The idea of Trump writing an autobiography didn’t originate with either Trump or Schwartz. It began with Si Newhouse, the media magnate whose company, Advance Publications, owned Random House at the time, and continues to own Condé Nast, the parent company of this magazine. “It was very definitely, and almost uniquely, Si Newhouse’s idea,” Peter Osnos, who edited the book, recalls. GQ, which Condé Nast also owns, had published a cover story on Trump, and Newhouse noticed that newsstand sales had been unusually strong.
Newhouse called Trump about the project, then visited him to discuss it. Random House continued the pursuit with a series of meetings. At one point, Howard Kaminsky, who ran Random House then, wrapped a thick Russian novel in a dummy cover that featured a photograph of Trump looking like a conquering hero; at the top was Trump’s name, in large gold block lettering. Kaminsky recalls that Trump was pleased by the mockup, but had one suggestion: “Please make my name much bigger.” After securing the half-million-dollar advance, Trump signed a contract.
Around this time, Schwartz, who was one of the leading young magazine writers of the day, stopped by Trump’s office, in Trump Tower. Schwartz had written about Trump before. In 1985, he’d published a piece in New York called “A Different Kind of Donald Trump Story,” which portrayed him not as a brilliant mogul but as a ham-fisted thug who had unsuccessfully tried to evict rent-controlled and rent-stabilized tenants from a building that he had bought on Central Park South. Trump’s efforts — which included a plan to house homeless people in the building in order to harass the tenants — became what Schwartz described as a “fugue of failure, a farce of fumbling and bumbling.” An accompanying cover portrait depicted Trump as unshaven, unpleasant-looking, and shiny with sweat. Yet, to Schwartz’s amazement, Trump loved the article. He hung the cover on a wall of his office, and sent a fan note to Schwartz, on his gold-embossed personal stationery. “Everybody seems to have read it,” Trump enthused in the note, which Schwartz has kept.
“I was shocked,” Schwartz told me. “Trump didn’t fit any model of human being I’d ever met. He was obsessed with publicity, and he didn’t care what you wrote.” He went on, “Trump only takes two positions. Either you’re a scummy loser, liar, whatever, or you’re the greatest. I became the greatest. He wanted to be seen as a tough guy, and he loved being on the cover.” Schwartz wrote him back, saying, “Of all the people I’ve written about over the years, you are certainly the best sport.”
And so Schwartz had returned for more, this time to conduct an interview for Playboy. But to his frustration Trump kept making cryptic, monosyllabic statements. “He mysteriously wouldn’t answer my questions,” Schwartz said. After twenty minutes, he said, Trump explained that he didn’t want to reveal anything new about himself — he had just signed a lucrative book deal and needed to save his best material.
“What kind of book?” Schwartz said.
“My autobiography,” Trump replied.
“You’re only thirty-eight — you don’t have one yet!” Schwartz joked.
“Yeah, I know,” Trump said.
“If I were you,” Schwartz recalls telling him, “I’d write a book called ‘The Art of the Deal.’ That’s something people would be interested in.”
“You’re right,” Trump agreed. “Do you want to write it?”
Schwartz thought it over for several weeks. He knew that he would be making a Faustian bargain. A lifelong liberal, he was hardly an admirer of Trump’s ruthless and single-minded pursuit of profit. “It was one of a number of times in my life when I was divided between the Devil and the higher side,” he told me. He had grown up in a bourgeois, intellectual family in Manhattan, and had attended élite private schools, but he was not as wealthy as some of his classmates — and, unlike many of them, he had no trust fund. “I grew up privileged,” he said. “But my parents made it clear: ‘You’re on your own.’ ” Around the time Trump made his offer, Schwartz’s wife, Deborah Pines, became pregnant with their second daughter, and he worried that the family wouldn’t fit into their Manhattan apartment, whose mortgage was already too high. “I was overly worried about money,” Schwartz said. “I thought money would keep me safe and secure — or that was my rationalization.” At the same time, he knew that if he took Trump’s money and adopted Trump’s voice his journalism career would be badly damaged. His heroes were such literary nonfiction writers as Tom Wolfe, John McPhee, and David Halberstam. Being a ghostwriter was hackwork. In the end, though, Schwartz had his price. He told Trump that if he would give him half the advance and half the book’s royalties he’d take the job.
Such terms are unusually generous for a ghostwriter. Trump, despite having a reputation as a tough negotiator, agreed on the spot. “It was a huge windfall,” Schwartz recalls. “But I knew I was selling out. Literally, the term was invented to describe what I did.” Soon Spy was calling him “former journalist Tony Schwartz.”