Police Say Hookers Drug and Mug Rich Men in Plush Midtown Hotels

“Wanna feel my gun?” said Gary Napoli, motioning toward his ankle.

It was late at night and Mr. Napoli was standing at the cocktail bar of Fifty-Seven Fifty-Seven, the elegant restaurant in the Four Seasons hotel. He looked nonchalant, just another guy out for some laughs. He was wearing a gold hoop earring in one ear and sipping from a Bailey’s Irish Cream on the rocks. He was checking out every woman in the place.

Mr. Napoli, an undercover sergeant with the New York Police Department’s vice squad, had a pistol in an ankle holster and a wallet full of phony identification cards. No, Fifty-Seven Fifty-Seven is not one of his usual hangouts. He was there on business, looking into a little problem that police say has been plaguing upscale midtown hotels lately: prostitutes who pick up businessmen and rob them.

On the night of Jan. 21, Mr. Napoli was posing as a publishing executive. He was a little worried, he said, because of the earring. Shouldn’t he have worn the more discreet diamond stud, rather than the gaudy hoop, to more convincingly play the role of Manhattan media macher ? But the hoop had brought him luck, and so that’s what he wore.

The man standing beside him at the bar was Rod MacDonald, a vice squad detective who was playing Mr. Napoli’s “college buddy” from their days at “SUNY Buffalo.” Both officers made a point of wearing dark socks for this assignment, rather than the white socks they usually favor. Mr. MacDonald, who had a Four Seasons room key in a pocket of his tweed blazer, was sipping Champagne. And why not? Drinks were on the N.Y.P.D.

The undercover men had heard that “escorts” have been slipping “mickeys”-usually powerful liquid sedatives meant for animals-into their clients’ drinks, then “rolling” them. The hapless john would wake up in an empty room, pants down and pockets empty.

At around 11:15 P.M., Mr. Napoli was keeping a sharp lookout for possible perpetrators; his partner seemed a little weary. “It’s one of the nicest hotels in the city,” Mr. MacDonald said. “We haven’t seen anyone tonight.”

His frustration was understandable. Fifty-Seven Fifty-Seven, at 57 East 57th Street, is clean, orderly, even a little intimidating, and it looks nothing like a crime scene. You reach it by way of a grand white staircase leading out of the Four Seasons’ monumental lobby. The restaurant-designed by I.M. Pei, like the rest of the hotel-manages to be coolly minimalist and plush at the same time. The New York Times dubbed Fifty-Seven Fifty-Seven “one of the city’s stateliest dining rooms” and said it “makes everyone sit up a little straighter”; the Zagat restaurant survey called it a “modern masterpiece.” They serve truffles in the mashed potatoes.

Seated at the lounge’s tables are future Stepford wives in pearls and cashmere, bankers with their mothers, headhunters and their clients, frightened out-of-towners, men in suits nibbling cheese biscuits and throwing back $11 Scotch-and-sodas.

In among them all, there she was. A middle-aged woman in a mottled fur coat. Maybe she didn’t look like a hooker to the civilian eye, but she got Mr. Napoli’s attention. For one thing, the night was a little warm for fur-and the conversation between the woman and the man in the banquette did not look entirely natural.

She had long brown hair, teased, and her bangs were curled. Bright red lipstick, heavy foundation makeup. The man in the banquette appeared to be turning down her advances. What could be worse than being blown off by some potential john? That’s when the “publishing executive” at the bar started checking her out in earnest. Oh, he was a cad.

She made eye contact with Mr. Napoli. That was her first mistake.

From the Oak Room to Your Room

With street-level prostitution on the downswing, members of the oldest profession are having to look for more creative ways to keep the deals flowing, so now some of them are leaving the street corners and brothels, or else turning off their beepers, and moving directly into the realms of the city’s Rolex class.

According to Lieut. George Pagán, the commanding officer of the detective squad at the 18th Precinct in north midtown, there have been at least four incidents of prostitutes “rolling” clients in upscale midtown hotels lately. In one case, a police strip-search revealed a vial containing a horse tranquilizer hidden away in the panties of one prostitute they arrested. Police officers said they have received complaints of “prostitutes” rolling clients from the Waldorf-Astoria Hotel, the Plaza Hotel’s Oak Room and the eighth-floor revolving lounge at the Marriott Marquis.

A Plaza spokesman had no comment on any such complaints; the Marriott Marquis did not return calls seeking comment by press time; a Waldorf-Astoria spokesman said the hotel was not aware of any such complaints, adding, “Certainly if we see any activity that looks suspicious, or if somebody’s acting in an improper manner, then security would be notified.”

In a further dispatch from this unlikely crime front, another alleged victim said he met a woman at the Plaza and invited her back to his room-only to end up drugged and mugged in an elevator. He woke up naked in a Brooklyn hospital with little memory of what had gone on the night before. When the man went to the police, he said he had invited the woman into his room at the Plaza because she had asked him for a glass of water, said Capt. John Costello, the executive officer of Manhattan’s vice division; the “glass of water” line rings bells with vice squad cops. It’s the kind of thing they hear from men who are embarrassed to admit they would pay for sex in the first place, but feel compelled to report the incident because they were robbed and assaulted.

And when johns aren’t making up tales to hide their own sins, they’ll often keep their mouths shut about having any contact whatsoever with a prostitute, whether they end up robbed or not. Who needs to make an official complaint pertaining to any ugly activities that may have gone down while they’re in swank hotels on business, away from the wife and kiddies? And the hotels aren’t much help in ridding themselves of such crimes, either, often preferring to sweep anything that might be of interest to the vice squad under the rug.

“Hotels don’t like to admit these things,” said Lieutenant Pagán. “It’s like asking the principal of a school, Do you have a drug problem? Of course they’ll say No.”

Anonymous police sources said that if there were four or five cases last year that were actually documented, there were probably over 20 more that weren’t.

Lieutenant Pagán added that hotels seem to go to the police only when the problem gets out of hand. Some hotel managers, he said, may even phone in complaints anonymously to police precincts.

The Lady in Fur

At the Four Seasons restaurant on Jan. 21, Mr. Napoli watched as the lady in the mottled fur coat moved past the bar. Their eyes met, and he caught up to her by the maître d’s desk.

A little while later, Mr. Napoli told the rest: “I walked toward her, said hello, how are you, why are you leaving so soon.… And she said, ‘The bar’s more or less dead.’ She said she was going to the Plaza-the Oak Room. She asked me what I do for a living … and I said to her, Oh, what do you do for a living, and she said she was a professional escort, and then, more or less, she told me that her fee was $500 … for anything you want within reason-sex, oral and straight, striptease, massage. Nothing beyond that. No bondage or anything like that.”

Mr. Napoli told her to wait. Then he returned to the bar, picked up his partner and they made the arrest.

They told her to keep quiet as they walked her to the squad car, reading her the Miranda rights as they moved down the grand staircase. Once they got her into the squad car, her only request was that the police move her own car so it wouldn’t be towed. She had exactly $500 on her, giving Mr. Napoli the impression that his fictional alter ego wouldn’t have been her first client of the evening. He got two precinct cops to move the car, which allowed him to note down the license number for “intelligence” purposes. They booked her at the station. She said her name was Tina James. Then she gave them two addresses that proved to be fake.

Rick Curtis, an anthropologist at the John Jay College of Criminal Justice who studied midtown street-level prostitution several years ago, attributes the seeming rise in hotel prostitution on broad-based changes in the sex trade. “When [I] started out in 1993 and 1994, there were quite a few complaints about women working around 56th Street and Sixth Avenue, and there were several hotels there. But by the time I got over there, in 1994, it had decreased fairly significantly,” he said.

The number of prostitute-related offenses in Manhattan has gone down, from 5,275 in 1992 to 3,115 in 1996, according to Police Department records.

“We began to see kind of a broadening, if you will, of the sex industry,” Mr. Curtis said. “Lap dancing had become more mainstream. You had more upscale guys going [to strip joints] with platinum cards, and it was fairly lucrative. So a lot of women that might have tried to work the street … were attracted to new opportunities.”

The Sentence

It’s no secret that more goes on at chichi hotels than just debutante balls and panel discussions. Most recently, the Plaza Hotel got a public relations migraine on Feb. 4 when police arrested actor Daniel Baldwin, whom they found naked and surrounded by empty crack-cocaine vials in his room.

Exactly a week after the arrest of Ms. James, the scene at Fifty-Seven Fifty-Seven was much the same. Both the crowd at the bar, which was several people deep, and the three rooms of tables were full of men in Zegna suits and Hermès ties, many of them older and sans wedding bands, and a few dames in furs, some powdering their faces, some smoking cigarettes. The actor Michael Keaton, in town for an appearance on Late Show With David Letterman , was there in a black T-shirt; he chatted with a waitress for a while before settling in at his table until last call.

A long-haired blonde in a mink walked in and sat down at the far end of the bar, whipped out her cell phone and began dialing. An investment banker went over to talk to her. Her name, she told him, was Diane; she was a fashion designer-in fact, she said, she had designed the very dress she was wearing that night, a long black sleeveless number that showed off her brassiere.

He bought her a second Absolut and soda. She told him she used to work as the executive dining room hostess at a Wall Street investment house, and that she was trying to call some guy named Larry in Miami. When the banker asked her if she had a cold-she kept sniffing loudly-she said, “Whaddaya mean , do I have a cold? I’m going skiing tonight.” Eventually, she put her hand on his inner thigh and said, “So, are you going or staying?” Another couple was in the sparring stage: The man said he was an investment banker, and the woman said she was a “Daddy’s girl.” Meanwhile, yet another couple was deeper into the game, necking furiously at the bar as the lights went up after last call.

Some Wall Street princes prize the pickup scene at Fifty-Seven Fifty-Seven. “If I wanted to go meet a girl and, like, suck face with her, I’d probably go there, because it’s a pretty high hit rate,” said one investment banker, a Fifty-Seven Fifty-Seven regular. “But it’s not like going somewhere downtown and doing that, where I’m like, fuck, anything can happen to me.”

Yeah, that’s what he thinks.

But how can hotel and restaurant managers distinguish between the pros looking to turn a trick (and perhaps filch a wallet or two) and the women the banker described as the “businessman groupies-you know, the nonpaid people doing the same thing”?

Brian Honan, a spokesman for the Four Seasons, said you can’t turn anyone out of a bar because he or she might look cheap or suspicious. “It’s discriminatory, illegal, all that … no matter what somebody looks like, they certainly have rights,” he said. “When the line’s crossed is when someone’s privacy has been invaded by unwanted solicitation or attention.”

Mr. Honan, for what it’s worth, denied the arrest conducted by Mr. Napoli and Mr. MacDonald-and witnessed by The Observer -had occurred. “We’ve never had an arrest on property,” he said.

Rick Curtis, who interviewed pimps and prostitutes for his study, said hotel managers “definitely let the women know that they’re not welcome there. And a lot of women will just go to another hotel.” Still, added Mr. Curtis, “It’s definitely well known that a lot of women will just pay off the bartenders and doormen” to avoid being ratted on.

Mr. Costello admitted the N.Y.P.D. has de-emphasized its focus on hotel prostitution, mainly because the pros and the johns are usually discreet. “It’s just one of those things that goes on,” he said. “It’s time-consuming, and there are other priorities.”

Besides, he added, trying to curtail the oldest profession may simply be an exercise in frustration. “If there was a rash [of hotel incidents] or, God forbid, somebody really gets hurt as a result of this,” he said, “then, of course, we would try to … assist with that investigation.”

As for the hotels, said Mr. Costello, “If it’s bad for business, they wanna put a stop to it, too.”

But Mr. Pagán pointed out that perhaps the hotel call girls aren’t so threatening after all. “Women just walk into a bar,” he said, “they order a drink, they sit there, [and] they’re very well dressed, pretty women and actually what they do is they dress up the bar and attract customers. And unless [management’s] been getting complaints from guests, they don’t chase them away that easily.”

Tina James, the woman nabbed at the Four Seasons, pleaded guilty. She spent a night in the lockup at the 18th Precinct. The next day, the Midtown Community Court ordered her to attend a health seminar and sentenced her to one day of community service.

Police Say Hookers Drug and Mug Rich Men in Plush Midtown Hotels