Michael Kruse is a senior staff writer for Politico.

The week before Thanksgiving in 1985, a 39-year-old Donald Trump announced his plan to make sure nobody would ever forget him.

At a showy news conference at his sleek, glass-wrapped Grand Hyatt in midtown Manhattan, and later that evening at a cramped, tense community meeting in the cafeteria of the John Jay College of Criminal Justice on the Upper West Side, Trump unveiled drawings and models of his vision for the old Penn Central rail yards on the bank of the Hudson River. It wasn’t just the largest undeveloped tract of land in Manhattan; it was “the greatest piece of land in urban America,” he crowed. And on those 76 acres, he intended to build nearly 8,000 apartments and condominiums for up to 20,000 people, almost 10,000 parking spots, some 3.6 million square feet of television and movie studio space, and some 2 million square feet of “prestigious” stores. There would be no fewer than six 76-story towers, and looming atop it all one unprecedented skyscraper twice that height. It was a behemoth endeavor meant to go, his promotional materials proclaimed, “beyond the grandeur and excellence that has become synonymous with projects bearing the Trump name.”


This was supposed to be his legacy. Not Trump Tower. Not a clutch of casinos. Certainly not a political office of any kind.

In a metropolis of superlatives, he was striving to be New York’s biggest builder, a cocksure maker of tangible, unmissable things—and here, now, he wanted to build a city within the city, a conspicuously separate entity, of a style and scale no one had accomplished, not even the man who had shaped modern New York, Robert Moses. It was, in the words of the New York Times, his “bid for immortality.” First, he called it Television City; then, simply and unsurprisingly, Trump City. That centerpiece skyscraper would be the world’s tallest building, and he was going to live at the top.

And he failed.

Confronted over the span of two decades with a complicated thicket of social and governmental interests, frustrated by the incremental realities of bureaucracy and stymied by a disciplined, well-funded and committed opposition, Trump raged and feuded with nonpliant politicians and intractable citizens and critics from an established intellectual elite. In the end, nothing even approaching his grandest ambition was ever built. No other chapter in Trump’s long life reveals more about the man who now inhabits the Oval Office. “It’s all a wonderful sort of mosaic,” says Jim Capalino, one of New York’s most prominent lobbyists, who worked for Trump at the time, “of all of the characteristics and all of the personality traits and bluster and bravado and insecurity that are … shaping his presidency.”

The behavior of Trump during his manic first year and a half as president that has most confounded observers has its clear precursors in the war he waged on the edge of Manhattan. Evident then as now are a bullheaded disregard for nuance and detail, unpredictability magnified by impulsivity—and ultimately a peculiar strain of pragmatism some see as admirable and others consider merely cold-eyed. The insights the saga provides into Trump could fuel a playbook for the current “resistance” battling him and his administration—but also serve as a reminder of the strengths that make him nearly impossible to back into a corner. Thwarted by his opponents and weakened by the consequences of his own worst attributes, Trump actually did come away with something. Television City never happened, and Trump City never happened, either, but Trump nonetheless pocketed millions of dollars. Buildings were built. And some of those buildings still bear—at least for now—the name Trump Place.

An aerial map of New York City with a red box overplayed to show the location for the proposed “Trump City” development. | Wikimedia Commons

“I’ve always given Trump credit,” says Roberta Brandes Gratz, a journalist and an urban critic who was one of his harshest foes, “for recognizing that defeat was staring him in the face—and switching gears.”

“He was a survivor and a chameleon,” says Rich Herschlag, chief borough engineer for Manhattan in the 1990s. And as much as some people see a string of losses, Herschlag came to view the actual result on the Upper West Side as a triumph for Trump, likening it to the “umbilical cord” connecting the man then to the man now. “Without it,” he says, “it’s pretty safe to say he would have been selling blenders on cable television.”

Trump found a way to win after all—with the help, remarkably, of enemies he converted to allies. What looked like Trump’s white whale in the ’80s ended up in the ’90s being key to his ability to dodge personal financial ruin and permanent reputational stain. He got to keep selling—not blenders on cable television, but himself, on NBC, in prime time, with “The Apprentice,” which amounted to the groundwork for his presidential bid.

“I think he thought he got away with something there,” says Brendan Sexton, a former president of the Municipal Art Society, an organization more than a century old that promotes historical preservation and sensible development in New York—and that tangled with Trump in this instance before ultimately teaming up with him. “And maybe he did.”

I asked Sexton what lessons he took from his experiences with Trump on the Upper West Side.

“That what he does, he has been successful at,” he said. “And that it’s important to recognize that, or you go into the next discussion overconfident, thinking that he couldn’t possibly pull this crap off. And you wake up six months later, look around, and wonder, ‘How the hell did he pull that crap off?’ And that’s a real danger. And it keeps happening.”



***

Trump’s obsession with the site he ultimately wanted to turn into his own city started when New York was a fiscal wreck and desperate for any new economic activity.

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In the mid-1970s, Trump obtained options to develop three of the choicest assets of the bankrupt Penn Central Railroad—the crumbling Commodore Hotel at Grand Central Station, the West Side rail yards running from 30th to 39th streets and those running from 59th to 72nd streets. The properties needed a developer “who seemed best positioned in the New York market to get rezoning and government financing,” Ned Eichler, a vice president of Palmieri and Co., the firm appointed to dispose of the real estate of the bankrupt railroad, told reporter Wayne Barrett in the Village Voice in 1979. Zoning, Eichler told Barrett, is a “highly political activity,” especially in New York, and there had not been a “rezoning of this magnitude on a piece of property this politically sensitive in the recent history of the city.” Eichler’s assessment was that Penn Central would benefit from having a developer who was “very, very high in his political position.” Trump was not yet 30 and completely unproven, but thanks to his father’s considerable wealth and political connections, he was just that kind of developer.

The Palmieri people in charge of the Penn Central properties had pegged the younger Trump to be in some sense as desperate as the city was—desperate to earn the approval and affection of his flinty, businesslike father by outdoing him. John Koskinen was the commissioner of the Internal Revenue Service in President Barack Obama’s second term. Back then, though, he was a Palmieri principal along with Eichler. While Eichler did the railyards negotiations, Koskinen handled the Commodore. He found Trump “irrepressible.”

Bernard Gotfryd/Getty Images

“He had a tremendous amount of energy,” Koskinen told me.

Trump took his option on the Commodore and turned it into the Grand Hyatt. He took his option on the yards from 30th to 39th Streets and turned it into a brokerage fee from the city and the state; the land would ultimately house the Jacob K. Javits Convention Center. Before doing either of those two things, though, he took his option on the yards from 59th to 72nd Streets, the true jewel of the lot, he always believed, and pitched 20,000 apartments—an audacious proposal that would have surpassed, in one fell swoop, the real estate empire his father spent a lifetime building in Brooklyn and Queens.

Members of the Upper West Side’s politically potent Community Board 7 scoffed—the proposal was too discordant with the character of the neighborhood, they thought, and simply too big. Over the next few years, Trump downgraded to 14,500 units, then 8,000, but they kept rebuffing him. Meanwhile, New York’s ongoing financial crisis had ended the generous public subsidies on which Trump’s father had gorged. It was 1979. Trump was stalled. Otherwise wrapped up in the early stages of the construction of Trump Tower, in addition to his initial maneuverings in Atlantic City, Trump let his option lapse. “The toughest business decision I ever made,” he would say in The Art of the Deal.

In the fall of 1984, though, one of his staunchest foils looked out her window and spotted Trump standing by the West Side Highway in what she termed his “Fountainhead pose”—feet planted, hands on hips, his face a picture of conviction. Sally Goodgold called everybody she could reach, according to Barrett’s biography of Trump, to warn that he was going to buy the yards. She was right. Ten years earlier, he had gotten the site from Penn Central for no money down; now, in January 1985, for $115 million, he got it back—not only an option but actual ownership.

In the whole scope of his life, with the obvious exception of Election Day 2016, and maybe the night of the finale of the first season of “The Apprentice,” Trump never was riding higher than at that moment. Trump Tower was then gleaming and new, a beacon for unabashed wealth. “The Empire and Ego of Donald Trump,” read the headline in the New York Times in 1983. “The Secret to Donald Trump’s Success,” said the cover of GQ in 1984. To that point, he had experienced little else.

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The Times in April 1985 compared Trump to the late Robert Moses—“New York’s master builder,” according to the paper’s obituary—who over nearly half a century in various public offices oversaw construction of the Triborough Bridge, the Verrazano-Narrows Bridge, the West Side Highway, Jones Beach State Park, 658 playgrounds and 416 miles of parkways. Moses amassed his power methodically as a head-down insider, and he exercised it ruthlessly, believing what mattered the most was the blunt, black-and-white ability to “get things done.” Said the Times, “If Mr. Moses were to be born again, he’d probably return as Mr. Trump.”

“Trump did want to be identified with him,” Robert Caro, who wrote the definitive biography of Moses, The Power Broker, told me. “For a time, I used to hear—people would say to me—‘Donald Trump is the next Robert Moses.’ … But I always felt he himself was behind people saying that, if you know what I mean—that he wanted to be the next Robert Moses. And that’s really a terribly revealing thing. Moses, he didn’t let people stand in his way. He targeted—he not only evicted all these people, … he hounded them out like cattle. He targeted poor neighborhoods and particularly poor neighborhoods that were black … and Puerto Rican … because he felt they were the most defenseless against him.”

Caro continued: “To admire him is to say a lot about yourself.”

“Defining power in this age is certainly different than it was 25 years ago,” Trump told the Times in 1985. “Things were done less delicately. You used to be able to bull something through, but power today is much tougher to achieve.” He added, “I’ll say that I don’t think of myself as having power, and yet if I want to do something I seem to be able to get it done.”

And now what he wanted to get done was what he had wanted to get done in the first place. He wanted another shot at a legacy-cementing project on the old Penn Central yards. The mammoth mall. The giant garage. All the apartments and the very tall buildings and the even taller building that would have taken the record from the Sears Tower in Chicago. “New Yorkers want to have the world’s tallest building,” Trump said. “And, frankly, so do I,” he added.

Before and After At left, Manhattan’s West Side rail yards in 1974. At right, the Riverside South development in 2008. | Wikimedia Commons; Busà Photography/Getty Images

He billed it as a potential “tremendous psychological boost to New York.” As important or more, Trump wanted to live in the penthouse, he said to Jerry Nadler, the Brooklyn-born Democrat who has been in Congress since 1992 but at the time was a member of the New York State Assembly representing the Upper West Side. “Above the clouds,” Trump told him.

And he wanted to break ground in 1987, which for a project of this magnitude was tantamount to tomorrow. The opposition that had derailed him before, gathered again at John Jay, gasped at the realization that they were going to have to fight another round against Trump—this time an ascendant, emboldened Trump.

“He gave a schedule of anticipated rapid approval by the city and anticipation of rapid start of construction, which seemed wildly ambitious to those of us who knew about the public process that you’d have to go through,” Steve Robinson, a young architect then who became intimately involved with the neighborhood’s opposition, told me. “But that’s what he said: ‘This is it, and this is when I’m going to get my approvals, and this is when I’m going to start construction.’”

Ruth Messinger, who was the neighborhood’s City Council member at the time, was at the meeting, too. “It was like, ‘I’m sure this is what you want, and here I am, and isn’t this great?’” she said in a recent interview. “Like, ‘I’m an emerging developer, I’m a great person, I can sort of do things that are good for me, and they’re good for everybody else, and here’s what I’m going to do for you.’”

There was no misunderstanding. This was the message Trump meant to convey.

“He was not that interested in anybody telling him that he had to rethink or resize his expectations,” said Capalino, the lobbyist. “He wanted what he wanted. He was confident he could get it.”

“My track record,” Trump said, “is unparalleled.”



***

The timetable wasn’t the only thing that roiled the opposition. There was also what he was proposing: a sun-blotting row of hulking buildings plus the practically phallic tower shooting into the sky. As a piece of architecture, it was “laughable,” in Robinson’s estimation, “almost childlike.”

Paul Goldberger, at the time the architecture critic for the Times, dismissed the plan as “woefully simplistic.” He thought it looked like “rocket ships lined up in bleak open space.”

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Carter Wiseman, the critic for New York magazine, knew Trump from an earlier tour of Trump Tower. Trump “kept grabbing my arm, squeezing my arm, and saying, ‘Carter, you’ll appreciate this marble, this marble is quality marble,’” Wiseman told me recently. “And it looked like something that should have been in a men’s room in a whorehouse.” He had described Trump Tower in print as “an anonymous, 68-story shaft.” Now, though, as 1985 flipped to 1986, what Trump wanted to erect on the Upper West Side was no longer cartoonish and gaudy, Wiseman believed, but something more sinister.

“Trump’s vision for the Penn Yards is really based on a very old idea, one made popular in the 1920s—and since then universally discredited in theory and in fact,” Wiseman wrote. “Isolated towers from the fifties and sixties survive in most of the world’s major cities as reminders to planners that this brand of angst-inducing exclusivity is nasty to live with. Hard lessons have shown that the way to make a residential complex work is to create some sense of intimacy, or at least communal identity. But for all the adolescent, outdated striving for bigness, Trump is onto something thoroughly contemporary in the life of eighties New Yorkers. It is fear.”

Trump, after all, lived at the top of Trump Tower, high above the sidewalks and the subways, sealed off from the heart of a city he used for personal enrichment but not much else. For Wiseman, the issue wasn’t even so much the “brooding row” of buildings. It was that the development was an “island-upon-an-island,” aggressive in its separation from the city in which it stood.

Trump didn’t disagree. “I don’t want to cater to the community immediately surrounding Television City,” he told the Miami Herald. “I want to build my own thing.”

For many of the citizens of the Upper West Side, too, this was pointedly the most troublesome facet of Trump’s proposal. “He doesn’t give a shit what the zoning is, or what the neighborhood is, or what people think—he’s ready to impose his will,” says Gratz, who once called Trump “the Liberace of development.” So, Gratz, Robinson and a handful of others formed a group to try to stop him. They called it Westpride. They enlisted the help of boldface names who were neighbors—feminist Betty Friedan, comedian Jerry Seinfeld, “Superman” actor Christopher Reeve, political commentator Bill Moyers, the novelists Judith Rossner and E.L. Doctorow, and Caro, the biographer of Robert Moses. They held boat cruises and cocktail parties to raise hundreds of thousands of dollars. They used the money to hire attorneys and log public records requests. Robinson, who is writing about the experience in a book called Turf War: Stopping Trump on Manhattan’s West Side, expected to be published next year, says they wanted to do more than just “throw rocks and march in the streets.” Throughout the latter half of the ’80s, the membership and fervor of Westpride and like-minded, smart- or small-development organizations soared.

Among the Upper West Side Resistance Top row, left-right: journalist David Halberstam; Mayor Ed Koch, with Donald Trump; local political leader Ruth Messinger, with Mayor David Dinkins. Bottom: writer Betty Friedan; actor Christopher Reeve; author Robert Caro. | Getty Images

New York Mayor Ed Koch, meanwhile, tangled mightily with Trump. The frequently combustible relationship between two of the biggest, brashest personalities in the biggest, brashest city in America crested on the Upper West Side. “Ed always had this sense that Donald was looking for six quarters for a dollar,” says Capalino, a Koch aide before he lobbied for Trump. Trump “liked to assert that he was going to do this and everybody else was going to go along with it,” says Alair Townsend, one of Koch’s deputy mayors, who led the administration’s negotiations with Trump. “It didn’t happen.” Koch refused to give Trump tax breaks that would have aided his efforts to build Television City; instead, his administration gave them to NBC, which stayed at Rockefeller Center rather than move to Trump’s planned development or over to New Jersey. The administration probably “gave too much,” Koch aide George Arzt told me. “However, it undercut Trump—and he recognized that no longer did he have any plan, and he yelled and screamed about it.”

Trump responded to Koch and the other prongs of this resistance in ways that would be familiar to anyone who watched his presidential campaign, or has paid even cursory attention to his tenure in the White House. He lashed out, sneering at the community activists, considering them a “small group of devout enemies” who didn’t have “enough to do.” He called Koch “a horrible manager” and a “moron,” and said he should resign. “If Donald Trump is squealing like a stuck pig, I must have done something right,” Koch shot back. “Piggy, piggy, piggy,” the mayor added.

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Vitriol wasn’t Trump’s only tactic. He tried to butter up women, many of whom found his overtures eye-rolling and unwelcome. Trump always called Townsend “hon” or “deary,” she told me. “He would consistently call me Ruthie—and there’s no one in America who calls me Ruthie,” Messinger says. “He obviously thought it was cute or seductive or something. I thought it was disgusting and stupid and out of touch.”

In 1987, Trump changed architects—but not his objective. He fired Helmut Jahn, his flashy first pick from Chicago, when he realized Jahn’s gargantuan design would never get green-lighted by the necessary city agencies and boards. And he hired Alex Cooper, acknowledged throughout the city as something like the antithesis of the flashy Jahn. Cooper was respected for his tasteful community-integrated work. For Trump, then, it was a savvy political play—except he remained unwilling to decrease the size or to give up on the world’s tallest building. Cooper’s design was scarcely any smaller than Jahn’s.

“There is absolutely no doubt that it will go through,” he told the Times. “This will be the biggest project in the history of the city,” he said in the magazine Manhattan, inc. And in 1988, Trump changed the name of the prospective development; Television City became Trump City. He did that, he said, “because I’m so happy with the way the job has developed and the tremendous response I’ve gotten.” These fact-free assessments only got bolder after his original start date for construction came and went.

The reality, though, was that he was stuck.

“Mr. Trump has so far suffered only defeats with Television City,” Goldberger wrote in the Times that year, offering an insight that would be all the more trenchant in the years and decades to come. “It would seem that Mr. Trump does not so much avoid failure as know how to land on his feet and change course so deftly that no one catches on.”

Flummoxed by political headwinds and the disciplined activism of the Upper West Side, Trump shifted his attention to the acquisition of things other people had made rather than creations of his own. In a frenetic, debt-burdened shopping spree, he bought a yacht, the Plaza Hotel, the half-finished structure of a third casino and an airline, the Eastern Airlines Shuttle—which he rebranded as the Trump Shuttle. And he started talking about running for president. He wasn’t really running, not yet, he told Newsweek, “but if I did … I’d win.”

And then the gleam of Trump’s burgeoning empire started to tarnish.

Tabloid bombshells in early 1990 about the breakup of Trump’s first marriage bled into less sensational but even more alarming headlines about his deteriorating financial situation. They appeared everywhere from USA Today and the Wall Street Journal to Businessweek and Forbes. The news jumped to TV. The tenor of the coverage of the fall of Trump was a mixture of voyeuristic fascination and tsk-tsk schadenfreude. “If Donald Trump does become the victim of overweening ambition, that will hardly be a new chapter in human nature,” political analyst Jeff Greenfield said on ABC’s “Nightline.” Trump was, it turned out, more than $3 billion in debt. “Trump was invincible,” Caro told Newsday that June. “Now he’s not, and I think that will help. Too often people used to say that you can’t fight Trump. He’s too big. … But I don’t think he has that invincible image anymore.” It was in this context that his opponents on the Upper West Side presented something they had been working on—an alternate plan for the 76-acre plot, drastically reduced, considerably more in tune with the neighborhood as a whole.

That’s when Trump did something that shocked them.



***

“Trump City,” Capalino said in Newsday in August 1990, “is absolutely central to Donald’s view of how history will judge him—whether or not as one of the 20th century’s greatest urban planners and developers.”

Four months later, though, Trump outright gave up on that goal. His bid for immortality would be replaced by a struggle for survival.

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The moment of this massive hinge in his life came early one morning a couple weeks before Christmas. The Upper West Side resistance, 30 or so members, according to Gwenda Blair’s biography, gathered in a conference room of a law firm of a Westpride leader. Their meeting was scheduled for 7 a.m. Trump arrived right on time. His opponents’ alternative idea had been in the newspapers already, so it wasn’t a total surprise, but they wanted to deliver to Trump in person a formal presentation of their plan. It featured a park by the river, smaller, shorter buildings—and no world’s tallest building. And it wasn’t called Trump City but Riverside South.

“He looks at it, and he says, ‘I love it, it’s great.’ He said, ‘I want to build that,’” says Robinson, one of the architects, along with Paul Willen, environmental planner Dan Gutman and others who had devised the alternative.

One question from Trump: “He said, ‘By the way, how many square feet is it?’” Robinson recalls. “And somebody said, ‘Seven million.’ And he said, ‘Oh, I can’t do that.’ He said, ‘You know what this property cost me?’ And Bruce Simon, who’s one of the most powerful labor lawyers in the country”—one of the founders of Westpride—“said, ‘Donald, what’s your number?’ And Trump said, ‘I’ve got to have at least 11 million, 12 million square feet.’ That’s when Bruce stood up and said, ‘Donald, it was a pleasure to meet you—we really don’t have anything to talk about.’”

At that, though, Trump quickly relented again. “Trump said, ‘Wait, wait—wait a minute,’” Robinson says. “‘Sit down, sit down—let’s talk.’”

And then … “he agreed,” Kent Barwick, the president of the Municipal Art Society at the time, told me recently.

“It wasn’t much of a negotiation,” Barbara Res, a construction manager on Trump Tower who had returned to work for Trump as a vice president in the early ’90s, told me. “He pretty much gave them what they wanted. Basically, they gave him a plan, and he said, ‘OK.’”

“He had to,” Robinson says. “He was dead in the water.”

“He came to the meeting,” Gutman adds, “and in effect capitulated.”

The New ‘Master Builder’? Trump was compared to Robert Moses, top left, at first. Paul Willen, right, helped draw an alternative plan, Riverside South, above. | Joe Scherschel/Getty Images; Paul Willen; Paul Willen and Stephen Evanusa

And that was the end of Trump City. In a news conference at City Hall, they announced this unlikely alliance. “All you folks convinced me to do really what was right,” Trump told them, and everybody else.

For Willen, the architect, it was stunning—and telling, too. “Not everybody understood what happened, and how remarkable that was,” he told me. “Yet it was somehow characteristic of Donald Trump. The 180-degree turnabout he made revealed something about his audacity and his willingness to … go in any direction at any moment.”

But this flip-flop didn’t play in public as comeuppance for a greedy developer. Quite the opposite. Good-government types lauded the unconventional compromise. And Trump earned plaudits from public officials and mostly glowing headlines for his more conciliatory stance. The optics were not altogether ideal but came nowhere close to egg on the face. Trump biographer Blair called it “a coup.” He went, said Blair, who lived on the Upper West Side at the time, from “being evil developer to being civic-minded guy.”

“Instead of having all these banshees, you know, causing him trouble, now he’s going to be standing in a photograph with the Parks Council, the Municipal Art Society, the National Resources Defense Council,” Barwick says. “All these virtuous people are suddenly on his side.”

“He used them,” Ethel Sheffer, a community board member, told me, “so that he could be standing up there with the good guys.” The key for Trump, though, was this: “They believe,” Sheffer says, “they were using him.”

“He’s a very good deal-maker,” Richard Kahan, who helped broker the agreement between Trump and his former adversaries, told the Times back then. “It’s quite extraordinary that a man can work on a project for four or five years”—longer even than that, counting the ’70s—“and then be able to change direction so quickly and make a brand-new start. Whether he’s doing it out of self-interest or in the public interest, the result is good for everybody.”

And it was in fact good for Trump. The Riverside South coming-together, “his abrupt about-face,” Goldberger wrote in 1991, “hit urban development circles with about the same impact that the news that the Soviet Union had given up on Communism had in political circles. Don’t laugh; there are more similarities between Mr. Trump and the Soviet Union than one might think. After all, the developer and the country are motivated by the same impulse: survival. Mr. Trump knew that it would be a freezing day in August before his own plan could ever win approval and, like any skillful politician, he jumped on the opposition bandwagon so deftly that he made it look like his own.”

“I didn’t surprise anyone as much as I surprised myself,” Trump would say in a subsequent book, The Art of the Comeback. “After I decided to go with the civics, I went around Manhattan telling people this was either the dumbest or the smartest decision I’d ever made in business.”

It was one of the smartest. Because the partnership loosened the logjam and made the proposed project palatable to the politicians who needed to support it—from Messinger, by then the borough president in Manhattan, to Mayor David Dinkins, who had succeeded Koch, to New York Governor Mario Cuomo. And because of what it allowed Trump to do next: find a buyer.

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In 1994, Trump and a consortium of Hong Kong businessmen worked out a deal. In essence, they would be the cash, and he would be the face—they would pay $90 million to assume the more than $250 million Trump owed on the property to Chase and other banks, plus approximately $6 million in back taxes, according to the South China Morning Post at the time, and he would keep a 30 percent ownership stake and be responsible for day-to-day permitting and construction. The agreement almost ended just before both sides signed contracts because Trump got angry and “used a string of foul language, including racial epithets regarding Asians,” a lawyer close to the negotiations told American Banker in August of that year. But the Hong Kong businessmen shrugged their shoulders. “Doing business with Mr. Trump is anybody’s guess,” a spokesman for the group said at the time. “We are linked up with Mr. Trump purely because of this piece of land.” It was, in other words, a good enough deal for them to put up with the periodic boorishness of the seller.

It was a good deal for Trump, too, though. He had filed for corporate bankruptcy four times in 1991 and ’92, but the Riverside South sale to the Hong Kong group helped him avoid having to file for personal bankruptcy. By the end of that year, he was being called “the king of comebacks” on CNN. “Trump is definitely back,” Trump said.

“The Hong Kong guys saved him,” says Arzt, the Koch aide.

“It was absolutely essential to him not dying,” Res adds.

And Trump played his prescribed part in the partnership. Construction started in 1997—a decade later than he had predicted. The project was smaller. It wasn’t fully or even mostly his. But his name was on it. “In a way, it is my greatest construction achievement,” he said. And in 1999, in front of Trump Place, he let the magician David Blaine get “buried alive” for a week in a plexiglass coffin. It’s something Houdini wanted to do, Blaine explained, but he died before he could. It was a showy ode to the art of the escape. Reporters swarmed. The lesson Trump would take from the spectacle? “You can do things in your own mind that you don’t think you can do.” Moreover, he let Blaine do the stunt on the site for a reason that was far more obvious. “I did it,” Trump told the New York Post, “because everybody gets to see the buildings.”



***

Today, hardly anybody talks about the buildings. Trump Place is not Trump Tower. It’s not even the Grand Hyatt. Trump Place is just … buildings. One afternoon not long ago, I walked the length of the old Penn Central yards, up, then back. Three of the buildings that once said Trump Place no longer do. Residents angry about his election had the large gold letters removed. A judge in Manhattan recently ruled that people in another one of the buildings could make the same choice. I stood there and squinted in the sun to make out the scantest visible remnants of his name. I considered the obvious metaphor. But it’s not right. Trump’s not fading away. And what Trump got from the Upper West Side was of such significance that it makes this still one of the most important plots of land in his life.

What he got from these 13 blocks wasn’t what he wanted, not even close, not in 1975, not in 1985—but he still got a lot. He got to keep going.

He made a lot of money, too, albeit not as much as he could have. Even so, the coffers filled up, especially after the company he sold to in 1994 sold to another company in 2005—a transaction that gave Trump small but lucrative stakes in a pair of office towers in New York and San Francisco. He publicly derided the deal as not good enough and filed a lawsuit, claiming he could have done better, which a court dismissed as nonsense.

But perhaps most importantly, from Television City and Trump City and Riverside South and Trump Place, he got an education. And the lessons Trump took from his decades of attempting to develop the property, in the indeterminate way he absorbs what he does, were lessons, too, for the people who worked against him, and then with him.

“He took command of the ground,” Barwick says. “The whole posture wasn’t, ‘OK, you’ve got me, I’m going to give in to your will.’ He shared—or pretended to, at least—shared the vision.” And that was after years of demanding, so unyieldingly, so much more. “He turned quickly. He’s capable of turning on a dime.”

Mogul to President Trump peers out over New York from a helicopter in 1987. After his election, “Trump Place” was stripped from three buildings. | Joe McNally/Getty Images; Peter Foley/Getty Images

“I also think he recognized this was a defeat that he had to turn into a victory, and he enlisted us in a way that did that for him,” Gratz says. “And we went along with it because we knew we could have a major impact.” Someone was going to build there, they decided, and they wanted some say over it. “And that park and those designs and that street grid and all the urban features are there not because he has any clue how to do these things, none, zero, zip—nor does he care—unless he’s forced to. And we forced him.”

What, then, could the “resistance” today learn looking back at Trump’s experience on the Upper West Side?

“You have to find a way to get him over a barrel,” Gutman told me. “You have to back him into a corner or get him over a barrel.”

And what did Trump learn?

“Did he learn from the Television City debacle that he shouldn’t get too big, too fast, too loud? No,” Sexton says. “He put something out that was so big, so fast, so loud, it scared the hell out of people, and they mobilized to oppose it—that was an actual tactical blunder by him. But it doesn’t seem like he learned the lesson of not doing that anymore.”

And why would he have? Ultimately, Sexton says, he wasn’t punished.

“So maybe what he learned,” he says, “is—yeah—think big, talk big, make a big splash. And let the other guys fight to keep up with him.”

On the Upper West Side, Trump was overbearing, tactless and tone-deaf. His proposals were extreme, offensive and ill-conceived. Many of the people who fought him thought they beat him. They prevented him from doing what he actually wanted to do. But those buildings were built. That money was money he made. It’s the Trump paradox: He’s the most successful failer of all time. Because what really happened with what became Trump Place was that he created such a disturbance for so long that his opponents literally did his work, designing his development for him, which saved him, which enabled him to maintain a veneer of credibility, which allowed “The Apprentice” to present him as it did, which let him run for president. The election was an apt capstone. He lost (the popular vote), but he won (the Electoral College). And so, his transactional, bluff-and-bluster, react-to-me life became a candidacy, and now a presidency, that is driving change on a far larger canvas than just the New York skyline.