What the hell happened to Rudy Giuliani? It’s a question much of America was asking in the winter of 2020 while watching the former mayor of New York debase himself in the service of Donald Trump’s attempt to overturn a presidential election. As he made ever more outlandish claims about electoral fraud, brown hair dye running down his sweaty cheeks, his flatulence so clamorous it became a meme, he was unrecognizable from the once heroic symbol of Manhattan’s endurance after 9/11.
Giuliani went from being given an honorary knighthood by Queen Elizabeth II in 2002 to holding an unhinged press conference next to a sex shop in 2020. From Time magazine’s Person of the Year to selling happy birthday messages for $400 on the Cameo app, “America’s mayor” had become Trump’s poodle.
Was Giuliani’s decline inevitable or might the better angels of his nature have prevailed? This is the question that Andrew Kirtzman sets out to answer in his second Giuliani biography (the first covers the period before 9/11). A veteran New York reporter, Kirtzman was with the mayor on the fateful morning that the twin towers fell and knows his inner circle well. The result is a riveting rubberneck of a read, mortifying and meticulously reported.
Rudy’s Roots
Giuliani was born in 1944 to a blue-collar Italian-American family in Brooklyn. His father, Harold, was a violent criminal who served time for robbery and wielded a baseball bat for his mafioso brother-in-law. Kirtzman suspects that the damage done to young Rudy by this “pathologically self-centered” man was “incalculable”.
His mother, Helen, however, was “controlled and focused”, putting “heavy pressure” on him to succeed. Giuliani’s sharp intellect got him to law school at New York University. He worshipped the Kennedys in those days, but had conservative instincts: while his fellow students got stoned, he wore suits and enjoyed “listening to Verdi in his room”.
Giuliani was always driven by a strong sense of his moral purpose and wanted to become a prosecutor or a priest. Yet he was also a hypocrite and cheated persistently on his first wife, Regina. “He was pretty wild. He hit on everybody. All the time,” one former friend recalled. Giuliani quickly moved on to a second wife, Donna, with whom he had two children, Andrew and Caroline.
He opted for prosecutor over priest and rose through the legal ranks, landing the prize role of US attorney for the Southern District of New York in 1983.
Rudy Giuliani worshipped the Kennedys, but had conservative instincts: while his fellow students got stoned, he wore suits and enjoyed “listening to Verdi in his room.”
From there his ascent was meteoric. He helped to break the Mafia, prosecuting New York’s “five families”. He took down significant white-collar criminals including Michael Milken, the junk bond king. Having lost one election for mayor of New York in 1989, he ousted David Dinkins from Gracie Mansion in 1993 and became prince of the city.
As mayor of Gotham, Giuliani styled himself as a cross between Batman and Savonarola, seeking to drive the filth from crime-ridden New York. He hired the tough guy police commissioner Bill Bratton and applied the “broken windows” theory, ensuring that no small act of vandalism went unpunished. Crime dropped almost 60 percent during his tenure and the murder rate plummeted.
Yet there was also unapologetic racial targeting. Giuliani’s Black deputy mayor, Rudy Washington, was stopped and frisked so often, he was given a special badge to show overzealous officers.
In 2000 Giuliani decided to take on Hillary Clinton in the race for New York senator, but prostate cancer and revelations of an affair with Judith Nathan, who became his third wife, knocked him out of contention. His two terms as mayor were drawing to a close when the aircraft hit the World Trade Center, catapulting him to global fame.
Charging around a smoldering Manhattan in Churchillian fashion, he became the face of America’s response, an icon of resilience. He was courageous, brash and eloquent. He was tireless too, sleeping four hours a night and attending more than 200 firefighter funerals.
Yet from the moment he left office things went downhill. He cashed in on his reputation and consulted for all manner of shady clients, from Purdue Pharmaceuticals (of opioid crisis infamy) to MEK, an Iranian militia. A “creeping decadence” set in. At one point he had six homes and 11 country club memberships, and in six months he spent $12,000 on cigars and $7,000 on fountain pens. On one private flight to Europe he was furious that the jet didn’t stock cashmere blankets.
When he finally ran for the Republican presidential nomination in 2008, the campaign flopped. His 9/11 halo had dimmed and his social liberalism made him ill-suited to win over the Republican heartlands.
At one point he had six homes and 11 country club memberships, and in six months he spent $12,000 on cigars and $7,000 on fountain pens.
Depressed and defeated, he was offered sanctuary by Trump, who used the tunnels under Mar-a-Lago to sneak him and his wife in for dinner. When a club employee was caught photographing Nathan, Donald and Melania Trump had them fired.
Two old lions of New York, Trump and Giuliani delight in each other’s alpha bravado and are bound by mutual respect and self-interest. One key difference, though, is that Giuliani drinks, while Trump is sober. “He was shit-faced,” is how Nathan describes Giuliani before one damaging fall.
As Giuliani’s relevance began to wane, Trump became his last ticket to the big time and he threw his lot in with the property tycoon’s underdog 2016 campaign.
Despite his loyalty, Giuliani was passed over for secretary of state, becoming Trump’s media attack dog and personal lawyer instead. His media appearances were frequent, frenetic and seemingly well lubricated, but because of his closeness to Trump he was able to do real damage. First in Ukraine, where he cooked up a “big bowl of spaghetti”, leading Trump to threaten to withhold arms from a newly installed President Zelensky unless he announced an investigation into Joe Biden’s son Hunter.
That earned Trump his first impeachment. In November 2020 Giuliani helped to put Trump on a path to a second. “Just pick a state and say that we won!” was his election-night advice. By January 6 he was exhorting an angry crowd of Trump fans in Washington to resist a democratic election result through “trial by combat”. The infamous assault on Congress followed.
As of today, Giuliani’s law license has been suspended. He’s facing lawsuits and investigations for his role in January 6 and is squabbling with Nathan in court over the scraps of his fortune.
So what did happen to him? Kirtzman’s view is that he didn’t so much change his stripes as surrender to his worst instincts and need for validation. “A powerful man bereft of self-doubt can accomplish great things. Or cause tremendous damage.”
Kirtzman has written a comprehensive and devastating portrait of an American life at once great and dismal. It is all the more devastating because, despite his criticism, the author clearly admires the mayor’s squandered talents.
Giuliani may yet have further to fall, but a once golden legacy is irreparably tarnished. Does he worry about this, a journalist asked recently. “I don’t care about my legacy,” he responded with characteristic contempt. “I’ll be dead.”
Josh Glancy is special correspondent for The Sunday Times
