The Making of Donald Trump: 2000-2015

Part four of our series looking at the media's coverage of the man before the MAGA

​​​​Welcome back to Culture Club, a feature where David and I write about what we’ve been reading, watching, playing, and listening to, for paid subscribers. Please enjoy this free preview, and consider upgrading to support two struggling journalists at once! — Talia

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Photograph by Richard Burbridge

“Most people, when they write about me, write about me like I’m a machine, like I’m some kind of motherfucker,” Donald Trump told Esquire’s Tom Junod in 2000. “I couldn’t be as successful as I am if I was just a machine and a motherfucker. One of these days, I’d like for someone to try to find another side of me.”

It’s time to return to one of the scariest stories in recent American history — the mainstream media’s coverage of Donald J. Trump as he rose from fledgling real-estate mogul to tabloid laughingstock to president of the United States. Time and time again over the last fifty years, Trump has alternately courted and jousted with the media — just when one outlet would expose some bit of his legal or ethical malfeasance, another would redeem him as an urban swashbuckler out to make his mark on the Manhattan skyline. As we’ve seen in previous excursions down the archival rabbit hole, Trump was a disaster as a developer, squandering the empire his father had left him to manage. But he was a hell of a showman. And so, following failures both personal and professional, he rebranded himself — as a brand.

At the turn of the 21st century, as demonstrated by this week’s collection of articles, Trump was back from the wilderness of bankruptcy, but far from the center of the action. He cashed in on his celebrity, licensing his name, and slapping his likeness on beverages, buildings, and board games. Then, with the January, 2004, launch of “The Apprentice,” he was back, riding the reality-TV wave right into living rooms across America.

If “The Apprentice” was the first step in Trump’s transformation from hokey New York curiosity to household name, it was his embrace of racist conspiracy theories that made him a political force. “Donald Trump has appointed himself spokesman for some of the nastiest impulses in American politics,” the editors of The New Republic wrote in 2011. “The sooner the Republican mainstream rejects him, the better. And we liberals should be cheering them along as they do.” Five years later, he was on the cover of Rolling Stone. As Trump mounts yet another bid, and as his legal woes mount in courtrooms throughout the country, it’s worth revisiting how he got to this point, and who helped smooth his path.

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Lessons in the Simple Humanity of Donald J. Trump, America’s Host
By Tom Junod
Esquire, March 1, 2000

He could be the first man ever to run for president as a function of his wanting, of his covetousness, of, yes, his greed; the first man to ever posit the presidency as the pinnacle not merely of male ambition but of male desire; the first man who could come right out and say he was running for president for power and prestige and publicity and pussy without hiding his might behind the pieties of public service. He could be the first presidential candidate allowed to say “fuck” in an interview, as well as the first to relish openly the prospect of fucking a supermodel in the Oval Office, as well as the first to drive a fucking Lamborghini. “You see, I don’t give a shit,” he once said to me during a discussion of his “negatives,” which included, in his words, “the fact that I date extraordinarily beautiful women.” “That is one of the things about me,” he said. “I don’t care. I don’t give a fuck.”

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Unreal Estate
By Charles V Bagli
New York Times Magazine, April 14, 2002

Last month, Donald J. Trump put a $58 million price tag on the 20,000-square-foot penthouse apartment of Trump World Tower. A week earlier, Trump and his Japanese partners signed a contract to sell the Empire State Building for $57.5 million. Sure, the vast duplex — about 10 times the size of the average American home — has wraparound windows and 18-foot ceilings atop Manhattan's tallest residential tower. But is an apartment on First Avenue across from the United Nations worth more than the city's tallest and most famous skyscraper? It boggles the mind. But let's do the math.

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Jeffrey Epstein: International Moneyman of Mystery
By Landon Thomas Jr.
New York, October 28, 2002

Epstein likes to tell people that he’s a loner, a man who’s never touched alcohol or drugs, and one whose nightlife is far from energetic. And yet if you talk to Donald Trump, a different Epstein emerges. “I’ve known Jeff for fifteen years. Terrific guy,” Trump booms from a speakerphone. “He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side. No doubt about it — Jeffrey enjoys his social life.”

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Photograph by Michael Edwards

What I’ve Learned: Donald Trump, 57, Builder, New York
By Cal Fussman
Esquire, January 1, 2004 

I was walking down Fifth Avenue with Marla Maples in 1991. This was at the peak of the bad market. Across the street I saw a man in front of Tiffany with a tin cup. I looked at Marla and said, “You know, right now that man is worth $900 million more than I am.”

When I told Marla this, she didn’t run away. Of course, I would have saved a little money if she had.

I had a lot of friends who went bankrupt and you never hear from them again. I worked harder than I’d ever worked getting myself out of it. Now my company is much bigger than it was in the eighties — many times. The Guinness Book of Records gave me first place for the greatest financial comeback of all time.

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Due Diligence on the Donald
By Charles V. Bagli
New York Times, January 24, 2004

The first episode of Donald Trump's new hit reality show “The Apprentice” began with an introduction. As usual, Mr. Trump did the honors. Over aerial views of Manhattan's glittering skyline, he intoned, “My name is Donald Trump and I’m the largest real estate developer in New York.” The camera panned across Trump International Hotel and Tower at Columbus Circle, and he continued: “I own buildings all over the place, modeling agencies, the Miss Universe contest, jet liners, golf courses, casinos and private resorts like Mar-a-Lago.”

For millions of viewers, the show is an opportunity to watch 16 remarkably ambitious people compete for a $250,000-a-year job with Mr. Trump. But for those who follow the New York real estate market, the show provides something else: a hilarious look at Mr. Trump’s blend of fact, image and sheer nerve. Even when the show plays a bit with the truth, it's an excellent primer — sometimes unintentionally so — on Mr. Trump’s peculiar brand of success.