What happened to Rudy Giuliani? The question seems to come up often, and when it’s raised I sometimes think back to the man I met back in June 1983—lean and ambitious and with a mischievous smile. He was the new U.S. attorney in Manhattan, and I was the courthouse reporter for the Associated Press. I liked what I saw. He was bursting with energy and enthusiasm; he leaned forward as if he were a runner about to begin a race, ready to make news.

I was especially impressed by his insider-trading prosecutions. Before Giuliani, judges treated the offense as barely criminal, handing down minimal sentences. But Giuliani made the case that it was just another form of cheating and should be punished that way. Similarly, he labored mightily to change the city’s corrupt political culture. He became a sort of “Shell Answer Man” (for those who recall the TV commercial) on matters of ethics in government, sought out constantly for his opinion.

In time, I looked to report on his limitations: his inclination to exaggerate and hog credit for himself; his low regard for civil liberties; his vitriolic attacks on critics, even federal judges. I noticed how his self-serving, high-profile style squandered the credibility of the nation’s most prestigious prosecutorial office in the eyes of the no-nonsense judges of the Southern District of New York.

But never would anyone have predicted that he’d end up where he is now: suspended from the practice of law for ethics violations and the subject of many investigations. How could a man who seemed to have a strong sense of right and wrong become the chief enabler of the “Big Lie” that Donald Trump was cheated out of victory in the 2020 presidential election?

Political journalist Andrew Kirtzman has written an engaging and very well-reported book aimed at answering that question. He provides what I believe is the most thorough [1] account to date of how Giuliani and Trump developed their relationship, including details that will be valuable to historians. Kirtzman reports in one of the book’s scoops [2] that Giuliani’s close friend Maria Ryan sought a “general pardon” for him from Trump shortly after the January 6 attack. He provides the most complete picture yet of the downward spiral in Giuliani’s personal life, showing how it is entwined with his professional downfall. There is also a terrific account of Giuliani at his apex, his stirring leadership on September 11, 2001. On that day, Kirtzman had rushed down to the World Trade Center after jets struck the Twin Towers, then somehow found the mayor in the midst of the chaos and tagged along at his invitation.

As a political reporter for the politics-intensive cable-news station New York 1, Kirtzman chronicled Giuliani’s 1994–2001 mayoralty closely. He published a biography of Giuliani in 2000, Rudy Giuliani: Emperor of the City, that was quite stinging, but generously credited the mayor with being “a leader whose accomplishments rank among the most dramatic in urban history.”

So: What happened to Rudy Giuliani?

“His descent was the result of a series of moral compromises made over the years as the temptations of power and money grew. There were any number of opportunities to do the right thing when he did the opposite,” Kirtzman writes in the book’s introduction. “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 paradox of Giuliani, he writes, “was that he viewed all of his actions through the lens of morality, even when they were morally questionable.” In Giuliani’s worldview, leaders had a responsibility “to enforce a moral order…. The language of morality would govern his words, his politics, his personal life. His belief in the infallibility of his views rendered him impervious to criticism and self-doubt, which would prove to be his greatest asset and his eventual undoing.”

Commonweal readers may recognize [3] Giuliani’s pre–Vatican II Catholic education in this; Giuliani studied under Christian Brothers at Bishop Loughlin Memorial High School in Brooklyn and at Manhattan College, and for a time considered the priesthood. Kirtzman doesn’t go deeply into the role religion plays in Giuliani’s life, dealing instead with his moral streak.

Giuliani seemed to have his high ideals intact as he left a post as the number three official in the Justice Department to take the lesser but higher-profile job as U.S. attorney in Manhattan in 1983. Kirtzman’s chapter on Giuliani’s years as a federal prosecutor breaks no ground, however, and misses opportunities to examine some episodes relevant to his inquiry.

Once Giuliani enters the political arena with his first mayoral campaign in 1989, Kirtzman is adept at showing the compromises he says Giuliani made in the quest for power and glory. He notes, “Like the president he would serve decades later, Giuliani had an instinctive ability to press the outrage button at whim.” During his first (and quite effective) term as mayor, he “fomented public uproars to shatter the complacency that allowed city services to decline, crime to rise, and budget deficits to soar. But as his political aspirations grew, he increasingly created these spectacles to serve his own needs.”

Facing a two-term limit as mayor, Giuliani prepared to run for the Senate against Hillary Rodham Clinton. He set out to redefine himself as a social conservative—positioning himself to reap contributions from Republican donors nationally—and went to war against the Brooklyn Museum for exhibiting a painting of the Virgin Mary splotched with elephant dung and dotted with cut-out images of sexual organs. Offensive as the painting may have been, there was no legal basis for Giuliani to evict the museum from its city-owned building, as he attempted to do. The museum quickly won a federal court order finding that Giuliani had violated the First Amendment. (It was one of twenty-five cases the federal appeals court cited [4] in a 2000 ruling that took note of the “relentless onslaught” of First Amendment cases the city had lost over the previous four years.)

Giuliani dropped out of the race for Senate, citing a prostate-cancer diagnosis as the reason. But at the same time, the turmoil in his private life came into full public view.

I have to admit that as a reporter in City Hall and later as an editor supervising coverage of city government, Giuliani’s widely rumored marital infidelity was a story I was always happy to be second on. Kirtzman persuades me that in retrospect, it was newsworthy.

He reports that Giuliani’s cheating began with the first of his three marriages, to Regina Peruggi, a talented woman who later became a college president. The story presented to the public was that when they married, Giuliani thought he and Peruggi were third cousins, but that they were in fact second cousins. This was the supposed basis for their divorce and subsequent annulment from the Catholic Church.

Peruggi has not publicly discussed their relationship, but Kirtzman quoted Peruggi’s close friend Pat Rufino, who says that “[h]e cheated on her pretty much the whole time they were married.” Bob Leuci, the police informant whose relationship with Giuliani is the subject of the movie Prince of the City, based on a corruption probe Giuliani led as an assistant U.S. attorney, said the same: “He hit on everybody, hit on them all, all the time. He bounced around the Village. He was pretty wild.”

Giuliani’s second marriage, to television newscaster Donna Hanover, who became the city’s first lady, went a similar route. Giuliani announced both his decision to divorce her and his relationship with another woman, Judith Nathan, without telling her. Hanover went to New York’s Cardinal John O’Connor for counseling. Giuliani hired a celebrity divorce lawyer, Raoul Felder, who showed off his skill at publicly besmirching his clients’ exes.

Giuliani’s second term was distracted and problematic. He married Nathan, leaving his friends “puzzled that this famously ascetic man was increasingly focused on money and material things, and had chosen in his mate a woman who was passionate about both,” according to Kirtzman. As he left the mayoralty at the end of 2001, Giuliani “lost his grip on the zealous mission that had driven him his entire career, which was to wield power and impose his view of right and wrong on others.”

He made a series of moral compromises to become rich—helping Purdue Pharma elude accountability for the opioid crisis, for example. Giuliani “leveraged his mayoralty to make himself spectacularly wealthy,” Kirtzman writes. He bought a $4.77 million, nine-room co-op on Madison Avenue, a $3.2 million, nine-bedroom house in the Hamptons, took on a $6.8 million divorce settlement with Hanover, obtained memberships in eleven country clubs, and bought two more homes, according to Kirtzman, who maintains that the former mayor’s “creeping decadence was an outgrowth of a painful reality, which was that his power had drained away.”

He began an ill-fated run for president in 2006, but even though he led national polls of Republican voters, his campaign fizzled and he dropped out before the end of January 2008, with just one delegate vote to his credit. This, Kirtzman writes, was when Giuliani fell apart, and when Trump stepped in to help [5] pick up the pieces.

Nathan is quoted as saying that Giuliani fell into a deep melancholy. She couldn’t get him out of bed, she says; he hardly ever went out and he drank more heavily. “He was in what, I knew as a nurse, was a clinical depression,” she says. These are details only Nathan and Giuliani would know, Kirtzman writes, but he notes that their friends confirm that they dropped out of sight for several months. That was when Trump took Giuliani into Mar-a-Lago, his Palm Beach hotel and estate. “Giuliani would never turn his back on Trump, much to his detriment,” Kirtzman notes.

As Giuliani returned to his previous life, he developed a list of clients that reads “like a collection of villains from James Bond films,” Kirtzman contends: a far-right Serbian politician; a Peruvian presidential candidate whose father, former president Alberto Fujimori, had been convicted of murder and kidnapping; dubious business and political figures from Ukraine; an Iranian organization the State Department had listed as terrorist.

“Giuliani wasn’t changing his stripes as much as surrendering to his worst instincts,” Kirtzman argues. “The prosecutor who wrecked lives in search of fame; the mayor who destroyed reputations in pursuit of power; the husband who cheated on his wife—these men lived side by side with the leader who comforted grieving widows, and raced to help his friends in hard times.”

Anyone following the January 6 congressional hearings and Trump-impeachment proceedings knows the rest of the story. Giuliani seized on his bond with Trump to find the spotlight. With a dramatic narrative and a mixed sense of indignation and sadness, Kirtzman chronicles Giuliani’s often outrageous conduct as he defends Trump against impeachment, baselessly accuses Joe Biden of corruption, and uses what he knows are unsupported claims in his effort to undo a democratic election. His work was so haphazard that there were “laughingstock episodes,” even for many within the Trump White House.

Kirtzman’s reporting is impressive, as are his narrative skills. In the end, though, I didn’t feel that the conclusion to this morality play was decisive. Near the end of the book, he comments, “Somewhere early in life Giuliani developed a moral certitude that protected him from fear and self-doubt. He was infatuated with his sense of virtue, and viewed those who opposed him as either moronic or corrupt.” Kirtzman quotes a young woman who served as Giuliani’s press secretary during those chaotic days of challenging the 2020 election results: “He believed what he was doing was right. That’s all the motivation he needed.”

Maybe so. But after all these years, I still have a high enough opinion of Giuliani to believe he knows what he’s been doing is wrong.

Giuliani
The Rise and Tragic Fall of America’s Mayor
Andrew Kirtzman
Simon & Schuster 
$30 | 480 pp.