By Eleanor Hildebrandt and Emily Sawaked
COLD OPEN
Archive – Air traffic control: We have a problem here, we have a hijacked aircraft headed towards New York … No, this is not an exercise, not a test.
ELEANOR: On one of the most harrowing days in New York City history, one man stood above everyone else.
Archive: Mayor, what’s the situation right now? The situation is that two airplanes have attacked, apparently.
ELEANOR: Rudy Giuliani is blocks away when two airplanes fly into the Twin Towers. The mayor knows he has to take charge to help New Yorkers in the city’s darkest moment.
Archive – GIULIANI: Come with us. Come with. Well let’s talk a little later, okay?
EMILY: Giuliani is level-headed, focused on bringing the city together. He addresses the nation.
Archive – GIULIANI: And I want the people of New York to be an example to the rest of the country and the rest of the world that terrorism can’t stop us. American democracy is much stronger than vicious cowardly terrorists and we’re going to overcome this.
ELEANOR: Giuliani is such a calming force and strong leader that he’s named Time Magazine’s Person of the Year. He becomes America’s mayor. And is even talked about as a possible presidential candidate.
And then, nearly two decades later, he’s once again in the middle of another crisis. Another threat to democracy.
EMILY: But this time, Giuliani is leading the charge. Donald Trump loses the 2020 presidential election, but claims it was stolen from him. And Rudy Giuliani becomes his lead lawyer, bringing lawsuits claiming voter fraud. He’s all over the press, swearing that Trump won.
POLITICO – GIULIANI We get to see the machines that are crooked, the ballots that are fraudulent, and if we’re wrong, we will be made fools of.
EMILY: That moment would lead to Giuliani’s downfall.
NEWS TAPE : Also tonight, Rudy Giuliani just took another blow in his home state of New York. The former Trump attorney and New York City mayor, now stripped of his law license over efforts to overturn the 2020 presidential election. (0:00- 0:12)
CNN WOLF BLITZER: A federal judge has just ordered former Trump attorney and New York Mayor Rudy Giuliani to hand over some of his most valuable possessions, including his Manhattan penthouse apartment, to the two Georgia election workers he defamed. (0:00- 0:16)
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ELEANOR: America’s Mayor was suddenly a laughing stock.
The Daily Show Trevor Noah: Rudy Giuliani. Former aide to Donald Trump and lawyer who makes all his clients look innocent in comparison. Since his role in the attempt to overthrow the 2020 election, Giuliani has largely disappeared from public view. Like a snail retreating into its shell, but way more disgusting.
ELEANOR: To people who knew Giuliani for years before working for President Trump, he’d become unrecognizable.
Ed McDonald: Yeah, I think he’s changed. I think, when he lost power, he and his, he got old. He was desperate to stay relevant.
Charlie Perkins: I can’t believe he’s so cynical that he’s been doing what he’s been doing and destroying his life and career and reputation and legacy for something he doesn’t, at the end of the day, believe in.
It’s hard for me to understand how a former prosecutor who’s as smart as he is could believe in something that is so patently false.
ELEANOR: Rudy Giuliani was a rising star in New York City for the majority of his life. He had one of the highest approval ratings of all time among New Yorkers. He was even knighted by the Queen of England. So, how does that person end up bankrupt and ridiculed? How did America’s Mayor end up betraying the very values he built his career on?
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EMILY: And one more thing – We reached out to Rudy Giuliani several times over many weeks to ask him to participate in this podcast. We sent registered letters to his home in Manhattan and in Florida. We left messages on his social media accounts, and we asked some of his long-time friends to reach out to him on our behalf. In the end, we never did hear back from Giuliani.
ELEANOR: Over the next six episodes, we did our best to include his voice in the telling of this story, using archives that go back all the way to the 1980s.
SHOE LEATHER THEME
ELEANOR: I’m Eleanor Hildebrandt.
EMILY: And I’m Emily Sawaked.
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.
ELEANOR: This is season 6, Giuliani: The Unraveling. You’re listening to episode one, The Fight.
Scene 1:
ELEANOR: May 28th, 1944. A Sunday in New York City. By midday, it was 84 degrees. Franklin Delano Roosevelt was in his fourth term. Bing Crosby was breaking records, his famous song “I Love You” was on jukeboxes everywhere.
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And Rudolph William Louis Giuliani was born to Helen and Harold Giuliani in East Flatbush, Brooklyn. Their only child.
EMILY: Helen and Harold Giulani were born and raised in New York City. The Giulianis were the children of Italian immigrants. Helen was one of seven. Three of her brothers were police officers, a fourth was in the fire department. A fifth, Leo, was involved with the mob. He was a bookkeeper and a loan shark.
ELEANOR: Helen dreamed of being a teacher. Harold wanted to be a boxer, skills he would later teach his son. When he was 26 years old, Harold spent a year and a half in Sing Sing, a New York prison. A journalist named Wayne Barrett dug up Harold’s criminal past. He found old court and police records. Harold had robbed a milkman at gunpoint in 1934.
EMILY: When Harold got out of prison, he married Helen. He worked as a plumber and a barkeep. According to the same journalist, Wayne Barrett, Harold also spent time doing grunt work for the mob. He wrote about it in a book back in 2000 that Giuliani’s father, quote:
“broke legs, smashed kneecaps, crunched noses.”
EMILY: It’s unclear whether Giuliani knew the extent of his father’s work with organized crime. Harold eventually left the mob, and became a plumber.
ELEANOR: Harold was also a baseball fan. When the Giulianis lived in Brooklyn, the Dodgers were the borough’s team.
Archive – 1952 WORLD SERIES: Baseball is all in Brooklyn today. It’s October 1 in Evansfield. And the frenzy is caused by the dramatic Dodgers and their participation in the World Series of 1952.
EMILY: But Harold was a Yankees fan. And he wanted his son Rudy to be one too.
BOB RAVALLO: Not only did he grow up in Brooklyn as a Yankee fan. His father, now I don’t know how often, but his father would have him wear a Yankee uniform, which probably other kids took exception to that.
ELEANOR: That’s Bob Ravallo. He met Rudy Giuliani in college.
RAVALLO: So, I guess that was beginning, the beginning of him becoming toughened up.
EMILY: When Giuliani was 7, his parents moved the family from Brooklyn to a house in Long Island.
ELEANOR: It was a big move for the family. His parents bought a newly built house in Long Island. The neighborhood is quiet in North Bellmore.
ELEANOR: So we’re in Long Island, and these are, this is a substantial amount of space. This also very much gives me vibes of like suburban communities.
EMILY: I mean, they’ve got front yards and backyards. There’s like every single, it looks like every single house here has cars. We are right in front of Giuliani’s house.
MATTHEW TREIBER: Just a split level, three bedrooms, two-and-a-half baths.
ELEANOR: That’s Matthew Treiber. He owns the house now. We knocked on his door this past March.
TREIBER: They’re plain and ordinary, built in the fifties.
EMILY: Giuliani got his first job delivering newspapers in the neighborhood. He took the money from his paper route, and walked into a record store one day. He bought two records: George Frideric Handel’s opera Julius Caesar and Peter Ilyich Tchaikovsky’s The 1812 Overture. He had no idea what they would sound like. But he went home and dropped the needle.
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ELEANOR: He fell in love with opera. He would sit in his room and listen alone. He loved the right and wrong of it all — the good versus evil — that morality played itself out in the music.
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Scene 2:
EMILY: Giuliani went to Bishop Loughlin Memorial High school. It was an all boys Catholic school in Brooklyn. He commuted more than three hours by public transportation to the school. Every day. Each way.
ELEANOR: He played baseball and he founded his school’s opera society. He also tried his hand at politics for the first time. He ran the campaign for a fellow classmate for senior class president. But, they lost. It was Giuliani’s first time losing an election.
EMILY: John Maceli went to the same Catholic high school. Maceli didn’t really notice Giuliani until his senior year, when they shared a homeroom for the first time. According to Maceli, Bishop Loughlin was a tough school to get into. So, the boys worked hard to stay there.
Maceli: You know, you could cut up in class, but people were not. They never sort of got out of control.
ELEANOR: Maceli and Giuliani had never hung out together, except for one Wednesday.
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It was October 19, 1960. John F. Kennedy was scheduled to parade down Broadway Avenue in his motorcade. He was campaigning for president.
Archive – CAMPAIGN TAPE: Kennedy, Kennedy, Kennedy, Kennedy… Do you want a man for president who sees it through and through?
EMILY: JFK was set to become the first Catholic president, and according to the Bishop Loughlin yearbook, a young Giuliani wouldn’t stop talking about it. It says that he was famous for, quote, “telling everyone how wonderful JFK is.”
ELEANOR: Giuliani wanted to meet his hero. So, he went around the school asking his classmates to skip with him. To go to the parade.
Maceli: I wouldn’t say I was apolitical, but I wasn’t certainly as political as a lot of people were. And, I don’t know, I just probably wanted to be out of school.
EMILY: So, Maceli agreed to go with Giuliani. They took the train to Manhattan. The parade down Broadway took off just after noon.
Archive – news tape: A wild affair. With mounted policemen trying to control a crowd that was estimated at several hundred thousand. Almost as soon as the motorcade started up lower Broadway people began crashing through the sidewalk barriers.
ELEANOR: Soon, the perimeter of the avenue began to fill up with a crowd of people. Everyone was excited to see Kennedy and his wife, Jackie Kennedy. There were barriers along the streets to separate the crowd from the couple.
Maceli: I’m sure there were a lot of police, but you didn’t really see a lot of them.
EMILY: And then Giuliani made a bold move. He jumped the barriers and ran toward Kennedy.
Maceli: And I mean, I don’t you know, nowadays nobody would have been able to run out into the street and shake his hand, you know.
EMILY: He was ecstatic.
Maceli: And then he came back. And, you know, he was a big smile on his face.
EMILY: The saying “you never wash that hand again” seems juvenile, but it’s fitting. Giuliani had just met one of his heroes. His parents were Democrats. He was a Democrat. So, that handshake was monumental for young Giuliani.
ELEANOR: It was his first brush with a U.S. president. But it certainly would not be his last.
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Scene 3:
ELEANOR: Giuliani graduated high school in 1961. He enrolled in Manhattan College in the Bronx. Another all-boys, Catholic school. He was a political science major. Giuliani lived at home with his parents when he was in college. Most students did back then.
EMILY: Giuliani was interested in becoming a lawyer, or a priest. Both appealed to his moral code – the idea that in both cases there was a rule book for right and wrong. He pledged the Phi Rho Pi fraternity. One thing we heard consistently – Giuliani liked to be involved. Sometimes, he was intense. But he always made an effort to be active in his community.
ELEANOR: Bob Ravallo was one of Giuliani’s fraternity brothers.
Ravallo: We had lunch together every day. We would have, once a, once a week official meetings.
EMILY: Giuliani and Ravallo took three classes together: calculus, religion, and a comparative government class. Ravallo says Giuliani was a much better student in the government class than he was.
Ravallo: For him, it was a natural. Rudy was, he was an interesting guy. He, I mean, much more than the rest of the fraternity brothers, he he had a sense for politics. He was at that time, he was much more into it than I was.
ELEANOR: Ravallo and Giuliani went to the fraternity’s dances together. They double dated. And Giuliani became close with every member of the Ravallo family. At one point, Giuliani even helped Ravallo pick out a puppy for his sister’s birthday.
Ravallo: I remember my father telling the two of us how, how proud he was of us. So, that, that was a big deal. You know, for me, and I’m sure it made him feel good too. Rudy, beneath his tough exterior, he, he was a bit of a sentimental guy.
ELEANOR: Ravallo often had dinner at Giuliani’s house. He remembers Helen Giuliani, Rudy’s mom. She would cook Italian for the boys’ visits. Ravallo says she was opinionated.
Ravallo: I don’t. I don’t know how far her formal education was, but it sticks, it sticks in my mind that she was very bright. And she was, she was what I would describe as a good Italian mom. Rudy respected her tremendously.
EMILY: He also met Giuliani’s dad. At this point, around 1963, Harold had inherited his brother-in-law’s bar.
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Ravallo: I remember with Rudy, we visited his father in the, in the bar. And I remember his father giving us a warning to behave ourselves. I mean, the the bar was all filled with what you would call Merchant marine sailors, and they were really a tough lot. I mean, Rudy was a tough guy, but we would not want to tangle with those guys. They looked mean.
ELEANOR: Ravallo and Giuliani were good friends. He says Giuliani was someone you could trust whenever and wherever.
Ravallo: If you were in a tough position. How could I say it? If I had to be in a foxhole, I would like Rudy beside me.
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Scene 4:
ELEANOR: In Giuliani’s second year of college, he was elected class president. He ran for reelection in his junior year. And lost. That’s the year he became pledge master in his fraternity. He was in charge of the new class. Sal Scarpato was one of those eight pledges.
Sal Scarpato: But he would withhold love, okay, or respect if he didn’t like what you were doing. Very effective, okay? … Rudy would make you feel bad if you did something that was against what he wanted you to do as a pledge.
EMILY: Scarpato got into the fraternity. And he decided to run against Giuliani for fraternity president. Giuliani won easily. Scarpato finds it funny now.
Scarpato: I don’t think I got two votes.
EMILY: But he did become the fraternity’s vice president. Second in command to Giuliani.
ELEANOR: And according to Scarpato, there were two kinds of people in the fraternity.
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Sal: The tigers and the pussies.
Eleanor: So who was on, who do you remember being on which side?
Scarpato: That’s character assassination. I won’t comment on it.
Eleanor: Do you remember what side you were on?
Scarpato: I would consider myself one of the tigers, yes.
Eleanor: And what did that mean back then?
Scarpato: I think he used the right word, okay? The tigers were more rowdy.
Scarpato: Definitely put Rudy on the other side.
EMILY: At that time, Giuliani was considered to be a goody-two shoes. The tigers were trouble makers. They would attend parties, drink, and cause mischief. The other group of boys – the pussies – were far more dedicated to their education.
Scarpato: He tended to be always worried about the future, not careless in what we did.
Scarpato: His whole life he was much more conservative, much more. conscious of life, every action has consequences.
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ELEANOR: What Scarpato and the other fraternity brothers remember most about Giuliani is his intelligence. His rigor. Giuliani’s moral code made him a rule follower. He wasn’t a big partier. He got his work done. There was nothing unruly about Rudy Giuliani. But he did have a temper.
EMILY: Scarpato and a few other fraternity brothers spoke to the New York Daily News about it in 1997. Another frat brother said Scarpato and Giuliani were quote, “two hotheaded Italians, constantly challenging each other.” He called Scarpato the most vocal “tiger” in the fraternity.
EMILY: Outside of the fraternity, Giuliani was also a columnist for the school’s newspaper. It was called the Quadrangle.
ELEANOR: He wrote a column during his senior year. It was titled “Ars Politica” which is Latin for the Art or Skill of Politics.
EMILY: Giuliani was engaged. He was focused. Giuliani had a hand in everything he could get a grasp on. And when he latched onto something, he held on. Tight.
Scene 5:
ELEANOR: Under Giuliani’s leadership, things in the fraternity were changing. He rebranded Phi Rho Pi. It wasn’t just about parties or pranks anymore. It was clear to the brothers that Giuliani was a natural born leader.
EMILY: But he didn’t always want to listen to the brothers. Bob Ravallo remembers one meeting. Giuliani was in the front. Leading the charge. Ravallo was sitting in front of Sal Scarpato.
Ravallo: I guess Sal raised his hand, probably a lot … He was making noise to be recognized. He picked up a bottle. I think it was a bottle of 7Up. It could have been a bottle of Sprite, okay, both green.
ELEANOR: Ravallo remembers the plastic bottle sailing over his head. Scarpato had thrown it at Giuliani.
Ravallo: I believe he deliberately aimed to miss, okay, because he couldn’t be that bad of an aim. It missed by quite a bit. And yeah, he caught Rudy’s attention.
EMILY: After that, Giuliani disciplined the fraternity. He brought structure to the group. The fraternity changed its rules.
Ravallo: Well right after that, the next meeting. We passed a rule that from now on, all meetings have to follow Robert’s rules of order.
ELEANOR: The book was written by a U.S. Army officer. I know it well, I was given a copy when I joined the high school debate team. It’s a guide on how to run a meeting. It’s very generic, some would even say boring. Everyone gets to speak, but it has to be on the agenda. It’s about efficiency. Here’s Bob Ravallo again:
Ravallo: All of us and I, I still have two copies of it today, including my original copy of. We bought copies of Robert’s Rules of Order. That made a difference in running the meeting. Everybody got a chance to talk by themselves without being interrupted, so we really ran a good meeting.
EMILY: He knew how to rein in a crowd, even if he did not always get his way. Here’s Jerry McCarthy, the secretary of the fraternity:
McCarthy: Well, I’m sure the fraternity did pretty much what he wanted us to do or what he was interested in.
ELEANOR: Giuliani even tried to push his fraternity brothers into Opera.
McCarthy: and he used to keep telling us that we’ve never heard real music, as beautiful as that, which has been written by Verdi or Puccini or a couple of the others.
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And I, most of us had no idea what he was talking about.
ELEANOR: Sal Scarpato remembers this one time. They were in a meeting. Sal wanted to talk about a party.
Scarpato: I think it was a particular group of girls where I wanted to suggest we have a get-together, a party. wasn’t my job to select sororities.
ELEANOR: He wanted to talk about what sorority girls to invite. But Giuliani wouldn’t hear it. It wasn’t on the agenda.
Scarpato: and according to him and his interpretation of Robert’s rules of order, I didn’t even get a chance to bring it up as new business. So after a couple of go-arounds and not getting my point across, I provoked him and he said, we can’t settle it here.
EMILY: So, the brothers left the meeting room. They ventured out into the Bronx to take care of business.
Scarpato: Let’s go down to the football field, which is a couple of blocks away from where we’re meeting. And we went down and beat each other up for a while.
ELEANOR: Scarpato and Giuliani traded blows and then, all returned to normal. Like nothing had ever happened.
Scarpato: We came back, we started the meeting, and I didn’t get to bring my point up.
Scarpato: I think his father was a boxer at one time. And that’s where Rudy learned his pugilistic skills that he used very effectively.
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EMILY: At this point, his father Harold had run into some trouble after taking over the bar. Previously, he was the one who did the grunt work for the mob. Now, the tables had been turned on him..
Scarpato: He owned a bar at the time.
Scarpato: He often talked about the problems that his father had with the um, for better term, the mob in New York, giving him, interfering in his business … and Rudy was always talking about he wanted to become an attorney and then a district attorney and go after the mob. So he kind of was on a mission.
ELEANOR: And that mission would begin in 1965. At New York University’s Law School. It was the first time Giuliani would go to school with women. The first time without Catholic prayer in every classroom.
Scene 6:
EMILY: NYU Law was home to students from around the country. It was a mostly white school. Students were required to wear business suits to every class. The school was also divided between students who were active in the Civil Rights and anti-Vietnam War movements and those who weren’t.
ELEANOR: Rudy was against the war, but he did not protest it. He didn’t want to get arrested. In his first year at NYU, he was the guy who sat in the front row of class. George Wendell (when-dul) went to law school with Giuliani.
George Wendell: He was always one of these people who seemed to express himself and wanted to make himself known.
EMILY: Giuliani was on the law review, too. It’s a scholarly journal focused on legal issues. Many universities have more than one.
ELEANOR: While Giuliani was in law school, he started pursuing a woman named Regina Peruggi.
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He’d known her since he was a kid. They were second cousins, They’d spent summers together growing up. At first, Giuliani suggested that Bob Ravallo, his fraternity brother, date Regina. But that didn’t go anywhere. Ravallo remembers double dating with Giuliani and Regina.
Ravallo: She was a sweet girl. She was sort of the, the love of his life and I never heard him express so much affection for anyone as he did for his wife.
EMILY: Giuliani’s mother didn’t approve of the relationship, according to Wayne Barrett’s book. She thought they weren’t compatible.
ELEANOR: Regina was a soft spoken and introverted girl. Giuliani was larger than life. Charismatic. But Ravallo was right. He was smitten with her.
EMILY: After graduation, Giuliani proposed to Regina. That was late May. That same year, Regina and Giuliani were married. On October 26, 1968. In a Catholic ceremony. Ravallo was an usher in the wedding party. At a church in the Bronx.
Ravallo: The biggest thing I remember about the way they looked up, it was, it was a very attractive, traditional wedding. And the reception I would describe as, you know, traditional.
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ELEANOR: It is legal in the state of New York to marry your second cousin. Even the Catholic church says it’s okay. But with one caveat. You have to tell the church that you’re cousins.
EMILY: And that’s something Giuliani and Regina never did. They didn’t tell the priest. One rule Giuliani didn’t follow. At least not according to our reporting. It’s a small detail. But one that will matter later in Giuliani’s life.
ELEANOR: But for now, Giulani turns all his focus to one thing: becoming a prosecutor. Enforcing the law. Helping decide what is right. And what is wrong.
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ELEANOR: Shoe Leather is a production of the Columbia Graduate School of Journalism.
This episode was reported, written, and produced by me, Eleanor Hildebrandt.
EMILY: And me, Emily Sawaked.
ELEANOR: Joanne Faryon is our executive producer and professor. Peter Leonard and Rachel Quester are our co-professors. Special thanks to Columbia Digital Libraries. Additional editing help from Bryant Urstadt.
EMILY: 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. Our Season six graphic was created by me, Emily Sawaked.
Some of the source material in this episode include Andrew Kirtzman’s book “Giuliani: The rise and tragic fall of America’s mayor” and Wayne Barrett’s book “Rudy!: An investigative biography of Rudolph Giuliani.”
ELEANOR: Special thanks to Andrew Kirtzman, Stuart Karle, Dale Maharidge and Sydney Mimeles. We’d also like to thank Director of the Archives and Special Collections at Manhattan University Amy Surak for her assistance with accessing Giuliani’s college documents. Thank you for listening.