Michael Kruse is senior staff writer at Politico Magazine. Taylor Gee and Lakshmi Varanasi contributed to this report.

Trump Tower opened in 1983—a gleaming, ostentatious building in a grimy, troubled city. At its base was an orange marble atrium with a waterfall and a clutch of boutiques that sold only the highest-priced jewelry, shoes and clothes. Outside, it was impossible to find a subway car not covered with graffiti, and a growing homeless population jangled cups for change; inside, the tower’s apartments were billed as “totally inaccessible to the public” and meant exclusively for “the world’s best people,” developer Donald Trump crowed. And in the aftermath of the fanfare-fueled debut of his eponymous tower—his grandest achievement as a builder, the most singular and physical manifestation of his ego and ambition—Trump walked into the bank of shiny gold elevators and ascended to his triplex penthouse.

If that elevator ride marked his ultimate arrival in New York, it also was a departure of sorts—up and out of the dirty, rattled, crime-ridden metropolis in which he came of age. In the 1970s, the city had teetered on the brink of bankruptcy and been terrorized by a serial killer. In the 1980s, murders soared toward 2,000 a year, and muscled volunteers calling themselves the Guardian Angels patrolled the subways in red berets in an effort to put frightened riders at ease. This was a nadir of New York—and Trump used it to his advantage, leveraging the city’s anxiety and uncertainty to secure the tax breaks that helped kickstart his career.


Ever since, his view of New York, and of urban areas in general, has remained as hardened as Mafia concrete. The Trump take on the city was evident in 1989, as he fanned the racially charged public frenzy around the Central Park Five rape case. Almost a decade later, it was on appalling display in his revealing pit stop as “principal for a day” at an impoverished South Bronx elementary school. During last year’s campaign, it inspired his statistically flimsy rhetoric about urban blight. And in the White House, it has informed his budget proposals that will punish cities in particular.

Almost uniquely among famous city-dwellers, Trump has made his bones railing against cities, constructing escapes from them, taking from them while complaining about them—and, most remarkably, in his bid to be president, describing America’s now often prosperous cities in an alarming, arm’s-length way that resonates with many white rural voters and suburbanites but with few people who actually have lived in a city at any point in the past decade or more.

“How could a guy who lived in New York have these provincial, redneck attitudes?” says Ken Auletta, who grew up in Brooklyn and writes for the New Yorker. “I’m not sure I have an answer—other than, obviously, he lived apart. He got into his elevator.”

The Bronx, early 1980s In 1982, filthy train cars, crumbling infrastructure, crime and graffiti brought New York subway ridership to its lowest levels since 1917. | John Conn

What went wrong between Trump and cities? The roots of this antagonistic relationship go back to before even Trump Tower. Trump grew up in perhaps the most suburban setting possible within New York’s municipal boundaries, in a columned mansion in quiet, leafy Jamaica Estates, Queens. His real estate developer father had his office in Coney Island in Brooklyn. But in 1971, at 25, Trump left to pursue wealth and fame in what he considered the most important arena—Manhattan. He chose to live on the tony Upper East Side.

The city, for the admittedly shallow, ever-transactional Trump, was a place not to be experienced so much as exploited. The interest was not mutual: To most of New York’s elite, whose acceptance he sought, Trump was far too brash and gauche. He was an outer-borough outsider, bankrolled by his politically connected father. He wanted to be taken seriously, but seldom was. “He’s a bridge-and-tunnel guy, and he’s a daddy’s boy,” Lou Colasuonno, a former editor of the New York Post and the New York Daily News, said in a recent interview. “There were people who laughed at him,” former CBS anchor and current outspoken Trump critic Dan Rather told me. While his loose-lipped, in-your-face approach appealed to blue-collar types in spots in Brooklyn, Staten Island and Queens, many in Manhattan, Rather says, considered him “repulsive.”

For Trump, as inhospitable as he found the city on the street, the parlors of high society were equally problematic—and he created a refuge. It was some 600 feet in the sky, where the faucets were gold, the baseboards were onyx and the paintings on the ceiling, he would claim, were comparable to the work of Michelangelo in the Sistine Chapel. At the top of Trump Tower, biographer Tim O’Brien told me, he could live “at a remove from the city and its amazing bloodstream of ideas and people and culture”—“encased,” added fellow biographer Gwenda Blair, “within this bubble of serenity and privilege.”

Times Square, 1980 In 1981, Rolling Stone called the section of 42nd Street bordering Times Square the “sleaziest block in America.” | Richard Sandler

Out his bronze-edged, floor-to-ceiling windows, Trump could see Central Park to the north and the Hudson River to the west. He could see south to the Empire State Building and the twin towers of the World Trade Center. He could see the tops of yellow cabs and the tiny people moving around on the sidewalks some 60 stories down. What he could not see, though, or hasn’t, is the transformation that has taken place, as New York morphed from what it was in the ’70s and ’80s into the cleaner, safer enclave for the smart and the rich that it is today. The trend has held throughout America as well, as rural and suburban areas started to sag while urban cores became hip engines of growth and innovation.

Cities changed. Trump did not.

How, at a moment when American cities are at a peak of wealth and success, can Trump argue so persistently against them? The answer starts with the New York that made him.



***

The deal in the ’70s that launched Trump, the refurbishment of the decrepit, aging-brick Commodore Hotel into the sleek, glass-wrapped Grand Hyatt by Grand Central Station, would not have happened—could not have happened—if New York hadn’t been a barely functioning hellhole. It required his father’s money, credit and clout. Just as definitively, it depended on his father’s long-standing relationships with the mayor (Abe Beame) and the governor (Hugh Carey), both of whom had deep Brooklyn ties. But it was the precise timing that led to the tax breaks, and they are what made it work. “It is made possible,” says Kim Phillips-Fein, the author of Fear City, her acclaimed, recently published book about New York in that era, “in large part by the city’s fiscal desperation.”

The Manhattan Trump inserted himself into was at a low point, reeling and vulnerable, and the city as a whole was listing. In October 1975, President Gerald Ford said he was “prepared to veto any bill that has as its purpose a federal bailout of New York City.” “FORD TO CITY: DROP DEAD,” read the blunt headline in the New York Daily News. Only two months later, Ford in fact would pledge $2.3 billion in federal assistance to the city, but budget cuts nonetheless necessitated layoffs of public employees in New York for the first time since the Great Depression. That included cops. “WELCOME TO FEAR CITY,” warned flyers distributed by the protesting police union to arriving tourists.

Image Subway, 1980 In 1979, police logged 250 felonies per week on the New York subway system. | Bruce Davidson/Magnum

In 1976, an elderly couple who had lived in the Bronx for more than 40 years killed themselves. “We don’t want to live in fear anymore,” they wrote in their joint suicide note. And 1977 was worse. The serial killer David Berkowitz, or “Son of Sam,” murdered six people and wounded another nine before he was caught that summer—“NO ONE IS SAFE,” blared the front of the New York Post—and the citywide blackout in muggy mid-July triggered rampant looting that was seen by many as evidence of an angry, anxious populace, a city on the edge. “This wounded Paris, this hemorrhaging Athens,” Jack Newfield and Paul Du Brul wrote that year in their book, The Abuse of Power: The Permanent Government and the Fall of New York.

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This is the context in which Trump was able to cross the Queensboro Bridge in a Cadillac convertible and ultimately secure “the most extraordinary structure of city and state tax breaks ever arranged,” in the words of the late Wayne Barrett in the Village Voice—unprecedented public subsidies of some $360 million over 40 years. “He leveraged the fear that was rampant in New York, of the city going bankrupt, of racial unrest, of manufacturing fleeing, of imminent collapse,” Blair says. The city helped Trump much more than Trump helped the city. But ever one to tell and sell his story before others can backfill facts, Trump pitched his breakthrough deal as an act of civic-minded selflessness. “I think we’ve proven people still have a lot of confidence in the city,” he said in 1977 to a reporter from the New York Times.

The Commodore Hotel he plucked for $10 million from the scrapheap of the bankrupt Penn Central railroad sat at 42nd Street and Lexington Avenue, adjacent to Grand Central Terminal—an area that now feels like most of the rest of money-soaked Midtown Manhattan but at that point felt “like shit,” says Barbara Res, who was working for Trump on the Commodore project. There were cat-killing rats in the basement of the hotel, she recalls, and prostitutes operating out of its rooms. City leaders worried the area would turn into another Times Square, which had become a low-class bazaar of peep shows and pornography dives. “The Commodore was really run-down, and Grand Central was in really bad shape,” Res says. “You didn’t think of it as a nice part of New York at all.”

For Trump, this beleaguered city was a personal stage as well, a kind of backdrop against which he could shine. Clad in three-piece, flared-leg suits, riding around Manhattan in a limousine with DJT license plates driven by a laid-off cop playing the role of armed-guard chauffeur, Trump preferred East Side bars and hot spots frequented by fashion models—Harper’s and McMullen’s and Maxwell’s Plum, and the sweaty, celebrity-spotting bacchanal at Studio 54, where he “would watch supermodels getting screwed,” he would say later to O’Brien, the biographer, “well-known supermodels getting screwed on a bench in the middle of the room.” Trump wasn’t out to get drunk—he was, and is, a teetotaler—but to be seen.

If he had expected New York to grant respect the way it had handed out tax breaks and opportunities for sheer publicity, he was mistaken. Critics in the pages of the Times called him “overrated” and “totally obnoxious.” It bothered him that he could put up such a glossy building and still be so readily dismissed as an arriviste. “If I were Gerry Hines in Houston,” he told Marie Brenner for a profile in New York magazine in 1980, referring to the billionaire real estate entrepreneur in Texas, “I would be the most important man in the city—but here, you bang your head against the wall to try to get some nice buildings up, and what happens? Everybody comes after you.”

But Trump attacked New York, too. He had, for instance, valuable art deco friezes jackhammered off the face of the Bonwit Teller building during its demolition—even after he had promised to donate them to the Metropolitan Museum of Art. It was a literal and visceral assault against the exact sort of New Yorker who found him so distasteful.

1981 Many New Yorkers welcomed the so-called Guardian Angels, private citizens who patrolled subways to deter crime. Others considered them vigilantes. | Getty Images

They were “nothing,” Trump said. They were “junk.”

They were not, said a man from the Met. “They were irreplaceable architectural documents.”

“Obviously,” huffed an editorial in the Times, “big buildings do not make big human beings.”



***

The building that took the place of Bonwit Teller was Trump Tower, a branding achievement that, once finished and polished, made Trump a new echelon of famous around the country and even the world. In the city, though, it did not broadly elicit the esteem from the elite that he craved.

An anonymous sniper in a story in Town & Country described him as a “corporate vandal.” The Times said his critics called him “a rogue billionaire, loose in the city like some sort of movie monster.” As Trump grew increasingly acquisitive in Atlantic City, people in Manhattan diminished him as “a casino operator in New Jersey,” essentially de-New Yorking him.

“He was,” says Pete Hamill, the longtime columnist who had stints as the editor of both the Post and the Daily News, “an object of mockery.”

Early ad copy for Trump Tower apartments embraced the escapist imagery of the elevator. “You approach the residential entrance—an entrance totally inaccessible to the public—and your staff awaits your arrival,” the come-on cooed. “Quickly, quietly, the elevator takes you to your floor and your elevator man sees you home. You turn the key and wait a moment before turning on the light. A quiet moment to take in the view—wall-to-wall, floor-to-ceiling—New York at dusk. Your diamond in the sky. It seems a fantasy. And you are home.”

1979 About a dozen undercover policemen, armed with battering rams and hydraulic drills, forced their way into this fortified apartment. They confiscated boxes of drugs, but the distributors got away. A few years later, crack cocaine would arrive in the city, beginning a decade-long epidemic. | Leonard Freed/Magnum

Once ensconced in his tower—Trump’s office was on the 26th floor, and he and his first wife and their three young children moved into the penthouse in early 1984—his vantage point had literally changed. George Arzt, a prominent public relations man in Manhattan, then was a reporter for the Post, and Trump, he told me recently, used to call him a lot. “And he would say, ‘I’m looking down from my office … ’” A close former employee would get similar calls from Trump from the penthouse. “One of the things he does a lot,” this person said in a recent interview, “is look down.”

Trump looked down at Wollman Rink, the ice skating facility in Central Park, which the city had spent six years and $12 million trying unsuccessfully to renovate—and he decided in 1986 he should be the one to fix it. Mayor Ed Koch and the city accepted his offer, and he did repair the rink, in less than six months and some $800,000 under budget. In the end, Trump not only celebrated what he had done—he highlighted what the city had not. “I guess it says a lot about the city,” Trump said at the grand opening, “but I don’t have to say what it says.”

He looked down in the mid-1980s, too, at his plot of land over on the West Side—on which he wanted to put six 76-story buildings, 8,000 apartments and the world’s tallest skyscraper. It never happened, partly because Ed Koch refused his request for a billion-dollar tax break. Trump, as always a mixture of public-subsidy suckler, self-appointed savior and plainspoken critic of the city, lambasted the mayor—“a moron,” “a disaster.” “Greedy, greedy, greedy,” Koch retorted. “Piggy, piggy, piggy.”

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From the opening of Trump Tower until earlier this year, when his address became 1600 Pennsylvania Avenue, Trump never moved. In the three and a half decades he lived at 721 Fifth Avenue, New York, New York, “one of the greatest residential addresses in the world,” he would say, the city below him changed dramatically.

New York’s comeback from the trauma of the ’70s was bumpy and unbalanced. Wall Street in the ’80s boomed, as did Trump’s Fifth Avenue, but the homeless population spiked, poverty continued to punish slums in Brooklyn and the Bronx, and the fear of crime still gripped the city. When the white vigilante Bernhard Goetz shot four black teens who allegedly tried to rob him on a train in Lower Manhattan in 1984, many New Yorkers all but cheered. A tip line set up by the Daily News was inundated with calls professing sympathy and support—for the shooter. “It did not seem to matter to the callers that the blond man with the nickel-plated .38 had left one of his four victims … with no feeling below the waist, no control over his bladder and bowels, no hope of ever walking again,” the newspaper wrote a week after the crime. “To them the gunman was not a criminal but the living fulfillment of a fantasy.”

Such was the psyche of the city in 1989, when a 28-year-old white, female, Wellesley- and Yale-educated investment banker was beaten and raped in Central Park. Five black and Hispanic teenagers were arrested, charged and convicted—wrongly, on coerced confessions, it eventually turned out. At the time, though, the case became “a milestone in the public’s sense of helplessness,” as the Times put it. News coverage clamored about these “wilding” teens, “animals on a feeding frenzy.” “WOLFPACK’S PREY,” said the headline in the Daily News. The judge who sentenced them said in court that they had made Central Park a “torture chamber of mindless marauding.” He lamented that “the quality of life in this city has seriously deteriorated.”

Clockwise, from left Subway, 1980; Lower East Side, 1980; Subway, 1980; Brooklyn, 1981. | Bruce Davidson/Magnum (2); Jamel Shabazz (2)

Trump, who in the ’70s had identified the city’s insecurity and fear and found a way to benefit from it, now tried to do so again. He paid a reported $85,000 to put in four New York newspapers a full-page ad that called for the death penalty. “What has happened to our City?” he wrote in the ad. “What has happened to the respect for authority, the fear of retribution by the courts, society and the police for those who break the law, who wantonly trespass on the rights of others? What has happened is the complete breakdown of life as we knew it.” He seethed about “roving bands of wild criminals” and “crazed misfits” and longed for a time when he was a boy, when cops in the city roughed up “thugs” to give people like him “the feeling of security.”

“The ad for the first time reveals all the rest of the things that anybody would want to know about Donald Trump,” columnist Jimmy Breslin wrote the next day in Newsday. Trump had “destroyed himself” with the ad, Breslin wrote, “for all demagogues ultimately do that.”

Getty Images; Library of Congress

The more complicated, uncomfortable reality, though, is that what Trump said in his ad about the Central Park Five was not universally unpopular around the city. Far from it. And he might not have been beloved—but that didn’t mean he wasn’t being listened to. The ad spawned stories in the Washington Post, the Chicago Tribune, the Los Angeles Times and USA Today, as well as a spate of letters to the editor in New York.

It read like a crystallization of how he saw the city, that city, in the ’70s and ’80s—and it reads, in retrospect, as a searing preview of the race-based, law-and-order rhetoric that powered his presidential campaign.

“Mayor Koch has stated that hate and rancor should be removed from our hearts,” Trump said in the ad. “I do not think so. I want to hate these muggers and murderers … and I always will.”

“Let’s all hate these people,” he said on CNN, “because maybe hate is what we need if we’re gonna get something done.”



***

The convictions in 1990 of the innocent Central Park Five coincided with surprising news of a different sort: that Trump’s own balance sheet was even worse than the city’s had been. The riches-to-riches kid from Jamaica Estates actually was billions of dollars in debt. “CASH-TASTROPHE,” screamed the Daily News. Arzt, the Post reporter who by now was the head of New York’s Fox affiliate, did a whole week of special shows on Trump’s collapse. He couldn’t help but notice that his ratings more than doubled. “He is a ratings generator,” Arzt told me recently. “People like entertaining, and he’s entertaining—and there are a lot of people who hate him.” Some of the surge in viewership, Arzt figured, was simple schadenfreude.

Image Clockwise, from left New York, 1981; Manhattan, 1987 (LL Cool J); 34th Street, 1989; 57th Street, 1985.

To the consternation of those who loathed him, though, this was not the end of Trump. As he spent the first half of the ’90s trying to avoid filing for personal bankruptcy—he pulled it off, of course, thanks to family money, permissive banks and corporate bankruptcies—New York and other cities began to boom, while leaving behind the areas at their outer reaches, practically reversing the dynamic that defined the socioeconomic tides of Trump’s formative ’70s and ’80s. Once-derelict downtowns became trendy, glistening capitals of commerce, juice bars, yoga studios and million-dollar condos. Harlem’s first Whole Foods is set to open in July.

But Trump’s view of cities did not appreciably keep pace with this shift. Throughout his presidential campaign, he talked to his crowds about the “horrible” “inner cities,” the “terrible” “inner cities,” the “crime-infested” “inner cities,” the “inner cities” that were “sad,” the “inner cities” that were “suffering,” the “inner cities” that were “almost at an all-time low,” the “inner cities” that were “more dangerous than some of the war zones that we’re reading about.”

“You look at the inner cities,” he said in Florida less than a month before the election, “and you see bad education, no jobs, no safety. You walk to the grocery store with your child, and you get shot. You walk outside to look and see what’s happening, and you get shot.”

“We’re going to work on our ghettos,” he said in Ohio less than two weeks before the election. “The violence. The death … ”

The Bronx, 1981 Crime on the subway became so common that, starting in June 1985, at least one police officer rode every train between 8 p.m. and 6 a.m. as part of an effort to restore public confidence in the transit system. | Martha Cooper

American cities have problems, to be sure, but people who live in them didn’t recognize the way Trump talked about them. And on November 8, cities rejected him. And the city in which he was born and raised and in which he has lived and worked his entire adult life rejected him resoundingly. Every borough other than Staten Island posted a landslide against him—Hillary Clinton garnered 88 percent of the vote in the Bronx, 86 percent in Manhattan, 79 percent in Brooklyn, 75 percent in his native Queens. He was booed at his own polling place—Public School 59, on 56th Street, less than half a mile from Trump Tower. The first native New York president since Franklin D. Roosevelt was elected by people not in the city, but in depressed, drug-ravaged small towns and outer suburbs—by people whose profound disconnection from urban America left them open to the twisted version of the “city” that Trump described.

“It’s amazing,” says Mitchell Moss, a professor of urban policy and planning at New York University. “He operates out of New York City, but his Weltanschauung”—Trump’s worldview—“is a suburban golf course, a suburban country club.”



***

“New York is either going to get much better or much worse, and I think it will get much better,” Trump had predicted in the Times back in 1976. But he added: “I’m not talking about the South Bronx. I don’t know anything about the South Bronx.”

In 1997, he had a chance to learn—on a trip to P.S. 70 to be “principal for a day.”

Trump was seven years removed from his near-fatal, early-’90s failures—and still seven years away from his NBC-aided full resuscitation in the form of “The Apprentice.” He had talked about running for president in the late ’80s, and he would talk about it again in 1999 as a member of the Reform Party, but mostly he was known for being known at the time, famous for being famous, and publicity was his fuel.

In this respect, his visit to the school made sense. It was set up through a program run by an organization called PENCIL—Public Education Needs Civic Involvement in Learning. The point, the president of PENCIL told the Times, was twofold: to give students a burst of inspiration from a person seen as a success and “to bring in people who should see the schools and who wouldn’t otherwise.” Trump fit the bill. He had told the Times, after all, that he had “never even thought about” sending his children to public school, which he explained was “one of the advantages to wealth.”

P.S. 70 was home to 1,700 students crammed into classrooms meant for 300 fewer students. All but 3 percent of the children were poor enough to qualify for free lunch. The chess team was having a bake sale to rent a bus to take them to a national competition in Tennessee.

Thousands of successful and prominent people had been PENCIL “principals,” giving schools money and books, as well as their attention and time. Trump, on the other hand, came off to the educators in the South Bronx like a Victorian lady forced to walk through a slum, clearly ill at ease with the real grit of street-level urbanity. Trump was scheduled to stay all day. He ended up leaving before noon.

Central Park, 1986 After renovations of Central Park’s ice rink dragged on for six years, Donald Trump persuaded Mayor Ed Koch to let him fix the rink—in four months. | Harry Benson/Getty Images

Before he departed in his limo, on a tour of the school, according to a report from The 74, a news organization covering education in America, Trump took a tissue from his pocket and used it so he wouldn’t have to touch the railing on some stairs. In the cafeteria, a mop-wielding science teacher on lunch duty joked to Trump, “How are you with mopping up vomit?”

“I don’t do vomit,” said Trump.

At the bake sale for the chess team, he dropped a gag $1 million bill into a basket—then gave them a relatively meager $200 instead.

Hundreds of fifth-graders gathered in the auditorium to listen to Trump. “Is there anyone here that doesn’t want to live in a big, beautiful mansion?” he asked them, the Times reported. “You know what you have to do to live in a big, beautiful mansion?”

“You have to be rich,” one student offered.

“That’s right,” Trump said. “You have to work hard, get through school. You have to go out and get a great job, make a lot of money, and you live the American Dream.”

“Money does not buy happiness, but it helps,” he said to the students. “Always remember that.”

And he asked them to write their names on pieces of paper so he could pick 15 of them to come get a free pair of sneakers at the new Nike store in Trump Tower—a building smack in the center of rich, bustling, flourishing Manhattan, a building, he told them, that was in “the inner city called 57th and Fifth.”