What the Hell Happened to Rudy Giuliani?

How the former prosecutor and 9/11 hero ended up like this.

George Pataki, Kofi Annan, and Rudy Giuliani at ground zero.
New York Mayor Rudolph Giuliani (right) gives a tour of the World Trade Center attack site to New York Gov. George Pataki and U.N. Secretary-General Kofi Annan on Sept. 18, 2001, in New York. Timothy A. Clary/AFP/Getty Images

If you look at the political history of the past decade, from his failed presidential run in 2008, to his demagogic Republican convention speeches, to his colorful Fox News appearances, Rudolph Giuliani’s emergence on the scene as Donald Trump’s most visible legal surrogate is not particularly surprising. It’s easy to forget that Giuliani, who is now attacking federal law enforcement with glee and warning of dark conspiracies and storm troopers, was once the United States attorney for the Southern District of New York and sold himself to New York voters during his two terms as mayor as the paramount protector and defender and patron of the criminal justice system in its entirety.

To try to understand the arc of Giuliani’s career, I spoke by phone with Andrew Kirtzman, a former New York journalist and current president of Kirtzman Strategies, a bipartisan political consulting firm, and the author of Rudy Giuliani: Emperor of the City. During the course of our conversation, which has been edited and condensed for clarity, we discussed Giuliani’s transformation, why he’s gone all in for Trump, and how to understand his lack of loyalty to the Department of Justice.

Isaac Chotiner: Have you been surprised by the past several weeks?

Andrew Kirtzman: I’m not totally surprised. Giuliani has always had this knack for knowing how to insert himself right in the center of a story. So when this whole thing began, I was a little skeptical he was going to limit his involvement to taking a meeting with Robert Mueller and wrapping this up in two weeks. Once Giuliani is in, he stays in. The only question in my mind was what kind of role he was going to play with Trump: Was he going to calm him down or wind him up? And I think we have gotten our answer the last few days.

He may have a knack for inserting himself right in the center of a story, but Giuliani is also someone very concerned with his image. And yet he doesn’t seem to mind embarrassing himself for Trump. How do you understand that contradiction?

It’s been a gradual evolution. The turning point was, I think, the 2008 race, and it all fell apart. The luster of his brilliant performance on 9/11—and I don’t use the word performance cattily; I think it was brilliant—it lost its power. He has been casting about for a role ever since. If you look at his trajectory after that race, it’s not really pretty. He took a whole bunch of clients who were foreign dictators, and others who were unsavory, and he geared his efforts towards making money and also playing in a sketchy international realm.

He got very “in” with the Palm Beach crowd and the Hamptons crowd and just lost touch with who he once was. His activities in public have grown increasingly out there, from questioning whether Obama loved the country to questioning Hillary Clinton’s health. It was all part of the losing of his image as nonpartisan healer from Sept. 11, and it has just gotten more and more extreme.

Part of the image you talk about was wrapped up in this idea of him as the paramount man of law enforcement. Is the upshot that this part of his image was less sincere than we might have believed?

I keep thinking about his decision in 1994 to endorse Mario Cuomo over his fellow Republican George Pataki for governor. To me, that always stands out as a signal event in his career. For one thing, it was incredibly brave and independent of him. But in addition, what we learned from that episode is that it is his belief that when you enter the fray, it is all or nothing. You go all the way or not at all. His attacks on Pataki in that campaign were venomous. It was quite a sight to behold the Republican mayor going after the Republican gubernatorial candidate. And that has been a mark of his personality and political strategy his whole career. If you are in for a dime, you are in for a dollar. There is no half-way, polite way to do anything in Giuliani’s world.

During his time as mayor, Giuliani had this crime-fighting image as this guy who was tough and rude, but he was also written about as a technocrat. What do you think happened to that part of his political personality, if it indeed existed?

The short answer is that that part of his personality went out the window a long time ago. You are absolutely right: He ran for mayor in 1989 when he was less than prepared, lost to David Dinkins, and then spent much of the next four years studying up on the issues, and learning about experiments in other cities that were working, and learning about “broken windows” and other things that were really forward-thinking back then. That was one of the best things about watching him as mayor from 1993–1997. He was iconoclastic and fearless in pursuing stuff. But that Giuliani is not really the Giuliani we have seen for a long time. He has made the transition to political partisan since then.

Do you feel you have a sense of his current ideology?

I am not talking about his ideology as much as what he was all about, and also the sense of pragmatism and idealism. At some point in his second term, he saw that it was in his best interest to cast his lot with Republicans, and has thrown all his chits into the right-wing pile, and he seems comfortable with that identity. For people who voted for him in New York in the 1990s, there has been a huge amount of anger and disappointment. In New York, I think the majority of people, aside from Staten Island, really dislike him.

What was Giuliani’s relationship with Trump like when he was mayor?

A lot of us New York reporters have been talking to each other about when this all began. None of us could recall any moment when the two of them were particularly close during his time as mayor. The most high-profile collaboration was the video of Giuliani in drag going shopping with Donald Trump, and it was obvious from that that they were pretty simpatico. But I don’t recall them being close. Giuliani’s friends at the time tended to be the people who were close to him politically. It is a very small crew wherever he has gone, and Trump was not it.

I am not asking you to diagnose him, just to be clear. But when you watch him on television now, versus 15 years ago, how do you think he seems?

The brilliant thing about Giuliani from the time he was prosecutor through Sept. 11 was this very lawyerly, factual way of communicating. Even when he was attacking someone, he was extremely persuasive. And that persuasive quality really disappeared at the Republican convention for Trump. It was just a horrible, horrible spectacle. I can’t get into his head as to what happened, but it is depressing. I was with Giuliani on Sept. 11 and experienced that morning with him. I was overwhelmed by his leadership and his calm and his methodical approach to putting things back together, and the inspiring way that he calmed the city and lifted our spirits. It’s always been kind of fashionable in certain liberal circles to hate Giuliani, but I was never on that bandwagon. At all. I have seen him display greatness, and that is why it is so sad to see what he has transformed into.