By Hope Talbot and Deep Vakil
Newly crowned as America’s Mayor, Giuliani looks set to cash in on his newfound popularity. He shoots for the White House and misses. After disappearing from the spotlight, he decides to make a comeback working for someone who could very well be his last legal client: President Donald Trump. This episode was reported, written, and produced by Deep Vakil and Hope Talbot.
TRANSCRIPT
OPRAH WINFREY (archival): “I know you want to hear from him. He is the man of the hour, a man whose extraordinary grace under pressure in the days since this attack has led him to be called “America’s Mayor.”
HOPE TALBOT: From the ashes of 9/11, Rudy Giuliani’s reputation soars to new heights.
So, what do you do when your popularity peaks?
MUSIC IN
HOPE: For Giuliani, he chooses to run for President.
DEEP VAKIL: This is the story of how Rudy Giuliani became one of America’s most prominent politicians. And it’s also the story of his fall from grace – how America’s Mayor lost out on being America’s President. For years after his failed presidential bid, Giuliani vanished from the spotlight. Until his reappearance, alongside President Donald Trump.
HOPE: I’m Hope Talbot
DEEP: and I’m Deep Vakil.
HOPE: And this is Shoe Leather, an investigative podcast that digs up stories from New York City’s past to find out how yesterday’s news affects us today.
DEEP: This season, we’re taking a deep dive into the life and career of Rudy Giuliani. One of the most influential politicians in New York City’s recent history. Before he went to work for President Donald Trump, before he was disbarred, bankrupt …before all the trouble…Giuliani rose to prominence as a prosecutor and a politician.
We wanted to know, how did America’s mayor end up going from presidential hopeful … to participating in a lie that shook the foundations of American democracy?
This is Shoe Leather season 6, Giuliani: The Unravelling. You’re listening to our sixth and final episode: Rudy Gone Wild.
HOPE: In this final episode, we follow Giuliani’s choices after 9/11 – fresh out of office as mayor, his failed presidential bid, and his decision to join President Trump.
MUSIC OUT
HOPE: Deep and I are in an office building in Staten Island. We’re with Matthew Mahoney.
Laughter
MATTHEW MAHONEY: There’s not much reason to come out here.
HOPE: We’re looking at photos from Mahoney’s time working for Giuliani.
DEEP: I see a couple posters up here from campaigns…
MAHONEY: Oh yeah!
DEEP: The one where you’re next to Rudy at the presser.
MAHONEY: Oh yeah, that’s from 98, maybe 99…that’s an early one.
HOPE: Mahoney started working as an aide to Giuliani during his second term as mayor. He was an advance man – his job was to get places before Giuliani did and make sure that things are all set before his boss arrived.
DEEP: 9/11 presented new challenges for both of them. Mahoney describes days filled with back-to-back funerals where Giuliani wants to mourn alongside the city’s residents.
MAHONEY: They were grueling, they were grueling, and they were non-stop, and everybody worked really, really hard.
HOPE: Giuliani asks to see psychiatrists who specialise in trauma.
MAHONEY: We sat with him and he said, I don’t always know what to say to people. I’m afraid I’m going to say the wrong thing. I’m afraid I’m going to make things worse …
HOPE: He even gathers old rivals, former mayors, to help guide him.
MAHONEY: And he even brought in Mayor Dinkins, who – they hated each other, Koch. He brought them all in to sit with him and say, what else should I be doing?
DEEP: Giuliani’s approval skyrockets. Just six weeks after the attack, his approval rating hit a high of 79 percent. Oprah dubs GIULIANI America’s mayor. Time Magazine names him Person of the Year. A few months later, he’s even knighted by the Queen of England.
RUDY GIULIANI (archival following his knighthood): “if I go back to Brooklyn and tell them I’ve been knighted, and I ever ask them to refer to me as “Sir.” Woah boy. Something like this’ll happen…”Aye, what’s this sir stuff?”…”You some kinda big shot?”
HOPE: So, when Giuliani’s time as New York City’s mayor ends on December 31st, 2001, he leaves a hero.
GIULIANI (archival from Farewell Address as Mayor of New York City): “Thank you! Thank you very very much! … Although I have to leave you as the mayor soon. I resume the much more honorable title. Of a citizen. Citizen of New York. And citizen of the United States.”
DEEP: As America’s Mayor steps away, Giuliani’s fame is about to be met with fortune.
DEEP: Giuliani doesn’t wait long to cash in on his fame. In fact, he doesn’t wait at all.
HOPE: Mathew Mahoney remembers the idea of a consulting business coming up a couple of months before the end of Giuliani’s term.
MAHONEY: And there were a couple of discussions that were very tight-knit.
HOPE: During another phone interview, Mahoney tells us how he got a call from Giuliani’s former chief of staff, who asks Mahoney:
MAHONEY: What are you doing when this is over? … They said, well, Rudy wants you to come work with him. I was like, awesome. What are we doing? Business. Okay. What’s the name of the company? Don’t know yet. Where’s the office? Don’t have one yet. What’s the name? We don’t know yet. Okay. What am I going to make? More than you make now. I’m in!
DEEP: They name the firm – Giuliani Partners. It’s a consulting business. Giuliani has connections in government – that his wealthy clients would like to tap.
HOPE: That’s exactly what happens with Purdue Pharma, the drugmaker. You’ve probably heard the name associated with being responsible for the opioid crisis. In the 2000s, the government is trying to hold the Sackler family — who owns Purdue Pharma — accountable. But Giuliani and his law firm get involved, and help the Sacklers avoid jail time. On top of that, Giuliani’s consulting firm helps the family navigate the PR fallout.
TOM DAVIS: Look, you have a shelf life. And 911 resurrected him. He was in the political trash heap prior to that time.
DEEP: That’s Tom Davis. He’s a seven-term Republican congressman from Northern Virginia. In 2002, he tells New York magazine that Giuliani is “the hottest political property in America today.” Davis knows that, because he’s leading the fundraising arm of House Republicans.
DAVIS: That’s how I got to meet him and we utilized him from there. I also got him some speaking gigs. He charged 100 grand a speech after that, and I got to a couple of speaking gigs, but everybody wanted to hear him.
HOPE: The 2002 midterms come along. The first nationwide elections after 9/11. Giuliani’s stardom becomes an asset.
DEEP: Davis is a moderate Republican. And so is Giuliani, at the time. That makes him the perfect campaigner in swing districts.
DAVIS: His politics were a little more moderate than a lot of Republicans because he represented New York City. So, you know, on some of these abortion guns, these kind of issues and stuff like that. He wasn’t waving the flag for these conservative groups because he had to be electable in New York. But in these swing districts, he was he was America’s mayor. He’s led them from the ashes after 911. And so if you’re a candidate looking for swing voters, which were the keys in these districts, Rudy Giuliani was the man.
DEEP: The Republican party has a blowout year in 2002. Not only do they flip the Senate that year, they also add more seats to their House majority.
HOPE: Around that time in November 2002, Giuliani is in Paris on a business trip.
MUSIC IN
HOPE: He asks Judith Nathan to marry him – his third marriage. They marry six months later, and among the attendees is Donald Trump.
GIULIANI (archival of his wedding day): And I would like to introduce my wife, Mrs. Giuliani. And you can see how fortunate I am with a lucky man. I am going to have a beautiful lady and a wonderful person as my wife, and I want to thank Mayor Bloomberg for allowing us to use Gracie Mansion. [JUDITH NATHAN:] And I want to say thank you to the people of New York, the support that we’ve had.
MUSIC OUT
DEEP: Two years later, in 2004, the Republican Party holds its national convention in New York City. The party is nominating George Bush for a second term. Giuliani has a primetime speaking spot.
GIULIANI (archival at RNC in 2004): At the time, we believed that we would be attacked many more times that day and in the days that followed. Without really thinking, based on just emotion, spontaneous, I grabbed the arm of then-Police Commissioner Bernard Kerik and I said to him, ”Bernie, thank God George Bush is our president.
HOPE: Giuliani is biding his time. Just one year later, his team starts planning for the 2008 presidential run. Here’s Matthew Mahoney again.
MAHONEY: My job was to get him ready to run for president if he wanted to. … that enhanced the business, right? If someone thought he had the potential to be president or vice president one day, well, you have more reason to be aligned with him, you know?
DEEP: By now, companies like General Motors, JP Morgan, and even Lehman Brothers, are paying Giuliani $100,000 dollars to speak. He gives so many speeches in 2006, he averages one roughly every three days – they earn him 11 million dollars. And according to a 2007 article in the Washington Post, Giuliani Partners makes more than $100 million in the first five years of being in business. The money is flowing from all directions.
HOPE: There’s a campaign called Draft Rudy that forms to convince Giuliani to run. A committee registered with the Federal Election Commission raises more than $60 million from donors. Giuliani’s star is rising. Again. He’s newly married. He has the financial backing of his firms. And the biggest prize of all seems within reach: President of the United States.
DEEP: After teasing a presidential bid for months, Giuliani finally commits to the race in early 2007. He announces his bid in a nonchalant interview with Larry King.
Larry King Live Theme Music (archival, 14 February 2007)
LARRY KING: Are you running or not?
GIULIANI: Yeah, I’m running. Sure.
KING: So you’re running.
GIULIANI: Yeah, I’m running.
KING: What led to the decision?
GIULIANI: I think I can make a difference. The country needs leadership. We’re going through a war on terror, or at least, a terrorist war on us.
DEEP: For mayor, Giuliani’s pitch was that he took on the mob. Now to become president, he declares terrorism his new enemy. He is running on the strength of his image as America’s Mayor.
MUSIC IN
GIULIANI (archival): “I’ve been tested by having to provide leadership through crisis. Through difficult crises. Not just September 11th.”
GIULIANI (archival): We must remain, on offence, on the terrorist war, and on the United States.”
GIULIANI (archival): “I think Bush got the big question of his presidency right, the big decision he made on September 20th 2001, when he put us on offense against Islamic terrorism.”
HOPE: After a while, it became a gimmick. AND America started to take notice, including Democratic Presidential candidate Joe Biden.
JOE BIDEN (archival from Democratic Candidates Debate 2007): “Rudy Giuliani — there’s only three things he mentions in his sentence, a noun, a verb, & 9/11”
MUSIC OUT
HOPE: At the time, the country is beginning to turn against the War on Terror. U.S. troops fail to overcome insurgent groups in Iraq. But President George W. Bush doubles down, and sends more troops. Giuliani doubles down too — on his support for the war.
GIULIANI (archival): “The major issue today is the war on us. In fact, it’s the major issue for Republicans, Democrats, and Independents.”
HOPE: And his campaign starts to suffer by association.
DEEP: Still, this criticism isn’t going to stop Giuliani. In the summer of 2007, he’s out connecting with voters on the campaign trail.
WMUR-TV (archival): “The only Yankee fan who could draw a crowd in Red Sox nation this time of year. Rudy Giuliani signed copies of his book, Leadership, at the Red Arrow diner. … The latest poll shows Giuliani is the clear national front runner.
HOPE: Giuliani is a Republican who supports gay marriage and abortion. He jumps to an early lead, with the help of support from independents. But he also speaks to the conservative base.
GIULIANI (archival of speech at NRA Conference): “This is my wife calling, I think. Hello dear. I’m talking to the members of the NRA, would you like to say hello? I love you, and I’ll give you a call as soon as I’m finished, okay? Okay, have a safe trip, bye bye. Talk to you later dear, I love you.”
DEEP: Giuliani is charismatic. Voters know his name. It allows him to sail through much of the initial campaign season.
MUSIC IN
DEEP: But even with Giuliani’s popularity, cracks begin to emerge in his campaign strategy. Here’s Matt Mahoney again.
MAHONEY: Where it really started to go south was the team we had put in place in New Hampshire consisted of New Hampshire people and a couple of Rudy Old Guard folks who sounded the alarm every day. We need to be doing more, we need to be doing different things. We’re not getting the support that we need for the national campaign. And the national campaign guys saying we know Iowa’s going to be a bust, maybe New Hampshire is too. Maybe it’s time to rewrite this decade-old story.
HOPE: Why does any campaign care about Iowa and New Hampshire? Well, since the 1970s, these two states are the first to vote in the Republican primary calendar. They act as a litmus test for wanna-be presidents. They don’t always predict who will win the primaries, but they prove if the candidate has popular support. Maybe even enough support to win the whole race. To secure the Republican nomination, Giuliani needs to drum up support in those two states. But he doesn’t do that. Instead, his campaign sets its sights on…Florida.
MUSIC OUT
JUAN MANUEL BENÍTEZ: Rudy Giuliani’s campaign was a little strange. … Rudy Giuliani was counting on New Yorkers in Florida who had lived through his time as mayor, who had a good memory of his mayoralty. So he was banking on that.
DEEP: That’s Juan Manuel Benítez. He’s a New York City-based political reporter and a professor of local journalism at Columbia University. He covered Giuliani’s presidential campaign in 2008.
BENÍTEZ: Rudy Giuliani thought that his best bet was going to be Florida. He didn’t invest time or money on Iowa or New Hampshire and he waited and waited
ASSOCIATED PRESS (archival): “Rudy Giuliani has spent more time in Florida than any other candidate. But he says he still needs a little more time for his message to catch on. But, with the January 29th primary approaching, and new polls showing Giuliani’s support dwindling, time may be running out.”
MUSIC IN
HOPE: Giuliani’s bet doesn’t pay off.
BENÍTEZ: He was a distant third. He only got 15 percent of the vote, which every single one of those votes was a really expensive proposition after the huge investment he made.
HOPE: Instead, John McCain wins the Florida primary.
MAHONEY: Most people got drunk. Most of the staff got drunk. I mean in Florida that was the end. … it was, it’s depressing. We knew right then and there that Florida was the last state of our hope.
DEEP: After doing so poorly in Florida, Giuliani’s campaign had little hope for surviving. And so he drops out of the race.
GIULIANI (archival of speech dropping out and endorsing McCain): “I am very proud to endorse my friend and fellow Republican a hero John McCain of Arizona for president of the United States of America. God bless you John.”
HOPE: Rudy Giuliani had aimed for the highest office. And lost. And even though the campaign is over, it’s in debt. 2.4 million dollars. Giuliani works off that debt, while elections come and go. He rules out running to be the next governor of New York State, and two years later, he rules out running for the White House again in 2012.
DEEP: Years go by. Giuliani’s popularity fades. Google searches for his name plummet.
MUSIC IN
DEEP: Until 2015. President Barack Obama is now nearing the end of his second term. Giuliani is at a private fundraiser in New York City for Wisconsin Gov. Scott Walker, who is running in the 2016 presidential race. Politico reporter Darren Samuelsohn is covering the fundraiser. He breaks the news about something Giuliani says at the event. Something that puts him at the center of media attention for the first time since he dropped out some eight years ago.
JOHN KING ON CNN (archival): Rudy Giuliani says this: “I do not believe, and I know this is a horrible thing to say, but I do not believe that the president loves America. … He doesn’t love you, and he doesn’t love me. He wasn’t brought up the way you were brought up and I was brought up through love for this country.”
DEEP: The comment is immediately picked up by news anchors and debated by pundits.
NBC NIGHTLY NEWS: “Firestorm over what the former mayor of New York City said about President Obama.”
CNN (archival): “It’s like he says this stuff to get a reaction, it actually reflects more poorly on him than it does on the President. Shows how desperate he is … As a citizen, he can say whatever he wants, but as a leader, he was America’s Mayor after 9/11 and god bless him for what he did after 9/11. … I look at him differently as a citizen. He has the free right to say that. I look at him as much more desperate and deserving of less respect after saying something like that.”
MUSIC OUT
DAVIS: he’d been out of power a while and you start to suck it up, suck, suck up to power. Right? You drink the Kool-Aid. …
DEEP: That’s Tom Davis again, the retired congressman
DAVIS: The money runs out after a while. People you know, you’re not the new new thing in terms of attracting clients. The speeches decline. You’re looking for relevance. You see that opening.
DEEP: And that opening is about to get even bigger. Scott Walker does not win the Republican nomination that year. Donald Trump does. Giuliani throws his support behind him.
GIULIANI (archival from NBC 26): “Donald Trump’s not a perfect man thank God. I think there was only one perfect man. Some people think they’re perfect but they should see a psychiatrist, they need help. But he is a man who learns from his mistakes, grows from his mistakes and has been able to do things, and I’ve watched him do it, that nobody else can do.”
DAVIS: When he saw the magic that Trump brought on the campaign trail, that he wanted to be part of it while other people, they came out of more moderate swing constituencies who were running the other way. … he saw the value of first to himself and maybe to the country that maybe this guy is somebody worth working for.
DEEP: Giuliani and Trump go back more than 25 years, at least up to 1989 when Trump co-chaired a Giuliani campaign fundraiser. They’d attended each other’s third weddings. Trump had donated to Giuliani’s campaigns in the past. Now Giuliani was campaigning for Trump.
GIULIANI (archival from RNC in 2016): “It’s time to make America one again. One America! What happened to, there’s no Black America, there’s no white America, there’s just America. What happened to it?”
DEEP: And when Giuliani speaks at the Republican National Convention in 2016, he reminisces about his time as mayor.
GIULIANI (archival from RNC in 2016): I know we can change it because I did it by changing New York City from the crime capital of America to the safest large city in the United States. What I did for New York, Donald Trump will do for America.
HOPE: Giuliani backs the winning horse. Trump beats Hillary Clinton – in an upset. After the election, Giuliani is briefly considered for a Cabinet role as the Secretary of State. But within weeks, questions begin swirling about the integrity of the election.
ABC NEWS (archival): “Calls for an independent prosecutor to look into the ties between Russia and the President’s campaign growing louder tonight. … This comes amidst growing calls for an official investigation from both sides of the aisle. A prominent Republican calling for a special prosecutor. And that the Attorney-General should recuse himself.”
HOPE: In 2018, the Russia investigation is heating up. Trump is in need of a new lawyer. And he turns to someone who he knows from his New York days.
WOLF BLITZER ON CNN (Archival): “Pamela, you’re also learning that there may be a high-profile new member of the president’s legal team.” [PAMELA:] “That’s right. We’re learning that Rudy Giuliani, a former mayor of New York City, a longtime ally of President Trump will now be joining the legal team.”
DEEP: It may look like Giuliani is on his way up again. But it will be the beginning of a long downfall. At around the same time Giuliani joins the Trump team, Judith Nathan, his wife of 15 years, files for divorce.
DEEP: Less than a month into working for Trump, Giuliani gives an interview to Sean Hannity on Fox. Where he slips up some less-than-flattering information about his client. His client, who is denying making hush money payments to an adult film star during his 2016 campaign.
GIULIANI ON FOX (archival): “Having something to do with paying some Stormy Daniels woman 130,000, I mean, which is gonna turn out to be perfectly legal. That money was not campaign money. Sorry I’m giving you a fact now that you don’t know. It’s not campaign money, no campaign finance violation.” [HANNITY:] “So they funneled it through the law firm.” [GIULIANI:] “Funnelled it through the law firm and the president repaid it.”
HOPE: In that interview on national television, Giuliani admits that Trump did in fact pay the hush money to Stormy Daniels. An admission that would prove costly down the line. A New York jury would later find that Trump broke the law by hiding the hush money payments to Daniels. The case would turn him into the first president convicted of a felony.
HOPE: In another attempt to take the spotlight off Trump and Russia, Giuliani tries to bring into focus the Biden family’s dealings in Ukraine…
PBS NEWSHOUR (archival): “In this case, both The Washington Post and The New York Times say they followed Rudy Giuliani’s money to show that he was trying to really negotiate a lucrative consulting deal with the government of Ukraine while he was, at the same time, urging the top prosecutor there to look into Joe Biden and Hunter Biden.”
HOPE: The Ukraine saga would eventually result in Trump’s first impeachment in late 2019. But it’s not until 2020 that Giuliani displays his unwavering loyalty to Donald Trump.
HOPE: In 2020, Trump loses his second Presidential election to Joe Biden. But within hours of the polls closing, Trump declares himself the winner, and demands vote counts be stopped.
DONALD TRUMP (archival): “This is a fraud on the American public.This is an embarrassment to our country …we were getting ready to win this election, and in fact, we did win this election.”
DEEP: Through legal challenges, Trump launches a campaign to overturn the results of the election. Giuliani helps lead many of those challenges. As Republicans began contesting the outcome, Giuliani emerges as a central voice.
DEEP: He speaks at a press conference at the Four Seasons. No, not the fancy hotel chain. A parking lot. Of a landscaping company. In suburban Philadelphia.
GIULIANI (archival): “Thank you for coming…. I’m an attorney for the President…I’m here to describe to you the first part of a situation that is extremely troubling…This is outrageous, an enormously important contest with a very very suspect method of voting.”
HOPE: On January 6th, 2021, Giuliani takes the podium on the National Mall in Washington, D.C.
GIULIANI (archival): “I’m willing to stake my reputation, the President is willing to stake his reputation on the fact that we’re going to find criminality there…Let’s have trial by combat!”
HOPE: Later that morning, hundreds of Trump supporters breach the Capitol building, trying to disrupt the certification of Joe Biden’s victory.
DEEP: Still, Trump leaves office. And Joe Biden is sworn in. For Giuliani, there is a reckoning.
CNN (archival): “Accountability may be coming for some of the people who helped promote the big lie about the 2020 presidential election. Dominion voting systems is suing Donald Trump’s personal lawyer Rudy Giuliani for defamation and is asking for $1.3 billion in damages.”
MSNBC (archival): “Rudy Giuliani was disbarred temporarily, with permanent disbarment likely. …”
CNN (archival): “From America’s Mayor to disgraced attorney. A panel recommends that former Trump adviser and New York mayor be disbarred in Washington.”
HOPE: With all of this, Giuliani becomes a laughing stock.
NBC (archival): Sacha Baron Cohen is back with his significant style of political satire… The scene in question shows Rudy Giuliani after an interview in a hotel with an actress playing Borat’s teenage daughter…Giuliani appears to take off his microphone and then lays on the bed, and puts his hands in his pants for a few seconds. The whole thing recorded by what seemed to be hidden cameras.
INSIDE EDITION (archival): The President’s attorney held a press conference today continuing to stick to his unfounded claims that there was massive voter fraud in the election. … Rudy Giuliani getting hot under the collar today. “I don’t know what you need to wake you up!” He was sweating so much that his hair dye was running down his face.
HOPE: As we’ve retraced his life, we kept hearing the same thing: Giuliani is not the person he used to be.
PAUSE
HOPE: Once a man so determined by right and wrong, so deeply religious that he nearly became a priest, and so interested in moral codes that he became a lawyer…
PAUSE
HOPE: This is the man who participated in a lie. A lie so significant, it led to an insurrection and shook the foundations of American democracy.
PAUSE
HOPE: Today, Rudy Giuliani hosts his own podcast.
Archival, Giuliani Podcast: Good Evening! This is Rudy Giuliani, and this is America’s Mayor, Live!
HOPE: After years of defending the big lie, Giuliani continues to face legal action. In 2023, Giuliani lost a 148 million dollar defamation lawsuit against two election workers in Georgia. It forced him to file for bankruptcy.
DEEP: He’s even facing felony charges under the RICO Act, which you heard about in the third episode. The very act that he used to put mobsters away in the 1980s. He has been forced to sell off his classic Mercedes, his luxury watches, and his favourite sports memorabilia: rings commemorating the Yankees winning the World Series.
GIULIANI (archival from Reuters): “The reality is…I have no cash, it’s all tied up…so right now, if I wanted to call a taxi cab, I can’t do it. I don’t have a credit card, I don’t have a checking account. I have no place I can take cash out, except the little bit that I saved, and it’s almost down to nothing.”
PAUSE
CREDITS
HOPE: This episode was reported and produced by me Hope Talbot
DEEP: and me Deep Vakil.
Joanne Faryon is our executive producer and professor. Peter Leonard and Rachel Quester are our co-professors. Additional editing help from Asthaa Chaturvedi.
Shoe Leather’s theme music – ‘Squeegees’ – is by Ben Lewis, Doron Zounes (zoo nez) and Camille Miller, remixed by Peter Leonard. Other Music by Blue Dot Sessions.
HOPE: Our Season Six graphic was created by Emily Sawaked (suh-wah-kid).
One of the sources in this episode is Giuliani: The Rise and Tragic Fall of America’s Mayor, by Andrew Kirtzman.
Special thanks to Andrew Kirtzman, Stuart Karle, Dale Maharidge, and Sydney Mimeles.