If everything works out, it may be the last great political deal brokered in a smoke-filled room. On a balmy June night in 1999, Judith Nathan was having a drink at Club Macanudo, a cigar bar on East 63rd Street. Her companion was Dr. Burt Meyers, an infectious-disease specialist at Mount Sinai hospital and one of the many physicians she had befriended as a hospital sales rep for Bristol-Myers Squibb. Nathan, then 44, was at ease amid the upmarket manliness, a woman of the world among many middle-aged men of the world, including, that night, the mayor of the City of New York, Rudolph Giuliani.
Club Mac, with its wooden Indians, leather sofas, and “state-of-the-art ventilation system,” had become a well-known late-night haunt for the mayor. Perhaps it was also something of an escape: He was still living at Gracie Mansion with his second wife, television personality Donna Hanover. Here, he could kick back with a tumbler of Glenlivet and relax with City Hall aides and political associates. Sometimes a woman would approach him, interrupting his cigar-smoking to express her admiration, maybe get an autograph. Perhaps flirt mildly. So it wasn’t surprising when Nathan, a pretty woman with rich brown hair, came over and said hello.
This story of how they met had to be pieced together from accounts by Giuliani intimates because the couple refuses to talk about it. Even during their gauzy TV interview this past March with Barbara Walters—who was a guest at their wedding in 2003—which was a custom-made moment to safely peddle this type of personal anecdotage, Judith demurred. “That’s one thing I would kind of like to keep private,” she said, allowing only that “it was by accident.”
A few days after their fateful meeting, the mayor had an aide retrieve Judith’s business card from his desk drawer at City Hall, then he phoned and asked her out. They took in a movie at Loews Kips Bay, The General’s Daughter, which is about a cover-up at West Point. At dinner afterward, at Peter Luger Steakhouse, they were chaperoned by a couple of City Hall staffers.
Later, on the occasion of their marriage, Giuliani would tell the Times’ “Vows” columnist that “our attraction was instantaneous. There was something mystical about the feeling.” He evoked an appropriately operatic moment from one of his favorite novels, Mario Puzo’s The Godfather, when Michael Corleone spotted his Sicilian bride, Apollonia. “It was,” Rudy said, “the thunderbolt.”
When she met the mayor at Club Macanudo, Judith Nathan couldn’t have imagined the complexity of the relationship she was getting into. At that point, the considerable successes of Rudy’s mayoralty were in the past and his future was uncertain. He may have looked like a catch, but he certainly did not look like a potential president. There was talk of a Senate run. Now, in a Cinderella-like reversal, Judith Giuliani, with her husband’s help, is auditioning for a vast and contradictory role: romantic partner of America’s Mayor, wholesome third wife, definer of gender roles, and emblem of respectable femininity for an entire nation. So far, her attempts to play this impossible part have been riveting, if sometimes comic.
Rudy Giuliani has always been the most insular of politicians, operating within his personal tribe, at odds with most everyone outside. The prime value is extreme loyalty, and for those in possession of that quality (think Bernard Kerik), much else is forgiven. Like George W. Bush, he and his team create their own reality and wait for the world to follow.
Judith Giuliani is the latest to join this coterie, and by far the most important. He’s given her influence into all facets of his professional life. He has often referred to Judith as his “closest adviser.” In a 2003 TV interview, Rudy claimed that Judith is “an expert we rely on” at Giuliani Partners. “She gives us a lot of advice and a lot of help in areas where she’s got a lot of expertise—biological and chemical,” Rudy said as Judith watched him and nodded vigorously. “And since we do security work, that’s an area of great concern—you know, another anthrax attack, a smallpox attack, chemical agents. She knows all of that.” Famously, he told Barbara Walters that Judith would be able to sit in on cabinet meetings, acting at the time as if this were a perfectly ordinary responsibility for a president to give his wife.
At other times, their presentation has been lovey-dovey to the point of queasiness. Their displays of affection got so gooey during the taping of the Walters interview that the ABC News doyenne is said to have joked, “Enough already!” They held hands and cooed; he called her “baby” and she called him “sweetheart” as they kissed on the lips. At one point, after he absolved her of responsibility for his divorce from Hanover and his alienation from their two children (“She’s done everything she can. She loves all the children”), Judith, who was serenely feminine in a sea-green sweater, with another, lavender sweater tied casually around her neck over it, French preppy style, reached out to caress his cheek. When Walters asked her if she was “bothered” by her affair with the married mayor, Judith responded, blandly, “It was a rocky road, absolutely. But when you have a partnership that is based on mutual respect and communication, the two of you know what’s going on.”