The Legend of Donald Trump

The money, the ego, that hair—profiles of the bilious billionaire by Tom Junod, Erik Hedegaard, and others.
5 stories

In his latest attempt to make the 2012 election about himself, Donald Trump unveiled his "October Surprise" yesterday: He would donate $5 million to Barack Obama's favorite charity if the president would release his college application and transcripts, as well as his "passport information" by October 31.

The president responded to the outrageous stunt by joking with Jay Leno last night that the conflict with Trump “dates back to when we were growing up together in Kenya.” The whole incident was classic Trump. On one hand, he looked a bit silly. On the other hand, publicity!

Headlines have always mattered to the man.

In Jonathan Van Meter's 2005 profile of the Trump children, he recounted a time when "in the winter of 1990, life as Donny knew it began to unravel. Donald was courting a pretty young girl from Georgia named Marla Maples, right under Ivana’s nose," he wrote. "The whole thing blew up in their faces on the slopes of Aspen. Donald moved ten flights down in Trump Tower, and war was declared. Liz Smith broke the story in the Daily News just before Valentine’s Day, when Ivana called Smith to a secret meeting at the Plaza Hotel to tell her that Donald was having an affair." A cheating husband. An angry wife. The only novel part of the scandal was Trump's reaction: "The story stayed on the front pages of the tabloids for three months, which, as Donald likes to point out, must be some kind of a record." Would anyone else brag about that?

Tom Junod went to see Trump during his 2000 "I'm running for president" phase. "It had always struck me how square he was," Junod mused. "He grew up in Queens, the son of a successful builder and developer, and his idea of rebellion was doing what his father had done--but bigger, better, and in Manhattan. Now, at fifty-three, he looked like a guy who had never thought to join a student protest when he'd gone to school and so, upon his return, was giving the kids what he thought they wanted: peace signs. He appeared, in fact, to be exactly what he is: a determinedly unironic man whose career has been made possible by a culture of determined irony--by a culture that allowed him to matter precisely because it had decided he didn't matter at all."

The presidential run led to more headlines.

"Trump thrives on an audience and a foil, and today, inside his Trump World Tower offices in New York City, he has both," Sheelah Kolhatkar wrote in her 2011 profile. "He's sitting behind his desk, stacked with magazines and newspaper clippings about himself, discussing his proto-Presidential campaign whose sudden momentum seems to have surprised even him... He wants the doubters and the haters and the petty critics and the other real estate people to know that not only could he do a better job than President Obama—that, if he were in charge, he would kick China's and Saudi Arabia's butts and have jobs flowing back into the U.S. within months—but that he's been goddamn successful at business."

Still, Daniel Roth suggested that he hasn't been quite as successful as he pretends. "In Trump's reality show, The Apprentice, he and two lieutenants monitor contestants as they backstab their way to a $250,000-a-year job as president of one of his companies. In Trump's real life he has managed—by force of personality, insane attention to certain details, charisma, bluntness, self-promotion, and connections—to build an empire of steel, marble, beauty pageants, casinos, and some of the most incredible moldings you'll ever see. The total value? If you believe Trump, $6 billion," Roth wrote. "But few people actually believe him. And there's good reason. Trump is the Reality Tycoon. He lives his life straight out of the Survivor handbook: Start with the truth, then add enough drama, celebrity, sex, and what might very charitably be called creative editing to make something entirely outlandish."

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I mean, he called to ask about my mother.

Mar 2000