War Stories

How Did Rudy Giuliani Come to This?

The Giuliani of the ’90s was far from perfect, but he wasn’t a ranting, bug-eyed ideologue.

Close-up of Rudy Giuliani listening to a question.
New York City Mayor Rudolph Giuliani listens to a reporter’s question during a press conference at City Hall in New York on April 27, 2000. DOUG KANTER/Getty Images

As Rudy Giuliani writhes in his bed at Georgetown University Medical Center, his mind might well be leafing through the storied chapters of his life and how it came to this—the hero of 9/11, “America’s Mayor,” once a plausible candidate for president, now suffering from COVID-19 as a result of the devil’s pact he struck with Donald Trump.

His eight years as the mayor of New York City at the turn of the century were packed with controversy, mainly of his own stubborn making, but he was never the ranting, eye-bulging water boy of an ideologue that we’ve seen of late at political conventions, press conferences, and gonzo legal proceedings.

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The Giuliani of the 1990s and early 2000s was, for the most part, a pragmatist: an economic conservative but a social liberal, in favor of gun control, abortion rights, gay rights, and immigration reform. As the Boston Globe’s New York bureau chief from 1995-2002, I talked with Giuliani several times. (When the city was in financial straits, he viewed publicity in out-of-town papers as economic development.) In the summer of 1996, I asked him why he wasn’t at the Republican National Convention, which was going in San Diego. “It’s not my sort of thing,” he replied. “I’m much closer to moderates in both parties than to extremists in either.”

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He wasn’t just saying what he might have thought I wanted to hear. He venerated New York’s Democratic governor, Mario Cuomo, and had even endorsed him in his 1994 race against Republican challenger George Pataki. (Pataki won and never forgave Giuliani for his betrayal.)

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In 2000, Giuliani started to run for the U.S. Senate against Hillary Clinton, who’d been guaranteed the Democratic nomination, in what many foresaw as the year’s most exciting political contest—and a possible foothold to bigger things for both candidates. Then in May came a triple whammy. Giuliani announced he’d been diagnosed with prostate cancer. A few days later, he confirmed reports that he was having an extramarital affair and, a few days after that, announced he was separating from Donna Hanover, his wife of 16 years (who learned about it from TV news). Then he dropped out of the Senate race, saying he needed to focus on his health. After Clinton phoned to wish him well, he described his once and future nemesis this way: “She’s a nice lady.”

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At the press conference where he bowed out of the Senate race, Giuliani made some other comments, the likes of which no one had ever heard him make before or since. “Politics is not as important as I thought it was,” he said, adding that he was now going to focus on “what’s important in life.” In the 18 months remaining in his second and final mayoral term, he would try “to overcome some of the barriers that maybe I’ve placed”—a clear and rare reference to the deep distrust he’d sown among Black and Hispanic New Yorkers. Two months earlier, he’d unsealed and publicized juvenile court records of Patrick Dorismond, a 26-year-old Black security guard who had been shot and killed by an overly aggressive undercover cop. Now Giuliani said he’d “made a mistake,” admitting that he should have “conveyed the human feeling that I had—of compassion and loss for a mother,” adding, “Maybe it’s something when you confront your limits, your morality. You realize you’re not Superman, you’re just a human being.”

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Is it possible that when he recovers from the coronavirus (if he recovers—he’s 76 and, by appearances, in less than stellar shape), Giuliani will rediscover his compassion, as he did 20 years ago?

Maybe, but probably not. Too much has gone down, too much of his brighter side has been whacked and whittled away for a Scrooge-on-Christmas-morn revelation to come easily. This takes us back to our story of Rudy’s rise and fall.

His moment of conscience, even back then, didn’t last long: Soon enough, he resumed denouncing critics as “jerks” and “idiots,” demanding slavish loyalty from his underlings, and ignoring Black and Hispanic New Yorkers, to whom he never did make his promised overtures.

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And yet something about that moment may have lingered to enable his universally admired response to the terrorist attack on the World Trade Center. By that time, he had moved out of the mayor’s mansion and was staying with two men he knew—an openly gay couple—in their apartment. After the 9/11 attack, he stayed up at night reading Winston Churchill’s memoir of the London blitz and raced around the city all day, leading the mourning, rallying cultural leaders to reopen their doors and bring New York back to life, and serving as the city’s public face to the rest of the nation, urging people to come visit, lobbying Congress to boost funding. He ended his second term four months later as popular as ever.

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Then he started to believe his own hype.

He gallivanted around the country, making lucrative speeches, presenting himself as an expert not just on city planning and crime-fighting (with some justification) but also on terrorism and world politics (with no basis whatsoever). He ran for president in 2008 (the conventional wisdom was that he would face Hillary Clinton in the general election, making real the canceled promise of the Senate race eight years earlier), but shut down his candidacy after spending $50 million and winning just one delegate. The problem, he surmised, was that his views were too far left for the national Republican mainstream.

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So he turned right—and, along with his party, never stopped turning. It is hard to say how much of his switch in views was opportunistic and how much was real, but, at some point for most people evolving in this way, it doesn’t matter. In olden times, one of Giuliani’s greatest pleasures was to have a hot dog and a beer while watching his beloved Yankees play baseball. (In the early days of his Senate run, he skipped a fundraising lunch in Albany, for which tickets had already been sold, to attend the team’s season opener.) In the past decade or so, he’s been seen chortling at parties in the Hamptons, Palm Beach, and Mar-a-Lago, and on the very few times when he’s ventured to Yankee Stadium, he’s been booed. And so, he may have fumed, to hell with his old allegiances and pleasures.

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Now he’s sweating through the toxins that his new companions transmitted to him and that he’s no doubt passed on to others with whom he’s mingled at myriad gatherings in Trumpworld, where particles of laughter spew forth at wrought concerns about “Covid Covid Covid Covid” and where masks are verboten as emblems of the deep state and the resistance.

Giuliani is tagged as the 53rd Trump insider to contract the coronavirus. Given the several Christmas parties to take place at the White House, he is unlikely to be the last. Chris Christie, the former New Jersey governor who helped Trump prepare for debates with Joe Biden, is one of the few victims who emerged from his ICU kicking himself for stupidly not wearing a mask at those gatherings and urging other Americans not to make the same mistake. What will Giuliani say if and when he limps out of his hospital? It is too late for words of regret and renunciation to reclaim his much-tarnished legacy. But hey, it couldn’t hurt.

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