The Making of Donald Trump: The Nineties

Part three 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

There are few faces I hate quite as much as Donald Trump’s, and this week it was everywhere. Even before “the most famous photograph in the world” was officially released on Thursday night, twitter was rife with speculation, predictions, and fake versions of presidential mugshot. It’s hardly surprising that betting sites were giving odds on Trump’s weight, skin tone, and whether he would face the camera with a grimace or a grin. Given everything we know about him, it wouldn't surprise me if he put money on a scowl before heading to central booking. He was always going to cash in.

“There were only a few ways the Donald Trump mugshot could go,” wrote Hunter Harris. “Would he go with a demure grin, the taunting smize of 2000s celebutantes? Or would he strike his familiar pose, his presidential headshot, squinting and threatening? Or would he try to pull off a grin?” As we now know, he went with “squinting and threatening,” an expression that’s been likened to a twerp kid’s passport photo, Mama Fratelli, and “The Grinch Who Stole Georgia.”

I’m so sick of that face. As regular readers of this newsletter know, I’ve spent way too much time this summer mucking about the reeking dungheap of Donald Trump’s career. Having already covered his rise in the seventies and fall in the eighties, this week I’ve assembled a collection of magazine and newspaper stories documenting his scandal-wracked nineties. There are tales of bankruptcy, divorce, sketchy business deals with the Russians and Chinese, private plane trips with Ghislaine Maxwell, and a potential presidential bid. And photo after photo of that yam face with its ludicrous hair, smirking, squinting, smiling, scowling. I hate it even more when I think that behind those beady little eyes resides a tyrant whose stated goal is to dissolve American democracy, and he may succeed. He's probably betting on it.

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Trump the Soap: Stay Tuned…
By John Taylor
New York, March 5, 1990

“Can you believe it?” Donald Trump asked me.

We were talking on the telephone. It was the morning of February 14, the day the true dimensions of the hysteria over the Trumps' split became apparent, the day the Post ran its DON JUAN headline and accompanying story about Marla's St. Moritz hideaway, the day the News featured Mike McAlary on Donald and Liz Smith on Ivana, and Newsday, though its front-page photo of Nelson Mandela showed an astonishing lapse in editorial judgment, tried to answer the question “Does Ivana Trump have a case?” Though Trump himself had said in a recent interview with Playboy that “the show is Trump and it is sold-out performances everywhere," even he had underestimated the fascination with him.

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Pages from the Donald J. Trump Scrapbook, 1990-96
By Jamie Malanowski
Spy, August 1990

In the previous installment of the Donald J. Trump Scrapbook the following events transpired: Trump attempted to slough off his glamorous, reconditioned wife, Ivana, in favor of young, pliable nineties edition Marla Maples; he opened the horrifically kitschy and monumentally leveraged Taj Mahal casino; he saw his net worth devalued by 70 percent in Forbes magazine; he floated the idea of selling his airline and other assets in what he claimed was an effort to become a “king of cash”; and he became the subject of speculation about his ability to service the $3.2 billion debt that is the basis of his empire. Now the saga continues…

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After the Gold Rush
By Marie Brenner,
Vanity Fair, September 1990

This past April, when his empire was in danger of collapse, Trump isolated himself in a small apartment on a lower floor of Trump Tower. He would lie on his bed, staring at the ceiling, talking into the night on the telephone. The Trumps had separated. Ivana remained upstairs in the family triplex with its beige onyx floors and low-ceilinged living room painted with murals in the style of Michelangelo. The murals had occasioned one of their frequent fights: Ivana wanted cherubs, Donald preferred warriors. The warriors won. “If this were on the ceiling of the Sistine Chapel, it would be very much in place in terms of quality,” Trump once said of the work. That April, Ivana began to tell her friends that she was worried about Donald's state of mind.

She had been completely humiliated by Donald through his public association with Marla Maples. “How can you say you love us? You don't love us! You don't even love yourself. You just love your money,” twelve-year-old Donald junior told his father, according to friends of Ivana's. “What kind of son have I created?” Trump's mother, Mary, is said to have asked Ivana.

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All of the People All of the Time
By John Connelly
Spy, April 1991

With his bluster and his extravagance and his tabloid love life, Donald Trump has always been a source of considerable entertainment. If we're honest, we all have to admit that after his every achievement in greed or vanity we've said to ourselves, Heck, you've gotta love that guy! Like some funny, impossibly venal puppet in a Punch-and-Judy show, Trump has always given us a good laugh. In fact, Trump’s image as a buffoon is just another example of how the press has protected him from real scrutiny for so long. While one would prefer not to be considered a joke, that is not so bad if it distracts people from seeing what one really is: a charlatan, a liar, a cheat.

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Donald Trump Gets Small
By Harry Hurt III
Esquire, May 1991

Given the kind of year he has had, Donald J. Trump might be forgiven a little ego candy. His net worth, once extravagantly overestimated at $1.7 billion, may be as low as negative $295 million. The Taj Mahal and some of his biggest real estate ventures are in various stages of bankruptcy negotiation. His other two casinos, Trump Plaza and Trump Castle, are fighting to stay afloat. In fact, the Castle only made its last bond payment in December because Trump’s father bought $3 million worth of chips there and left them in the casino cage. He may still have to part with at least one of his three Atlantic City casinos before the year is out...

“You know,” he muses philosophically as we return to our ringside seats after the grandstand tour, “it really doesn’t matter what they write as long as you’ve got a young and beautiful piece of ass.”

“But,” he adds after a pause that suggests this is a distinction with a difference, “she’s got to be young and beautiful.”

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Donald Trump’s Tower of Trouble 
By Wayne Barrett
Village Voice,  December 17, 1991

When Trump Tower opened in 1983, its golden entrance, 80-foot waterfall, and rose-peach-and-orange-colored marble atrium quickly established themselves as the most photogenic symbols of Trump glamour. Donald launched a $2 million promotional campaign, complete with a lavish brochure promising the ultimate in luxury — hairdressers, masseuses, limou­sines, helicopters … all at your service with a phone call to your concierge — mak­ing the tower the place to buy. In a mas­terstroke of media deception, he even floated the rumor that Prince Charles was thinking of moving in at Fifth Avenue and 56th Street. But the clientele never did get that exclusive…

Actually, your Trump Tower neigh­bors are as likely to be Medicaid cheats, coke dealers, mobsters, or those who may have gotten a touch too friendly with mobsters.