SPEAKER_1: It's November 1997, election night.
SPEAKER_1: In Meadton, Manhattan, at the Hilton's Grand Ballroom, the crowd applauds Rudy Giuliani.
SPEAKER_1: He has won his second term.
SPEAKER_2: It was kind of clear he was going to win.
SPEAKER_2: 93 was a nail-biter.
SPEAKER_2: 97 was not a nail-biter.
SPEAKER_2: He was going to win the election.
SPEAKER_1: That's JD Dapper.
SPEAKER_1: He's a reporter who covered Rudy Giuliani extensively at the time.
SPEAKER_1: He remembers Giuliani's victory speech.
SPEAKER_2: It was very much not a hard-core speech that would nowadays be considered kind of a speech to the base.
SPEAKER_2: It was a speech to everybody.
SPEAKER_2: Big, tense speech.
SPEAKER_1: Adam Goodman was there too.
SPEAKER_1: He was Giuliani's media advisor, hired to support Giuliani with his campaign for re-election.
SPEAKER_3: And so in that ballroom that night, it was pure elation by all of us, not just because the campaign was very successful for re-election, but because we knew we were all a part, in some fashion, of a transformative moment in the most incredible, maybe one would argue, most important city in the world.
SPEAKER_2: And at that time, I think it's fair to say that a lot of people in New York, a lot of political scientists in New York, a lot of politicians in New York, thought, this guy's got a future.
SPEAKER_4: Politicians, union leaders, advisors, they all joined Giuliani to celebrate his re-election.
SPEAKER_4: But one person is missing from the party.
SPEAKER_4: His wife, Donna Hanover.
SPEAKER_4: What Giuliani didn't know was that his second term was about to become more turbulent than he might have expected.
SPEAKER_4: Both in his personal life and his leadership of the city.
SPEAKER_2: Things are going in the right direction.
SPEAKER_2: But then what happened over the course of that second term is these abuses happened.
SPEAKER_2: These horrible incidents happened.
SPEAKER_2: You can put a force out in the streets to stop crime, but you also have to have management of that force, or else it's going to become a wrecking ball.
SPEAKER_2: And I think that's kind of what happened.
SPEAKER_1: But in this moment, everything is still possible for Rudy Giuliani.
SPEAKER_4: Election day is not yet over when the New York Times dubs Giuliani King Rudolph.
SPEAKER_1: And he was, until he wasn't.
SPEAKER_4: Giuliani's celebratory moment at his 1997 victory party could have been lifted from the disaster romance Titanic.
SPEAKER_4: About halfway through the film, Leonardo DiCaprio's character Jack leans out over the stern of the ocean liner and shouts the phrase.
SPEAKER_1: Halfway through his mayorship, Rudy Giuliani seems to be just as confident.
SPEAKER_1: But just like in Titanic, treacherous waters lie ahead.
SPEAKER_4: And it's the people closest to him.
SPEAKER_5: I had hoped to keep this marriage together.
SPEAKER_1: And his fellow New Yorkers.
SPEAKER_1: Who would bear the consequences?
SPEAKER_1: I'm Alice Finno.
SPEAKER_4: And I'm Peter Shea.
SPEAKER_1: 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.
SPEAKER_4: 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.
SPEAKER_4: Before he went to work for Donald Trump, before he was disbarred and bankrupt, before all the trouble, Giuliani rose to prominence as a prosecutor and a politician.
SPEAKER_1: In this episode, we look at Giuliani's second term as mayor.
SPEAKER_4: This is Shoe Leather, season 6, Giuliani, The Unraveling.
SPEAKER_1: You're listening to episode 5, King Rudolph.
SPEAKER_1: To understand what went wrong in Giuliani's second term as mayor, you have to understand what went right the first time he was elected.
SPEAKER_1: So let's back up, to the end of Giuliani's first term.
SPEAKER_1: His success in making the city safer resonates with New Yorkers.
SPEAKER_1: So the mayor decides to run again, building his campaign for reelection on his tough on crime policies.
SPEAKER_7: Crime down more than 50 percent.
SPEAKER_7: Murder down an amazing 65 percent.
SPEAKER_7: New York became a model for police in this country and around the world.
SPEAKER_6: You have to deal with murder.
SPEAKER_6: You have to deal with rape.
SPEAKER_6: You have to put more resources into that than you do dealing with street-level drug dealing or street-level prostitution.
SPEAKER_6: But you can't ignore that either because then you create a lawless environment.
SPEAKER_1: In the 1997 mayoral race, Ruth Messinger is Giuliani's main opponent.
SPEAKER_8: Tonight New Yorkers will get their first look at Rudy Giuliani and me side by side.
SPEAKER_8: It is seriously a contest between two candidates with different styles and different priorities.
SPEAKER_1: Messinger was Borough President of Manhattan when she became the first woman to receive the Democratic nomination for mayor.
SPEAKER_1: I reached out to her to ask what she remembered about the race.
SPEAKER_9: I wouldn't say I was this pleased with what Giuliani was doing.
SPEAKER_9: I was this pleased with all the things he wasn't doing.
SPEAKER_9: So I decided it was worth challenging him, but I didn't get much coverage.
SPEAKER_9: I got some supporters, but I didn't get much media coverage.
SPEAKER_4: Messenger's campaign brings attention to schools and education.
SPEAKER_4: It is a weak spot for Giuliani, who has cut the school budget significantly in the previous years.
SPEAKER_4: At the time, there are issues of overcrowding in schools and reports that some students were forced to have classes in bathrooms due to a lack of space.
SPEAKER_9: Whatever he did to overhaul the police department, doesn't seem to be bringing that interest or that energy to any other city agency.
SPEAKER_4: But Giuliani himself was confident about his track record.
SPEAKER_4: He portrayed Messenger as too liberal for the city and reminded people of the decrease in crime every time he had a chance.
SPEAKER_3: What he was actually doing was helping to unify the city, unify them around common ground, the common ground about quality of life, about being safe when you walk down the street.
SPEAKER_1: That's Adam Goodman again, Giuliani's media advisor.
SPEAKER_3: To some extent, Hispanics and Asian Americans and African Americans, they came to understand that.
SPEAKER_1: In 1997, Giuliani receives more votes from black and Hispanic people than he did in 1993.
SPEAKER_1: He ends up winning with a 16-point margin over Messenger.
SPEAKER_10: I would like to now introduce the mayor of the city of New York, the Honorable Rudolph W.
SPEAKER_10: Giuliani.
SPEAKER_6: Thank you very much to all of the people of the city of New York for giving me four more years as your mayor, the greatest job in the world and the greatest city in the world.
SPEAKER_6: I want to first thank my family for their love, for their kindness, for their support, for their help.
SPEAKER_1: On the Ivovis inauguration, Giuliani hires 1,600 new police officers, bringing the size of the police department to over 40,000.
SPEAKER_6: Now is the time to make our efforts redouble, stronger, to fight harder, and to see if we can make these reductions in crime permanent and make them happen even more.
SPEAKER_1: Giuliani was doubling down on the very thing that got him elected, fighting crime.
SPEAKER_1: It's an effective strategy.
SPEAKER_1: 76% of New Yorkers approve of his handling of crime.
SPEAKER_1: But Giuliani's growing political ambition will not stop in New York.
SPEAKER_1: The mayor seems increasingly drawn to the national spotlight.
SPEAKER_1: In the first months of 1998, Giuliani positions his second term on issues that might seem inconsequential compared to his first term.
SPEAKER_1: He pushes welfare reform, revitalizes the Times Square theater district, and endorses financial incentives to benefit the owners of the New York Yankees.
SPEAKER_1: Giuliani spars with the Daily News and other New York media outlets.
SPEAKER_1: In 1999, he bars press conferences from the steps of City Hall, only for a judge to later receive the rule.
SPEAKER_1: And this also got his future to think about.
SPEAKER_1: Because of New York City's major term limits, he has to think about what's next for his political career.
SPEAKER_4: In November 1998, Democratic Senator Daniel Patrick Moynihan announces that he will not seek another term.
SPEAKER_4: If his name sounds familiar, that's because Moynihan was the man who told a much younger Giuliani he had to wait his turn before becoming a federal judge.
SPEAKER_4: That was back in Episode 2.
SPEAKER_4: Moynihan has represented New York and the US Senate for 21 years, and he wields a lot of power.
SPEAKER_1: Giuliani is immediately expected to be a candidate.
SPEAKER_4: The camera-ready Rudy expands beyond local television and starts showing up on national television shows, including appearances on Late Night with Conan O'Brien, Ladies and gentlemen, Mayor extraordinaire, his honor, Rudy Giuliani.
SPEAKER_4: Saturday Night Live.
SPEAKER_6: Hello, everyone.
SPEAKER_6: It's great to be here hosting Saturday Night Live.
SPEAKER_4: And maybe most appropriately, Law and Order.
SPEAKER_11: Good morning, Mayor Giuliani.
SPEAKER_9: Good morning, Mr.
SPEAKER_9: Mayor.
SPEAKER_6: Nora and I worked together on many organized crime cases.
SPEAKER_6: She was always nervous, but always brilliant.
SPEAKER_1: Well, it is a little daunting coming in behind Adam Schiff.
SPEAKER_1: But then, a new candidate with even more star power enters the race.
SPEAKER_1: On July 7, 1999, on his farm in upstate New York, Senator Moynihan walks out for a press conference.
SPEAKER_1: With him is Hillary Clinton, the wife of then President of the United States Bill Clinton.
SPEAKER_12: Yesterday, Hillary Clinton established an exploratory committee as regards candidacy for the Senate, United States Senate from New York, a seat in which I will vacate in a year and a half.
SPEAKER_12: I think she's going to win.
SPEAKER_12: I think it's going to be wonderful for New York.
SPEAKER_13: Well, I want to thank Senator Moynihan and my friend Liz Moynihan.
SPEAKER_4: Moynihan stands next to Clinton, dressed in linen pants and a frumpled button-up.
SPEAKER_4: Clinton is immaculately tailored in a pressed blue pantsuit.
SPEAKER_4: Moynihan looks like an old boxer, escorting a new young fighter into the ring.
SPEAKER_4: Giuliani just got a new opponent in his battle for the Senate, and this one is a heavyweight.
SPEAKER_1: Clinton has never won elected office.
SPEAKER_1: She has risen in politics alongside her husband.
SPEAKER_1: In Bill Clinton's second term, his presidency and his marriage were nearly sunk by the scandal of his affair with White House intern Monica Lewinsky.
SPEAKER_7: Indeed, I did have a relationship with Ms.
SPEAKER_7: Lewinsky that was not appropriate.
SPEAKER_7: In fact, it was wrong.
SPEAKER_1: Hillary Clinton's public approval numbers have risen during the Lewinsky scandal.
SPEAKER_1: She has become a prominent figure in democratic politics.
SPEAKER_1: Republican Rudy Giuliani and Democrat Hillary Clinton are positioned for a brutal battle to win the open New York Senate seat.
SPEAKER_14: For months, the stage for the most celebrated Senate race in the country appeared set.
SPEAKER_14: The city's mayor versus the nation's first lady.
SPEAKER_15: Oh, they're beautiful.
SPEAKER_4: Are you getting all well?
SPEAKER_4: Giuliani campaigns hard on his record as prosecutor and two-term mayor.
SPEAKER_4: He tries to draw a distinction between his record and Clinton's lack of leadership experience.
SPEAKER_4: He also tells the press that Hillary ought to go back to Arkansas, the state where her husband used to be governor.
SPEAKER_4: Clinton is a fast learner and quickly shows her adeptness at campaigning.
SPEAKER_13: But then let's also get rid of the obstacles of high taxes, high utility costs, poor transportation, and let's take advantage of training people so they can get the jobs of the new global economy and move forward.
SPEAKER_4: By February 2000, six months before the election, Clinton and Giuliani are in a dead heat, with the mayor leading by just one percentage point over Clinton in a statewide poll.
SPEAKER_1: Giuliani is in a fight.
SPEAKER_1: Through his campaign for Senate, Rudy sees a path for life after the mayorship.
SPEAKER_4: But then, something happens that would fundamentally change the way New Yorkers see Giuliani and his leadership.
SPEAKER_1: Patrick Dorismond has just finished his shift as a security guard.
SPEAKER_1: He heads to a bar with a friend for a few drinks.
SPEAKER_1: It's March 16th, 2000.
SPEAKER_1: It's after midnight when Dorismond decides to go home.
SPEAKER_1: He's Asian-American, and he lives in an apartment in Flatbush with his girlfriend and his one-year-old child.
SPEAKER_1: Dorismond is standing outside the Wacamba cocktail lounge in middle Manhattan.
SPEAKER_1: He's waiting for a taxi with his friend when an undercover narcotics officer approaches him and asks for drugs.
SPEAKER_1: The encounter escalates quickly into a confrontation.
SPEAKER_1: There are conflicting reports of the events from that moment.
SPEAKER_1: What we know is that in a matter of minutes, Dorismond is shot and killed.
SPEAKER_1: He was 26 years old.
SPEAKER_1: He would have turned 27 the following day, St.
SPEAKER_1: Patrick's Day.
SPEAKER_4: That morning, Giuliani holds a press conference.
SPEAKER_4: According to a New York Times article from the time, he says, quote, I would urge everyone not to jump to conclusions and to allow the facts to be analyzed and investigated without people trying to let their biases, their prejudices, their emotions, their stereotypes dictate the results, unquote.
SPEAKER_4: Tensions between the black community in the city and the police department are already high.
SPEAKER_4: This is the third time a black unknown man has been killed by the NYPD in the past 13 months.
SPEAKER_15: The young African immigrant died when four plainclothes cops shot him 19 times, firing 41 bullets, then staking the wallet in his hand for a gun.
SPEAKER_4: The killing of Amadou Diallo is still vivid in people's minds.
SPEAKER_4: Only three weeks have passed since the officers who shot Diallo 41 times were acquitted.
SPEAKER_4: During the Giuliani administration, the tactic of stop and frisk was widely used by the NYPD.
SPEAKER_4: Based on this policy, police officers could stop anyone they found suspicious and search them.
SPEAKER_4: This led to the disproportionate targeting of black people.
SPEAKER_4: In April 1999, stop and frisk reports from the street crime unit of the NYPD show that about 64% of the people stopped were black, 20% Hispanic and 6% white.
SPEAKER_1: As I was looking into the case, I submitted a public records request to the NYPD to get the police incident report and other documents that could tell me more about the shooting.
SPEAKER_1: After a few weeks, I received two short documents.
SPEAKER_1: Most of the information was redacted, but I saw that the Dorismont shooting was not classified as a stop and frisk incident.
SPEAKER_1: In this case, the officers had approached Dorismont as part of an undercover operation.
SPEAKER_1: Within 24 hours of the shooting, Giuliani does something unexpected, something that will attract heavy criticism.
SPEAKER_1: He releases Dorismont's sealed criminal record.
SPEAKER_6: Well, the reality is, what those records demonstrate is a propensity to violence.
SPEAKER_6: That is important for people to know in judging whether the police officers were telling the truth that he began the violence and caused his own death, or the witness who says that the police officers struck him first, but his record was relevant to his propensity for violence.
SPEAKER_4: But Dorismont has never been convicted of a crime.
SPEAKER_4: He was accused of robbery and assault, but the charges were either dropped or reduced to disorderly conduct.
SPEAKER_4: One of them was sealed because he was 13 when the incident happened.
SPEAKER_1: A few days later, Giuliani speaks about the case on Fox News Sunday.
SPEAKER_1: He says Dorismont was no altar boy.
SPEAKER_1: He's being metaphorical, but in fact, Dorismont was an altar boy.
SPEAKER_1: He went to school at Bishop Laughlin.
SPEAKER_1: If the name sounds familiar to you, it's because it's the same Catholic school that Giuliani attended.
SPEAKER_16: I remember the mom in her broken English going, Mr.
SPEAKER_16: Giuliani, my son goes same school as you.
SPEAKER_16: My son no criminal.
SPEAKER_1: That's Yolette Williams, the head of the Haitian American Association of New York.
SPEAKER_1: She helped the family organize Dorismont's funeral.
SPEAKER_16: He was killed, not only it was a senseless killing, but to make him pass as a criminal was really upsetting.
SPEAKER_16: It was as upsetting as the killing.
SPEAKER_1: Williams remembers the protest that broke out the day of Dorismont's funeral.
SPEAKER_16: The funeral procession turned out to be like a march.
SPEAKER_16: And for the funeral service, the priests really had to control even the media.
SPEAKER_16: The priests did not allow everyone to come in.
SPEAKER_16: A lot of elected officials were there, many community leaders, and so, and family and friends.
SPEAKER_16: So that's why there was so many people outside, and people were barricaded.
SPEAKER_16: But a lot of people from the community, the Haitian community came, and people were very upset by this.
SPEAKER_4: That day, about 5,000 people joined the procession to escort Doorsman's body to the church.
SPEAKER_4: Protesters chant and hold signs calling for Giuliani's resignation.
SPEAKER_4: Then, clashes with the police erupt.
SPEAKER_4: 27 people are arrested, and 23 officers are injured.
SPEAKER_4: Giuliani must go on!
SPEAKER_6: Giuliani has to step down!
SPEAKER_16: Enough is enough!
SPEAKER_17: Giuliani, you don't have no heart!
SPEAKER_4: Giuliani defends what he did.
SPEAKER_6: I laid out the facts that were being ignored by the press so that they could do basically what they're doing now, which is create a vacuum, seal the public off from certain facts, and blame it completely and clearly on the police officers.
SPEAKER_6: I haven't reached a judgment.
SPEAKER_6: And actually, I have no right to reach a judgment.
SPEAKER_6: A grand jury and a jury reaches a judgment.
SPEAKER_1: A grand jury ultimately decides not to file criminal charges against the officers.
SPEAKER_1: The Dorismont family sues the city for wrongful death and settles.
SPEAKER_1: A poll conducted days after the shooting shows the mayor has the lowest job approval ratings of his seven years in office.
SPEAKER_1: Giuliani has also lost points in the Senate race against Clinton.
SPEAKER_1: At the beginning of April, the First Lady has a 49 to 41 percent lead over Giuliani.
SPEAKER_1: For the first time, Clinton is leading the race.
SPEAKER_4: A few weeks later, Giuliani holds a press conference.
SPEAKER_4: He has a major announcement.
SPEAKER_6: Good morning.
SPEAKER_6: I was diagnosed yesterday with prostate cancer.
SPEAKER_6: My father had prostate cancer, which is the reason why I went and got tested for it.
SPEAKER_6: It brings up very painful memories.
SPEAKER_6: And I miss my father every day of my life.
SPEAKER_6: And he's a very, very important reason for why I'm standing here, as the mayor of New York City.
SPEAKER_1: The 55-year-old mayor of the largest city in the nation is suddenly vulnerable.
SPEAKER_1: One of the reporters asks him a question.
SPEAKER_18: Has this made you think about the values in life and what's important?
SPEAKER_6: Absolutely, sure, yeah.
SPEAKER_6: I don't mean between yesterday and today.
SPEAKER_6: Just the contemplation of it for the last two weeks makes you think about what's important in life and what are the most important things.
SPEAKER_6: But you should be thinking about that anyway.
SPEAKER_6: It just reminds you to think about what you should be thinking about.
SPEAKER_1: Reporters want to know how the diagnosis will impact his political career.
SPEAKER_19: Could you at least tell us what you think or how, if at all, this affects the Senate race?
SPEAKER_6: I have no idea.
SPEAKER_6: I think in fairness to me, to the Senate race, to the Republican Party, all the parties and everybody else, you need some time to think about it.
SPEAKER_6: And I really need to know what the course of treatment is going to be.
SPEAKER_4: In the weeks after the public admission, City Hall receives hundreds of emails and letters of support from around the country.
SPEAKER_4: Polls also say that New Yorkers believe Giuliani is still a strong candidate to take on Clinton.
SPEAKER_4: But the cancer diagnosis complicates the already tight race for Senate.
SPEAKER_4: Members of his inner circle, like Adam Goodman, are unsure if their boss will even continue with the campaign.
SPEAKER_3: We were writing against Hillary Clinton.
SPEAKER_3: We were thinking, oh my god, this is going to be the biggest campaign of the year in America.
SPEAKER_3: I got a call one day.
SPEAKER_3: And they said, you know, Rudy just came back from the doctor and it's not good.
SPEAKER_3: He's got prostate cancer and he's going to decide, yet to decide, what to do.
SPEAKER_11: He had a very contentious relationship with the media.
SPEAKER_4: Alice Hennigan was a reporter and columnist for Newsday in the 1990s.
SPEAKER_11: He treated us like shit and we gave him quite a bit back, I would say.
SPEAKER_11: I don't think he was personally popular.
SPEAKER_11: I mean, the reporters didn't like him, didn't particularly identify with him.
SPEAKER_11: Although I think anybody that covered him in those years had to recognize that he had skills.
SPEAKER_11: He aimed recklessly too high politically by deciding to launch a campaign for Senate.
SPEAKER_11: All of this stuff coming at it essentially the same time.
SPEAKER_11: And in the middle of it, getting a prostate cancer diagnosis.
SPEAKER_11: So you've got all that stuff coming on top of each other.
SPEAKER_11: Looking back, it's hard to remember exactly the order they all came in, but they all they all crashed down on his head at once.
SPEAKER_1: Just one week after Giuliani announces he has cancer, the New York Post snaps a photo of Giuliani dining with a quote, a mystery woman.
SPEAKER_1: The paper identifies her to be Judith Nathan, a pharmaceutical sales representative and former nurse.
SPEAKER_1: The article insinuates that Nathan and Giuliani had dined together before, even quoting the restaurant manager as calling the mayor one of our favorite customers.
SPEAKER_1: At the time, Giuliani is still married to the journalist Donna Hanover.
SPEAKER_1: The Post article says that Hanover declined to comment.
SPEAKER_1: The next day, when asked about his relationship with that mystery woman at a press conference, Giuliani says, She's a good friend, a very good friend.
SPEAKER_6: And beyond that, you can ask me questions and that's exactly what I'm going to say.
SPEAKER_1: Back at the Gracie Mansion, Giuliani's private life is about to be made very public.
SPEAKER_4: When the New York Post publicizes Giuliani's relationship with Judith Nathan, the focus of the New York media turns to the mayor and his wife, Donna Hanover.
SPEAKER_4: Within a week, the story is picked up by the Village Voice, Newsday, the Daily News, even the New York Times.
SPEAKER_1: Throughout her husband's mayorship, Donna Hanover seldom talks to the tabloid media, but her job as an anchor for New York One News means that she can't avoid the press forever.
SPEAKER_1: Here's Seneca again.
SPEAKER_11: She was not easily accessible to us as a reporter.
SPEAKER_11: She wasn't hanging out with reporters when Rudy was in Gracie Mansion.
SPEAKER_1: And here's Charlie Perkins, one of Giuliani's advisors.
SPEAKER_20: They had, from my eyes, a wonderful, loving relationship.
SPEAKER_20: Donna was a journalist.
SPEAKER_20: She'd gone to Columbia Journalism School.
SPEAKER_20: She understood New York City politics.
SPEAKER_20: She was a calm, moderate person.
SPEAKER_20: And I think she had a huge impact.
SPEAKER_1: But the press attention and Judith Nathan herself will not go away.
SPEAKER_1: It's May 10th, 2000.
SPEAKER_1: One week after Giuliani's relationship with Judith Nathan becomes public, and two weeks since he's diagnosed with cancer.
SPEAKER_1: Giuliani holds yet another press conference, this time in Bryant Park.
SPEAKER_1: Reporters ask him about the state of his marriage.
SPEAKER_6: It's very, very painful.
SPEAKER_6: For quite some time, it's probably been apparent that Donna and I lead in many ways independent and separate lives.
SPEAKER_6: But I don't think I'm saying anything that you haven't all written, that over the course of some period of time, in many ways, we've grown to live independent and separate lives, and we should probably strive toward formalizing that.
SPEAKER_4: It's a moment that comes as a surprise to his wife.
SPEAKER_4: She, like the rest of the world, learns of her husband's decision to end their marriage from this press conference.
SPEAKER_4: Three hours later, in the afternoon of that same day, Hanover reads a brief statement to a collection of New York media outside the gates of Gracie Mansion, the home she has shared with Rudy and their children since her husband was sworn in as mayor six and a half years earlier.
SPEAKER_5: Today's turn of events brings me great sadness.
SPEAKER_5: I had hoped to keep this marriage together.
SPEAKER_5: For several years, it was difficult to participate in Rudy's public life because of his relationship with one staff member.
SPEAKER_5: Beginning last May, I made a major effort to bring us back together and Rudy and I reestablished some of our personal intimacy through the fall.
SPEAKER_5: At that point, he chose another path.
SPEAKER_5: Rudy and I will now go forward to discuss the possibility of a legal separation.
SPEAKER_4: Donna Hanover speaks for less than one minute and takes no questions.
SPEAKER_4: Jade Adapter is reporting for New York television station WABC 7, the day of the news conference.
SPEAKER_2: I've never been at a news conference where every reporter looked at each other and went, what the fuck?
SPEAKER_2: Excuse my language, but this was unprecedented.
SPEAKER_2: He basically says he's having an affair and he's getting a divorce from his wife.
SPEAKER_2: I mean, it was all in a news conference that wasn't even called for that.
SPEAKER_4: Those close to Giuliani are shocked too, like Charlie Perkins.
SPEAKER_20: I thought his behavior then was atrocious, and I like Donna very much.
SPEAKER_20: And his announcing in a press conference that he was divorcing his wife was beyond the pale.
SPEAKER_20: That may be an example of how I think he kind of lost his way in the second term.
SPEAKER_1: The news spreads across the country.
SPEAKER_1: The marriage of Rudy Giuliani and Donna Hanover is over, and in a spectacular way.
SPEAKER_12: Rudy Giuliani's candidacy is toast, it's history.
SPEAKER_21: I think it's so hard at the human level to see how Rudy Giuliani can endure this.
SPEAKER_21: But man, he's got a marriage to put together, he's got a wife who's angry, he's got a new girlfriend he cares a lot about, and he was very human in expressing that.
SPEAKER_21: He's got children to reassure, and he's got a Senate race that the whole world is going to be looking at to focus on.
SPEAKER_1: Giuliani's admission of the affair and the public insult of separating from his wife during a press conference for many New Yorkers is unforgivable.
SPEAKER_1: Giuliani and Danover had been married for 17 years.
SPEAKER_1: Danover stays in Gracie Mansion with their two children, Andrew and Caroline, until the end of the mayor's term.
SPEAKER_4: After the separation, Rudy Giuliani moves to a guest room at Gracie Mansion, and eventually, he'll pack up and leave the house entirely.
SPEAKER_4: Now, he still has two other fights on his hands, his battle against prostate cancer and his campaign for the Senate against Hillary Clinton.
SPEAKER_1: Giuliani has been the subject of one controversy after another, but the race is still on.
SPEAKER_1: About a week after he announces the separation from his wife, a Quinnipiac College poll shows that Clinton is leading 44% to Giuliani's 43%.
SPEAKER_22: That was an extremely, potentially competitive race.
SPEAKER_22: Both candidates had high negatives.
SPEAKER_1: That's Lee Miringoff, the Director of the Marist Institute for Public Opinion.
SPEAKER_1: He conducted polls during the race.
SPEAKER_22: I don't remember a time when the political atmosphere of New York was any more intense than it was then.
SPEAKER_22: I mean, these were two heavyweights going toe to toe, and I remember we were polling regularly on that race.
SPEAKER_4: The two candidates faced different struggles, as the media intensely covers the tumultuous events of Giuliani's life, Clinton is overshadowed.
SPEAKER_4: On his end, Giuliani doesn't seem very interested in winning the race.
SPEAKER_4: While Clinton visits all 62 New York counties, Giuliani barely travels outside of New York City.
SPEAKER_4: When an upstate fundraising event conflicts with the opening day at Yankee Stadium, Giuliani cancels the fundraiser, saying, Long before I was a politician, I was a Yankee fan.
SPEAKER_1: Adam Goodman, who worked on Giuliani's campaign for mayor, is now working on his Senate run.
SPEAKER_3: I never saw Rudy necessarily being entirely happy as one of 100 voices in the United States Senate.
SPEAKER_3: Remember, he was an executive.
SPEAKER_3: I mean, as the mayor, you're an executive.
SPEAKER_3: As a senator, you're a legislator, and you're just one of many votes.
SPEAKER_3: And so I think to exchange that kind of job, where it's Rudy, Rudy, Rudy all over the streets of the five boroughs, to, oh, hi, Senator.
SPEAKER_3: I think that wasn't necessarily the most compelling life change he was looking forward to.
SPEAKER_3: I think intellectually, he willed himself to do it.
SPEAKER_3: It wasn't the same Rudy that I worked with back in the 90s.
SPEAKER_3: It was just a different Rudy.
SPEAKER_3: I can tell you in his heart of hearts, there was not a better act, second act, after being mayor for two terms for Rudy.
SPEAKER_1: On May 19th, 2000, three weeks after his cancer diagnosis, Giuliani calls a press conference.
SPEAKER_6: I guess because I've been in public life so long, in politics, I used to think the core of me was in politics, probably.
SPEAKER_6: It isn't.
SPEAKER_6: When you feel your mortality and your humanity, you realize that the core of you is, first of all, being able to take care of your health and make sure that you're in good health, and to deal with a disease like cancer in the most effective way possible, so you can be useful to the people that you really care about and really care about you.
SPEAKER_6: I've decided that what I should do is to put my health first.
SPEAKER_6: This is not the right time for me to run for office.
SPEAKER_1: And with that, Giuliani leaves the Senate race.
SPEAKER_1: His redoubled efforts to fight criminality in the city backfired after the Doorsman shooting.
SPEAKER_1: His public announcement about ending his marriage further damaged his reputation.
SPEAKER_1: And all of that, together with his prostate cancer diagnosis, cost him the Senate seat.
SPEAKER_1: With 18 months left to his term, Giuliani commits to devote the remainder of his time as mayor to New Yorkers.
SPEAKER_1: What he didn't know was that New York and the United States were about to change forever.
SPEAKER_17: It's 852 here in New York, I'm Bryant Gumbel.
SPEAKER_17: We understand that there has been a plane crash on the southern tip of Manhattan.
SPEAKER_17: You're looking at the World Trade Center.
SPEAKER_17: We understand that a plane has crashed into the World Trade Center.
SPEAKER_17: We don't know anything more than that.
SPEAKER_17: So you have no idea right now?
SPEAKER_23: Oh, there's another one.
SPEAKER_23: Another plane just hit.
SPEAKER_15: Oh, my God.
SPEAKER_23: Another plane has just hit another building.
SPEAKER_5: It flew right into the middle of it.
SPEAKER_23: Explosion.
SPEAKER_15: My God.
SPEAKER_23: It's right in the middle of the building.
SPEAKER_23: That, yes, that was definitely looked like it was on purpose.
SPEAKER_4: On the morning of Tuesday, September 11, 2001, Rudy Giuliani is having breakfast at the Peninsula Hotel in Midtown Manhattan.
SPEAKER_4: He's told that a plane has struck one of the World Trade Center towers.
SPEAKER_4: He and his staff head to the scene.
SPEAKER_4: They see medical staff and stretchers lined up in front of St.
SPEAKER_4: Vincent's Hospital.
SPEAKER_4: Giuliani knows that the situation is serious.
SPEAKER_4: But the reality is worse than he fears.
SPEAKER_4: Both towers collapse later that morning.
SPEAKER_4: The attacks on the World Trade Center kill more than 2,600 people and shock the world.
SPEAKER_1: In one of the darkest moments in American history, Giuliani shines.
SPEAKER_1: The mayor races to the World Trade Center site to direct the city's response to the attacks.
SPEAKER_1: As the south tower falls, the mayor and a handful of staff leave town, literally running for their lives.
SPEAKER_1: But Giuliani regroups and takes whatever control he can of the city in a morning full of confusion and horror.
SPEAKER_4: Throughout his second term, Giuliani struggles through mistakes both personal and political.
SPEAKER_4: He can't seem to get out of his own way.
SPEAKER_4: But on the morning of September 11th, 2001, less than four months before leaving office, he projects calm and control.
SPEAKER_3: Suddenly, Rudy Giuliani is at the center of the universe, trying to hold this country together.
SPEAKER_3: Well, before George Bush, the president, could kind of parachute in and do his piece.
SPEAKER_3: He was there, and boy was he trained for the moment.
SPEAKER_3: I mean, when Rudy, when that, when the planes hit, he wasn't looking around to his team saying, what do we need to do?
SPEAKER_3: He knew what to do.
SPEAKER_6: I feel terrible for the people that we lost, some of whom I talked to just 15 minutes before we lost them.
SPEAKER_6: And the city is going to survive.
SPEAKER_6: We're going to get through it.
SPEAKER_6: It's going to be a very, very difficult time.
SPEAKER_6: I don't think we yet know the pain that we're going to feel when we find out who we lost.
SPEAKER_6: But the thing we have to focus on now is getting the city through this and surviving and being stronger for it.
SPEAKER_3: And more than that, because of the prostate cancer, he had something he didn't have in the early years, at least not publicly.
SPEAKER_3: He had empathy.
SPEAKER_3: He had heart.
SPEAKER_3: I think his mortality gave him that.
SPEAKER_3: And that quality, more than anything else, I think he did in those days after the planes hit the World Trade Center.
SPEAKER_3: That is what people will remember the most.
SPEAKER_3: He was real.
SPEAKER_1: Maybe this is what fate had in store for Giuliani all along.
SPEAKER_1: This episode was reported, written and produced by me, Alice Finno.
SPEAKER_4: And me, Peter Shea.
SPEAKER_1: Joanne Farion is our executive producer and professor.
SPEAKER_1: Peter Leonard and Rachel Quester are our co-professors.
SPEAKER_1: Additional editing help from Vanessa Grigoriadis.
SPEAKER_4: Shoe Leather's theme music, Squeegees, is by Ben Lewis, Doran Zunes and Camille Miller, remixed by Peter Leonard.
SPEAKER_4: Other music by Blue Dot Sessions.
SPEAKER_4: Our Season 6 graphic was created by Emily Sawackett.
SPEAKER_1: Some of the sources in this episode include Andrew Kirschman's books, Rudy Giuliani, Emperor of the City, and Giuliani, The Rise and Tragic Fall of America's Mayor.
SPEAKER_1: And documents provided by the New York City Municipal Archives.
SPEAKER_4: Special thanks to WNYC New York Public Radio for Archival Tape, Andrew Kirschman, Stuart Karl, Dale Maharage, Sydney Mimiles, and Sarah Janerum.