America's Mayor Wants a Job

On a steamy Tuesday afternoon in August, Rudy Giuliani and I met in the lounge of the Grand Havana Club, the private domain of some of the richest and most celebrated cigar aficionados in New York City.

Giuliani, accompanied by two aides, was on his way to Greenville, N.C., to deliver a motivational talk to an assembly of middle managers. Colin Powell would be there, too. I asked him what he got paid for his oratory these days. “I can’t tell you that,” he said with a loud laugh. “But it’s a lot.” His booking agency, the Washington Speakers Bureau, lists him in its “heroes” category, along with Congressional Medal of Honor recipients and astronauts. Some nations reward their favorite sons with knighthoods. In America, the prize is speaking fees.

In his long career, Rudy Giuliani has been a crime-busting prosecutor, a transformational mayor, and a failed candidate for the Republican presidential nomination. He’s flirting with another run this year. The odds are heavily against it, but if he were to improbably get elected, he would be the first president since Eisenhower for whom reaching the White House would be an anticlimax. Nothing will ever top Giuliani’s legendary leadership in the terrifying days and nights that followed 9/11.

This year marks the 10th anniversary of the attack, and although time has dimmed visceral memories of that day, Giuliani remains an icon for many. There are still bars and restaurants, and not just in New York City, where people stand and applaud when he enters the room. The Grand Havana Club, however, is not one of them. When he walked in, a few members looked up from their newspapers or their conversations to nod a greeting, but no one called his name or came over to say hello. For two hours, the only interruptions were from the impassive server, who delivered Giuliani’s standard lunch of Kobe beef sliders washed down with Diet Cokes, and a brief “Yes, dear. OK, dear. I’ll take care of it, dear” phone call from home. No man, not even Rudy G., is a hero to his waiter or his wife.

Lately, Giuliani has made several exploratory campaign trips to New Hampshire, a state whose libertarian leanings theoretically fit his style and platform. “If he decides to go for it, he will run up there like he is running for governor of New Hampshire,” says Jake Menges, one of Giuliani’s closest political consultants. “It will be an all-out effort.”

But sitting in the Grand Havana lounge puffing on a La Gloria Cubana, Giuliani didn’t seem like a man prepared to go schlepping through the frozen hamlets of New Hampshire, grubbing for retail support. Like his boyhood idol, Joe DiMaggio, Rudy retired with the cheers of the crowd still ringing in his ears. But once out of office, he had nowhere to practice his art. All he could do was get rich, which he did, joining a Big Oil Texas law firm, starting his own security-consulting business, and tossing off six-figure inspirational speeches. By 2008, his net worth had reached $30 million—and presumably it has only grown since then.

Money isn’t everything, though. People expected more from Rudy, and he expected more from himself. After 9/11, he appeared to have virtually limitless political potential. His leadership after the attacks smoothed some of the rough edges of his mayoralty, washed away memories of his messy personal life. But he hasn’t capitalized on that potential.

He went into the 2008 presidential campaign as the odds-on favorite to win the nomination to succeed George W. Bush. Giuliani liked his odds, too. “I looked at the other candidates, and let’s say I didn’t see anyone better,” he told me. But he ran a lackadaisical race in the New Hampshire primary and came in fourth. In Florida, putatively Giuliani territory, he blew past admiring crowds of transplanted Italian and Jewish New Yorkers without bothering to mingle or engage and fumbled the race. He was surprised, he told me, by the defection of the Jews, less so by the Italians.

“There’s still some resentment there about my prosecution of the Mafia,” he said. “The only place anyone has ever thrown eggs at me is on Arthur Avenue.” Giuliani arrived at the 2008 Republican National Convention with zero delegates and a tarnished image.

“It humbled him,” says Andrew Kirtzman, one of his biographers. “The magic was gone.”

Heroism is intoxicating, and Giuliani misses it. He also feels that a man of his talents has a major contribution to make to a country in trouble. “The question,” he told me in a detached tone, “is whether I can win the nomination in the party that views me as too moderate.”

He claims to be bemused by this image. “I’m as conservative as anybody running. Ronald Reagan is my political role model. I wrote two speeches for him when he was president.” As mayor, Giuliani said, he not only tamed crime, he balanced budgets, reduced entitlements, and shrank the size of government, all without raising taxes. These are accomplishments that should win him Tea Party acclaim. But then, unsolicited, he added that he would have raised taxes if it had been necessary. Honesty, especially in a party dominated by an ideological tax-cutting purity, is not necessarily the best policy.

Giuliani’s problem is not his security or economic politics. He is close to the Tea Party on both. But the winner of the GOP nomination will most probably be the candidate whose ideology and personal style reflect the deepest beliefs and social mores of the ascendant Republican right wing. Giuliani’s casual New York metrosexuality and pro-choice stance, not to mention his very public adultery and disinclination to moralize on personal matters, put him at odds with a party that increasingly looks like a traveling Pentecostal tent revival. Nothing less than a full-blown national-security emergency would remake him as the man of the hour.

Which raises the question: why is he flirting with a primary run? One answer is that speculation keeps him in the news and strengthens the lucrative Giuliani brand. But he has less crass motives as well.

“Rudy is an action junkie,” says Kirtzman. And there isn’t much action talking to middle managers in Greenville.

“I love Washington, D.C.,” Giuliani told me. “I’d be very happy to serve again.” I mentioned two positions that seem up his alley—secretary of defense and attorney general. “Those are both great jobs,” he agreed, “great opportunities to serve the country. I would be honored to perform either one.” He added that he has visited 55 foreign countries in recent years, a remark I took to mean that he would welcome an appointment as secretary of state.

Under the circumstances, Giuliani is disinclined to express negative opinions about the GOP’s current crop of 2012 candidates. Why alienate a potential future boss? He told me that he feels an executive kinship with governors Perry and Romney, but Perry, who endorsed Giuliani in 2008, is a personal friend and political ally. Giuliani and Romney are not what you would call pals.

“How can you compare Mitt Romney to Rudy?” Menges asked me in a conversation before my interview with Giuliani. “What did Romney ever do besides save the Winter Olympics?”

The old Rudy Giuliani was known for bellicosity; the epic battles of his mayoralty were fought on racial issues against Al Sharpton. “To most whites, Giuliani was the savior of the city who brought back civility and economic prosperity,” Sharpton wrote in 2002. “To blacks, he was an unbending, nasty man who presided over a police department that had no regard for black life.” The two adversaries are now mellow members of the same club. “Al was in here last night,” Giuliani told me. “Joking around, he offered to help me in New Hampshire by campaigning for Michele Bachmann. I told him, don’t do it, she’s got enough headaches already.”

Still, Giuliani is mindful of the persistent potency of racial issues in American politics. At one point in our conversation, he wondered aloud if Obama would play the race card in the 2012 election. Giuliani has a low opinion of the president’s abilities.

“He grew up and lived in a make-believe world, and he came to office without a clue. I don’t sense that he has any practical intelligence.”

Obama and Giuliani will meet at this year’s Ground Zero commemoration of 9/11. The president, Giuliani concedes, has earned antiterror chops by taking out Osama bin Laden and waging an aggressive drone campaign against Al Qaeda in Pakistan. Giuliani is also not critical of the state of preparedness. “A terror attack can always defeat any intelligence system; that’s just a fact,” he said. “An attack will always expose the one thing no one thought of. You try to prevent that, but what matters most is the response. New York City was well prepared on Sept. 10, 2001, and it is even better prepared today.”

Some Giuliani critics say that preparations were not so great. He has been criticized for the inability of police and other emergency-system radios to communicate with one another, and for his decision to put the command center downtown. There were also, inevitably, complaints from some of the bereaved families who thought something could have been done to anticipate the attack.

But the indelible fact is that in the height of the chaos and the panic of the worst foreign attack on American soil in modern history, Rudy Giuliani stepped up and took control. He made decisions instinctively as he strode through the wreckage of downtown Manhattan. He said the right things and, for the most part, did the right things. And he showed courage. “The one time I faltered was when I heard that Father [Mychal] Judge, the chaplain of the fire department, was dead. I always leaned on him when I had to tell a bereaved family about a loss, and now he was gone. I felt a real flash of fear when I realized he wouldn’t be with me to face that.” But he managed to overcome even that loss. “I don’t want to be falsely modest. I think I did a good job,” he said.

I asked if having weathered the challenge of 9/11, he sometimes wonders, late at night, if there are future tests he might not meet so well. His eyes widened and he said, “I can’t think of any. No.”

Would Giuliani consider running for mayor in 2013?

“I know I’ve called it the world’s best job, but it’s something I’ve already done,” he said. “I like going forward, not backward.” But what if there is another attack on the city, or some other crisis? He paused. “It’s a hypothetical question, really. But you never say never.”

Mayors of New York eventually become memorialized in concrete. Fiorello LaGuardia has an airport. Ed Koch got a bridge. Even the disgraced James J. Walker has a little park named after him in the West Village. I asked Giuliani what he would like his namesake to be. “Yankee Stadium,” he said and, when he saw I was writing it down, quickly added that he was kidding. “They need to keep Yankee Stadium the way it is.” How about Central Park? “Central Park?” he said. “Real-ly?” He laughed, took a deep drag on the La Gloria Cubana. “They’d have to get rid of the smoking ban, though. That’s for sure.”