Who Trolled Amber? - Trump and Rudy: A bare-knuckle romance - Episode 2

Episode Date: October 9, 2023

Twenty years ago, Rudy Giuliani was “America’s mayor”. Now he’s been indicted, along with Donald Trump, for allegedly attempting to overturn the 2020 election in Georgia. Will Rudy die in jail for The Don?Listen to the three part series today. For the premium Tortoise listening experience, curated by our journalists, download the free Tortoise audio app. For early and ad-free access to all our investigative series and daily and weekly shows, subscribe to Tortoise+ on Apple Podcasts.If you’d like to further support slow journalism and help us build a different kind of newsroom, do consider donating to Tortoise at tortoisemedia.com/support-us. Your contributions allow us to investigate, campaign and explore, and to build a newsroom that is responsible and sustainable. Hosted on Acast. See acast.com/privacy for more information.

ACAST powers the world's best podcasts. Here's a show of glamour and scandal and political intrigue and a battle for the soul of a nation. Hollywood Exiles, from CBC Podcasts and the BBC World Service. Find it wherever you get your podcasts. ACAST helps creators launch, grow, and monetize their podcasts everywhere. Acast.com Tortoise September 11th was election day in New York City.

Giuliani had already served almost eight years as mayor, and there was a primary to select the Democratic candidate for mayor. And so at New York One, we were all braced for a very long night for election returns. So we were all, you know, sleeping late, getting rested for a long night. And I was in bed and the phone rang. It was my mother. And she was frantic. The attacks of September the 11th, 2001, tipped the world into a new age of fear. the 11th, 2001, tipped the world into a new age of fear. They put Rudy Giuliani into a new orbit. In the space of a few hours, he became a global icon. Andrew Kurtzman has written a biography of Rudy Giuliani. Back in 2001, he was a reporter covering City Hall for New York One News. His mother was calling to tell him to switch on the TV.

His mother was calling to tell him to switch on the TV. Both towers of the World Trade Center were smoking. There was billowing smoke coming from them. And so I, you know, bolted out of my apartment and I ran downstairs and I jumped into a taxi and I terrorized this taxi driver to take me towards the World Trade Center when everyone was fleeing it. me towards the World Trade Center when everyone was fleeing it. And on the way down there, I watched the first tower implode. Kurtzman's editor at New York One had given him a simple instruction, find Giuliani. The cab driver went, I guess, a few blocks further towards the World Trade Center and then slammed on his brakes and screamed at me to get out. I was probably four blocks north of the Trade Center. So this frantic woman came to the cab and saw that I was getting out. And she looked at me like I was crazy. And she was like,

don't get out. I was, you know, I'm a reporter. I've got a story. And so she jumped in the taxi feeling like she had won the lottery by finding a taxi. And I'm left out on the street and it's deserted and it's covered with white ash. It's as though there were a nuclear explosion and there was no humanity in sight. Kurtzman assumed Giuliani would be in or near his Office of Emergency Management, his Situation Room, which he had personally located inside the World Trade Center. But, you know, I was let off several blocks north of it and there was a police officer there and he saw me and he screamed at me. He said, get off the street. It's going to blow. Get off the street. And I said, I need to find Giuliani. And he said,

oh, Giuliani, he's right there. And Giuliani was literally at the corner with many of his mayoral aides and the police commissioner and the fire commissioner, and they're covered in ash because they were even closer to the building and had, you know, escaped with their lives from it. And they were standing in the middle of the street trying to figure out what to do and also kind of dazed. And Giuliani saw me and he waved me over. He's like, Andrew, let's go. For the next four days, Andrew Kurtzman barely left the mayor's side. He'd covered Giuliani as closely as any reporter in New York. He'd seen his political fortunes fade in his second term.

And now, in extreme close-up, he saw the man come back to life. Rudy Giuliani was the one unquestioned winner of 9-11. It revived his brand, gave him options, gave him money, and it left him, according to one poll, more popular than the Pope. At this rate, Donald Trump would be lucky to get him to return his calls. This is episode two of Trump and Rudy, a bare-knuckled bromance. One thing was clear. There was no point trying to get to the emergency control room in the World Trade Center.

So we started this, I guess, two-mile odyssey marching up Church Street trying to find a place to relocate city government. And City Hall was closed. The police department was closed. There were all potential terrorist targets. And we didn't even have a car. I mean, it was this kind of ragtag group, you know, covered in dust, you know, trying to figure out what to do. It was an extremely helpless situation. It felt as though kind of civilization itself was being attacked.

So who'd take charge? Not the president. He was being hurried out of harm's way on Air Force One in central Florida. But it wasn't obvious it would be Giuliani. In Kurtzman's biography of Giuliani, he writes that the mayor learned the hard way. He had to react fast if he wanted to dominate coverage of a disaster. There'd always be others eager to stand in front of the cameras. This time, he seized the moment, and he did it almost effortlessly. It was Giuliani who was kind of the calmest one there. And, you know, it was almost as though his leadership abilities were a reflex. He just launched into giving orders very quietly, very methodically, asking a lot of questions of his aides.

And talking to the world through Andrew Kurtzman's camera operator. But it was clear he was in charge. And, you know, for a lot of us, that was really reassuring. through Andrew Kurtzman's camera operator. But it was clear he was in charge. And, you know, for a lot of us, that was really reassuring. I mean, I think for a lot of the world, that was reassuring because everyone saw it on television. But I was two feet away from him, and I was relieved. I mean, I thought I was watching kind of a historic moment

where someone rose to the occasion to kind of take command of an inherently disorganized situation would be a light way of putting it. And it was very impressive, very impressive. This goes on for days. He is the face of the world in threat. He's the face of the West. Hank Sheinkopf, the political consultant, was transfixed. His metaphor of choice? Giuliani as vampire, feeding off the catastrophe. He's the face of the Western world versus this great attack from the East. He becomes everything that he always wanted to be. He's restored as the greatest outsider who is now leading the world from the inside, whether they like it or not.

At a memorial service 12 days later in Yankee Stadium, Giuliani was introduced by Oprah Winfrey. I know you want to hear from him. He's the man of the hour, a man whose extraordinary grace under pressure in the days since this devastating attack has led him to be called America's mayor. The moniker stuck. He's the mayor of New York City. Ladies and gentlemen, Rudy Giuliani. For those with eyes to see, there were signs almost at once that the legend was full of holes.

The reason he's the man of the hour, coming out of the dust with the dust cloud behind him in his Yankees hat is because he was coming out of the world's most stupidly placed security bunker. This is Eileen Markey, the reporter, now a journalism professor in the Bronx. The security bunker was on the seventh floor of a building that had already been attacked by terrorists. And so the reason we have those heroic images of him with the cloud of dust behind him is because he had gone to his absurd bunker.

And of course, it was inaccessible. And because it was inaccessible, it meant that New York, like, he just ran around for several hours looking for phone lines that would work. Later, Giuliani was blamed for the fact that police and firefighters couldn't talk to each other on their new radios. That led directly to dozens of firefighters' deaths. But when the 9-11 Commission tried to question him about the radios, he replied with a monologue about the drama of the day, and the challenge fizzled. In the meantime, Bush, Blair, Putin, Chirac, they all paid court to America's mayor. The world was his oyster. The question was what he would do with it.

He was a savior in a lot of people's eyes. And, you know, instead of using it, I guess, for, I don't know, more honorable purposes, right? He could have become the president of a foundation. He could have, I don't know, even if he stayed in politics, he could have run for governor or joined the Bush administration. But instead, instead he decided to cash in. He set up a consulting firm and got rich. He advised Mexico City on cutting crime. He hired himself out to a former cocaine smuggler who wanted to know how to apply for federal contracts. If the price was right, it turned out Giuliani would do pretty much anything. I guess the best example was Purdue

Pharma, which was the maker of OxyContin, which was hooking a generation of American teenagers on their product. And they came to Giuliani because the lawsuits were piling up and the federal investigations were heating up. And they hired Giuliani to, I guess, intimidate the Bush administration into easing up on Pertu Pharma. OxyContin, of course, is a highly addictive painkiller, and thousands of users were dying from overdoses. Giuliani, a prostate cancer survivor, had no qualms using his personal story to support a pitch that Purdue was helping sick people get

the pain control they needed. He could get his calls returned by anyone up to the president of the United States. And so there were meetings held with administration figures. And eventually a deal was cut in which Purdue Pharma paid a large fine, but was allowed to go on selling OxyContin and marketing it in the same way that it had before. And, you know, within years, thousands of American deaths had turned into tens of thousands of American deaths. There was something else about the deal Giuliani brokered. It ensured that not one member of the Sackler family, which owned Purdue Pharma and made about $10 billion from sales of OxyContin ever went to prison. and I'm the host of a new podcast called Hollywood Exiles. It tells the story of how my grandfather, Charlie Chaplin, and many others were caught up in a campaign

to root out communism in Hollywood. It's a story of glamour and scandal and political intrigue and a battle for the soul of a nation. Hollywood Exiles, from CBC Podcasts and the BBC World Service. Find it wherever you get your podcasts. ACAST helps creators launch, grow, and monetize their podcasts everywhere. ACAST.com. By 2007, Giuliani's personal net worth is $30 million. But wealth never suited him, Ken Friedman says. When I knew him, when I worked with him,

he was a modest, modest guy. He didn't care about fancy clothes and trappings. But he married a woman who did. That's Judith Nathan, his third wife, who'd moved into Gracie Mansion, the New York mayor's official residence, before his second wife moved out. Suddenly he had a very expensive lifestyle, which I've decided he never wore well.

He wasn't meant to be rich. which I've decided he never wore well. He wasn't meant to be rich. He didn't carry himself like old money, all right? He carried himself like new money. And his greed and need for relevance and access and money either turned him or triggered a personality that hadn't been exhibited before, but was there all along. There seem to be two ways of looking at Giuliani's turn to money, despairing and Trumpian. So what is Trump thinking of Giuliani at this point? It's probably fair to say the most damning word in the Trump lexicon is loser, and the most precious thing in his universe is money. And Giuliani is now a winner and rich. He ticks Trump's boxes, and Trump ticks his.

There were both bullies, and there were authoritaritarians and they saw a lot to admire in one another. But they also needed each other. And that was a pattern that went on from the very beginning. You know, there are any number of periods in the Giuliani-Trump relationship in which one benefited from the other. And it was a power dynamic that kept switching. It was a power dynamic that switched dramatically in 2008 when Giuliani ran for president. I'm Ben Smith. I'm the editor-in-chief of Semaphore. Back in 2006, I was a reporter for the New York Daily News, which was then I think the largest newspaper in America by print circulation. In the fall of 06, a source connected to another campaign gave me this incredible document that was just this extremely detailed playbook for how Rudy Giuliani was planning to run his campaign. And it came at a moment when people thought, oh, maybe he's thinking about it and made clear he was dead serious about it. It listed the vulnerabilities around his personal life, around his political stances that would wind up crippling the campaign. And it also just, the fact that it had leaked to me, in fact, was maybe the biggest story of all, because it revealed

a level of kind of chaotic lack of professionalism, basically, or for around a pretty serious effort. And yeah, and his team was hysterical about it. And I remember his communications director, Sonny Mindell, called me to scream at me and at one point told me, I believe it was to bow to Mecca, shithead. Andrew Kurtzman writes that the hero of 9-11 considered the presidency, quote, a natural progression. An advisor on his campaign said, quote, he felt that voters should have the opportunity to give him the job. But first, he had to win the Republican nomination,

and he had to win it as a New Yorker who believed in abortion rights, who waffled on gay marriage. The more Republican voters saw of him in the 2008 primary season, the less they liked him. That taught Donald Trump, that other New Yorker, a lesson that would change the course of history. But in the meantime, Rudy crashed and burned. His entire campaign lasted about a month.

And he dropped out in total humiliation, having acquired just one delegate. It was a complete disaster. And it was a pivotal moment in the Giuliani story because the 9-11 halo was tarnished. He was known thereafter as a failed politician, and it was devastating for him. Ken Friedman, who'd helped Giuliani become mayor, questions whether he ever really had the desire for the top job. He wanted to be president, but did he really want to be president? It looks like he just went through the motions, right,

to maintain his public image and exposure. Now he's a loser, right? Trump reminded him of that very often, that he lost, right? He lost. You're a loser, Rudy. This was not a sentimental relationship, but in a peculiar way, it had become closer than ever. Here's Andrew Kurtzman again, talking about Giuliani. He was driven by a need to be important, to be on the front page, to be powerful, need to be important, to be on the front page, to be powerful, also to be rich.

But it was power, I think, and recognition that really drove Giuliani. And suddenly he had lost his relevance after he lost that race. And he went into a deep depression. And he started drinking and couldn't get out of bed. And according to Judith, she moved him down to Florida to recuperate. The press found out. And then she went looking for kind of a refuge. And who came to their rescue but Donald Trump? Trump drinks Coke. Giuliani likes scotch. Giuliani likes cigars. Trump doesn't smoke. But they're both people people. Trump actually collects people, Hangshankov says. As for Giuliani,

one person who spent time with him says it was like being in Russia, where a businessman will dine alone with you, but a mafia don invites his bodyguards. Lunch with Giuliani was a full-table affair. The trouble was, at this point, Giuliani was in no state to be sociable. Trump reached out. He invited Rudy and Judith to stay at Mar-a-Lago, his mansion in Palm Beach. There are a lot of underground tunnels connecting the various areas of Mar-a-Lago. So it enabled Giuliani to travel unnoticed. So he and Judith were given this large bungalow by Trump. And when they wanted to leave or wanted to go to dinner, they would kind of walk underneath Mar-a-Lago and go to where they were going.

They spent a month there, venturing outside at their peril. side at their peril. And Judith told me a number of stories where Giuliani would, quote unquote, fall down shit-faced drunk. She said that she was constantly having to salvage situations, literally pick him up. There were times when he physically injured himself. She told me a story about how they decided to go to a movie one day and went to this mall where the movie theater was. And he was drinking and he literally fell out of the car and injured himself so badly he had to go to the hospital. And there was a gash above his eyebrow that made him worry that he was going to have to miss an appearance on Saturday Night Live. And sure enough, if you look at the video of his appearance on the set of Weekend Update, his makeup just barely covers this gash above his eyebrow. Now, looking back on your own campaign, would you have done anything differently?

Well, let's see, Seth. In July of 2007, I was the clear frontrunner for the Republican nomination. Now, only eight months later, I'm sitting here with you and Amy. So, to answer your question, yes, I would have done a few things differently. Great question, Seth. Thanks a lot. Most of the time, the Trumps left the Giulianis to themselves, but there was contact. One day, Judith told Kurtzman, she and Melania Trump were together at the beach club when they spotted a Mar-a-Lago staff member taking their picture.

And according to Judith, Melania called Donald. Donald came, you know, arrived at the scene, went to his employee, demanded to see his camera or his cell phone, whatever he was shooting with, and sure enough, saw that the guy had shot pictures of Judith and Melania and fired the guy on the spot. In November 2014, Giuliani appeared on NBC's Meet the Press with its host, Chuck Todd, and Professor Michael Dyson of Georgetown University. A grand jury was debating whether to bring charges against a white police officer who'd shot and killed an unarmed black man, Michael Brown, in Ferguson, Missouri, three months earlier.

Todd's question for Giuliani was how to make police forces in the U.S. look more like the people they policed. How do you make a police force that looks like the community they serve? Well, I mean, starting with Mayor Koch, Mayor Dinkins, myself. Things quickly got heated. We are talking about a significant exception. Ninety-three percent of blacks are killed by. Let me say, let me let me respond to that. I would like to see I would like to see the attention. I'd like to see the attention paid to that, that you are paying to this and the solutions to that. He's taking up time. Can I say this? First of all, most black people who commit crimes against other black people go to jail.

Number two, they are not sworn by the police department as an agent of the state to uphold the law. So in both cases, that's a false equivalency that the mayor has drawn, which has exacerbated tensions that are deeply embedded in American culture. Black people who kill black people go to jail. White people who are policemen who kill black people do not go to jail. If a jury can indict a ham sandwich, why is it taking so long? go to jail. If a jury can indict a ham sandwich, why is it taking so long? To understand what Giuliani was up to here, bear in mind he'd spent the Obama years gaining country club memberships and losing name recognition. The then Vice President Joe Biden found he could actually raise a laugh by mocking Giuliani for only ever saying one thing,

quote, subject, verb, 9-11, unquote. 9-11 was that long ago. Verb 9-11, unquote. 9-11 was that long ago. Giuliani's argument with Dyson on Meet the Press was strategic. It was a wave from the back of the class. Remember me? The dog whistler of 1993 was back, only more crass, more offensive,

more desperate than ever for attention. And Trump noticed. Trump had spent the Obama years gaining name recognition. He'd done so as host of the American version of The Apprentice and as a birther. To anyone who'd listen, he'd say there were questions to be answered about the president's place of birth, even though there weren't. He was considering his own run for the White House, but most people, even in his own party, still thought he was a joke. So when Giuliani went on Fox News a few months later to talk about Republican presidential contenders and said nothing about Trump, Trump phoned him in a lather. I'm running for president, he said, and you don't even mention me? That was when Giuliani realized Trump was serious.

A year later, Trump was the nominee, and Giuliani was giving a primetime speech in his honour at the Republican National Convention in Ohio. Three police officers had been killed a few days earlier in Baton Rouge, Louisiana, and Giuliani made them his subject. When they come to save your life, they don't ask if you are black or white. They just come to save you. He was red-faced, veering off script. The crowd loved it. It's time to make America safe again. It's time to make America one again. One America!

One America! time to make America one again. What America? What happened? What happened to? What happened to? There's no black America. There's no white America. There is just America. What happened to it? Where did it go? How was it flown away? Back in New York, people who thought they knew Giuliani thought he'd gone nuts. And something else was happening. In a hard-to-get-to part of Brooklyn, reporters and TV crews from all over the world were beating a path

to the door of an investigative reporter called Wayne Barrett. Barrett was dying. But before he died, these reporters wanted to get the skinny on this man called Trump, who was fighting Hillary Clinton for leadership of the free world. It was Barrett who'd taken on Eileen Markey and dozens of others as interns at the Village Voice in the 1970s and 80s. It was Barrett in 1979 who wrote a series of three long articles about the young Trump's business style. He was completely unimpressed by the Trump glitz. As Markey explains, he started with a few simple questions.

The city's hurting. Why are we giving money to the rich people? And who is this guy who keeps getting these deals, and why is he getting so many? He's not the most experienced developer. He's not the best. Where did he get his money? We know he got some from his father, but where did the rest come from? Where did he get his money? You know, we know he got some from his father, but where'd the rest come from? So all of that is to say, Wayne starts digging on who is Donald Trump in, you know, starts digging in 78, produces these, oh, they must be like 15,000 word articles, three 15,000 word articles in the Village Voice newspaper in February and March of 79. And they are, they're brilliant, they're detailed, they're exhaustive, they're exhausting.

I'm going to read you a little bit from one of them. So this is from this article that was published in January 15th, 1979. And it begins, Donald Trump, a 32-year-old self-proclaimed real estate colossus, price tagged at $200 million, the brash streetwise son of Brooklyn's largest apartment builder, transplanted from his father's box-like office at the Avenue Z tip of the borough to the Fifth Avenue penthouse, bound on both sides by his own stunning Manhattan ventures.

The New York Times puffs him as the city's number one real estate promoter of the mid-70s. the Fifth Avenue penthouse bound on both sides by his own stunning Manhattan ventures. The New York Times puffs him as the city's number one real estate promoter of the mid-70s, the Willen Zeckendorf of hard times. It goes on for another like 10,000 words about exactly how Trump has pulled strings, pulled in favors from his father, from his father's machine politician, political cronies, in all sorts of ways to get this first big contract, and then the next one, and then the next one. And the epitaph I wanted to read you is this. This is how this three-part series ends. The actors are pretty small and venial.

Their ideas are small, never transcending profit. In it, however, are the men elected to lead us and those who buy them. In it, unhappily, are the processes and decisions that shape our city and our lives. It's hard to overstate how fondly progressive New Yorkers remember Wayne Barrett. Read his work, Markey says, and... You get this whole lesson on machine politics, on public subsidies, on real estate development,

and a sort of dizzying network of favors and names and connections. And then he sums it up like that. And that was in 1979. Everything? Not quite. On October 7, 2016, the Washington Post published authentic footage of Trump on a Hollywood TV set in 2005. You know, I'm automatically attracted to beautiful women.

I just start kissing them. It's like a magnet. You just kiss them. And when you're a star, they let you do it. You can do anything. Whatever you want. Grab them by the pussy. You can do anything. Whatever you want. Grab him by the pussy. You can do anything. It was a Friday.

A month to go till the election. The Trump campaign looked finished. But if it was to fight on, it needed someone to defend the candidate on the Sunday morning news shows. And Rudy Giuliani stepped up. He did all five of them, CNN, ABC, CBS, NBC, and Fox. But in any event, we take to an extra degree of what he said. But the fact is that men at times talk like that. Not all men, but men do. You've talked like that?

He was wrong for doing it. I am not justifying it. I believe it's wrong. I know he believes it's wrong. I believe that this is not the man that we're talking about today. It wasn't pretty. Still, Trump's junior staffers thought Giuliani had done sterling work. He gets on the campaign plane at LaGuardia Airport. He sees himself as a conquering hero. And he gets some high fives from Trump's people, but he sits down with Trump who says, you know, Rudy, you sucked, right? You were low energy. And he just humiliated Giuliani and Giuliani just sunk into his chair.

Next time on Trump and Rudy, the big question. Will Giuliani die in jail for the Don? Thanks for listening. You can get early access to this and all our Tortoise investigative series, plus ad-free listening by subscribing to Tortoise Plus on Apple Podcasts, or for the best Tortoise listening experience curated by our journalists, download the Tortoise app. And please leave ratings and reviews.

It really helps. This episode was written and reported by me, Giles Whittle. The producer was Charlie Bell. The editor was Jasper Corbett, with sound design by Carla Patella. You can get anything you need with Uber Eats. Well, almost, almost anything. So no, you can't get snowballs on Uber Eats. But meatballs and mozzarella balls, yes, we can deliver that.

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