The Best American Crime Writing 2006

Mark Jacobson : The $2,000-an-Hour Woman

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 ingenue, 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 Jason, 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, every-thing.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 "nocti-vagous 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 tipp. 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 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 serving 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. I wanted to be Edie, 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.

1 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 become boyfriend and girlfriend."

At the time, Jason's top girl was Cheryl, a striking blonde 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: "With her, there's none of that shit like this is costing enough for a first-class ticket to London and the girl's in the bathroom for, like, half an hour. Natalia's this one, total this-is-all-about-you."

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, championship athlete. "I'm not a big sports fan, but I recognized him, the quarterback. 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!-$5200, 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 August 9 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."

Asked if the work affected her relationship with Itzler, Natalia says, "Sometimes he'd say, 'Everyone gets a chance to spend time with you except me.' I'd say, 'You're the one booking me.' "As for Jason, he says,"If she ever did it with anyone for free, it would have broken my heart."

Moving from Fifty-fourth Street following a nasty fallout with partner Bruce Glasser (each party claimed the other had taken out a contract on his life), Itzler ran NY Confidential out of his parolee apartment in Hoboken. One visitor describes the scene:"The place was full of naked women and underwear. It was a rain forest of underwear. In the middle on the couch is Jason with all these telephones, one in either ear, the other one ringing on the coffee table."

Seventy-nine Worth Street, with its twenty-foot ceilings and mezzanine balconies, where Jason and Natalia would move to in the summer of 2004, was a whole other thing. "Right away, we knew this was it," says Natalia. "The loft felt like home." As per usual, Jason would take much of the cost of the lease from Natalia's bookings-money she would never receive. But money was never an issue with Natalia. If Cheryl, Jason's first superstar, experienced "a rush of power when the guy handed me the envelope," for Natalia, collecting the "donation," while essential, had a faintly unseemly feel.

"Maybe it sounds crazy," she says, "but I never felt I was in it for the money."

For Jason, the loft was an opportunity to make real his most cherished theories of existence. "To me, the higher percentage of your life you are happy, the more successful you are," says Jason, who came upon his philosophy while reading Ayn Rand. "I was really into the 'Who is John Galt?' Atlas Shrugged thing. I thought I could save the world if I could bring together the truly elite people, the most beautiful women with the most perfect bodies, best faces, and intelligence, and the elite men, the captains of industry, lawyers, and senators. This would bring about the most happiness, to the best people, who most deserved to be happy."

Years before, Jason wrote out the precepts of what he called "The Happiness Movement." Assuming his findings to be big news, Itzler packed up the manifesto, a copy of his half-finished autobiography, and a naked centerfold picture of Elisa Bridges, his girlfriend at the time, and mailed it to Bob Woodward."I stuck it in this three-thousand-dollar Bottega Veneta briefcase so he'd notice it. He said I was a nut job and to leave him alone. I was so bummed I told him to keep the stupid briefcase."

On Worth Street, however, Jason (who says "the best thing about bipolarity is how much you accomplish in the manic phase") saw the chance to manifest his ideal. One of his first acts was to approach painter Hulbert Waldroup. Waldroup, a self-proclaimed "artist with attitude" who has been collected by Whoopi Goldberg and once appeared on the cover of Newsday along with his epic memorial to Amadou Diallo, was selling his work on the West Broadway sidewalk. "You're the greatest painter I've ever seen," Jason said.When Waldroup heard Itzler wanted to commission a ten-foot-by-ten-foot canvas of a "hot-looking" woman, he said the picture would never get in the door. No problem, Itzler said, Waldroup could do the painting inside the loft.

Waldroup soon had a job working the phones. "It was like I went in there and never came out," says Waldroup, now on Rikers Island, where he resides a couple of buildings away from Jason.

Seventy-nine Worth Street became a well-oiled machine, with various calendars posted on the wall to keep track of appointments. The current day's schedule was denoted on a separate chart called "the action board." But what mattered most to Jason was "the vibe… the vibe of the NY Confidential brand" (there was franchising talk about a Philadelphia Confidential and a Vegas Confidential). To describe what he was going for, Jason quotes from a favorite book, The Art of Seduction, a creepily fascinating tome of social Machiavellianism, by Robert Greene.

Discussing "seductive place and time," Greene notes that "certain kinds of visual stimuli signal that you are not in the real world. Avoid images that have depth, which might provoke thought, or guilt… The more artificial, the better… Luxury-the sense that money has been spent or even wasted-adds to the feeling that the real world of duty and morality has been banished. Call it the brothel effect."

Accentuated by the fog machine at Seventy-nine Worth Street, people seemed to come out of the shadows, float by, be gone again. "It was full of these familiar faces… like a soap-opera star, a politician you might have seen on NY1, a guy whose photo's in the Times financial pages," says one regular. In addition to Sinatra, music was supplied by the building's super, a concert pianist in his native Russia, who appeared in a tuxedo to play on a rented Baldwin grand piano.

"It was like having my own clubhouse," says Jason now, relishing the evenings he presided as esteemed host and pleasure master. He remembers discussing what he called a "crisis in Judaism" with a top official of a leading Jewish-American lobby group. Jewish women were often thought of as dowdy, Jason said. If the American Jew was ever going to rise above the prejudice of the goyishe mainstream, creativity would be needed. A start would be to get Madonna, the Kabbalist, to become the head of Hadassah.The official said he'd look into it.

Seventy-nine Worth Street was supposed to be Jason and Natalia's home, where they would live happily ever after. They had their own bedroom, off-limits to everyone else. "We were actually trying to live a semi-normal life, carry on a real relationship," says Natalia. "Jason felt abandoned after his mother died; my father left when I was very young.We sort of completed each other."

Natalia wrote her mom that she'd moved into a beautiful new place with a highly successful businessman. Her mom, a sweet cookie-baking lady leery of her daughter's life in New York, wrote back that she'd like to come down to visit. Natalia was going to put her off, but Jason insisted. Looking around the loft at the naked women, Natalia asked, "How am I going to have my mom come here?" Jason said he would close the place, and take the loss, for the time Natalia's mom was in town. Family was the most important thing, he said.

"Well," Natalia says,"Jason never closed the loft. My mom and I stayed in a little apartment uptown. Jason was supposed to come by to meet her, but it started getting late. Then the doorbell rings at 2:00 a.m. It's Jason, in his knee-length coat with these two nineteen-year-old girls. I'm totally flipping out: Like, what the fuck are you doing? He looked like the pimp from Superfly. My mom is saying, 'This is him?' But then Jason sits down and starts telling my mom I'm a great young actress and my career is going to take off, how living in New York is so terrific for me. He charmed her, completely. She left saying, 'Well, your boyfriend is kind of weird. But he's very, very nice.' "It was always like that."

Few expected Seventy-nine Worth Street to last very long. There were too many, as Natalia puts it, "variables."

For Jason, the main difficulty in running New York 's hottest escort agency while on parole was the curfew. Even though his lawyer on the Jersey Ecstasy case, Paul Bergrin, was eventually able to extend Jason's lights-out time to 3:00 a.m., he still had to leave his Worth Street happiness house to sleep in his apartment in Hoboken.

"Everyone's partying, having the best time in the world, and the Town Car is outside to take me back to goddamn New Jersey."

"It was a big strain," says Natalia. "I finally get home from my appointments. All I want to do is sleep in my own bed, and Jason is screaming about how we've got to go back to Hoboken. He hated to be alone out there.We had horrible fights. One night, I jumped out of the car right at the mouth of the Holland Tunnel and ran away. Broke my heel on a cobblestone."

The parole situation led to other traumas. Court-mandated drug tests caused Jason to alter his intake. Always "on the Cheech-and-Chong side of things," Itzler couldn't smoke pot, which turned up on piss tests. Instead, Jason, who never touched coke and often launched into Jimmy Swaggart-like speeches about the evils of the drug, dipped into his personal stash of ketamine, or Special K, the slightly unpredictable anesthetic developed for use by veterinarians. "They didn't test for it," Jason says by way of explanation. He was also drinking a $200 bottle of Johnnie Walker Blue a day. Natalia's drug use cut into her Perfect 10 appearance. One night, she cracked her head into the six-foot-tall statue of an Indian fertility goddess Jason had purchased for their room. Knocked cold, she had to go to the emergency room.

Still, the business charged on. It takes a singular pimp to think it is a good idea to stage a reality-TV show at his place of business, but Jason Itzler is that kind of guy."It was incredible," says independent producer Ron Sperling, who shot the film Inside New York Confidential. "Big-shot lawyers and Wall Street bankers flipped when they saw the cameras. Jason told them the movie was no problem. That it was a good thing. If they didn't want to be in it, they should just walk behind the camera. That's Jason. If he was a billionaire and no one knew about it, it wouldn't be anything to him."

Despite misgivings about legalities,VHl expressed interest in Inside New York Confidential. Arriving late, Jason swept into the meeting with several girls. Along for the ride was a young Belgian tourist whom Itzler had encountered only moments before on West Broadway. "You're beautiful," Jason told the young woman. "But your clothes look like shit." Itzler bought her $2,500 worth of threads in about ten minutes, convincing her she would be great in his TV show.

"He asked for a million dollars an episode," says a VHl exec. "We told him that was insane money, so he got mad and left."

Jason's manic spending increased. One afternoon, splashing on Creed Gold Bottle cologne ($175 per bottle) as "kind of a nervous tic," he bought twenty-six antique crystal chandeliers at $3,000 apiece. "We had so much furniture, there was nowhere to walk. I used to jump over the stuff for exercise," says Natalia."We had this room upstairs we called the Peter Beard Room. Peter likes to sit on the floor, so we got these beautiful Moroccan pillows. One day, I come home, and there's a Playboy pinball machine there, with Hugh Hefner's face on it. Then I knew there was no point saying anything."

Jason's class insecurities also cropped up. One night, upstairs at Cipriani's, Itzler went over to where Lizzie Grubman was sitting with Paris Hilton. He asked Grubman about representing NY Confidential. Grubman, whom Jason regarded as just another Great Neck girl with a rich dad under the glitz, supposedly sneered, "I don't do pimps." Returning to his table,Jason said,"I hate that bitch. She runs over sixteen people and thinks she's better than me."

Jason's Utopian house of happiness turned into a stage for an ongoing paranoid soap opera. Feeling his grip slipping, Itzler begged his former fiancee Mona to help with the day-to-day running of the place. Mona, who had helped organize things in the earliest days of NY Confidential, ran a tight ship. But there were complications. It had been only eight months since Mona had been Jason's girlfriend, living with him in Hoboken. They broke up, leading to an enormous screaming match during which Mona called the police, claiming Itzler attacked her. Jason disputed this, allowing he "might have squeezed her hand too hard, trying to get my keys back." Mona would drop the charges, but not before Itzler spent some time under house arrest.

Jason says, "Maybe I'm just soft, because after Mona wrote the judge a tear-stained letter how I never beat her up and how she loved me, I forgave her."With Jason's parole problems increasingly keeping him in Hoboken, Mona soon filled the power vacuum at Seventy-nine Worth Street. Her key ally would be Clark Krimer, a.k.a. Clark Kent or Superman, a muscle-bound young banker hired by Itzler to manage credit-card accounts. This way, those wanting to disguise their use of NY Confidential services would appear to be spending their $1,200 or so at venues like the fictitious Gotham Steak. Clark and Mona soon became an item, consolidating their power.

The Clark-and-Mona regime upset "the vibe" of Seventy-nine Worth Street, turning it into, in the words of one working girl, "just another whorehouse." First to feel the fallout was Natalia. As queen of the castle, Natalia always dismissed the jealousies of the other escorts as "stupid girl stuff." This was different. She says, "Mona was a psycho-bitch. She hated me, and now she was running the place." When clients called, instead of Jason's rapturous invocations of Natalia's charms, Mona said, "I've got this girl, she's six-one, a rower on an Ivy League college scull team. She's cheaper than Natalia and way better." Natalia's bookings fell off.

One November afternoon, Natalia arrived at the loft to find Mona standing in front of the door to her room-her room!- demanding she turn over her keys to the loft. "This is where I live. My home," Natalia screamed. Eventually, however, Natalia decided to move out.

Through this, people began telling Jason he'd better cool things out, not keep bringing parties of vacationing second-grade schoolteachers by the loft for fun.With guys in Con Edison vans watching the place from across the street, the least he could do was make sure the front door stayed locked.

"What do I have to hide?" Jason scoffed. "I'm not doing anything illegal."

Much of this self-deluding assessment was based on the contract Jason, utilizing his best Nova U. legalese, worked up between himself and the NY Confidential escorts.The document, signed by all the girls, stated they were "specifically forbidden" to have sex with the clients. Itzler showed the contract to Mel Sachs, the floridly attired defender of Sante Kimes, Mike Tyson, and, more recently, the pint-size exhibitionist-rapper Lil' Kim. Sachs made a couple of adjustments and said the contract passed muster, which was just what Jason wanted to hear.

"I'm bulletproof. Rich people don't go to jail," Jason proclaimed. He was certain that if anything came up, Sachs and Bergrin, a former Army major, could handle it."Mel's my personal Winston Churchill, and Paul's the tough Marine general," Jason rhapsodized, either unaware or not caring that Bergrin is currently under federal investigation for his alleged part in the death of a police informer slated to testify against one of his drug-dealer clients.

"Mel became my best friend," says Jason, always impressed by a man in a fancy suit."He was always in my place.We all loved Mel." Asked about these visits, Sachs, after some deliberation, said, "Well, Jason is a personable guy. I liked talking to him. It was an interesting place, full of fascinating conversation. A lot of business people, financial people, professional people."

Amid this gathering train wreck, one incident in November 2004 stands out as the beginning of the end. That evening, accompanied by a mutual friend, two mobsters, members of the Genovese family, according to Jason, stopped by the loft.

"I never did any business with them. I just thought it might open a new line of high-priced clients," says Jason, who bought a $3,500 Dior suit for the occasion, with a matching one for his bodyguard, a former Secret Service agent. The meeting had barely begun when a girl named Genevieve burst through the door. A tall blonde, she was returning from her first NY Confidential date, reputedly stoned out of her mind, and was demanding to be paid immediately. Told to wait, Genevieve started yelling, threatening to call the police to adjudicate the matter.

"What's wrong with that girl?" one of the mobsters asked. Itzler asked the bodyguard to quiet Genevieve down. But as the bodyguard approached, Genevieve pulled a can of pepper spray from her handbag and blinded him. With the bodyguard writhing on the floor, Genevieve locked herself in a room and called 911. A dozen cops and an engine company of firemen arrived.

There was some debate about whether to open the door, but the mobsters said,"It's the cops, you got to let them in."

"I'm looking at the security-camera monitors," remembers one witness. "In one is the cops, another the gangsters, the third the screaming girl, the fourth the Secret Service guy rubbing his eyes. That's when I thought I'd take a vacation from this place."

The encounter would end relatively harmlessly. "It looked like one of the cops recognized one of the gangsters," says the witness. "They started talking, everyone exchanged business cards and left."

After that, the cops started coming to the loft almost every day.

"They'd knock on the door, come in, look around, and leave," remembers Hulbert Waldroup. Almost always, they took a stack of Jason's distinctive metal rocket fuel for winners business cards. The card had become something of a collector's item at headquarters, one cop says. "Everyone wanted one." Rumor has it that one ended up on Mayor Bloomberg's desk, to the mayor's amusement.

When the big bust inevitably came down on January 7, the loft was nearly empty. Krimer and Waldroup were at an art gallery when someone's cell phone rang. The caller said no one was picking up at NY Confidential.That was a bad sign,Waldroup said.

Frantically, Krimer and Waldroup attempted to connect to the Webcam security system Itzler had installed so he could watch the activities at Seventy-nine Worth Street from his Hoboken apartment. The cam was available from any wired-up computer. But no one could remember the password. "Fuck!" screamed Krimer. Eventually the connection was made.

"The place is being raided, and we're watching it on the Internet," says Waldroup."The cops were like ants, over everything, taking all the files, ledgers, computers. On the couch were these people I'd worked with for months, in handcuffs. It was very weird."

Jason wouldn't find out about the bust until sometime later. "I was shopping for rugs with Ed Feldman, who is kind of a legend in the fashion business," Jason says. It was Feldman who, years before, had given the young Jason Itzler a copy of Budd Schulberg's all-time delineation of the Hebrew hustler, What Makes Sammy Run?

"Read it," Feldman said. "It's you."

Jason says, "I immediately checked into the Gansevoort Hotel and began partying. Had a couple of girls come over because I figured I wouldn't be doing that for a while. When the cops came, I thought, 'Well, at least I'm wearing my twenty-eight-hundred-dollar rabbit-fur-lined sweater from Jeffrey's, because who wants to look like a guy in a sweatshirt?'When they snapped on the handcuffs, all I remember thinking was how I thought NY Confidential would last for twenty-five years."

Almost six months later, Jason is still in jail. In the beginning, he was confident that his lawyers, Sachs and Bergrin, after all that money and all those free drinks, would bail him out. That did not happen. With none of his regulars, the trust-fund babies and famous artists Itzler considered his friends, rushing to his aid, Jason wound up in front of Judge Budd Goodman at the One Hundred Centre Street courthouse, penniless and lawyerless, tearfully asking to defend himself, a request that was denied. "Ask me if I feel like a sap," Jason says.

Down deep, he always knew that when all was said and done, after everyone had had their fun, he'd be the one to pay for it.With the Bush administration coming down heavy on sexual trafficking-the religious right's top human-rights issue-Robert Morgenthau's office is not of a mind to offer deals to loudmouthed brothel owners, not this election year. As a "predicate" felon from his ill-considered Ecstasy importation, Itzler's facing a four-and-a-half-to-nine-year sentence. Even if he beats that, there is the matter of his busted parole in New Jersey. Sitting in Rikers, playing poker for commissary food, once again Jason has a lot of time on his hands.

One of the things to think about is what happened to all the money that was made at NY Confidential. A common theory, one Itzler advanced in a recent Post story, is that Clark Krimer, who may or may not be cooperating with the D.A., took it all.

"He stole four hundred thousand dollars," Jason says. "He should be in jail. If anyone laundered money, it's him." Asked if it was possible that he, Jason, had managed to spend a good portion of the missing money, Itzler scoffs, saying,"Who could spend all that?"

When it comes down to it, however, Jason says he doesn't want to think about Krimer or the fact that Waldroup remains in jail even if he only answered the phones."I'm staying optimistic," Jason says, free of bitterness. "It is like I told the girls, if you smile a fake smile, keep smiling it because a fake smile can become a real smile."

"The problem with NY Confidential was it didn't go far enough," Jason says now. "If you really want to put together the elite people, the best-looking women and the coolest guys, you can't stop with a couple of hours. It has to be a lifetime commitment." Jason has consulted his prison rabbi, who presided over the recent Passover ceremony during which Itzler got to sit with recently arrested madam Julie Moya (ofJulie's) during the asking of the Four Questions.The rabbi told Jason that as a Jewish pimp who sold women to Jewish men, he was liable for the crime of kedesha. The rabbi did not, however, think this transgression necessarily prevented Jason from becoming a shadchan, or a traditional matchmaker.

"I'm thinking about the future, the next generations," Jason says from his un-air-conditioned prison dorm."I think I have a chance to do something good before I die.Who knows, the answer to the question 'Who is John Galt?' could be 'Jason.' "

As for Natalia, she is "keeping a low profile." Last week, she went to see Jason again. Thankfully he didn't talk too much about getting married inside the prison. Mostly they talked about the strange times they'd been through and how, even if it turned out the way it did, somehow it was worth it.

"I was a young actress who came to New York like a lot of young actresses, and I wound up with the role of a lifetime. I was the Perfect 10. I totally was. It wasn't the rabbit hole I expected to tumble down, but Jason and I…we werehappy… for a time, really happy."

Since she received hardly any of her booking money and is pretty broke these days, people ask Natalia if she's planning on coming back to "work." The other night, a well-known provider, who said she used to hate Natalia when she was getting those 10/10s, offered to "pimp her out."

"That would be a feather in my cap," said the escort. "To be the one who brought back the famous Natalia."

"No, thanks," said Natalia, which is what she tells her old clients who call from time to time. "I say I'm retired, in repose.They say, 'Come on, let me buy you a drink. I'll be good.' I tell them, 'Look, we had fun and I love you. But that is over.' Mostly, they understand. Some are willing to stay friends, some can't wait to get off the phone.They've got other numbers in their book."

That doesn't mean a girl has to stay home at night. New York, after all, is a big place, full of opportunity. In a way, things have gone back to the way they were before she met Jason. "Wiser, but not necessarily sadder," Natalia says.Tonight she's going downtown. It is always good to look good, so Natalia goes through what was a familiar ritual back in the days when she was the Perfect 10-getting her nails done at the Koreans' on Twenty-ninth Street, combing out her wavy hair. For old times' sake, she's got on what she used to call her "money dress," a short satin pink number with gray jersey inserts, with the shoes to match. About ten, she's ready. She goes out into the street, lifts her arm, gets into a cab, and disappears into the night.

Mark Jacobson is the author of several books including the novels Gojiro and Everyone and No One. His nonfiction books include 12,000 Miles in the Nick of Time: A Semi-Dysfunctional Family Circumnavigates the Globe, and the recent Teenage Hipster in the Modern World. He has been a contributing editor at Esquire, Rolling Stone, Natural History, the Village Voice, and works for New York magazine. He was born and lives in New York City.

The article that wound up getting called "The $2,000-an-Hour Woman" (my original title was "Rocket Fuel for Winners," after the rubric pimpmeister Jason Itzler had engraved on his metal business cards) wasn't easy to find. But once it got going it didn't let up. Partially this was due to the ever-fecund life story of Mr. Itzler, much of which actually appears to be true. Jason is one of those perfect journalistic subjects: a guy with a lot to say who can't wait to say it. In me he had a proper foil because, to reference Sydney Greenstreet in The Maltese Falcon, I like listening to a man who likes to talk. As long as that talk stays interesting. Itzler did, even if he did-and continues to-call me at least five or six times a day from his current residence at Rikers Island. That's the real torture for the Sammy Glicks of the world, getting locked up with a bunch of people who simply don't care what he has to say.

The piece's other leading figure, Natalia McLennan, would also wind up in Rikers sometime after the appearance of the story. This was too bad, since as the 1996 tap-dance champion of Canada and former Shakespearean actress (several productions as Juliet in Romeo and Juliet, also as Flute in A Midsummer Night's Dream) she is definitely not the Rikers type. Luckily, though, she was sprung after a month or so, although not before making the papers back in her Montreal hometown. Natalia, who does indeed have the proverbial heart of gold, did not hold me responsible for this unfortunate period of incarceration since, as she put it, "It wasn't exactly like I didn't expect something to happen after they put me on the cover of New York magazine without my clothes on." All told, I would say I met a better, more amusing, not to mention honest, class of people associated with New York Confidential than on my more usual beats, like state and national politics.