Rudy’s Choice

Rudolph Giuliani has never been a man to do things by half, to exercise restraint, to show moderation. He loves grand opera, and throughout his career on the public stage, he has performed with the full-throated gestures of a tenor playing to the last row. Subtlety has never been part of his repertoire. His style has been marked by an enthusiasm for overacting and overreacting, whether he’s dragging stockbrokers out of their offices in handcuffs as U.S. Attorney or trying, as mayor, to slash museum funding when he didn’t like an exhibit.

So perhaps it shouldn’t have been a surprise that when the glorious, soaring music of Giuliani’s success began to give way in recent weeks to the darker chords of serious trouble, the shift was one of sweeping, third-act operatic proportions. And when the curtain came down on his Senate run, we were left with the image of a man who seemed to have been transformed.

His performance at his withdrawal last Friday was truly moving. He seemed to have shed his hard outer shell like an old suit. He focused on the personal and talked about striving to be a better person. And he wanted to reach out to those who felt ignored. Stunningly, here was the mayor saying all the things so many people have been trying to get him to say for so long.

As the mayor stood there talking about how lucky he was because of all the people who loved him and all the people he loved, it was impossible not to think about the speed at which his life has been changed. First the cancer diagnosis and then the Nathan-Hanover-Lategano drama. It all had a through-the-looking-glass quality – after all, this was Rudolph Giuliani. Not exactly a man known for self-examination. Not exactly a slave to his emotions. Giuliani has built his entire public life on the themes of discipline, personal accountability, and control. Every fire, every shooting, every water-main break, Giuliani was there in his windbreaker letting everyone know he was in charge. It was always his cops and his crime-control strategies that made the city safe. Ask him why the schools are failing, and he’ll say it’s because he doesn’t control them. But it turns out that the arrogant tough guy, a politician who ridicules and exploits weakness in others, is just like everybody else.

“The Rudy that ran New York was the great moralist, the guy who was operating by his own description from a deep sense of right and wrong,” says Democratic consultant Hank Sheinkopf. “Now we learn he’s not the Rudy people thought they knew.”

“It’s very difficult to watch someone who’s been in control just lose it this way and have it all crumble at his feet,” says a veteran insider.

Many in the mayor’s inner circle were devastated by events of the past several weeks. “I can’t even begin to tell you how I feel,” says one of his confidants, sounding on the verge of tears. “He’s obviously in pain right now, and I’m worried about him. But clearly the first priority is his health. Everything else can be dealt with later.”

Another Giuliani insider, now out of the administration, sums up the situation thus: “It’s very difficult to watch somebody who’s been so in control just lose it this way and have it all crumble at his feet. And I have to say I don’t understand what’s going on here. I mean, I don’t understand his public pronouncements. I don’t understand Donna’s public pronouncements. And I don’t understand parading Judi Nathan around in public. I don’t understand it, and I don’t know why he’s doing it.”

Many longtime Giuliani insiders were crushed by all the damage they felt he’d done to himself politically. After all the years of work, and all the single-minded effort to build an unimpeachable record as an activist and a reformer, so much was lost so quickly. And the great irony was that despite the mayor’s overactive paranoia reflex, there was no convenient, culpable enemy: no great left-wing conspiracy to point to and no despicable Democrat to blame. Giuliani couldn’t even claim the usual suspects, the media, had done it. For the simple fact was, Giuliani himself had made his private life public, and his most potent enemy seemed to be his wife.

While Giuliani weighed his political options last week, he looked, aides said, eerily Hamlet-like in his inability to pull the trigger. Day to day, and sometimes more than once a day, he changed his mind about whether to run for the Senate.

Throughout this excruciatingly difficult period, the mayor was relying on the counsel of his two closest friends, former deputy mayor Peter Powers and Elliot Cuker, the restaurant owner, car dealer, and sometime actor. Both, according to sources, were telling the mayor not to run.

“Peter was very concerned about his health as well as the whole Catholic thing and the propriety of it all,” says one source. “He firmly believes family comes first. Elliot, on the other hand, is telling the mayor to get in touch with his feelings, to reach deep down, to feel his heartbeat, and to listen to his soul.”

Arrayed against Powers and Cuker were most of Giuliani’s political people, who obviously had a vested interest in Giuliani’s continuing the race. “Once he got his medical situation worked out,” says one of these men, “everything else, all the personal stuff, would have gone away by September, and I still think he would have beaten her.”

But finally, on an appropriately dark and rain-soaked Friday morning, the mayor made the decision that seemed – at least for him personally – to make the most sense all along. One after another, the people who work for him were summoned in groups: deputy mayors, top commissioners, key campaign staff. “He simply told us that the reason he’s not running is his health,” says one disappointed loyalist. “He said it’s simply too serious a disease to deal with and to take on a major campaign as well. People certainly weren’t surprised, and there were no tears. But everyone’s blown away. There’s a malaise here now, a dark cloud hanging over City Hall.”

But with all the questions raised in the past few weeks, the one that has hardly been asked at all is, in many respects, the most interesting. Why has he behaved so bizarrely? Why does the straitlaced Giuliani, who sees the world in stark black-and-white, good-and-evil, with-him-or-against-him terms, suddenly look like an indecisive, introspective, flawed hero in a Verdi opera? Why has the man who humiliated any reporter with the temerity to ask about his personal life (and for five years, there’s been plenty of reason to ask) suddenly laid himself bare in public?

Though everyone in the mayor’s inner circle has known about his relationship with Judi Nathan for months, no one seems to understand how he’s handled it. (It is, of course, another hallmark of Giuliani’s administration that none of his advisers dared discuss it with him.) “We were all scratching our heads about this,” says one Republican insider. “We all understood the possible ramifications, and we were dumbfounded as to why he would expose himself to this kind of risk.”

In an effort to explain it, a couple of Giuliani friends point to the impact of his illness. “When you get cancer, your life comes into focus,” says a confidant, “and you start to realize what’s important and start to face your own mortality. You realize you’ve only got so many years in this life, and you want to do what you want to do. I think that’s what this is about.”

His illness, however, explains only the past couple of weeks. It doesn’t shed any light on why the mayor thought it was perfectly all right to have Nathan along on New Year’s Eve, when Rudy-in-charge was managing the millennium celebration in front of the whole world. Literally. Or why he paraded her (again, literally) in public on St. Patrick’s Day.

For that matter, it doesn’t even begin to explain why barely two days after a trembling Hanover accused her husband of cheating on her twice in the past five years, Giuliani would flaunt his girlfriend. On a beautiful Friday evening, as Hanover was off to California with the kids to spend Mother’s Day weekend with her parents, the mayor went to dinner with Nathan. After a leisurely meal at Tony’s Di Napoli on the Upper East Side, a beaming Giuliani, accompanied by a claque of reporters, strolled with Nathan back to her apartment on 94th Street, where the two said good night. Rudy the Romantic?

“I have to believe,” says one former high-level member of the mayor’s staff, “that he probably hasn’t been listening to the people who’ve given him sound advice in the past. I know he’s now talking to Peter Powers, but it’s a little late. Looking at the strange way he’s been behaving, my guess is it’s Elliot Cuker who’s been giving him advice.”

This was a refrain repeated again and again by people close to the mayor: He shouldn’t be leaning so heavily on the advice of Cuker, loyalists told me, when making life-altering decisions. “Elliot likes to think of himself as the mayor’s Svengali,” says one Republican insider. “He exercises enormous influence over Rudy and he wants the mayor to remain mayor. He loves sauntering into City Hall with his bow tie and cappuccino. He loves having his parking permits and heading the Film and Theater Advisory Board and the Crystal Apple awards and producing the Inner Circle show. And most of all, he loves being able to say, ‘My best friend is the mayor.’ ‘My best friend the senator,’ to him, wouldn’t sound as good.” (Cuker denies this, saying he has no agenda and wants only what’s best for his friend. “I can afford to fly to Washington.”)

Cuker’s contributions notwithstanding, there is another explanation for the dramatic change in Giuliani’s behavior: He’s in love with Judi Nathan. That’s right, nothing more complicated than that. He’s a guy in love. You can see it when he talks about her, you can see it when he looks at her, and you can see it in the way he’s behaved recently.

Though all the talk has been negative – the mayor’s midlife crisis – and the language describing his situation has been laden with portentous overtones, the mayor actually looks – when he’s with Nathan – positively liberated. He looks buoyant, like he’s happy and having fun. Which is no small thing for a man who’s ordinarily as testy as Giuliani.

Not only was Judi Nathan with him on New Year’s and St. Patrick’s Day, but he took her to the annual Inner Circle dinner in March, an event thrown by and for reporters. Now, you could say this was simply an outrageous act of Gary Hart-like brashness (“Go ahead, follow me.”).

But even as arrogant as this mayor is – and as successful as he’s been in bullying the media – he still couldn’t have confidently believed he could parade his girlfriend in front of several hundred reporters and no one would report it. (As it turned out, of course, no one did.)

But taking his girlfriend everywhere is what a guy who’s in love does. He’s happy, he’s proud, and he wants to show off. Though one insider chalks this up to the mayor’s just being the mayor (“He’s not the kind of guy who’s gonna try and hide”), it’s unlikely he’d be so bold if the romance were less important to him. Was he trying to manipulate the media into breaking the story? Possibly. It is also possible he wanted it out to force his wife’s hand.

One political insider even says he believes that Nathan, who has certainly not wilted in the spotlight, pushed Giuliani to go public. This is, of course, the classic play for a woman seeing a married man, and – in the stereotypical scenario – what a woman in this circumstance wants is for the man to leave his wife.

In the middle of the Giuliani drama, there was a powerful image of the mayor sitting in the front of St. Patrick’s cathedral at Cardinal O’Connor’s funeral. There was President Clinton with Hillary; Al Gore with Tipper; George W. Bush with Laura; Governor Pataki and Libby; and, among this group, by himself, was Rudy Giuliani. Much was made of the symbolism of this haunting picture: the mayor, forever the loner, the battler, the man who seeks no counsel, needs no comfort, and is happy going it solo in a world of his own creation.

But the reality is that this impression of the mayor as an ascetic is completely wrong. All the fire, the passion, and the emotion spilling out of him in public and directed mostly at his enemies is apparently also at play in his personal life. All this time, he’s never been alone at all. He’s always had a woman to rely on, to trust, and to share the excitement of his work. It just happens not to have been his wife.

Knowing what we know now, we can go back and connect some of the dots, fill in some blank spaces, and answer some nagging questions about Giuliani and his mayoralty. It is even possible to gain some insight into the extraordinary relationship that dominated his first five years in office: the one with Cristyne Lategano.

At the beginning of the summer in 1995, I began to do the reporting for a piece about Lategano, then the mayor’s director of communications.

It was a year and a half into Giuliani’s first term, and from a public-relations point of view, things were not going well. Giuliani’s relationship with the press had been anything but a honeymoon, and the young, exuberant Lategano had become the scapegoat. Only 28 and with limited political experience, she was clearly in over her head. Her role as press secretary, always an important one in a new administration, was particularly critical in the Giuliani mayoralty for two reasons.

First, he was a Republican elected by a narrow margin in what was still a predominantly Democratic city. More important, however, he was a reformer whose politically brave assaults on the deficit and the business-as-usual bureaucratic Establishment made him the first potentially transformative mayor the city had had in years. Getting the message out is crucial in this kind of activist government, because it helps drive the policy.

Lategano’s press office was a disaster. It was so bad that many Giuliani loyalists believed it was threatening the success of his mayoralty. They were convinced that the torrent of negative press and the fact that Giuliani’s message and his accomplishments were being lost in a series of meaningless skirmishes were Lategano’s fault. She was responsible for crafting his image, and rather than being viewed as an achiever and a star, he quickly came to be seen as cranky and prickly and difficult to deal with (a perception that stuck and in fact has only gotten worse over time).

“I’ve covered eight mayors,” Channel 4’s éminence grise Gabe Pressman told me at the time, “and the relationship between this mayor and the reporters in Room 9 the City Hall press room is the worst I’ve seen in 30 years.”

The always irascible Jerry Nachman, then Channel 2’s vice-president of news and now the co-executive producer of Politically Incorrect, was even more scalding. “This is a jihad; it’s a holy war against the press. It’s beyond my experience,” he’d said. “Cristyne Lategano is an amateur.”

As the summer progressed the Lategano story took on another dimension. Not only was she the object of hostility both inside and outside the administration, but she was now also the subject of a whispering campaign. Rumors about the precise nature of her relationship with the mayor were being discussed at cocktail parties, over lunches, and in offices all around the city.

Ironically, Lategano’s closeness to the mayor was born out of her instinct for survival. “You have to understand,” one high-level member of the administration told me then, “she’s getting terrible press; she’s got this cabal of Rudy’s closest people trying to get her a boss or kill her. Her staff hates her because she treats them like shit. City Hall people hate her because she’s young and arrogant and she treats them like shit. The pressure to handle the William Bratton problem – his great P.R. – is growing, and everybody has identified her as the press problem.”

Instead of crumbling under the pressure, Lategano reacted brilliantly. She abandoned the press office – the mayor always believed the media were out to get him anyway – and began to ride with the mayor day in and day out. She was at Gracie Mansion in the morning so she could ride with him to City Hall. She traveled with him to every event, no matter how unimportant. She attended every meeting, and she was the last person to see him at night.

“She did not leave his side or that fucking ice-cream truck the mayor’s white Suburban for months,” one former aide said. “By the time she’d finished a couple of months of this, Peter Powers’s influence was diminished, Denny Young’s was diminished greatly, and Randy Mastro’s was diminished even more. Ray Harding was put in his place, and David Garth, who was the strongest proponent of getting somebody in there to fix the press office, was out. They had all tried to kill her, and she’d gotten them all taken care of.”

It was also during this period that the mayor’s daily routine began to change. Instead of going home at the end of the day, he was out every night of the week into the wee hours of the morning. Though much of this was the result of his tireless working style, his ability to function on little sleep, and his absolute joy at being the master of all he surveyed in the city, there was another element as well.

He was enjoying himself. Nearly every night, he could be found eating dinner at ten or eleven o’clock at McMullen’s or Limoncello or in more recent times at Coopers Classic Cars & Cigars (owned by Elliot Cuker). Sometimes he was with several staff members and Lategano, sometimes just with Lategano. While he hammered Commissioner Bratton and his clique for hanging out at Elaine’s, Giuliani had carved out his own thriving nightlife.

It was at this point that the rumors about his relationship with Lategano really heated up. Coy items ran in the gossip columns about shopping expeditions he’d gone on with her, and Newsday even printed mentions of the late-night dinners.

Proving an affair, of course, is almost impossible unless one of the participants talks. Otherwise, the best a reporter is likely to come up with is circumstantial evidence. (Semen-stained dresses are few and far between.) And there was a mountain of circumstantial evidence surrounding Giuliani and Lategano.

But I believed when I wrote my story in 1995 and I continue to believe now that whether the relationship was sexual is really irrelevant. What is relevant is that it became the most important relationship in his life: both in terms of its impact on his mayoralty and for him personally. Lategano was the person he spent all his time with, day and night, seven days a week.

By the beginning of last year, she was even being referred to as co-mayor. It was an all-consuming relationship that created a wall between the mayor and everyone else – including his wife. When Hanover said last week that her husband’s relationship with one staff member prevented her from participating in his public life, this is what she was talking about.

“What we at City Hall really resented was their complete disregard for the perception created by their behavior,” a former staff member and an ardent supporter of both Giuliani and Lategano told me last year. “Despite the widespread rumors, however unfounded we chose to believe they were, the mayor and Cristyne altered none of the actions that led to those rumors. There was a complete disregard for appearances.”

Given recent events, it’s possible to say that this is how a man in love behaves. If a man is seeing someone his friends believe is bad for him, and they say so, who ends up gone? It’s always the friends.

The most trenchant quote about the nature of their relationship in 1995 is just as penetrating today. “It may not be an affair of the heart, but it is an affair of the spirit,” said Hank Sheinkopf. “That’s where the intimacy cuts.”

After all the intensity between them and all the slings and arrows Giuliani and Lategano withstood, the relationship ended last May with barely a whimper. Lategano’s departure from City Hall couldn’t have been more unceremonious. Quietly, she took a leave of absence and never returned. By the fall, she’d been installed at the Convention & Visitors Bureau at a salary of $150,000 a year.

It was during this time, Hanover said, that she and Giuliani “reestablished some of our personal intimacy.” And for the first time in years, they were seen in public together: dancing cheek to cheek at the wedding of Howard Safir’s son last May.

“Who knows exactly what happened?” says a former staff member. “Did Cristyne tell the mayor she was in love with Nick Nicholas her husband now first, and he went berserk? Or does he tell Cristyne, ‘Listen, Donna and I are gonna try and make a go of it, so you have to leave ‘cause we can’t do it with you around’?”

In any event, the reconciliation with Hanover did not, apparently, go on for long. By last summer, Giuliani had already taken steps to set the current situation in motion: He’d begun to see Judi Nathan.

One Republican insider told me he believes the mayor is going to pay a price for his decision. “Scores of Republican leaders and tens of thousands of Republican voters across the state and around the country are going to look at his dropping-out as an abandonment of the cause. The cause is to stop Hillary Clinton, and if she wins, he will pay for the damage.”

But in the end, Hillary wasn’t the opponent he needed to focus on. “There were just too many uncertainties,” says a confidant. “The mayor is not a man who’s comfortable with the unknown or with taking risks.” Of course, the unknown will loom larger than ever in the months ahead. And as he said in that remarkable press conference a couple of weeks ago, now he’s going to need someone more than ever.

Rudy’s Choice