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.”