Secrets of the Megapimps

A visual interpretation of the governor’s very bad week by Andy Gray, Ogilvy & Mather, left, and Tom Godici and Greg Ketchum, Ogilvy & Mather, right. Photo: Mario Tama/Getty Images, right

Hearts have been broken, ideals betrayed, shock registered across the sociopolitical landscape. “Never saw this coming, not in a million years,” says one buddy of mine who went to Harvard Law with Eliot Spitzer. “Sure, he was a driven guy, but a good guy. He never impressed me as a manic horndog, not any more than anyone else.”

This is the basic response to the monumental Spitzerian crash-and-burn: surprise. Surprise that he would take such risks, surprise that he’d be so reckless/dumb to use a wire transfer in a business where everyone else, from truck drivers to CEOs, pays cash. Surprise that he would cheat so vigorously on the super Silda.

But there is one segment of the population that is not surprised. Not one bit. “Surprised?” says Lulu, who called herself Celine before she was named Robin, and who made “at least $150,000 a year” as a part-time “high-end” hooker before her retirement in 2005. “Look,” Lulu says, purring into the phone, “I’ve had famous clients—maybe not governors, but well-known business guys. People you read about in the Wall Street Journal, and let me tell you, if Michael Jackson or, like, the Dalai Lama came through the door, I might get surprised. But Eliot Spitzer? No way. What I’m selling, you never get surprised who’s standing at the counter.”

This is pretty much the opinion from the top end of the oldest profession: There’s just not much new ’neath the sun down here in the New York underground penthouse-sex division.

Posts on the Erotic Review, the sex-for-hire industry’s Bible blog, reflected more bemusement than disbelief. Initial speculation as to who “set Spitzer up” (on March 11, poster “Officer Krupke” said it had to be the Wall Street CEOs, who could now “return to business as usual: insider trading, backdating options, embezzling”) soon passed to discussion of the Luv Guv’s supposed refusal to wear a condom, leading one informant to say that in his experience, the Emperors Club VIP was “very safety-conscious,” where “everything was covered” and “daty” (sex-net for “dining at the Y,” or cunnilingus) was strictly off-limits. If “Kristen” favored her famous client with a “bbbj” (bareback blow job) on that fateful St. Valentine’s eve, the question around town was, “Did she spit-zer his jiz-zer?” One local $1,000 girl known for a thoroughgoing reading of the Times op-ed page said she knew right away it was a Democratic sex scandal, “because if it was Republican the hookers would have been guys.”

Someone who was certainly not surprised by Spitzer’s fall was Jason Itzler, erstwhile self-declared King of All Pimps. The now-41-year-old but still endlessly openmouthed Jason, whose exploits at his pricey NY Confidential whorehouse were previously described in this magazine (see “The $2,000-an-Hour Woman,” July 10, 2005), knew right away, before it came out in the press, that the Big Spit was a regular. “When I was in the business, if you had someone like him, you’d comp him. You comp him and comp him again, all the while jumping for joy because a client like that is like having the ultimate ‘get out of jail free’ card. But there’s a point you can’t comp him anymore. He’s using too much. You’ve got to begin charging. So if Spitzer was paying, and paying that much, he had to be serious addicted.”

Having served two and half years on Rikers Island for running a house of prostitution and money-laundering, Jason was now flogging his “next level” enterprise, DNA Diamonds, a legal matchmaking service that proposes to set up billionaires with fabulous women (i.e., “the girls with the best faces and the best bodies”) for the purposes of love and matrimony (only). “What can I say,” Jason says, in his gooiest prose, “I just like being surrounded by beautiful women and creating love, only this time it is for keeps.”

The Spitzer crack-up has been a bonanza for Jason, a man for whom any day he appears on “Page Six” is a good day. His best iron in the fire is his assertion that he put Spitzer’s “Kristen” into “the business.” This occurred, Jason has been telling Larry King and anyone else with a camera, back in 2004, when he met the woman now known as Ashley Alexandra Dupré at the Hotel Gansevoort, where she was a cocktail waitress. Impressed with the then-19-year-old’s, uh, “spirit,” Jason recruited her for his NY Confidential stable, renaming her “Victoria.” An immediate smash earner, “Victoria” was one of the girls Jason claimed to have dressed up as a cheerleader and sent over to Über-cocksman Charlie Sheen as a well-documented birthday present.

In the midst of this self-promotional blitz, Jason called to say not to worry, he was saving “the best juicy bit, what you can’t say on TV” for me. To wit: that even if Jason saw it as his right and duty to sleep with all the $1,000 NY Confidential girls, “Victoria” refused his advances. “She was like the only one,” Jason says. This rankled the so-called “King of All Pimps” primarily because “Victoria” had what all the other girls kept describing as “the most beautiful vagina in New York.”

By Thomas Allen, left, and Andy Gray, Ogilvy & Mather, right. Photo: Courtesy Foley Gallery, left

“It became the office joke,” Jason reports, “Victoria’s vagina and how I’d never even seen it.” This did not stop Jason from selling this facet of his charge’s anatomy. “You bet I did,” Jason remembers. “Big hedge-fund guys, the heaviest hitters, called and I’d say, this is the girl with the magic pussy, the best in New York. It bumped her price way up.”

It was all true, Jason said; if I didn’t believe him, I could call Natalia, his former girlfriend and queen bee of NY Confidential, the “$2,000-an-Hour Woman” herself. Having been sent to Rikers for a month following the agency bust, Natalia, now going by her real name, Natalie McLennan, was back in her Montreal home putting the final touches on her autobiography, The Price, due out this fall. She backed up her former boyfriend. “Believe me,” Natalia said. “Victoria and I, we did a lot of doubles. You do a double, sometimes guys want to, you know, watch. As soon as I saw her coochie, I told Jason, this is special.”

Was this it? The smoking, so to speak, gun in the entire Spitzer saga? Could it be as simple, as elemental, as that he couldn’t get enough of the girl with the magic pussy? Whatever the case may be, Spitzer’s downfall has been a vindication, an ultimate revenge, says Jason. “Ordinarily, I would have a lot of sympathy for a guy like this. But this guy helped shut me down. Put me in jail. Put all the girls out of work. Now he’s caught in his own trap. The biggest Dudley Do-Right becomes the King of Hypocrites.”

This was the kicker, Jason chortled: The girl he “trained” to be a high-priced whore took down Spitzer, prissy steamroller No. 1. It was, Jason said, “a Pygmalion thing.”

This invocation of the George Bernard Shaw classic of social transformation raises the question of what exactly goes into being a woman for whom someone like Eliot Spitzer would risk violating the Mann Act (the 1910 statute prohibiting the transport of a woman across state lines for “immoral purposes”—people previously prosecuted for this offense include Charlie Chaplin, Jack Johnson, and Chuck Berry). As any of the women sometimes seen in hotels like the Four Seasons and the Rivington knows, paid sex at the high end is almost never just about the fucking. For insight we consulted Amelia, a self-described “mid-multi-diamond Russian hooker” who commands as much as $1,500 an hour.

“I was trying out for these chorus parts on Broadway plays, and this guy approaches me. He tells me how much money I can make. I brushed him off, but I guess that’s where I really got the idea. I figured I could make myself into that high-end girl the guy was talking about. When they talk about the $500 girl and $1,500 girl, it is all in the details. I had to lose like ten pounds. I got a guy to take care of my teeth, made them pearly. I started to go to the $75 manicurist, not the $8 Korean. There were the shoes, the haircut, all that. You’re making yourself up for a part. These rich guys, some want that down-and-dirty thing, the $20 blow job in the car, like Hugh Grant. But most want this upscale fantasy. Their wives are already perfect, so you have to be more perfect. You give them perfect, plus—that’s what loosens them up.”

For many men, truly perfect means without a condom. “That’s the final taboo, that’s the last piece,” says one high-rolling businessman. “Not using one would mean that the girl cares for you because she’s making the big step. It’s an interesting psychology.”

Was this what Eliot Spitzer, the man who had everything, was looking for: perfect, plus? The thousands of hand-wringing hours of Spitzerian motivational psychology aside, there’s no doubt that it takes a lot to morph the man who was spoken of as a potential first Jewish president into the first black, blind governor of the state. One thing’s for sure, if Spitzer, the scourge of Wall Street, was caught in a stock finagle, no one would have cared, not this much. Sex is another matter altogether.

Questions float up. The hookers will tell you: Lies are easy; the truth is in the body language. That said, could there be any limit to the repression behind Spitzer’s tight frown, perhaps the tightest frown in history, during his initial apology speech? You wonder. Is there any redemption in throwing your whole life away just to scratch the itch of the unquelled libido? Where’s Norman Mailer when you really need him?

Face it, Spitzer might have been a prick, but at least he claimed to be our prick. That is the sad thing about this. This point was not missed even among the supposedly cynical precincts of so-called high-end prostitution. I asked Natalia, who had just done her own close-up on the Today show, how she really felt about Spitzer.

“You know, some guys, you give them a peek of the wild side … Well, you know. The last thing you want to do is mess up someone’s life. You could say he was really stupid. I mean, a wire transfer, wtf, dude! But I don’t like to use the word stupid. I’m going to say it was very unfortunate. The whole thing is very unfortunate.”

Chris Smith on Spitzer’s Downfall
Ariel Levy on Silda Spitzer
Slideshow: Artists Interpret Spitzer’s Bad Week

Secrets of the Megapimps