The rise and fall of Rudy Giuliani: how did we get here?

On Monday, former New York City Mayor Rudy Giuliani was indicted in Georgia. Prosecutors say he made false statements in connection with President Trump’s conspiracy to undermine the 2020 election.

New Yorkers, of course, have been following Giuliani’s career for decades: from his time here as a federal prosecutor to his two terms as mayor, to his ascension to the national stage of the Republican Party.

But how did he get here? How did he go from being known by some as “America’s Mayor,” to an alleged co-conspirator in a national scandal?

““He was just governed by his greed and by this almost primal need for relevance,” said journalist Andrew Kirtzman, who has written two books about Mayor Giuliani, including Giuliani, The Rise and Tragic Fall of America’s Mayor.

Kirtzman also covered Giuliani during his tenure as mayor, including during the September 11th attacks. He spoke to “All Things Considered” host Sean Carlson about Giuliani’s rise and fall, and the pivotal moments that shaped his trajectory. Below is a lightly edited transcript of their conversation.

Sean Carlson: Much of the recent controversy about Mayor Giuliani comes from his relationship to President Trump. How has their relationship evolved over time?

Andrew Kirtzman: Giuliani’s mayoral papers were available in the city archives, and what we found was a trove of communications between Giuliani and Trump and Giuliani’s aides and Trump. There was this terrific story in which Trump has decided to build the largest residential tower in the world, right next to the United Nations General Assembly building.

And there’s an agreement with the city, signed long ago, in which there can be no development higher than the General Assembly. Well, Trump, of course, wasn’t deterred. And there was this major kind of push to prevail upon Giuliani to reject this. Walter Cronkite, who was a resident of the area, protested. So did Walter Wriston, who was the president of Citibank at the time.

And Giuliani was not even returning their letters! And you could just tell from the increasing desperation and anger in these letters that these incredibly prominent people were being dissed by the mayor. Meanwhile, Giuliani was speaking at Trump’s mother’s funeral, his father’s funeral. So there has been an affinity between the two of them that’s gone on for a long time. And the relationship has only warmed, obviously, as time went on.

How did we get here with Giuliani? Love him or hate him, we’ve known him for a long time. And sure, he had his detractors as mayor, but he won two terms. He was popular enough to consider a presidential run … to an alleged co-conspirator in a national scandal?

The two pivot points in the Giuliani story are 9/11, when he became, as you know, this international hero. There was a poll taken at one point which showed that Giuliani was more popular than the Pope. He was knighted by the queen of England. He cashed in for hundreds of millions of dollars for Giuliani Partners who became, stratospherically wealthy. Things were going very well for him. And he decided to run for president in 2008 and he crashed and burned badly. He was the front-runner for a year. And then once the race began, he only lasted eight weeks in the primaries and left with only one delegate.

And that second pivot point is that 2008 humiliation. It was after that moment that Giuliani was out of the limelight and he started to fear for his relevance. I did many interviews for my book with people around him, including his ex-wife, who told me long stories about him drinking excessively, falling into a depression. And it was Donald Trump who took him in – literally. He brought Giuliani into Maryland. Go and let Giuliani recuperate for over a month.

Fast forward to 2016. No one was knocking at Rudy Giuliani’s door in the 2016 presidential race to endorse them except Donald Trump. Donald Trump needed Giuliani because he had no political support at the time. And Giuliani needed Donald Trump because Donald Trump was the only person with the potential to bring him back into power. The bond between the two of them has only increased. And, you know, Giuliani’s stuck to Trump to this day, even as he’s facing jail. He’s stuck to Trump.

One of the things that I struggle with when it comes to Mayor Giuliani is that I grew up with him being the guy who took on the mob as a federal prosecutor. He made law-and-order a huge part of his campaign and how he governed the city. It’s a big part of his legacy when we think of that era. So what do you think of the irony of him eventually becoming a criminal defendant himself?

It’s unbelievable, right? No one who lived during the 1980s could’ve believed that about Giuliani, who was venerated for his integrity. High crime era mafia had a run of a lot of industries. And Giuliani was kind of the adult. He was the one kind of setting the rules for right and wrong for Wall Street. For city government. He battled corruption. And of course, the mob. And he was at that point universally respected.

Fast forward 40 years, and I think all of this desperation for power and for money, little by little, moral compromise by moral compromise … Giuliani just became kind of an empty vessel. He was just governed by his greed and by this almost primal need for relevance. And, you know, it’s very sad. But also the other thing is, his age. He’s now 79 years old. He’s not a young prosecutor. And there’s an element of trying to kind of relive the glory days. You know, he pulled all this, like bumbling, legal, efforts during the 2020 election scandal, which only made him look ridiculous. It’s a sad story.

If you can recall, as Giuliani’s biographer, his responses to certain police scandals during his time: Abner Louima, Amadou Diallo. And his response to those stories when activists pressed him. How is that different to how he responds now to say, charges when people ask him difficult questions about things?

I think that there’s a significant difference. The Giuliani back in the ‘90s as mayor, you may have loved him, you may have hated him, but there was a rigor to his arguments. Today he’s off in a hundred different places. He’s made some horrendously bad decisions. And Ukraine, which got Trump impeached once. And then this in that election scandal, which got impeached a second time. I guess the one thread is this sense of him having a corner on morality, him being right when everyone else is wrong. And I think you saw that during the police incidents during the ‘90s when everyone was, criticizing him, the police force and Giuliani just kind of stood there like a one man barrier and refused to apologize. I think you were looking at a brilliant, brilliant man back in his prime and someone who is a shadow of that now.

That’s Andrew Kirtzman, who wrote Giuliani: The Rise and Fall of America’s Mayor, one of two books he’s penned about former New York City Mayor Rudy Giuliani. Andrew, thanks again for giving us a few minutes. We appreciate it.

Thank you.

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