Mayor of New York City is famously a dead-end job. The last New York mayor to win higher office was John T. Hoffman, and that was in 1868. He became governor. Every mayor since then has found the way up barred. And, for some, the way up turned into the way down.
The mayors are often a little surprised by this reversal of fortune. The assumption seems to be: If I can govern there, I can govern anywhere. This may or may not be true. What is true is that New York City’s mayors have had a hard time getting non-New Yorkers to vote for them. After all, you’re not likely to be elected President of the United States by promising to make the country more like New York. You basically have to run against your own home town.
When John V. Lindsay, who was elected mayor in 1965 and became one of the country’s highest-profile politicians, ran for President, in 1972, he was forced to drop out after finishing fifth in the Florida primary, where he had counted on getting the votes of retired New Yorkers. He quit politics after a 1980 New York Senate bid, joined two law firms, and made regular appearances on “Good Morning America,” but health problems and the collapse of both firms nearly wiped him out. In 1996, an ally on the City Council arranged for this once charismatic and commanding figure to be given two essentially ceremonial appointments in city government just so he could have health insurance.
Ed Koch (1978-89) ran for governor in 1982 and lost to Mario Cuomo in the Democratic primary after making disparaging remarks about life upstate. It’s a pretty basic rule in New York politics that you don’t do that if you want to be governor. After Koch left City Hall, his activities included movie reviewing, serving as a replacement for Judge Wapner on “The People’s Court,” and keeping alive his reputation as a great tummler.
Michael Bloomberg (2002-13), like Koch a three-term mayor, spent a billion dollars of his own money, a record, in the 2020 Presidential primaries and won a grand total of fifty-nine delegates before dropping out. He did carry American Samoa on Super Tuesday. He is now eighty years old and unlikely to run for anything in the future.
Bill de Blasio (2014-21) entered those Presidential primaries in 2019, while he was still mayor. His poll numbers hovered between one per cent and zero. This May, he announced that he was running for Congress in the 10th Congressional District, which includes western Brooklyn, where he lives. In July, after polls showed him running seventh, he dropped out. He says that he is leaving electoral politics.
Then there is Rudy Giuliani. Let’s pass over the dripping hair dye; the Pennsylvania parking-lot “election fraud” press conference, where a witness turned out to be a convicted sex offender; the on-air screaming matches with Piers Morgan, Chris Cuomo, and others; the embarrassing punking at the hands of Sacha Baron Cohen; his hosting a Russian disinformation agent on his podcast. At the end of the day, Rudy Giuliani is a lawyer whose counsel led to his client’s being impeached twice.
Since the 2020 election, Giuliani has had his law license suspended in New York and Washington, D.C. (Less consequentially, perhaps, Syracuse University is considering revoking his honorary degree.) Two of his former associates, Lev Parnas and Igor Fruman, have been convicted of federal crimes and sentenced to prison. Giuliani himself is a target in the inquiry into efforts to interfere in the results of the 2020 Presidential election in Georgia, and some observers, including Ken Frydman, a former press secretary from his 1993 mayoral campaign, think he will be indicted.
And he is being sued for defamation by Dominion Voting Systems for spreading falsehoods about its voting machines. He maintained, among other untrue things, that Dominion’s software had been invented in Venezuela for Hugo Chávez to steal elections.
During his last year as mayor, Giuliani claimed (amid divorce proceedings, so a grain of salt is necessary) that he was worth seven thousand dollars. But he got rich virtually overnight through a management-and-security consulting firm, Giuliani Partners, that he founded shortly after leaving City Hall—and shortly after September 11th had made him an international celebrity.
Giuliani Partners started out as a pure buck-raking operation. The Mayor and his partners had little if any experience in management consulting. And it would be a stretch to say that they had any experience in security, apart from having lived through the greatest security failure in American history. Many were cronies of the Mayor’s from city government.
As Andrew Kirtzman puts it in his lively new biography, “Giuliani: The Rise and Tragic Fall of America’s Mayor” (Simon & Schuster), they evidently calculated that “Giuliani’s fame and reputation for integrity could be squeezed like a washcloth for all types of moneymaking ventures.” They calculated correctly. In 2002 alone, Giuliani took in an estimated eight million dollars in speaking fees. A spinoff outfit, Giuliani Capital Advisors, made $84.7 million in 2004. By 2007, Giuliani’s worth was estimated to be thirty million dollars. At one point, he owned six homes, including a nine-room co-op on the Upper East Side and a house in the Hamptons, and had eleven country-club memberships.
But his work for Donald Trump has reportedly brought him to the brink of bankruptcy. When he tried to get paid for his services, Trump stiffed him. (Giuliani apparently failed to notice the one-way sign on the Trump loyalty street.) He now hawks collectible coins, health products, and cigars on his podcast, “Rudy Giuliani’s Common Sense,” and sells video messages on Cameo for four hundred dollars apiece. In April, he appeared on “The Masked Singer,” where he offered his rendition of “Bad to the Bone” in a rooster costume. This is someone whom Oprah Winfrey called “America’s mayor,” who was named “Person of the Year” by Time, who had an honorary knighthood bestowed on him by the Queen of England. What happened?
The rough answer suggested in Kirtzman’s book is that a posture of moral rectitude, instilled in Giuliani by his Catholic education and made into a powerful political weapon by a personality that, as a friend said, lacks the fear gene, succumbed to Mammon. Righteousness, as it often does, morphed into self-righteousness. After launching his career as a federal prosecutor and winning convictions of Wall Street inside traders like Ivan Boesky, Giuliani seems to have decided that riches were his due. Back in private practice, he began taking on all sorts of sketchy clients, from Purdue Pharma to the Mujahideen-e-Khalq, an exiled Iranian militia group that, in collaboration with Saddam Hussein, had slaughtered Kurds.
Of course, bad guys need lawyers, too. The trouble was that Giuliani was cashing in on a reputation for honesty and probity with unseemly avidity. He evidently didn’t care about how it looked. “His descent was the result of a series of moral compromises made over the years as the temptations of power and money grew,” Kirtzman writes. “By the time he reached an advanced age all those compromises left him an empty vessel, filled with a desire for power and little more. Alcohol, and a toxic marriage, were exacerbating factors, though not the cause.”
The “toxic marriage” was to Judith Nathan, a sales manager at Bristol Myers Squibb, whom he met in a cigar lounge on the Upper East Side in 1999 and who became his third wife. Kirtzman says that she was loathed by everyone in Giuliani’s circle, regarded as “deeply manipulative and obsessed with status and money.” As Giuliani’s former chief of staff Tony Carbonetti explained the matter to Kirtzman, “She’s a horrible human being.”
In Kirtzman’s account, Judith was demanding, questioned everyone’s loyalty, and seems to have had a death grip on her man, who was terrified of her displeasure. Giuliani’s children, Caroline and Andrew, stopped speaking to him for years. (Andrew later became a golfing buddy of Trump’s, worked in the Trump White House, and, this year, ran for the Republican nomination for governor of New York, with his father’s support. Despite the name recognition, he lost by twenty points.) The couple’s divorce, in 2019, was bitterly contested.
And alcohol does seem to be part of the story. Giuliani was always a red-meat, Scotch-and-cigars kind of person, but the drinking appears to have become serious after the debacle of his Presidential run, in 2008. That campaign was right out of the “New York mayor bombs on the big stage” playbook. In November, 2006, Giuliani was ranked the most popular politician in the country, and he went into the Republican primaries as the clear front-runner. In July, 2007, he was eighteen points ahead in the polls.
Then the New York curse kicked in. In November, Giuliani’s pal and business partner Bernard Kerik, whom he had named police commissioner (despite the fact that Kerik had never finished high school), was indicted on sixteen counts of corruption. (Kerik later pleaded guilty to some of the charges and served three years in prison. In 2020, he was pardoned by President Trump. In the Trump gift shop, pardons are cheap.)
There was also a brief to-do about the fact that Giuliani Partners had worked for the government of Qatar, a nation that had given haven to Khalid Sheikh Mohammed, who was named the principal architect of the September 11th attacks. And it came out that, while Giuliani was mayor, he had used the budgets of obscure city agencies like the Office for People with Disabilities to cover travel expenses, which some people connected to secret trysts he was having in the Hamptons.
Giuliani’s affair with Judith, while he was still married to his second wife, Donna Hanover, did not sit well with social conservatives in the Party’s base. (Giuliani had had his first marriage, to Regina Peruggi, annulled on the ground that they were second cousins. He did not inform her that he was doing this.) Nor were conservatives happy with his relatively liberal—that is, New Yorker—views on issues like gun control and abortion. A man who prospered through bluntness, he struggled to spin his positions rightward. In January, he finished sixth in the Iowa caucuses and fourth in the New Hampshire primary. He got two per cent of the vote in South Carolina.
Florida, as it had for John Lindsay, dealt the fatal blow. The campaign had doubled down in the state (those New York retirees!), but Giuliani took only fifteen per cent of the vote, good for third place. He dropped out of the race, his campaign having burned through sixty million dollars and ended up four million in debt. He had one delegate. Giuliani’s career in national politics was over before it had properly begun. He and Judith were taken in by an old friend, who let them stay at his estate, Mar-a-Lago. No one else would have them.
In the years that followed, Giuliani drank heavily. “He was always falling shitfaced somewhere,” Judith Giuliani told Kirtzman. (She denies saying it.) On Election Day, 2020, Giuliani—oddly, but presumably he was being compensated—did a thirty-minute show for RT, a Russian state television network, where he told his listeners that Hunter Biden served as Joe Biden’s bagman, collecting bribes for him. That evening, Giuliani showed up at the White House.
He was “definitely intoxicated,” Jason Miller, a Trump adviser, told the House January 6th Committee, when he insisted on seeing the President. And that, apparently, was when he advised Trump to announce that he was not conceding, because the election had been stolen—the first step on the road to January 6th and a second impeachment. Kirtzman says that we can be thankful for one thing Giuliani did in Trump’s post-election madhouse, which was to oppose the recommendation to call in the military and confiscate voting machines.
It’s natural when trying to understand a crash-and-burn peripeteia as spectacular as Giuliani’s to wonder whether he was all that great to begin with. How far did he really fall? Kirtzman, who covered Giuliani’s mayoralty as a reporter and as a host of “Inside City Hall,” on the news channel NY1, and who was with him on September 11th—this is actually his second Giuliani biography—reviews the entire career in this revisionist spirit. There’s new reporting and interviews; still, much of the critique covers familiar ground. The lapses and excesses had always been there to see.
Because he governed the city during a period of recovery, and because his comportment on September 11th was exemplary, Giuliani came to be regarded as a paragon of leadership. This was not unjust. A lot of political success is timing and luck. If the city’s economy or crime rate had gone south owing to circumstances beyond his control, he would have had to take the blame.
In a way, the most significant thing Giuliani did for New York City was to get elected. He ran against the Great Society liberalism that had dominated city politics since the Lindsay administration and that had developed a kind of institutional sclerosis, with the competing demands of various interest groups making governance almost impossible. When Giuliani came to office, more than a million people—a third of the workforce—held publicly funded government, health, and human-services jobs. Most of those people were unionized, and the bureaucracy was essentially feudal.
There was little transparency. Just by giving the impression of clear leadership, Giuliani changed the political culture of the city—something that became vividly apparent when he left office and was replaced not (as many expected) by Mark Green, the city’s public advocate, who was taken, fairly or not, as the representative of the old liberal order, but by a businessman, Mike Bloomberg.
The standard story of Giuliani’s mayoral career credits him with reducing crime and restoring fiscal sanity to city government. And the city did change dramatically on his watch. When he first ran for mayor, in 1989, nearly every municipal office in the city was held by a Democrat, and Democrats had a five-to-one advantage over Republicans in voter registration. But for the middle class the quality of life was deteriorating. The city was still struggling to balance the budget after its near-bankruptcy in 1975; there were almost two thousand murders a year; public spaces were occupied by drug dealers and homeless people. Times Square was a den of iniquity; you could not go into Bryant Park. The night air was filled with the sound of car alarms. People taped signs to the windows of their cars: “No Radio.”
In 1990, Time ran a cover story headlined “The Rotting of The Big Apple.” Eight hundred thousand people had moved out of the city in the nineteen-seventies, and in a poll conducted in 1991 sixty per cent of New Yorkers said they wanted to leave the city, and fifty-one per cent said they were planning to leave.
In the 1989 race, Giuliani lost to David Dinkins, who became the city’s first Black mayor, by only fifty thousand votes out of the 1.8 million cast. Four years later, he defeated Dinkins by just forty-seven thousand votes, helped by a strong turnout in Staten Island, the city’s whitest and most conservative borough. He became the first mayor in the twentieth century to be elected despite losing Manhattan. His crossover voters became known as Rudycrats. Under his administration, the quality of life improved enormously, and in 1997 he easily won a second term in a low-turnout election.
As Fred Siegel puts it in “The Prince of the City” (2005), a biased but insightful history of Giuliani’s political career (Siegel served as a senior adviser and speechwriter for him), Giuliani ran as “a Republican playing a Democrat playing a Republican.” In other words, he presented himself as a Republican Bill Clinton. Like Clinton, who declared that “the era of big government is over,” Giuliani was a “reinventing government” policy wonk. Like Clinton, he made a big deal of being tough on crime, calling for more police and more jail cells. He supported the Clinton crime bill, which is now regarded as having worsened the era of mass incarceration. (That act came back to haunt the Presidential candidacies of both Hillary Clinton and Joe Biden.) Like Clinton, Giuliani rejected the liberal belief that the way to fight crime is to improve social services. And, like Clinton, he turned welfare into workfare.
In New York, Giuliani implemented a “broken windows” policing policy, cracking down on minor crimes like subway-fare beating (not a small problem: a hundred and fifty-five thousand people were jumping the turnstiles every day), and car-window squeegeeing (a small problem: there were probably no more than a few dozen “squeegee men”). The crime rate dropped. Public spaces began getting cleaned up.
But what was happening in New York City was part of a national trend. Giuliani had strong tailwinds that would have sped the progress of any administration, and he may not have been as innovative as he was given credit for being. Quality-of-life policing had been introduced in New York by Benjamin Ward, Koch’s police commissioner, in 1983, and crime was already dropping under Dinkins. Between 1990 and 1994, subway felonies went down by seventy-five per cent and robberies by sixty-four per cent.
Broken-windows policing was instituted in the Dinkins administration by the chief of the transit police, William Bratton. (Giuliani made Bratton his first police commissioner, but pushed him out two years later, apparently annoyed that Bratton was hanging out at Elaine’s and hogging the media spotlight.) And the city’s budget stabilized, rectifying a cash-flow problem that had crippled mayors since Lindsay. Would these things have happened no matter who was mayor?
Much of urban America was blighted in the nineteen-seventies and eighties. Giuliani’s election was part of a wave of urban renewal across the country. Some cities, like Detroit and Baltimore, never recovered, but others, like Los Angeles, San Francisco, Boston, and New York, did get renewed and became magnets for young professionals.
Giuliani benefitted from the end of the crack epidemic, which was responsible for a lot of the robberies and street crime in the nineteen-eighties. And he benefitted from an aging population. Forty per cent of crimes are committed by people between fifteen and twenty-five, which means that a lot of the crime in the United States in the nineteen-seventies and eighties was an effect of the baby boom. As population growth flattened out, crime went down everywhere.
He inherited an improving economy, too. A major stimulus to economic growth in New York City was the Immigration and Nationality Act of 1965, which replaced the highly restrictive 1924 Immigration Act. Between 1980 and 1994, 1.4 million immigrants came to New York, effectively replacing the residents who had fled. Their entrepreneurship helped revitalize the city’s economy.
That economy was already undergoing a painful transition. Today, we have a hard time imagining New York as a manufacturing center. Yet the garment district was once a place where people made garments, just as the meatpacking district was once a place where people packed meat. Now the city’s economy is fuelled by the giant financial-services industry, the banking and investment houses and the law firms they employ—“Wall Street.”
But that behemoth didn’t spring up on its own. It was boosted by the policies of the Clinton Administration and of the chair of the Federal Reserve, Alan Greenspan, and by acts of Congress. In the course of the Clinton Administration, the Dow tripled, and the federal government started running a surplus. In New York, the Clinton boom helped gentrify parts of Manhattan and much of Brooklyn, and it rebuilt the city’s tax base, allowing the local government to accomplish things it could never have afforded ten years earlier.
By the end of his second term, however, Giuliani was running low on political capital. In 1999, he had entered the Republican primary for the Senate, expecting to run against Hillary Clinton, but before he had really launched his campaign he was diagnosed with prostate cancer (a disease that had killed his father) and pulled out.
In March, 2000, an unarmed Black man named Patrick Dorismond was shot and killed when police confronted him near the Port Authority Bus Terminal, and Giuliani went overboard in his defense of the cops. Just a year before, city police had killed another Black man, a West African immigrant named Amadou Diallo, firing forty-one shots before realizing that he was unarmed. Giuliani’s inclination then, too, was to defend the police. This made the affair much worse, of course, and it gave ammunition to his political opponents. But he didn’t learn from the experience. In the Dorismond case, he went after the victim. He authorized the release of Dorismond’s criminal records, including his sealed juvenile record, and he attacked Dorismond’s girlfriend when she praised him on television.
He was no altar boy, Giuliani argued—except that it turned out that Dorismond had been an altar boy, and attended Giuliani’s own high school, Bishop Loughlin, in Brooklyn. Dorismond was not engaged in any criminal activity when the police approached him, and he had never been found guilty of anything more serious than disorderly conduct.
Giuliani’s critics voiced anger at the way he had played racial politics. That divisiveness had a long history. Back in 1992, during Giuliani’s second mayoral campaign, members of the police union, the Patrolmen’s Benevolent Association, held a rally outside City Hall to demonstrate against Dinkins’s proposal to form a civilian board that would review allegations of police misconduct. Giuliani happily showed up and egged on the crowd. Many of the cops were drunk and shouted racist slogans. They marched onto the Brooklyn Bridge to disrupt traffic, and the demonstration devolved into a police riot. Giuliani left before the rioting started, but the incident was weirdly proleptic of his actions on January 6th, when he called out “Let’s have trial by combat” to the protesters. They took him at his word. Like Trump, he left before the rioting started. Light the fuse, then run.
And when he became mayor Giuliani never failed to exploit tensions between the N.Y.P.D. and the Black community. His stop-and-frisk policy, for example, was a plain case of racial profiling. Between January, 1998, and March, 1999, New York police frisked an astonishing hundred and seventy-five thousand people, half of them Black.
A few months after the Dorismond shooting, Giuliani announced his intention to separate from his second wife at a press conference. He had neglected to inform her of this, however, and a fight ensued over who would live in the mayoral residence, Gracie Mansion. In the end, Giuliani was the one who moved out. The press had a field day. New Yorkers had voted for a two-term limit for mayors in 1993 (the law would change in 2008, to accommodate Bloomberg), which meant that an already damaged Giuliani was staring at a political brick wall.
It’s callous to put it this way, but September 11th was a lucky break for him. It gave Giuliani’s career new life. He was on the scene right after the first tower was hit, and he had to run for his life when the second tower collapsed. But he is a tireless man, he can be eloquent, and he kept his nerve. Not having the fear gene came in handy. Giuliani stepped into a leadership vacuum left by President Bush, who was sequestered at an airbase in Nebraska, and spoke words of reassurance to New Yorkers and Americans. It was a testament to how far the city had come that, although the attacks inflicted a major wound, New Yorkers responded with compassion and manifestations of solidarity. It didn’t last, but it was striking.
When you drill down, though, the story isn’t so sterling. The city’s response to September 11th begins on February 26, 1993, when Islamic extremists detonated a truck bomb in the parking garage of the World Trade Center. More than a thousand people were injured, and six people died. Giuliani took the attack very seriously. He thought it showed that New York had become a target for international terrorism.
As mayor, therefore, he ordered the construction of a high-tech bunker where emergency response could be centralized. But he insisted that the center be within walking distance of City Hall, and so, despite police-department warnings that it would be impossible to secure, the Office of Emergency Management Command Center was constructed on the twenty-third floor of 7 World Trade Center. When the towers were hit, in 2001, the center was obviously useless. The administration had to manage the crisis on the run.
One of the facts that had emerged from the response to the 1993 bombing was that fire-department radios did not work inside the World Trade Center towers. Nor were the department’s radios synched with police-department radios. Although the city had had eight years to solve these problems, when the World Trade Center was attacked again the radios still did not function, and the police and fire departments, traditionally rivalrous organizations, still had not coördinated decision-making. On September 11th, even when it became clear that the lack of coördination was a serious problem, Giuliani did nothing to rectify it.
The breakdown in communications meant that 911 operators were telling people calling from inside the towers to stay put—standard advice in a high-rise fire situation—after the police department had determined that the towers were about to collapse, killing anyone who remained inside. It also meant that some firefighters inside the north tower never received the order to evacuate. At least a hundred and twenty-one firefighters died in the north tower. “There was an argument to be made,” Kirtzman concludes, “that Giuliani had cost lives on September 11 rather than saved them.”
This judgment seems a little severe. A truck bomb in a parking garage does not prepare you for the fiery holocaust that happened on September 11th. But it does explain why, when Giuliani entered the 2008 Presidential primaries, members of a group calling itself 9/11 Firefighters and Families went to New Hampshire to campaign against him. Although to the world Giuliani is the hero of September 11th, those people thought that he had failed them. Still, probably none of them could have imagined that he would end his career in a rooster costume. ♦
