All summer long, Rudy Giuliani has acted as if he’s in a contest with Donald Trump to prove who the most manic 70-something from the outer boroughs really is. It started at the Republican National Convention in Cleveland, where Giuliani raved and gesticulated about the podium like an Aztec priest offering up fresh beating hearts to Quetzalcoatl. He blamed President Obama for any and all racial division in the United States—“What happened to one America?!”—and Obama and Hillary Clinton for virtually every attack by Islamic terrorists over the past four years.

“There’s no next election. This is it! There’s no more time left to revive our great country,” he concluded apocalyptically, so overwrought that he seemed about to work himself into a stroke, barely able to get out or articulate words and simply shouting, “Greatness!” near the end of his speech.


On the campaign trail since then, Giuliani has led some of Trump’s most lunatic lines of attack, mocking Clinton for having failed a bar exam 41 years ago (and claiming it was covered up by the press); repeating the Trump camp accusations that the media are ignoring “several signs of illness by her” (“I don’t know if she goes home, goes to sleep. I think she sleeps”); insisting that Trump’s Milwaukee appeal for black people to abandon the Democratic Party was “the best speech that any Republican, at the least, has ever given” and reviving a monthslong feud with Beyoncé (Beyoncé!) by denouncing her for daring to pay tribute to Black Lives Matter at a concert. “I ran the largest and the best police department in the world, the New York City Police Department, and I saved more black lives than any of those people you saw on stage,” Giuliani bragged on Fox & Friends.

Anyone just tuning in must be wondering: What happened to “America’s mayor”? For millions of people outside New York, the lasting image of Giuliani is that of the man we all rooted for as he pushed his way through the streets of Lower Manhattan on September 11, 2001, and told us afterward, with almost heartbreaking gentleness, that “the casualties will be more than any of us can bear.” Giuliani that day went on television not only to urge calm, but to remind New Yorkers not to take out their grief on Muslims—“We should act bravely. We should act in a tolerant way”—and just days later held an interfaith prayer service in Yankee Stadium that brought Islamic clerics together with Christians and Jews. This season in political hell, Giuliani has seemed so addled, so much the campaign tool, alternately vicious and clownish in defense of The Donald, that at one point he even stuffed his most famed accomplishment down the memory hole, insisting of the Bush presidency, “Under those eight years, before Obama came along, we didn’t have any successful radical Islamic terrorist attack in the United States.”

It might seem like this summer has marked a sad break with that old Rudy, or proved him a sellout. But if you’ve followed Giuliani’s career, in fact it’s clear he swallowed the whole Trump persona many years ago—the race-baiting, the law-and-order pose, the incessant lying used to both steal credit and avoid responsibility. What we’re seeing this summer isn’t a crackup: It’s the inevitable, supernova explosion of what long ago became one of the most toxic and overrated political careers in our history. It’s tempting to count the 72-year-old Giuliani one more addition to the Island of Misfit Toys that Trump has gathered around him—another one of the political relics who, seeking to restore relevance, have found themselves denatured by the strange public power of Trump. But a better way to see it might be as a man seizing the star turn he never quite got—grabbing time in slow stretches of the campaign to stand on the national stage and play the role that was supposed to be his, exactly the way he thinks it should be played.

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What lies at the heart of Trumpism, and Rudyism, is the same, nostalgic impulse that has driven reactionary Republican populism for a half-century now—“The shining city on the hill!” as Giuliani managed to splutter at the convention, just before, “Greatness!” It’s no coincidence that Trump and Giuliani both came of age in the New York of the 1960s and ’70s, the time when the dream seemed to die, during the nihilistic, wholesale destruction of our cities.

Growing up in Flatbush, Rudy was a Democrat, like pretty much everyone he knew. Giuliani was first drawn to politics by John F. Kennedy’s run for the presidency in 1960; by 1964, when Hillary Clinton was still a Goldwater girl, he was writing in the school paper of Manhattan College in defense of civil rights and President Lyndon Johnson’s war on poverty, and calling Barry Goldwater “an incompetent, confused, and idiotic man.” By the time he got to law school at New York University, Rudy was opposed to the Vietnam War—from which he would get three deferments, thanks to a friendly judge—and a “real RFK Democrat, a liberal, except on law and order,” according to a friend quoted in the journalist Wayne Barrett’s invaluable book on the mayor, Rudy! An Investigative Biography of Rudolph Giuliani. Giuliani called Bobby Kennedy “irreplaceable,” “great and brilliant,” and his assassination stunned him. “He had the support of the minority community in a way no other white politician did, and he had the ability to communicate with the white middle class. There was no one else with a foot in both camps,” Giuliani said.

It was an astute assessment. Kennedy had taken the 1968 California primary, his last great race, with a coalition of working-class blacks, whites and Hispanics at the core of his campaign. His loss was, as it turned out, irreplaceable, and with his death American politics would continue to splinter along racial lines.

For a moment, it would look as though Giuliani might be the one to mend that rift. He voted for George McGovern in 1972, the same Democratic candidate a young Bill and Hill were working their hearts out to try to make palatable to the voters of Texas. With Richard Nixon’s landslide that year, though, both Giuliani and the Clintons swung right. The Clintons remade the Democratic Party in their own grasping, opportunistic image. In the 1970s, Giuliani would go to work for the Nixon-Ford Justice Department, first as an assistant U.S. attorney for the Southern District of New York, and then as associate deputy attorney general down in Washington. He switched his registration to independent sometime between 1973 and 1977, claiming he wanted to avoid any appearance of political partisanship in the cases he took up. He had apparently shaken off that concern by December 8, 1980, one month after Ronald Reagan’s election confirmed the country’s rightward shift, when he registered as a Republican just in time to be selected as the No. 3 man in the Reagan Justice Department.

“He only became a Republican after he began to get all those jobs from them,” his mother, Helen Giuliani, would say in 1988, as only moms can. “He’s definitely not a conservative Republican. He thinks he is, but he isn’t. He still feels very sorry for the poor.”

Giuliani was going to have to dangle a foot in both parties if he was to build a political career in his still overwhelmingly Democratic hometown. He wasn’t going to make it by hauling the Reagan administration’s water down in Washington, where he buried a case against a major arms supplier and argued, with a straight face, that Haitian refugees were ineligible for political asylum because “political oppression, at least in general, does not exist” under Jean-Claude "Baby Doc" Duvalier’s bloody regime.

By 1983, still just 39, Giuliani was back home, now in charge as U.S. Attorney for the Southern District, a longtime steppingstone toward higher office. Here, Giuliani could set his own agenda, going after all of the assorted nabobs running amok in Mayor Ed Koch’s wide-open New York: the Mafia, the masters of the universe down on Wall Street, corrupt municipal officials. It made for marvelous political theater. Giuliani declared his intention “to wipe out the five families” running the New York mob, and sent three Mafia family heads up the river with sentences of more than 100 years apiece. He ended the career of venal Koch cronies, and his prosecution of the Wedtech arms procurement scandal forced the resignation of two congressman and even his own boss, Reagan attorney general Ed Meese, whom Giuliani had one of his assistant attorneys publicly call “a sleaze.”

On Wall Street, Rudy nailed Michael Milken and Ivan Boesky and reinvented the perp walk for a new era of white-collar crime, manacling together 15 white financial executives arrested on drug charges and parading them through Foley Square downtown. He had other major traders hauled out of their offices in handcuffs or clapped in jail overnight, and if there were complaints that not all these cases held up in the end, who cared? In a New York that seemed given over to special privilege at the same time that it was being engulfed by crime, Rudy Giuliani from Flatbush seemed to be a genuine, working-class hero, administering justice with rare evenhandedness, as willing to pull down executives snorting coke as gang-bangers doing crack. Incredibly, he was able to pull the support of both Rupert Murdoch’s New York Post and The Village Voice, back when it was the best investigative paper in the country.

By 1989, Giuliani seemed like a lock to displace a sagging Mayor Koch, a Democrat, who was running for a fourth term. He attacked Koch from the left on homelessness, poverty, drug rehabilitation and AIDS, and refused to play what he called “the death penalty game.” In what Wayne Barrett aptly called his “Kennedyesque” speeches, Rudy railed against “the shame of racism” in New York, promising “a government of inclusion” and an “end to alienation.” By the spring of 1989, the Wall Street Journal was openly blasting Giuliani as too liberal—a “[John] Lindsay Republican”—and Senator Al D’Amato was fuming that if he won, Giuliani would leave the party, just the way liberal Lindsay had.

Perhaps he would have—and who knows what heights an independent or Democratic Giuliani might have risen to? But in August 1989, a mob of white Bensonhurst thugs chased down and shot to death 16-year-old Yusef Hawkins, a black kid who had come to the neighborhood to see about buying a used car. Soon, Reverend Al Sharpton was leading protest marches through Bensonhurst that were met in turn by white crowds screaming racial epithets and holding up watermelons.

The city was exhausted, wrung out by one more of seemingly endless racial confrontations of the Koch years. Koch lost his September primary by almost 100,000 votes to David Dinkins, the genteel, African-American borough president of Manhattan who was seen as a unifier. The whole narrative of the race shifted, and Giuliani found himself being pounded from both right (by Ron Lauder, the cosmetics heir) and left. Hopelessly entangled in social issues like abortion and gay rights, a flailing Giuliani now vowed to bring the death penalty back to New York, and tried to attack Dinkins over assorted personal scandals, as well as his association with various black “radicals.” These belated efforts to play the race card fell short, and turned off some New York white liberals. Come Election Day, Giuliani lost in a squeaker. “The Rudy who might have been mayor had Ed Koch won the primary would not be seen again,” Barrett wrote.

Rudy learned a lesson, and it was an ugly one. Much like George Wallace vowing, “I will never be outni---red again!” after losing his Alabama governor’s race in 1958, Giuliani turned the next four years into an almost nonstop campaign of character assassination and race-baiting against Dinkins, a fight the New York Times Magazine would dub “The Race Race.” Just as Giuliani at this year’s convention sought to blame all of the country’s racial divisions on President Obama, the Giuliani of 25 years ago brazenly accused Dinkins of “playing racial politics,” “whining” and hiding “behind black victimization.” Much like Trump today, he convinced himself that he could only have been beaten by voter fraud “in black and Dominican districts,” according to Barrett—something he seemed to use to justify doing anything and everything he felt necessary to win.

The dog whistles were over. Forget the Great Society. Rudy now endorsed the policy ideas emanating from the right-wing Manhattan Institute, all of which stressed the “tough love,” bend-over-and-grab-your-own-bootstraps prescriptions adopted for the urban poor today by the Trump campaign. Giuliani now wanted the “chronic” homeless banned from shelters after 90 days. Back in 1989, he had refused to march in the St. Patrick’s Day parade because its organizers refused to allow gays to march. In 1993, Rudy marched with the homophobes—and condemned Dinkins for not marching.

Nobody remembers it this way now, but the Dinkins administration compiled New York’s best record on crime since World War II, adding 6,000 more cops and enjoying a record, 36 straight months of drops in the crime rate. But for New Yorkers this was eclipsed by big headline events like the Crown Heights riot of 1991—a clash between African-Americans and Orthodox Jews that Giuliani would insist on calling a “pogrom,” implying that it was countenanced by Mayor Dinkins. The crime statistics had turned around, and quality of life was slowly but visibly improving in much of New York, but that’s not how people saw it at the time—in part thanks to Giuliani’s relentless, Trumpian campaign to tell them it was a still a cesspool.

Even once-liberal elements of the press internalized Giuliani’s apocalyptic view of his own city. Richard Cohen, in an October 1993 column in the Washington Post the month before the election, scoffed that, “Aside from the deranged, there's not a single Gothamite who thinks it has gotten better under Dinkins—no matter what his statistics say,” while the Times’ James McKinley concluded, “Mr. Dinkins will never be able to prove his policies have curbed crime.” John Taylor, in Time, conceded that New Yorkers might actually be safer, but that they felt less safe, because the crimes still going on—though he did not give a specific example—were Trumpishly hellish: “Entire families are executed in drug wars. Teenagers kill each other over sneakers. Robbers casually shoot victims even if they have surrendered wallets. The proliferation of carjackings means people are no longer safe even in their automobiles.”

With actual facts about the crime rate effectively banished from the debate, pundits could feel free to embrace the throwback notion pushed by Giuliani that America’s real urban problem was not so much poverty or racism, but black people demanding special treatment, much like their tribune in city hall. Black-scolding reached a sort of frenzy that April, when New York’s great stuffed owl of a senator, Daniel Patrick Moynihan, gave his famous, “Defining deviancy down” speech, in which he asked “what in the last 50 years in New York is now better than it was” back in 1943, and concluded that nothing was better, especially crime. Moynihan received almost universal adoration for these supposedly bold words, the media having failed to notice that crime was at record lows in 1943 because most of the city’s young men were off fighting something called World War II. Or that there was a deadly race riot in New York that year anyway, set off by a cop shooting a black soldier. Or that Harlem had been officially “off-limits” to visiting white servicemen, or that black people were effectively banned from all of the city’s best restaurants, hotels, colleges, hospitals, or jobs in 1943.

Whatever. The Giuliani campaign, and its attendant press corps, was as far past facts as the Trump campaign is now. The perception became the reality. Despite the yearslong decrease in crime, a 1993 New York Times poll found that 58 percent of all New Yorkers felt that it had increased since a black man became mayor. Giuliani charged that Dinkins “might as well have a ceremony in which he turned the neighborhoods over to the drug dealers. As far as I’m concerned, there is no future in surrender.”

It worked, even in some of the most progressive districts of Manhattan. Polls showed that in their 1993 rematch, Giuliani was especially “making gains among Upper West Side liberal women defecting from Dinkins on the crime issue,” according to his biographer, Fred Siegel, and this time it was Giuliani who was able to pull out a close race, taking 64 percent of New York’s white Democrats, and 77 percent of all whites.

Once in office, Giuliani didn’t really do anything. As it turned out, the man who would be Bobby Kennedy had no great vision for the city he had lived in almost all his life. Mostly, he watched as the stock market ticked up during the Clinton boom, the tourists poured into the Times Square that Koch and Mario Cuomo had rehabilitated, and the revolutionary CompStat program—instituted by Police Commissioner William Bratton, the man Dinkins had brought in—drove crime rates down. All the increased revenue, plus the dramatic lessening of the AIDS and crack crises, made managing the city easier than ever before. Even so, under the Giuliani administration, there was no real effort to keep the city’s middle class, and its small businesses from being driven out by New York’s skyrocketing real-estate prices—just huge, ineffectual tax breaks handed out to corporate giants, in the name of keeping their business in town. It was the beginning of a philosophy that has prevailed to this day in New York, in fact if not in rhetoric: the only thing to be done for the city is to fill it with more and more rich people.

Still, enough of white New York loved their shiny new city to return Rudy to office in 1997 by over 12 percentage points. People of color would increasingly feel themselves under siege, subjected to continual “stop-and-frisk” humiliations by the police and arrests for minor infractions, selectively applied. They came originally from Bratton’s adopting the philosophy of “broken windows” and “quality of life” policing, but Rudy backed them to the hilt, and gave the police permission to keep doing them even when they were ordered to cease and desist by the courts.

The same sorts of disturbing racial incidents that had marred the Koch years—and which would, years later, spark Black Lives Matter—returned. When one Abner Louima was arrested, tortured and raped with a toilet plunger in his cell by cops in what turned out to be a case of mistaken identity, Mayor Giuliani ordered an immediate investigation—then, months later, publicly threw out its findings. When four plainclothesmen mistook Amadou Diallo, a 23-year-old, law-abiding immigrant from Guinea for someone else and demanded to see his ID, he pulled out his wallet—and they fired 41 times, putting 19 bullets in him. Giuliani called his death a “tragedy,” but refused to say it was “a mistake.” When a 26-year-old security guard named Patrick Dorismond angrily attacked a pair of undercover cops who tried to get him to buy some crack, he was shot dead, too. Far from apologizing for police killing a young black man for refusing to buy crack, Rudy defended the cops and illegally unsealed Dorismond’s minor, juvenile delinquency record from years before, explaining that he was only trying to show that the dead man “was no altar boy.” In fact, it turned out that Dorismond had gone to the same Catholic school as Giuliani. And that he was an altar boy.

***

When a Washington Post reporter asked the mayor about what he had done for New York’s minorities, Giuliani famously shot back, “They’re alive, how about we start with that.” Then as now, he was utterly convinced that black people, in Milwaukee or New York, are largely incapable of understanding their own best interests, and that it is only the police who can keep them alive.

Term-limited, bored and aimless after his 1997 reelection, Giuliani resorted to the time-honored New York mayoral custom of hurling brickbats at pretty much everyone. He denounced, with equal fervor, Yasser Arafat, “sacrilegious” art at the Brooklyn Museum, and the Commonwealth of Virginia, which he insisted should feel “obligated” to continue accepting his city’s garbage in light of New York’s “substantial cultural achievements.” He let an extramarital affair and his increasingly sordid family life play out in the public press. And for all that he mocks her now, when he had a chance to put everything on the line and run against Clinton for a Senate seat in 2000, he ducked the race, citing a prostate cancer scare. As accounts of his affair and his internal organs filled the tabloid covers, he devolved quickly into something of a buffoonish figure, the TMI mayor.

September 11 rescued Giuliani from inanity, made him “America’s mayor,” the term first bestowed upon him by Oprah Winfrey, at that lovely, ecumenical service for the 9/11 victims in Yankee Stadium. There was still time to restore a little of the old Rudy. He wouldn’t have been the first politician to have gone off the rails and then got hold of himself. But even when it came to his best moment, the lying and Trumpian blame-shifting wouldn’t stop.

Rudy had been in the street on 9/11 only because his emergency “command bunker,” which he alone had insisted on putting on the 23rd floor of 7 World Trade Center, was destroyed in the first minutes of the attack; Giuliani blamed the decision, falsely, on the security expert who had opposed the idea. Infinitely worse, testifying before the 9/11 Commission, Giuliani lied on the graves of the 121 firefighters killed when the North Tower collapsed, by insisting that they had refused his orders to evacuate the buildings. In fact, they had never received any order to evacuate, due to his administration’s eight-year failure to correct a malfunctioning inter-services communications system.

No one much noticed. The details of what really happened on 9/11 came out only long after Time named Rudy its person of the year for 2001. Giuliani cashed in while waiting for a moment to run for president, splitting his time between his law firm, his security firm, even his financial consulting firm. Like Trump, he could suddenly do anything; all he had to do was put his golden name on it. But much like his first mayoral run, the race ended up confounding Giuliani. His adopted party looked askance at his gay friendships, his third marriage and his increasingly erratic behavior. Giuliani pushed Bernie Kerik, New York’s police commissioner for the last 16 months of his mayoralty, to serve as interim interior minister in occupied Iraq and as U.S. secretary of homeland security—ideas that ended up as an unmitigated disaster for all concerned, and ultimately landed Kerik in prison. Giuliani was found to have taken on any number of dubious clients, including an admitted drug smuggler, the makers of OxyContin, various penny stock operations under investigation by the feds, and, ironically, the government of Mexico City, looking to reduce crime.

Despite vituperative, quadrennial speeches that roused the galleries—in 2004, Rudy actually told the Republican National Committee that he grabbed Kerik’s arm in the midst of the 9/11 attacks and exclaimed, “Thank God George Bush is president!”—Giuliani was fading, still fighting a culture war that went all the way back to his youth, and that diminished with every passing year that New York grew still safer, richer and more orderly without him. Only the rise of Trump, with his need to convince America that we are all living in a hellhole, provided Giuliani with a new forum for his particular brand of race-baiting urban demagoguery.

On television, his joy at being relevant again has been almost palpable. His big, orange, jack-o’-lantern head—is Giuliani even trying to outsquash Trump?—reduced to a caricature of slitted eyes and flashing teeth, he lisped eagerly, nearly drooling, about what a good case he would make against Clinton on her emails.

The dumbest thing F. Scott Fitzgerald ever wrote was that American lives have no second acts. We are nothing but second acts, endlessly repeated, and no one has scrapped for more of them than those two, shining icons of a New York that seems very far away now.

They’ve known each other a long time, Rudy and The Donald, and earlier this year Giuliani referred to Trump as a “close personal friend,” and “not the man you see on television,” but “a gentleman” and “a good father.” By February, Rudy was coyly refusing to quite endorse Trump, but already calling him “the best choice for president” in the Republican field, and telling the Washington Post, “He calls to check things out, or I’ll call him to say, ‘Donald, you’re going too far’ or ‘What you said was great’ or maybe ‘Change it a bit.’ It’s nothing formal. It’s kind of a running conversation.”

Maybe Giuliani can help Trump figure out how to win, and if he can, I suppose there will be still another second act for him, too, perhaps a stint as secretary of homeland security, or all-around eminence grise to l’orange. If that day comes, both Rudy and The Donald can go on saying how they saved us from a city and a nation they insisted were on fire, even if they had to strike the match to get it going. Rudy was never crazy, no more than Trump is himself. He was simply a restless spirit, feeding on anger, searching for another body to use.