What Happened to Rudy Giuliani?
NEWS | 25 May 2026
Rudy Giuliani always loved opera. He founded his Brooklyn high school’s opera club at a time when other kids were digging rock and roll. The choice was deliberately defiant—counterculturally conservative and inspired by his Italian heritage. But it also reflected a sincere love for the sweep and drama of the music’s mythological struggles. Giuliani has lived an operatic life, full of highs and lows, and its final act has been a tragedy. But the full score is more interesting and instructive than its ending alone. A quarter of a century ago, Giuliani was a global hero, dubbed “America’s mayor” by Oprah Winfrey for his leadership after the terror attacks of 9/11, when he strode through the rubble of Lower Manhattan like a latter-day Winston Churchill. But in the years before that defining moment, for all of the controversies, Giuliani accomplished something that too many people have already forgotten: He turned around New York City after decades of decline. Giuliani has always been a mix of sunshine and shadow. He was a young man who had wanted to join the priesthood but chose to be a prosecutor instead, in part because he knew that he was too hot-blooded to keep his vows. In city hall, there was a constant struggle between the better angels of his nature and the darker impulses of his soul: the instinct to respond to a mosquito with a howitzer, the fact that he was more content to be feared than loved. Earlier this month, Rudy was suddenly hospitalized with pneumonia, sinking into a coma before recovering. This urgent reminder of his mortality prompted me to reflect on the arc of his life. I had a front-row seat to this daily wrestling match as a 27-year-old chief speechwriter in his second term. I learned a lot from him—and the lessons of his life, both positive and negative, should not be lost. Turn the tape back to the 1980s, when Giuliani made his name as the Italian American U.S. attorney for the Southern District of New York who took down the mob. This was a plot twist with political and cultural significance because Italian American politicians were often accused—at varying decibels—of being in hock to the Mafia. Despite his father being a secret ex-con and having an obsession with the Godfather films (his screen saver at city hall read Leave the gun, take the cannoli), Giuliani did more to dismantle organized crime and corruption than any prosecutor before or since. Those heroics opened the door to a mayoral campaign. David A. Graham: Rudy Giuliani’s attacks on democracy are attacks on people Politically, Giuliani instinctively triangulated between President Ronald Reagan and Fiorello La Guardia, the irrepressible Republican-Socialist mayor who fought Tammany Hall corruption in the 1930s and remains a touchstone for mayors to this day. Giuliani ran on both the Republican and Liberal Party lines, defeating David Dinkins in a 1993 rematch. He was loathed by many on the professional left, but his policy profile at the time could have been fairly described as law-and-order progressive: He was pro-choice, pro–gay rights, pro–health care, and pro-immigrant. He was a reformer, and he was relentless. His record deserves to be judged on its own merits. Before Giuliani became mayor, New York City endured a multidecade period of decline—accelerating during the tenure of the charismatic but operationally negligent John Lindsay, cratering toward the brink of bankruptcy under the diminutive Abe Beame, and recovering briefly through the bravado and competence of Ed Koch, before descending into a new form of urban chaos with the crack epidemic that coincided with the mayoralty of Dinkins, during which the city suffered roughly 2,000 murders a year. As mayor, Giuliani revolutionized public safety through quality-of-life policing and the CompStat process, which was developed by Police Commissioner Bill Bratton and his deputy Jack Maple, and pioneered data tracking that allowed police to be more proactive. It worked. The murder rate was cut by two-thirds on his watch, and the city had a 72 percent reduction in shootings and a 56 percent drop on the FBI Crime Index over eight years—far outpacing the 16 percent national decline in crime—undercutting the argument that Giuliani was simply surfing a national wave. In fact, New York drove the national crime decline, aided by funding to hire new police from the crime bill passed under President Bill Clinton, and thanks to a significant assist from then-Senator Joe Biden. But the crime decrease was just the top line. On the fiscal front, Giuliani turned a $2.3 billion budget deficit into a surplus, while reducing New Yorkers’ tax burden to the lowest level in three decades. He acquired close to 2,000 acres of new parkland. He invested more than $4 billion in the city’s schools, hired roughly 10,000 new teachers, expanded charter schools, fought against social promotion, and advocated for the Board of Education to be overseen by the mayor’s office. Giuliani fundamentally reformed welfare as well. When he took office, 1.1 million New Yorkers were on public assistance. He cut that number in half by adding work requirements and turning welfare offices into job centers. He believed that work is ennobling but that long-term dependence deprives men and women of their dignity. The same belief was the basis of his disdain for methadone clinics and his opposition to outdoor homeless encampments; he insisted that no one would allow their friends or family members to sleep on a street. He was, by this measure, a commonsense conservative. Perhaps the ultimate measure of his success was captured by a poll that he loved to cite, from a 1990 Time cover story that found that 59 percent of New Yorkers would live somewhere else if they could. By the end of Giuliani’s tenure, just 31 percent said they wanted to live someplace else. The transformation of New York was real and measurable—but it was often obscured by Giuliani’s unpopularity, which stemmed from his strident defense of the police, even in cases of excessive force, such as the killings of Amadou Diallo and Patrick Dorismond, as well as from the tabloid spectacle of a turbulent personal life. This hit a crescendo when he used a press conference to inform the mother of his two children, Donna Hanover, that he would be seeking a divorce so that he could pursue his relationship with Judith Nathan, who would become his third wife. Part of what was most appealing about the man up close was that he did not carry the pretense of most politicians. He understood that he was flawed and odd, but he also thought about politics in an uncommonly philosophical way. In private, Giuliani recognized that his 1950s Italian American upbringing did not enable him to see the same city as Spike Lee did. When he was going through his second divorce, his private soul-searching included reading Sigmund Freud in the mayor’s office at city hall. When discussing abortion in private, he would take the conversation back to his Catholic education and speak of Saint Thomas Aquinas and the ancient debate over when a soul enters a body. Trust me: This is not the way politicians typically talk or think. Then came September 11—with the operatic twist of the attack occurring on the morning of the primary election for his successor as mayor. It called forth all his latent strengths for the world to see. Giuliani embodied one of that day’s enduring lessons: You don’t have to be perfect to be a hero; you just have to do the right thing when it matters most. His popularity elevated the political newcomer Mike Bloomberg to the mayor’s office that fall and secured a continuation of the policies that had driven the city’s resurgence, under a leader with a very different personality. It was as if Batman had been succeeded by Bruce Wayne. The question that the era’s city-hall staff get asked most these days is “What happened to Rudy?” I can say only that after the 2016 death of his high-school best friend, campaign manager, and deputy mayor—Peter Powers—there were creeping and then galloping signs of decline: a lack of filter, a deterioration of judgment, and a diminished ability to connect with the better angels of his nature. Read: What Rudy Giuliani is really up to In part, Giuliani was suffering from the “ex-mayor’s disease”—an addiction to attention after years of dominating headlines with daily press conferences. But there was an undeniable partisan element to the descent as well. One of his characteristic aphorisms as mayor was that “to be locked into partisan politics does not permit you to think clearly.” He deeply believed and often said that “the law is a search for the truth.” Then came Donald Trump’s first presidential campaign. Giuliani was a reluctant convert, initially preferring New Jersey Governor Chris Christie or former Florida Governor Jeb Bush. He had never been close to Trump during his time as mayor but, driven by his growing animus toward Democrats under Barack Obama and Hillary Clinton—fueled by his immersion in the Fox News ecosystem—he fully embraced the role of prime-time attack dog. It is a strange fact about Giuliani that he seldom approved a negative attack ad on his own behalf, but he was quite willing to do one for someone else. So what happened to Rudy? He got locked in partisan politics and he stopped thinking clearly. He forgot that the law was a search for the truth and instead pushed Trump’s baseless Big Lie about a stolen election. He became susceptible to conspiracy theories, leading shady fishing expeditions in Ukraine that contributed to Trump’s first impeachment. I do not believe that his call for “trial by combat” on January 6 was just an innocent slip of the tongue. Giuliani lit his reputation on fire for Trump. His sycophancy has left him disbarred and broke. But no man should be judged entirely on their last act. History will remember his leadership on 9/11 long after the wild-eyed, hair-dye-dripping accusations are forgotten. Perhaps the greatest tragedy is that his sordid actions on behalf of Trump have made the real-world effectiveness of his policies less accessible to current and future mayors. If there is a cautionary coda, it is this: Rudy Giuliani would have been an even greater man if he had tried harder to be a good man.
Author: John Avlon.
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