These 10 articles reveal the full sweep of Trump’s outsize career

The man, the myth, the media maven

Colleen Killingsworth
Timeline
4 min readJun 14, 2016

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Brennan Linsley/AP Photo

1973: Race issues from the beginning

Trump was 27 when he first made the front page of The New York Times. The news was not good: The Department of Justice alleged that he and his father, Fred Trump, had refused to rent apartments to people of color.

1979: The family business, examined

“Trump won’t do a deal unless there’s something extra — a kind of moral larceny — in it,” a rival property developer told an investigative reporter from The Village Voice. “He’s not satisfied with a profit. He has to take something more. Otherwise, there’s no thrill.”

1983: Trump trumps Trump

Donald J. Trump alongside father, Fred Trump. Photographer: Dennis Caruso/NY Daily News Archive via Getty Images

Trump is no longer in his father’s shadow, The New York Times declared in a profile that described him a “brash Adonis” with a tendency toward “self-promotion, grandiose schemes — and, perhaps not surprisingly, for provoking fury along the way.”

1988: The short-fingered vulgarian

Ever heard Trump called a “short-fingered vulgarian”? This is where it began. The founding editors of Spy Magazine coined the infamous descriptor and triggered a years-long feud. “If you hit me, I will hit you back 100 times harder,” Trump is reported to have warned them.

1990: At last, a journalist who admires Trump

The Donald finally gets some media love—in Playboy. The skin mag described him as the “most daunting entrepreneur since the Astors, Vanderbilts and Whitneys”.

1997: Donald Trump, Performance Artist

“Every strand of his interesting hair…was where he wanted it to be,” reported the New Yorker writer sent to interview Trump, who had solidified his celebrity status and was divorcing his second wife. The profile paints a picture of Trump as performance artist, a man who “had aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul.”

2005: Wait, is he actually rich?

Photographer: Bebeto Matthews/AP Photo

What’s He Really Worth?” asked the New York Times. Back then the answer was a cool $900 million — in debt.

2015: From reality TV star to presidential candidate: not such a leap

Trump the reality TV host wasn’t much different from Trump the politician, concluded the Wall Street Journal after binge-watching Season One of the Apprentice: “He says he wanted to do ‘The Apprentice’ so that ‘the toughness, the viciousness of business could come out.’ The program is compulsively adversarial. Donald Trump is doing politics for the same reason and in the same way he did reality television.”

2016: The Economist is unimpressed with Trump’s business career

Economist.com

He has great wealth, much of it made well over a decade ago from a few buildings he has retained in Manhattan, including his favourite on Fifth Avenue. But he has not yet created a great company, raised permanent capital on public markets, gone global or diversified very successfully. Something to think about when you are sipping an $18 ‘You’re Fired’ Bloody Mary at the Trump Tower — or voting in a presidential election.”

2016: How Trump lives, as told by his longtime butler

Nothing paints the picture of the man, the myth, and the megalomaniac quite like this direct account in New York Times from his butler of 30 years, who reveals Trump’s “habitual, self-soothing exaggerations.”

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