The evolution of Rudy Giuliani is an epic tale. A celebrated crime fighter who brought down mafia bosses and put Wall Street crooks behind bars, he traded on trust and integrity to prove Republicans could still get elected as mayors of big cities. His empathy and leadership on 9/11 in New York City made him a global figure and a bona fide hero. How that man, who used to get standing ovations whenever he entered a room, morphed into former President Donald Trump’s conspiracy theory lackey peddling lies about the 2020 election is the subject of the new CNN Original Series, “Giuliani: What Happened to America’s Mayor?” The images of Giuliani’s early success paired with his later disgrace are striking and sad. I reached out to one key voice in the series, CNN political analyst John Avlon, who was Giuliani’s chief speech writer during his second term as mayor, including on 9/11, and later worked for Giuliani’s presidential campaign. Excerpts of our conversation about Avlon’s perceptions of the series and what happened to his old boss are below. A major character in the Trump saga WOLF: The Giuliani of today is at the fulcrum of so many of Trump’s problems. Giuliani’s dirt digging in Ukraine contributed to the first Trump impeachment. Giuliani helped enable the election denialism that led to the second Trump impeachment. How would you describe his place in Trump’s political history? AVLON: I think that among some hard-core Trump true believers, Rudy will be scapegoated as the source of Trump’s multiple problems. I think that’s an attempt to evade Trump’s responsibility for the chaos he himself caused. But you have got to hand it to him – Rudy is the first presidential lawyer whose actions contributed to not one, but two impeachments. That’s a special place in American history. And unfortunately, I think this tragic last chapter in his life will overwhelm the very positive, constructive role he played in different chapters of his life. I don’t think it’ll ultimately eclipse 9/11 and his leadership on that day. But he lit his legacy on fire in service of Donald Trump and got nothing in return except disgrace, ignominy, (possible) disbarment and a gutting of his personal fortune. He was also a crime fighter, a mayor and a hero WOLF: I think a lot of people will be surprised to learn about those earlier chapters. He’s this prosecutor who brought down mafia families and insider traders. He’s the mayor who cleaned up the city. How does that guy become the conspiracy theory pusher? AVLON: That’s, to a large extent, what the documentary is about. I think it is important for people to remember he was a leading lawyer of his generation, with an objective record of success in terms of dismantling the mob and taking on Wall Street. That alone would have made him a major figure in contemporary American politics. But then what he did as mayor was absolutely remarkable. George Will called it America’s most successful case of conservative governance. I worked for him in City Hall in his second term as chief speechwriter, and if you just look at the data of what he did, it’s remarkable: He cut murders by 68%, crime by 56%. He turned a $2 billion deficit into a multibillion-dollar surplus. He cut taxes for New Yorkers. He improved the quality of life. I think his policies ushered in an era of resurgence for urban America. In New York City, I think 20 years of Rudy and (Michael) Bloomberg together really helped turn around the city in fundamental ways. The tragedy – and I use the term advisedly because it’s self-inflicted, but it is tragic – is that the guy who believed that the law is a search for the truth ended up trying to defend his client in the court of public opinion using the law in pursuit of a lie. I think that he got caught in a right-wing echo chamber ecosystem, where he was totally invested in an alternate reality that was fundamentally hyperpartisan and therefore they couldn’t even conceive of losing fairly. And so at the end of the day, they tried to overturn an election, overturn our democracy on the basis of a pretty self-evident lie with no evidence. I’m not going to try to diagnose how he’s changed. But the filter in the judgment of the man I knew and was proud to work for is fundamentally off. Did Giuliani change or has he just been uncovered? WOLF: The perception is that he has changed as a person, but there are these interesting moments in the documentary that presage the Rudy of today. We see a riot of police officers at City Hall in 1992 that is compared with the riot at the Capitol. In ’89, he suggested but did not pursue the idea that there had been fraudulent voting. Has he actually changed, or has he just been uncovered? AVLON: Robert Caro has a great line about how power doesn’t corrupt, power reveals. I’m always more inclined to believe the adage that as people grow older, they get more so. There are moments, and the documentary makes a lot of them, to draw a narrative connection between the police riot and January 6th. The person I knew and worked for – those incidents did not define him on a day-to-day basis. Character counts. One of the things for good or for ill about Rudy, and something that I learned on 9/11, is you don’t have to be perfect to be a hero. Rudy was not one of these politicians who pretended to be perfect. He understood that he was a flawed human being and was actively interested in figuring out his flaws and what motivated him in certain low times. He was someone who thought philosophically about politics. If you talked to him about his position on abortion, for example, he would, in an unpretentious way, start talking about St. Thomas Aquinas, the debate about when life begins. He was also the kind of human who thought about becoming a priest and ended up becoming a prosecutor. But I think there has been a change in his judgment. The Trump orbit tends to attract people who are not at their best in terms of stability. Rudy found attention and relevance at the expense of his legacy and reputation. Does hero worship change a person? WOLF: It was instructive for me to revisit just how much of a national hero he was after 9/11. How do you think that specifically affected him? You saw it happen. AVLON: First of all, there is a misperception that’s partly partisan nature that Rudy was deeply unpopular before 9/11. That is statistically not true. That’s not to say he wasn’t controversial and divisive at times. What he would say is that when you’re turning around a ship at sea, you’ve got to throw your shoulder to the wheel. 9/11 was a classic case of the man meeting the moment. The New York Observer, which was often critical of Rudy, said that he distinguished himself almost overnight as New York’s greatest mayor. He became seen as sort of a modern-day Churchill and that was because of his instinctive response to an unprecedented massive attack. And it was also because of his empathy and his honesty. He was able to channel grief in a constructive direction. He was resolute. He said the number of people who died was more than any of us can bear, and he was an inspiration to a fundamentally shaken and horrified world. And it was extraordinary. For months and years afterward, he would be greeted with standing ovations when he walked in the room. I think it’s a little too simple to say that creates a presumption of that kind of reception wherever you go. But I think what it does is highlight how tragic the fall has been. And if he had kept his credibility as sort of a centrist Republican senior statesman who was tough on the issues that a lot of people care about – law and order, fiscal discipline, etc., including on social issues – he could have played a major stabilizing force within the Republican Party. He could have been somebody who parks and statues and streets would have been named after across the nation, because of his example of leadership on that day, which was the apotheosis of his career. That was a reflection of the true mettle and character. The GOP has changed along with Giuliani WOLF: You talked about him being a Republican in a Democratic city. He wasn’t the only big city Republican mayor. Los Angeles had one at the time. Republicans put up John McCain for president in 2008. Mitt Romney tried to be severely conservative, but these days he’s just about as moderate as Republicans get. Do you think Republicans are interested in moving back into that middle ground and governing a big city as opposed to just using it as a foil for their national ambitions? AVLON: It’s a great and important question. If you take the biggest possible step back at America’s historical political divisions, you’ll see that much bigger than Democrat / Republican or liberal / conservative is urban vs. rural. We need urban Republicans and rural Democrats to help bridge divides. When there were progressive Republicans back in the day, particularly in the Northeast, and conservative Democrats, there were a ton of problems. But you could always find governing majorities within divided government. You could cobble together coalition. The decline of urban Republicans and rural Democrats is enormously disruptive for the country in terms of further inflaming hyperpartisanship and polarization and the kind of distrust that already exists culturally kind of in our America. Republicans should care about playing in urban areas, and Democrats should care a hell of a lot more about playing in rural areas in red states. The Obama era as a turning point WOLF: We tend to think that it was proximity to Trump that radicalized Rudy, but there’s a riff in the documentary about Giuliani’s visceral reaction to the Barack Obama presidency, similar to how Trump reacted to Obama’s presidency, actually. I wondered how you felt about seeing that portion. AVLON: After his presidential campaign, he becomes more and more sort of isolated in that bubble. That right-wing ecosystem. It’s a form of acculturation where the hyperpartisan environment becomes kind of assumed. It’s the places you’re giving speeches. It’s the television networks you watch. You spend all your time with partisans. It isolates you from the act of responsibility of governing and uniting a very diverse city – even certainly he had challenges with that. I think that his animus toward Hillary Clinton and the Clintons was one of the things that drove him to embrace Donald Trump late in the (2016) campaign. By the way, he never endorsed (former New Jersey Gov.) Chris Christie or (former Florida Gov.) Jeb Bush, but he really was inclined to support either of them first, because they’re the kind of Republicans that he was. After he made that comment about Obama, I believe it was a fundraiser for (then-Wisconsin Gov.) Scott Walker, he actually called me at home to explain himself. (Read CNN’s report from 2015, when Giuliani said he didn’t think Obama “loves America.”) It was strange, because I think we just had our first son, and Margaret and I met working on his presidential campaign. (Avlon is married to the CNN political commentator and host of PBS’ “Firing Line,” Margaret Hoover). And he called me to, like, explain what he meant. I thought it was revealing of the right-wing media he had been ingesting, and also that somewhere there was a degree of guilt that he felt the need to explain himself to me, who worked for him before, a long time ago.