According to this week's New Yorker profile by Peter J. Boyer, he's New York
used-car dealer and actor Elliott Cuker:
It became clear at the start of Giuliani’s political career that his courtroom talents—the ability to break a witness o the stand, for example—were not especially useful in the task of charming voters. In Giuliani’s delivery style, ther was no trace of the natural politician. Apart from mechanical liabilities—including a lateral lisp that produces a slushy “s” sound—Giuliani was impaired by a native harshness that proved resistant to the remedies of his political advisers. I both runs against Dinkins, Giuliani’s campaign enlisted the candidate’s wife, Donna Hanover, in an effort to humaniz her husband through television ads. (These ads are now YouTube staples.) Old friends and trusted advisers, such a Peter Powers, despaired of ever coaxing a softer Giuliani to the fore. Then, about midway through his first term Giuliani turned himself over to a man named Elliot Cuker, who, in short order, had him squeezing into a dress
In Giuliani’s circle, Cuker functioned variously as the Mayor’s drama coach, his personal adviser, and his best friend. Born near Tashkent, Cuker had worked as an actor before establishing a successful business selling classic automobiles. During a stint in private law practice in the nineteen-seventies, Giuliani represented Cuker in a tax case, and the two men established a bond that both amused and puzzled Giuliani’s political associates. Cuker, unrestrained by deference, was credited by Giuliani with crafting a speaking style for him—a conversational persuasiveness—that became a political strength (and a source of vast wealth on the lecture circuit). “He was a dreadful speaker,” Cuker recalls of the early public Giuliani. “He was stiff, and his forehead would get drenched, with sweat running down both sides of the temples. He was extraordinarily uncomfortable speaking.”
Giuliani was a pliant student, making himself available to Cuker at all hours. “I’m a member of the Actors Studio,” Cuker told me, “and I had the key to the Actors Studio, and when everybody left I would take him there sometimes, like at ten o’clock at night, and work with him. But we worked everyplace.” Cuker’s aim was to force Giuliani away from his notes and toward spontaneity. “The fact is, I got close enough to him as a friend, at the time, that he had such trust in what I’m doing with him, that he let himself truly open up to me in a way that he really hadn’t done with anybody,” Cuker said. “And he’s become very spontaneous, as you can see. Very spontaneous.”
By the time Giuliani gave his third state-of-the-city address, in 1996, he left his notes on the lectern and, microphone in hand, walked about the stage, “talking” his speech. “Just talk to the people,” Cuker had advised. “Connect to the people.” Giuliani gave Cuker a parking pass at Gracie Mansion, and put him in charge of the annual Inner Circle political dinners—the municipal equivalent of the Washington Gridiron Club dinner, in which politicians and members of the press kid each other in skits and songs. Cuker saw the Inner Circle performances as another means of shaping the Mayor’s image. “I would rewrite a Broadway show to put Rudy into the show to help with what he needed at the time, politically, for his image,” Cuker recalled. “For example, when he was throwing Arafat out of Lincoln Center, people saw him as being very angry.” In 1995, during a United Nations celebration, Giuliani called Arafat a “murderer” and had him removed from a concert at Avery Fisher Hall. Cuker continued, “What I did was I chose the show ‘Grease,’ and I rewrote the show. And I put him on a motorcycle, and I showed him as a Hells Angel rebel back in school, and how it all started. So every show I did had a purpose.”
It was Cuker who was responsible for Giuliani’s turns in drag, which have also become a YouTube staple. “I am the one who convinced him that it would be a great idea to put him in a dress, soften him up, and help him get the gay vote,” Cuker says. “And, ultimately, it was his biggest bonus, because he got the gay vote—and the conservatives, who couldn’t believe that he had the balls to do something like that. It was a home run for him, and he got national attention. It showed that he had a sense of humor.”
Cuker accompanied Giuliani to the golf course and to Yankee Stadium, and talked with him on the phone a half-dozen times a day. When Cuker sensed that the Mayor needed a retreat, he opened a cigar bar—Cooper Classic Cars and Cigars, on West Fifty-eighth Street—which became Giuliani’s Elaine’s. “We were almost like brothers,” Cuker says now. “We were extremely close. He had a very strong trust in me, and he knew that I cared about him. And he knew that, whatever I did, I always tried to be there for him, and to help him with that other part of himself.”