The Best American Crime Writing 2006

by Mark Bowden

  FROM New York MAGAZINE

  JASON ITZLER, THE SELF-ANOINTED world’s greatest escort-agency owner, prepared to get down on his knees. When a man was about to ask for the hand of a woman in holy matrimony, especially the hand of the fabulous Natalia, America’s No. 1 escort, he should get down on his knees.

  This was how Jason, who has always considered himself nothing if not “ultraromantic,” saw it. However, as he slid from his grade school–style red plastic seat in preparation to kneel, the harsh voice of a female Corrections officer broke the mood, ringing throughout the dank visitors’ room.

  “Sit back down,” said the large uniformed woman. “You know the rules.”

  Such are the obstacles to true love when one is incarcerated at Rikers Island, where Jason Itzler, thirty-eight and still boyishly handsome in his gray Department of Corrections jumpsuit, has resided since the cops shut down his megaposh NY Confidential agency in January.

  There was also the matter of the ring. During the glorious summer and fall of 2004, when NY Confidential was grossing an average of $25,000 a night at its five-thousand-square-foot loft at Seventy-nine Worth Street, spitting distance from the municipal courts and Bloomberg’s priggish City Hall, Jason would have purchased a diamond with enough carats to blow the eye loupe off a Forty-seventh Street Hasid.

  That was when Itzler filled his days with errands like stopping by Soho Gem on West Broadway to drop $6,500 on little trinkets for Natalia and his other top escorts. This might be followed by a visit to Manolo Blahnik to buy a dozen pairs of $500 footwear. By evening, Itzler could be found at Cipriani, washing down plates of crushed lobster with yet another bottle of Johnnie Walker Blue label and making sure everyone got one of his signature titanium business cards engraved with NY Confidential’s singular motto: ROCKET FUEL FOR WINNERS.

  But now Jason was charged with various counts of criminal possession of a controlled substance, money laundering, and promoting prostitution. His arrest was part of a large effort by the NYPD and the D.A.’s office against New York’s burgeoning Internet-based escort agencies. In three months, police had shut down American Beauties, Julie’s, and the far-flung New York Elites, a concern the cops said was flying porn stars all over the country for dates. Reeling, pros were declaring the business “holocausted” as girls took down their Web sites and worried johns stayed home.

  Many blamed Itzler for the heat. In a business where discretion is supposed to be key, Jason was more than a loose cannon. Loose A-bomb was more like it. He took out giant NY Confidential ads in mainstream magazines (the one you’re holding included). In restaurants, he’d get loud and identify himself, Howard Stern–style, as “the King of All Pimps.” Probably most fatally, Itzler was quoted in the Post as bragging that he didn’t worry about the police because “I have cops on my side.” After that, one vice guy said, “it was like he was daring us.”

  Only days before, Itzler, attired in a $5,700 full-length fox coat from Jeffrey, bought himself a Mercedes S600. Now the car, along with much of the furniture at Jason’s lair, including the $50,000 sound system on which he blared, 24/7, the music of his Rat Pack idol, Frank Sinatra, had been confiscated by the cops. His assets frozen, unable to make his $250,000 bail, Jason couldn’t even buy a phone card, much less get Natalia a ring.

  “Where am I going to get a ring in here?” Jason said to Natalia on the phone the other night. He suggested perhaps Natalia might get the ring herself and then slip it to him when she came to visit.

  “That’s good, Jason,” returned Natalia. “I buy the ring, give it to you, you kiss it, give it back to me, and I pretend to be surprised.”

  “Something like that,” Jason replied, sheepishly. “You know I love you.”

  That much seemed true. As Jason doesn’t mind telling you, he has known many women since he lost his virginity not too long after his bar mitzvah at the Fort Lee Community Jewish Center, doing the deed with the captain of the Tenafly High School cheerleader squad. Since then, Jason, slight and five foot nine, says he’s slept with “over seven hundred women,” a figure he admits pales before the twenty thousand women basketball star Wilt “the Stilt” Chamberlain claimed to have bedded. But, as Jason says, “you could say I am a little pickier than him.”

  Of these seven hundred women, Jason has been engaged to nine, two of whom he married. “It was really only one and a half,” Itzler reports, saying that while living in Miami’s South Beach he married “this hot Greek girl. She was gorgeous. The first thing I did was buy her this great boob job, which immediately transformed her from a tremendous A/B look to an out-of-sight C/D look. But her parents totally freaked out. So I got the marriage annulled.”

  This aside, not counting his sainted late mother, Jason says Natalia, twenty-five, about five foot three and perhaps one hundred pounds soaking wet, reigns as the love of his life.

  Without Natalia, she of the smoldering brown eyes that have excited who knows how many hedge-fund managers, billionaire trust-fund babies, and NFL quarterbacks, Jason would never have been able to build NY Confidential into the sub rosa superhotness it became. It was Natalia who got top dollar, as much as $2,000 an hour, with a two-hour minimum. In the history of Internet escorting, no one ever matched Natalia’s ratings on TheEroticReview. com, the Zagat’s of the escort-for-hire industry. On TER, “hobbyists,” as those with the “hobby” of frequenting escorts are called—men with screen names like Clint Dickwood, Smelly Smegma, and William Jefferson Clinton—can write reviews of the “providers” they see, rating them on a scale of 1 to 10 for both “appearance” and “performance.”

  In 2004 Natalia recorded an unprecedented seventeen straight 10/10s. On the TER ratings scale, a 10 was defined as “one in a lifetime.” Natalia was the Perfect 10, the queen of the escort world.

  “Yo! Pimp Juice!… that her?”

  It was Psycho, a large tattooed Dominican (PSYCHO was stenciled on his neck in Gothic lettering) who was referring to Jason by his jailhouse nickname. Itzler nodded. There was no need to gloat. Moments before, Jason scanned the grim visiting room. “Just making sure I’ve got the hottest chick in the room.” Like it was any contest, Natalia sitting there, in her little calfskin jacket and leather miniskirt, thick auburn hair flowing over her narrow shoulders.

  Besides, half of Rikers already knew about Jason and NY Confidential. They’d read, or heard about, the articles Itzler had piped to his pulp enablers at “Page Six,” including how he could get “$250,000 an hour for Paris Hilton with a four-hour minimum.”

  But you couldn’t believe everything you read in the New York Post, even at Rikers. Natalia’s presence was proof. Proof that Jason, a little Jewish guy who still sported a nasty black eye from being beaten silly in his sleep by some skell inmate, wasn’t full of shit when he told the homeys that he was the biggest pimp in the city, that he got all the best girls. How many other Rikers fools could get the Perfect 10 to visit them, at nine o’clock in the morning, too?

  “Psycho…Natalia,” Jason said. “Natalia…Psycho.”

  “Hey,” Natalia said with an easy smile. She was, after all, a girl you could take anywhere. One minute she could be the slinkiest cat on the hot tin roof, wrapping her dancer’s body (she was the tap-dance champion of Canada in 1996) around a client’s body in a hotel elevator. Then, when the door slid open, she’d look classic, like a wife even, on the arm of a Wall Street CEO or Asian electronics magnate. She was an actress, had played Shakespeare and Off Broadway both. Ever the ingénue, she’d been Juliet half a dozen times. Playing opposite Jason’s however-out-of-luck Romeo was no sweat, even here, in jail.

  Not that Natalia had exactly been looking forward to coming to Rikers this raw late-spring morning. Riding in the bus over the bridge from East Elmhurst, freezing in her lace stockings as she sat beside a stocky black man in a Jerome Bettis jersey, she looked out the window at the looming prison and said, “Wal-Mart must have had a two-for-one on barbed wire.”

  It wasn’t that she didn’t miss J
ason, or the heyday of when they lived together at Seventy-nine Worth Street, the harem stylings of which came to Jason while getting his hair cut at the Casbah-themed Warren Tricomi Salon on Fifty-seventh Street. It was just that this marriage thing was flipping her out, especially after Jason called the tabs to announce the ceremony would be held inside Rikers.

  “Every little girl’s dream, to get married at Rikers Island,” Natalia said to Jason. “What are they going to get us, adjoining cells?”

  But now, holding hands in the visiting room, surrounded by low-level convicts, just the sort of people who rarely appeared in either of their well-to-do childhoods or in the fantasy life of Seventy-nine Worth Street—neither of them, pimp or escort, could keep from crying.

  “Are those happy tears or sad tears?” Jason asked.

  “Just tears,” answered Natalia.

  “Crying because your boy is in jail?”

  “That and…everything else.”

  It was a tender moment. Except then, as he always does, Jason began talking.

  “Don’t worry about this Rikers marriage,” he said, back in schemer-boy genius mode. “This isn’t the real marriage…When I’m out we’ll have the princess marriage…the white dress, everything. Your mom will be there. My dad…This is just the publicity marriage. You know: getting married at Rikers—it’s so…rock star!”

  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 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 super-fantasy, are willing to shell out seven hundred dollars 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 psychosocio-sexual drama crammed with equal parts genius (occasionally vicious) boychik 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, Itzler moved to New York with his mother, whom Jason 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 it 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 ha
d 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.”