Tootsie Cop

Giselle had the Fosse look down pat, the court records show, wearing a “see-through body stocking with a thong bikini bottom and a bikini top.” Nancy was more formal in her evening gown. But in her sporty combination skirt-shorts, white top, and fiery locks, Cindy was dressed for anything: coke deals, lap dances – and, by the party’s end, making ten arrests.

Since 1994, Hell’s Kitchen neighbors had complained to police about Club Edelweiss, a transvestite oasis and drug den that drew hookers to Eleventh Avenue and 44th Street. Each time the city brought a case against the club, it would close briefly and then reopen. Finally, police decided they needed a man on the inside to pinpoint the prostitutes, soak up the La Cage-meets-Caligula atmosphere, and buy enough coke to pave a handball court. Enter Detective Gerard McMahon – a.k.a. Cindy, undercover drag queen.

On seven nights last fall, McMahon pulled on a skirt and a wig, borrowed makeup from his sisters in blue, and sauntered over to Club Edelweiss. Though female cops often dress up for prostitution busts, McMahon went where no male cop had gone before – on duty, anyway. “This is the first time I recall using an officer in drag,” says William Daly, director of the Mayor’s Office of Midtown Enforcement. “He’s a good-looking man but not a very good-looking woman.”

But Cindy must have had a nice personality. In all, she made eighteen drug buys and witnessed an eyeful of male-on-male lap-dancing, plus one act of fellatio in the bathroom. And on November 21, on a raid with four officers who weren’t in drag, Cindy was a girl who couldn’t say no. “He made two agreements for prostitution, which he wasn’t even planning to do,” says city attorney Virginia Sullivan, adding, by way of explanation, “People would touch him and pinch him.”

This month, acting Supreme Court judge Eileen Bransten padlocked Club Edelweiss for a year. The court record is packed with details of drugs, hookers, and wardrobe choices: Cindy’s new friends included “a male wearing a white sports bra” and “a male wearing a miniskirt.” The city found its trump card a few hours after the raid, when proprietor Dino Eliopoulos denied he was a procurer. When one cop said, “Come on, you know what goes on in there,” Eliopoulos inexplicably agreed: “I guess so. I made money off them by letting them do drugs and prostitution in my place.” The judge found the remark incriminating, even though Eliopoulos took the Fifth during the trial.

Eliopoulos’s lawyer, Hal Weiner, is now suing the city for $5 million on civil-rights grounds. “Transvestites and transgendered people are probably the most despised people in the city,” he says. “You can probably find the same number of drug dealers and prostitutes at the Waldorf-Astoria bar, if you put the kind of effort the nypd put into this. All the drug arrests were stings; the sex was agreed to; and if lap-dancing is all they saw, they might as well raid fraternity houses.”

The defense lawyer never met Cindy. But he did see a picture of her in a red shoulder-length wig. When deposing Cindy’s alter ego, he couldn’t help but offer the detective some advice. “I said, ‘If you’re going to be a drag queen, you should dress better.’ ” If only the club’s clientele had been so discerning.

Tootsie Cop