about sexual trafficking and “sickened” by nightmarish exploitation of the street prostitute, Natalia says, “At the level NY Confidential was at, the guys I was meeting, I would have gone out with 80 percent of them anyway. People have so many misconceptions, preconceptions, about my life. Last year, I got a call to play an escort in a Broadway play. But the part was so dark, so icky, I said no. It didn’t fit my experience at all.”

  You never knew who might be behind the hotel door. Once, she was summoned to a guy’s room, told only that he was a famous, Super Bowl athlete. “I’m not a big sports fan, but I recognized him, the quarterbac
k. He turned out to be very laid-back. He mostly wanted to make me happy. In the middle, he looks up and says, ‘Well, you know me, I’m more of a giver than a receiver.’”

  What no one could have predicted, least of all Natalia, was how driven she would be. “I knew she was talented,” Jason says. “But once she started going, she was unstoppable, like the Terminator.”

  A glance at Natalia’s booking sheets raises an eyebrow. Annotated with Jason’s exhortatory commentary (“Awesome guy!—$5,200, wants to be a regular!” “Big Wall Street guy!” “Software king.” “Hedge fund heavy! Says he will give investment lessons!”), the records of Natalia’s bookings through June and July of 2004 reveal a workload exceeding 250 hours, or nearly a normal nine-to-five, at an average of $1,000 per hour, not counting little presents like fancy $350 underwear from La Perla.

  “Victoria’s Secret is all right,” Natalia says. “But you know you have a good client when you get La Perla.”

  Some weeks were particularly frenetic. From July 29 to August 1, she had a four-day date in the Florida Keys for which Itzler charged $29,000. The very next day was a four-hour appointment. August 3 was filled with a ten-hour appointment and another two-hour job. August 4, three hours. August 5, a three-hour followed by another four-hour. August 6, two hours. August 7, one four-hour job and a two-hour. August 8, she was off. But the 9th was another ten-hour day, followed by a pair of two-hour jobs on August 10.

  “It was like a dream,” Natalia says. “I never got tired.”