Ever wonder how a lifelong urbanite can resent cities as much as Donald Trump does? First you have to understand ’70s and ’80s New York.

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

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.” 

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.

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