“They Saw the World in This Dog-Eat-Dog, Manichaean Way”: The Ugly ’90s Roots of Rudy’s Bond With Donald Trump
Published November 10, 2019 in
Trump saw Giuliani harness racism, say-anything recklessness (“bullshit!”), and a 24-hour news cycle to win two terms as mayor of New York City. Those lessons became his blueprint.
Rudy Giuliani’s political career, and the whole Giuliani-era New York of the 1990s, began on a muggy September day in 1992 when some 10,000 police officers descended on City Hall in downtown Manhattan, ostensibly to protest Mayor David Dinkins and his call for new civilian oversight of the police. The day quickly descended into chaos; cops knocked over police barricades and stormed the steps of City Hall, swarming onto the Brooklyn Bridge and stopping traffic for almost an hour, and spilling out of the bars on Murray Street. According to longtime Village Voice reporter’s Wayne Barrett’s biography of Giuliani, the cops held signs that said “Dump the Washroom Attendant” and “Mayor, have you hugged your dealer today.” A pair of police officers stopped Una Clarke, the first female Caribbean-born elected official in New York, and one, cupping a beer in his hand, said to the other, “This nigger says she’s a member of the city council.”
And at the center of it all was Rudy Giuliani.
It had been three years since he lost his first bid for the mayoralty, the first real setback in his steady climb up New York’s political pole, one that had seen him hailed as a crime-fighting, corruption-busting hero from his perch as U.S. attorney for the Southern District of New York. But a new Giuliani emerged on that day in September, one who embodied all of the frustrations of New Yorkers embarking on the final decade of the 20th century, where crime and murder were rampant, racial tensions spilled out into the open, AIDS gutted the city’s art and club scene, and the city yearned for someone, anyone, who could quell the disorder and make it work again.
Giuliani spoke on the back of a flatbed truck, surrounded by drunken cops chanting, “Rudy! Rudy!” And he laced into Dinkins and the supposed culture of permissiveness he had brought to Gotham, speaking next to a chain-locked dummy in a police uniform and shouting “bullshit!” into a microphone.
It was supposed to be the end of Giuliani’s political career. The police riot brought him condemnation from all the usual circles in the city’s elite: The Daily News called his conduct “shameful” and “pandering”; the Times accused him of being “reckless” and his performance “barnyard.” He is “betting—irresponsibly—that divisiveness will win votes,” the paper editorialized.
But Giuliani never backed down, never apologized, and never even admitted to seeing much of the more alarming chants and protests that day.
Rather than killing Giuliani’s political career, it saved it. When he ran for office a year later, Giuliani accused Dinkins of being too willing to retreat “into black victimization.” He scored the backing of the police union, and ran up big numbers not just among outer-borough white voters, but among just enough white Manhattan liberals to eke out a roughly 2% victory over Mayor Dinkins.
We don’t know where Donald Trump was that day. His early 1990s were much like the city itself—Trump businesses declared bankruptcy four times between 1991 and 1992, and his efforts to become something more than a developer were floundering too. He was at the time engaged in an effort to develop a massive parcel of land on the far west side of Manhattan, a 57-acre project that would come to be known as Trump Place and Riverside South. A city councilman declared that the project would reverse the prevailing sentiment at the time, that the trajectory of the city was “all downhill.”
Meanwhile, Trump was learning that the public, the new 24-hour cable-news stations, the city’s ravenous press corps, and its gossip columnists, who were then among the highest-paid print journalists in the country, were interested in the saga of his private life as his divorce played out almost daily in the newspapers—not just the Post’s “Best Sex I’ve Ever Had” headline, which purported to be Marla Maples’s description of her new beau but turned out to be piped by Trump himself, but how the electricity mysteriously went out at ex-wife Ivana’s party at a building he owned; how he went to legal war with her over a thinly veiled tell-all novel about their marriage; and how he got Maples a leading role in The Will Rogers Follies on Broadway.
Giuliani and Trump did not know each well then, but they came into their own during the same decade in the same city—a city not yet the thundering world capital it is now, and not yet fully recovered from the near bankruptcy and strife of the 1970s and 1980s, a city where a politician could engage racially tinged support of law enforcement, nose-thumbing at respectable opinion, a teetering-on-the-edge political rally, an unwillingness to apologize, and still rise to the heights of power.
In other words, a political playbook put into action every day in a city about 250 miles away and nearly 30 years later. Trump surely never made a study of Giuliani’s executive-management style, but it is hard not to notice how he absorbed it. Giuliani delighted in insulting his constituents, especially if there was a microphone or a camera around. He willfully defied the city council and rulings from the courts in the name of all-out political war. And whenever he felt threatened, Giuliani went back to the people who elected him, the outer-borough middle-class (or lower) white voters who believed him to be the lone bulwark against a rapidly changing city.
The city elected Giuliani a year after the police riots, and he had no qualms about not just sweeping the homeless off the street and out of doorways, but criminalizing those who tried to help them. For his efforts, he spent most of his two terms as a civic and national hero, the crime-buster who tamed the bureaucracy and proved that urban America could work. The city of Night Court and Fame, dangerous and idiosyncratic, gave way to Seinfeld and Sex and the City—arch, ironic, awash with money.
Trump was surely too busy dealing with the aftermath of his businesses’ bankruptcies to be taking notes from Giuliani on how to be a political leader. Although he now calls Giuliani the greatest mayor the city ever had, the two were not close then. But it often seems like Trump is running in his head a playbook he learned from Giuliani. Remember Trump’s first months in office, when a snowstorm was bearing down on Washington, D.C., and he tweeted a photo of himself with the mayor and first responders? It was bizarre behavior from a president, but exactly what a take-charge mayor would do. And it was reminiscent of an incident that occurred after Giuliani was elected mayor, but before he was sworn in, when a 13-year-old boy was hit by a taxi and injured critically. The paramedics wanted to take him to the nearest trauma center. The boy’s mother wanted to take him to a different hospital. Giuliani intervened, arguing with the EMS to listen to the mother, their professional expertise and obligations be damned. And afterward he boasted of the incident. “What I said when I ran for mayor is that New York City is going to get a different kind of mayor,” he told reporters. “You’re going to get a hands-on mayor, somebody who acts to help the citizens of this city.”
Trump today can dominate the news with an errant tweet or by shouting over the whirling blades of the presidential helicopter on the White House lawn. Giuliani had different tools, but he readily deployed them. “There was just so much news,” said David Seifman, the City Hall bureau chief for the New York Post who covered every New York mayor going back to Ed Koch before retiring this year, still wincing at the onslaught the mayor could unleash. “People wanted to feel like someone was in charge, and Rudy gave them that.”
Leaders of New York other than Giuliani, and leaders of the United States other than Trump, have tended to their images carefully, fearful of overexposure, or of making a gaffe, or even of just wasting time on a constituency that lacked the power it believed itself to have. But Giuliani made it a point to put on a show. “At 2 p.m every day, Rudy would just whip his dick out and go yell at people,” said Rick Wilson, then Giuliani’s media consultant and now a prominent “Never Trump” Republican. “We had a strategy that we were going to go out and commit news every day. Politicians are raised to avoid controversy. Giuliani understood, and Trump understands, the value of a different model where you are trying to confront the media to divide the media from the people, so that the people don’t see the media as a legitimate source of truth and information.”
And just like Trump, even as he sits as leader of the free world, counts his Time magazine covers, and live-tweets his mentions on Fox & Friends, Giuliani’s DGAF attitude belied someone who was obsessed with seeing himself covered, who used to get in the “Ice Cream Truck,” the white GMC Suburban van that would whisk him around the city and turn on 1010 Wins and 880 and smile at the mention of his name. “Both of them grew up in a Page Six world,” said Wilson. “You are either making news or you are nothing.”
For Giuliani, that news, more often than not, meant playing to the lowest common denominator: whites largely living in the outer boroughs who had been dismayed by the turn the city had taken over the previous decade, who considered Bernhard Goetz, the “Subway Vigilante,” a hero. Giuliani let it be known that their New York was his.
The denouement in Giuliani’s tenure came late in his second term, when a few undercover police officers approached a security guard standing outside the Distinguished Wakamba Cocktail Lounge, a hole-in-the-wall bar in the garment district. One tried to buy drugs from the man, whose name was Patrick Dorismond. Dorismond, who’d been inside grabbing drinks with friends, told them he didn’t have any. A scuffle ensued, and Dorismond was killed. In the outrage that followed, Giuliani ordered Dorismond’s police records unsealed to show that he had several misdemeanor arrests, despite the fact that some people considered doing so against the law. Giuliani insisted that Dorismond was “no altar boy,” even though, in point of fact, he had been, and also went to the same Catholic school that Giuliani attended years before. “It was like Trump drawing with the Sharpie on the hurricane map,” said Mark Green, the city’s public advocate at the time and a consistent Giuliani foil. “He was violating the law, and violating this poor guy’s privacy, just to make a political point.”
It was a play Giuliani would run over and over; much as Trump warned before the midterms of a caravan of migrants coming to murder neighborhood children, whenever Giuliani got the chance, he would prey on the most disempowered groups of New Yorkers—squeegee men, falafel-cart vendors, ferret owners. He reportedly refused to meet with black elected officials in the city, no matter their rank or their concerns. “I don’t like to define people this way, typically,” former Manhattan borough president C. Virginia Fields, who was one of those elected officials the mayor refused to meet with, recalled. “But he was just an absolute, out-of-control racist.”
Giuliani, too, had begun to seem a bit unhinged. Megalomania and a desire to stage-manage every aspect of the churning city’s life began to eat away at his public standing. When New York magazine launched an ad campaign that ran on city buses with the tagline “possibly the only good thing in New York Rudy hasn’t taken credit for,” the mayor ordered the Transit Authority to take the ads down. “He wants to tell people what to eat and how to cross the street,” a Brooklyn city councilman told the Washington Post midway through Giuliani’s second term. “We elected a mayor. I don’t need a father.”
Between the winter of 1998 and the spring of 2000, Giuliani’s approval rating dropped an astonishing 37 points. Order had been achieved. The self-satisfaction of the Bloomberg years—where to want to live anywhere else meant that you were, in some sense, kidding—was dawning, and the constant conflict and drama of Giuliani’s New York had become exhausting.
The rest of the world moved on. New York ceased to be the City of Fear and became the City of Fun. Al Sharpton, a pariah in Giuliani’s New York, was welcomed into City Hall in Michael Bloomberg’s, and race relations cooled. The public demanded not just safety, but accountability from the police. Middle-class families stayed in the city to raise their children.
But neither Giuliani nor Trump moved on. This bifurcation, the division of us and them, became a permanent state of their consciousness, their only trick, still being played 20 years later. And the arsenal of tactics has hardly evolved; it’s simply been repurposed to deal with new circumstances.
So it makes sense that, these days, Giuliani is the rare figure in Trump’s orbit whom the president seems hesitant to toss aside, despite his glaring insufficiency to the current moment. They are creatures of the same town, of the same time. “I think for both of them, it was this period they just remain sort of forever stuck in,” said Wilson. “They started seeing the world from the window of a fortified limousine, and they saw the world in this dog-eat-dog, Manichaean way. They just stopped evolving.”
