<i>JAMES: Smart, charismatic,</i> ruthless, a little megalomaniacal. <i>JIM: Ambitious, righteous, and then self-righteous,</i> personable for a little while. [chuckles] <i>JONATHAN: Divisive, commanding,</i> <i>relentless.</i> <i>MAGGIE: Pugilistic, erratic, extremely smart,</i> reckless. WILLIAM: Forceful, combative, energetic. <i>DAN: Confident, tireless,</i> annoying. <i>JOURNALIST: After 9/11 nearly two decades ago,</i> <i>Giuliani was a national hero, America’s Mayor.</i> <i>Now he’s under federal investigation.</i> <i>What happened to this guy?</i> <i>[pensive electronic music]</i> <i>♪ ♪</i> - I’ve been on the “Metro” staff there for close to 20 years. - I’ve been a reporter in New York for nearly 40 years. - I’ve written ten books. Rudy Giuliani is a major character in three of those ten books. - Former city hall bureau chief when Rudy Giuliani was mayor. - I was assigned to do an assessment of Rudy Giuliani’s eight years as mayor. - My first days in city hall when he was mayor were January 1999, and I knew absolutely nothing about him or what I was doing. - Giuliani came on the scene during a very raw era in New York. [traffic clamoring] - Giuliani was the U.S. Attorney in the Southern District. He was the prosecutor in New York City. <i>MAGGIE: And we all read about the Gambino family, the Gotti family.</i> If you grew up in New York, this is what you were familiar with, and it wasn’t some distant memory. - Judges, prosecutors, not to mention cops were on the take, so to speak. <i>It was an enormously powerful force</i> in New York City. <i>DAN: Giuliani was fascinated by organized crime,</i> both from a professional perspective and also from a personal perspective. - Rudy grew up for a while in Brooklyn with a family that had its troubles. - His father, who was kind of a plumber and bartender, was also kind of an enforcer for a loan shark in a gambling operation at the time. <i>[dynamic music]</i> <i>MAGGIE: And Giuliani made cracking down on the mob</i> a centerpiece of his time as U.S. Attorney. [indistinct chatter] JONATHAN: The way that he goes about prosecuting these guys is in and of itself incredibly theatrical, which is to say he goes after all of them in one fell swoop. <i>REPORTER: “Big Paul” Castellano...</i> <i>REPORTER: Ralph Scopo. REPORTER: Anthony “Fat Tony” Salerno,</i> <i>all indicted today.</i> RUDY: This case charges more mafia bosses in one indictment than any ever before. - The message one gets and the messaging is <i>that this guy’s a saint.</i> - Also he orchestrated the campaign against insider trading. He nailed them. He brought all this to a halt. <i>RUDY: If you violate the law,</i> <i>whether it’s insider trading or tax evasion</i> <i>or fraud or bribery,</i> the overwhelming general rule is you go to prison. [indistinct speech] <i>JAMES: He seemed honest.</i> <i>He seemed very straight-forward.</i> He was good with the press. <i>He was a grandstander.</i> <i>He was a showboater.</i> <i>♪ ♪</i> - All the defendants received <i>the maximum sentences that the law provides.</i> <i>I think that’s the kind of message that you have to send.</i> <i>JAMES: He was on the side of law and order.</i> I mean, he was pursuing criminals. He got a lot of credit for that, <i>and it fueled his successful campaign into politics.</i> - On the day I become mayor, the old political system that is dragging this city down is out! [crowd cheers] <i>DAN: At that time, New York City</i> was seeing something upwards of 2,000 murders a year. <i>♪ ♪</i> <i>JIM: Almost five or six murders a day,</i> and the way Giuliani himself framed the narrative was that <i>he was gonna save the city.</i> <i>DAN: The opponent at that time was David N. Dinkins</i> <i>an African-American Democrat, well-entrenched</i> in the New York political establishment. <i>JAMES: He ran as a Republican in a heavily Democratic city,</i> and he made no bones about it. He was not Mr. Politically Correct. He was not playing to the liberal core of the city by any means. CROWD: [chanting] Rudy! Rudy! [cheers and applause] - I’ll not remain silent while our city is in trouble. <i>DAN: Giuliani won. He was an aggressive leader.</i> <i>And there was a feeling at that time that</i> that kind of aggressiveness was needed. - He focused on closing down sex shops, <i>which had been pervasive</i> <i>across Times Square and all over Eighth Avenue.</i> <i>NEWS ANCHOR: The broken windows theory:</i> <i>if you take care of the small problems,</i> <i>the big ones will follow.</i> - The biggest effect that it has—had is it saved lives. - And he was pretty effective at it. - It was astonishing. <i>All these problems, to this day</i> <i>I don’t really know how it happened,</i> <i>but they did go away.</i> <i>NEWS ANCHOR: New York is now the safest</i> <i>large city in America.</i> - Murder is down now more than at any other time in the last 28 years in New York City. <i>DAN: Giuliani absolutely had an effect</i> on the direction the city was going. <i>♪ ♪</i> <i>MAGGIE: The second term for Rudy Giuliani was fraught.</i> It was fraught fairly quickly. <i>People who had spent a lot of time with him</i> would describe it to me as him almost drunk on power. <i>JIM: The tactics that were employed</i> started to go bad. <i>There were cops</i> <i>put into position for which they were not trained.</i> - The accusation about Giuliani’s NYPD when Giuliani was mayor <i>was that they basically had permission</i> <i>to run pretty roughshod</i> over minority communities. <i>REPORTER: Tonight New York City’s police defend</i> <i>the shooting by an undercover officer.</i> <i>♪ ♪</i> - A young man in his 20s named Patrick Dorismond <i>was out with some friends.</i> <i>KEVIN: I was standing next to Patrick</i> when three men, who appeared to seem like derelicts, approached us for weed. - Dorismond told him to get lost, <i>kind of shoved him off and they kind of got into,</i> not realizing that he was squaring off with a cop. - I then saw Police Officer Vasquez throw the first punch at my friend Patrick. <i>JIM: Before you knew it,</i> Dorismond ended shot. - I heard one of them say... [muttering softly] - It’s okay. - Cop that shot, motherfucker. <i>[somber music]</i> <i>JIM: People said, “Look, Dorismond’s death</i> <i>is a byproduct of these hyper-aggressive tactics.”</i> Giuliani went on the rampage. - He engaged in a fight, created a situation of violence, and that ultimately ended in his death. <i>♪ ♪</i> - He managed to blame Dorismond for the entire event and make no concession whatsoever to say we have to think about how we patrol, what we’re doing out there. - I follow the rule of giving the police the benefit of the doubt. - You know, his tactics were always to attack your critics, give no ground, don’t apologize, and notably he didn’t apologize for it. JIM: It was as if Dorismond was just road kill. <i>♪ ♪</i> What mattered was Giuliani was right. REPORTER: Why did you rush to judgment? - I didn’t. I laid out the facts that were being ignored by the press. - The Dorismond case also plays into the issues with race that dogged Giuliani’s entire mayoralty. <i>You have the Abner Louima case where several police officers</i> brutalized a Haitian immigrant. <i>Amadou Diallo, who is reaching for his wallet</i> <i>outside of a building in the Bronx,</i> <i>and several police officers</i> <i>mistake him for a rapist</i> and fire off 41 shots, just killing him. <i>♪ ♪</i> Plus Giuliani had almost no relation with anybody who happened to be a person of color in the city. REPORTER: What is your answer to those who say that Giuliani is out of control, Giuliani is the chief lawless one in the city? - Oh, come on. All right, let’s move on to a serious question. <i>♪ ♪</i> <i>DAN: I think the public had, um, by this point, realized</i> that Rudy really, really enjoyed the spotlight, but more and more of what was happening was, a recognition of his abrasiveness. - I’m answering these questions because I’m the mayor of the city. Bull[bleep]! That really is pretty outrageous. I think I’ll have a serious reporter ask the question. Excuse me if I don’t think this is entirely phony nor do I have any confidence that it will be reported fairly tomorrow. - So you want me to walk you through the story of the mayor and the ferret? Okay. <i>[pleasant jingle] </i>[chuckles] <i>RUDY: This is Rudy Giuliani back again, on the air.</i> <i>We’re gonna go to David in Oceanside.</i> - Mayor Giuliani at that time had— I think it was a weekly radio program. <i>I think it was David from Oceanside—called up.</i> He was upset that the city, uh, bans, uh, having ferrets as a pet, but Giuliani doesn’t even give him a chance to talk. <i>RUDY: I think you have totally and absolutely misinterpreted</i> <i>the law because there’s something deranged about you.</i> <i>DAVID: The law— RUDY: Concern that you have</i> <i>for ferrets is something you should examine</i> <i>with a therapist.</i> <i>DAVID: Don’t go insulting me again.</i> <i>RUDY: I’m not insulting. I’m being honest with you.</i> <i>Maybe nobody in your life has ever been honest with you.</i> - It’s a dopey little moment in the eight years of the Giuliani administration, <i>but in a weird way it seemed to reflect</i> <i>Giuliani’s incivility.</i> And it became part of his persona. - He goes after people who cross him. He doesn’t forget. <i>No slight is too small for him to remember it</i> and to extract his revenge when the time comes along. - He’s a bully, you know? For real. He picks on little people. - You could feel the city wearying of this guy. - Short-tempered, um, egotistical. - I think he’s a hard-nosed son of a bitch. <i>JIM: He had kind of worn down the public,</i> and the public was tired of him, and maybe he was tired of the public too. - And then he was expected to be riding off into the sunset of his mayoralty in the summer of 2001, and nobody had any reason to believe that was gonna change. <i>WILLIAM: I was actually having breakfast that day</i> <i>in lower Manhattan, and the first plane</i> flew over pretty much where we were sitting, and it felt shockingly low. <i>We ran to the corner,</i> <i>and I saw coming towards me Rudy and his group.</i> And they were, you know, covered with dust as I guess pretty much everybody was. Rudy saw a crew from New York 1, and Rudy told his press secretary, you know, “Go get that guy.” <i>He just spoke into the camera.</i> - You should walk out of southern Manhattan and walk north as these people are doing right here. - He was urging people to stay calm. <i>He was very much in control,</i> and it’s what made him America’s Mayor. [low chatter] <i>JIM: At one point in the afternoon,</i> <i>someone asked him how many causalities</i> there were going to be, and... you know, his answer was <i>true and sorrowful and almost liturgical.</i> - I don’t think we really want to speculate about that. The number of causalities will be more than any— any of us can bear ultimately. - That line always stays with me, and it was... Sorry. It was hugely upsetting, and, um— And I think it was, uh... It was an understated way of describing what everyone else was feeling, which was that we couldn’t comprehend what was happening. <i>[solemn music]</i> <i>♪ ♪</i> - What I remember about Giuliani during that time was an appearance that he made on “Saturday Night Live.” - Good evening. Since September 11th, many people have called New York a city of heroes. Well, these are the heroes. [crowd cheers and applauds] [band plays gently] <i>JIM: And Paul Simon performed</i> “The Boxer.” - ♪ In the clearing stands a boxer ♪ ♪ And a fighter by his trade ♪ <i>JIM: And there was a phalanx of...</i> [voice breaking] firefighters and cops. <i>[somber music]</i> <i>MAGGIE: Giuliani was there, and he was there with Lorne Michaels,</i> <i>the creator of “Saturday Night Live.”</i> And it ended with Lorne Michaels saying— - Can we be funny? [crowd laughs] - Why start now? [crowd laughs, cheers] - The message was, we’re gonna be okay. <i>[somber, pensive music]</i> <i>MAGGIE: You don’t really know what an elected official</i> is going to be like until they’re in a moment of crisis. You just don’t, <i>and it was—it was the best day</i> <i>of his public life.</i> <i>♪ ♪</i> - After 9/11, Rudy became a rent-a-hero. <i>♪ ♪</i> <i>He was your guy to come</i> <i>and talk about the brave firemen</i> and the brave police officers. <i>He embraced that as his new brand.</i> - He founded a security company called Giuliani Partners. <i>- He was someone who could</i> <i>advise you on how to prevent terrorism</i> or to set up a strong emergency response structure. - He went around the world building up that business. He, uh, capitalized on his reputation as America’s Mayor quite handsomely. - And by the end of 2006, it was clear that he was gonna run for president. - Our democracy means we disagree with each other, but when you come and try to take away from us our freedom, when you try to come here and kill our people, we’re one, and we’re gonna stand up to you, and we’re gonna prevail. <i>I’m Rudy Giuliani, and I approved this message.</i> <i>REPORTER: Rudy Giuliani is not just getting in.</i> <i>He’s also taking off.</i> LARRY: You think they’ll vote for you? - I think they will, I think they will, and I think they will on the basis of leadership. <i>REPORTER: Giuliani is relying on the halo effect of 9/11.</i> - I’ve been tested in crisis, I’m ready to lead, and the time is right now. - There was something about the 9/11 moment that Giuliani embodied that he was not able to ever step away from in a graceful way. - Right before September 11th— - First report I got on September 11th— September 11, 2001— - And somebody actually finally stuck a pin in him. - Rudy Giuliani, probably the most under qualified man since George Bush to seek the presidency... - And it was Joe Biden. - Rudy Giuliani— there’s only three things he mentions in a sentence: a noun, a verb, and 9/11. I mean, there’s nothing else. <i>There’s nothing else. </i>- And... that was true. - Giuliani did not like that line. I don’t think that he ever forgot that Biden said it. <i>REPORTER: Florida was a crushing blow</i> <i>to former New York City Mayor Rudy Giuliani,</i> <i>who GOP sources say now plans to end his candidacy</i> <i>and endorse McCain.</i> - It was a spectacular flameout. - He spends millions and millions of dollars and he gets one delegate? <i>SARAH: His ego was profoundly bruised.</i> <i>He was almost catatonic</i> and was absolutely miserable in defeat. <i>MAGGIE: And his business suffered.</i> He couldn’t sell himself as this model of leadership and know how, and I think that he got <i>more frustrated and angry</i> <i>with, uh, a life that hadn’t quite worked out</i> <i>the way he had believed it was going to.</i> - And he faded from relevance.... until 2016. [chuckles] - Oh, you dirty boy, you! Oh, oh! Donald, I thought you were a gentleman. Hm! - You can’t say I didn’t try. <i>MAGGIE: Donald Trump and Rudy Giuliani</i> <i>had been friends for a very long time.</i> I think that they saw some similarity and style. <i>SARAH: They’re are these bombastic,</i> <i>larger-than-life figures in New York City.</i> They’re creatures of New York. - They’re both outer-borough guys looking in. They feel as though something is always being put over on them by the establishment. - They harbor their resentments against the elite together. But now look where they are. <i>KENNETH: In 2016, their relationship</i> takes a new turn when Rudy is among the first sort of establishment Republicans to really throw his support behind Trump. - Donald Trump is the agent of change. <i>He will make America once again.</i> - He was the only person who went on TV to defend Donald Trump after the infamous “Access Hollywood” tape dropped. - He realized that he was wrong. <i>I think he made a full and complete apology for it.</i> <i>MAGGIE: That has always stayed with Trump,</i> and I think he turned to Giuliani in a time of need again. <i>[dramatic music]</i> <i>REPORTER: Robert Mueller has the power to investigate...</i> <i>DONALD: There’s been no collusion, no obstruction.</i> I think it’s very bad for our country; it’s a shame. <i>MAGGIE: At some point, President Trump felt like</i> <i>he needed to take a more aggressive tact,</i> and he started quietly, without really telling anyone, talking to Giuliani about becoming his lead lawyer. <i>REPORTER: The president tapping Rudy Giuliani for his legal team</i> <i>REPORTER: This comes after weeks of basically</i> <i>the president’s legal team trying to find</i> <i>other members to join.</i> - And it gets him into the situation where he is today. <i>[tense music]</i> <i>KENNETH: After he leaves the mayor’s mansion in New York,</i> <i>Rudy was kind of a hero</i> all around the world, but particularly in Ukraine, and Rudy has a number of people with whom he stays in touch with in Ukraine, people who he had done business with. And then it all kind of comes together <i>with Rudy’s work on the Mueller report.</i> <i>♪ ♪</i> - Trump is furious that this investigation had cast a cloud over his presidency for two years, and Giuliani sets out to exonerate the president, to find a way to clear his name. But instead of turning to Russia, Giuliani turns to Ukraine. <i>KENNETH: And what Rudy alleges is that</i> <i>it was Ukraine and not Russia that actually did the hacking</i> of the Democratic National Committee to make it appear as if it was Russia that was doing the hacking. That has been thoroughly debunked by the Mueller report and by the U.S. Intelligence Community. <i>But it is through that investigation</i> that he stumbles across this other potentially beneficial thing that relates to the Bidens. <i>♪ ♪</i> <i>The story that Rudy pushes is that</i> <i>Joe Biden used his position as vice president</i> <i>to push for the firing of a prosecutor</i> <i>in Ukraine who was investigating</i> <i>the oligarch that was paying Hunter Biden,</i> <i>as a board member, to try to help his son.</i> It’s a lot more complicated than Rudy presents and actually Rudy is misrepresenting some key elements of that story. - I don’t know better. I am outraged by the behavior of these networks. - Watching him on television, you don’t know what he’s gonna say. - No, it isn’t truth. Truth isn’t truth. <i>ELISABETH: And he’s taken</i> his personality that I used to see in city hall in places I never imagined he’d go. - Laura, I’m a pretty good lawyer, just a country lawyer, but it’s all here. - It’s hard for me to ignore the fact that Biden hit Giuliani at a point that Giuliani considers a pride point with this line about “a noun, a verb, and 9/11.” <i>BIDEN: “A noun, a verb, and 9/11.”</i> - It’s hard for me to disconnect that from the fact that Giuliani has been singularly focused on the Bidens for the last two years. <i>♪ ♪</i> - Giuliani was going back and forth with Ukraine officials about how they needed to commit to these investigations. <i>KENNETH: In the midst of this, Trump makes a decision</i> to delay this military assistance that has been allocated by congress to Ukraine through the state department and defense department. And he doesn’t really offer any explanation and it’s sort of a big mystery. <i>- But the day after Mueller testified,</i> <i>Trump picked up the phone</i> <i>and he asked the president of Ukraine</i> whether he’ll work with Giuliani and his Attorney General Bill Barr, to investigate his political rivals in the hopes of undermining them coming into the election. - We begin with breaking developments involving that controversial whistleblower complaint. - This is a really big story. This is, I think, the biggest story we’ve covered since Trump became president. - He sought to pressure the Ukrainian leader to take actions to help the president’s 2020 reelection bid. - You did ask Ukraine to look into Joe Biden. - Of course I did. <i>ELISABETH: And Rudy’s right in the middle of it.</i> - I’m announcing the House of Representatives is moving forward with an official impeachment inquiry. - Well, the presidency’s at stake, and the future of the country’s at stake, and Trump himself is tweeting about this is “a coup,” <i>this will ignite a civil war in the country.</i> So there’s a lot of dangerous thoughts out there. - Why are you—the president’s personal attorney— what is your personal mission? - Wow. - What’s your mission? - To disrupt the world. - At the heart of the Ukraine issue are the actions of Giuliani. How much was he pushing the Ukrainians to do these investigations? <i>The House is moving forward with impeachment proceedings,</i> and now the president must contend with an investigation by his own justice department into his personal lawyer. The department is looking at his ties to Ukraine. Was Giuliani mixing his representation <i>of the president with his representation</i> <i>of the oligarchs?</i> <i>The investigation of Giuliani is the latest development</i> in the fallout of the Ukraine scandal that has engulfed the White House in the past few weeks. <i>It will be an incredible distraction for the president.</i> He hated the Mueller investigation and the cloud that it casts over his administration. He hated the investigation of Michael Cohen, and now as he tries to fend off impeachment he has his own department looking at Giuliani. - Leadership is more than just effective administration. There’s a moral component to leading as well. It’s not enough for our leaders to follow the law. They must set an example for others to follow. <i>[ambient pensive music]</i> - It is hard to fully process how we arrived at this moment. <i>The Giuliani of 20 years ago</i> <i>would have called this kind of thing really reckless.</i> <i>He would have been really dismissive of a lot of what</i> <i>Rudy Giuliani in 2019 is saying,</i> <i>and it can be hard to reconcile the two thoughts.</i> <i>JOURNALIST: Here’s the twist.</i> <i>Giuliani is now being investigated</i> <i>by the U.S. Attorney of the Southern District of New York</i> <i>and that’s the same position</i> <i>that made him famous more than 30 years ago.</i> <i>JAMES: He was a figure of massive admiration.</i> Why he then would pursue a path that brought a lot of that into question is a little perplexing to me, but maybe the alternative was simply bask in reflected glory and that’s not Giuliani. I mean, he would have— <i>He’s got to be in it.</i> <i>JIM: You’re seeing a most unusual spectacle of a person</i> clinging to the spotlight. <i>JAMES: Giuliani wakes up every day</i> <i>and kind of must be pinching himself saying,</i> “I’m in the middle of every— I’m Mr. Important.” We’re doing a whole TV show on him. He loves that. <i>♪ ♪</i> - Um... Enabled. He is the imprimatur of the president of the United States to do what he’s doing. - Conspiratorial. - He’s still very smart, but he’s also very pugilistic. - I mean, crusading in some sense. - I think there is a theory that as we all get older we just somehow become more of what we’ve always been, for better or worse.