(AP/G. Paul Burnett)

He's always been a jackass: I read Donald Trump's favorite book — his own — so you don't have to

In 1987's "The Art of the Deal," Trump's obnoxious early roots are on full display


Scott Timberg
October 19, 2015 8:45PM (UTC)

What’s the appeal of Donald Trump, who continues to be immensely popular among Republican voters despite longstanding predictions that his support would fade?

One of the key lines in Mark Leibovich’s much-quoted New York Times magazine story is that Trump preaches the secular version of prosperity gospel, “the idea that you follow a minister because he is rich and has his own plane and implicitly and sometimes explicitly promised that you, too will be rich.”

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That complicated and entirely baseless promise is part of what attracted countless readers to the mogul’s first book, “The Art of the Deal,” which came out in 1987 and remained stuck at the top of the bestseller list for almost a year.

The book also reveals some of Trump’s unpleasant qualities, even though he wrote it with a co-author and was clearly doing his best to seem charismatic, reasonable, and good-natured.

The book is a series of victory laps about the deals Trump was proudest of – his acquisitions of various hotels and casinos in what it sometimes a blow-by-blow of phone calls, zoning battles, and financial exchanges. Through it all, Trump remains sunny, confident, happy-go-lucky. “I don’t do it for the money,” he tells us at the book’s beginning. “I’ve got enough, much more than I’ll ever need. I do it to do it. Deals are my art form.”

Though he also describes the relentlessness of his time on the phone – more than 50 calls a day, sometimes more than 100 – he also makes it all look easy. “I play it very loose. I don’t carry a briefcase. I try not to schedule too many meetings. I leave my door open. You can’t be imaginative or entrepreneurial if you’ve got too much structure. I prefer to come to work each day and just see what develops.”

Wow, that sounds great. This is the young Trump, one not ranting about immigrants or insulting women. (He tells us, in fact, that “I’ve hired a lot of women for top jobs.”) A kind of breeziness blows through much of the book. Much of this comes, surely, from the airbrushing that’s typical of many books in which an author wants to seem likable. But it also comes from the fact that Trump, despite what one reviewer called a “streetwise” tone, was from the start an entitled child of privilege who had his father’s money to play with.

Trump credits his success to trusting his instincts, knowing the market, aiming high, and so on. But while he praises his developer father as “my most important influence,” he seems entirely unconscious of the fact that his ability to “think big” and all the other business-book bromides his tosses out would be impossible if he didn’t start the game with significant riches. When Trump was in college, for instance, he and his father purchased a 1,200 unit apartment complex in Cincinnati, Swifton Village, for about $6 million: It becomes Trump’s first big deal.

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His description of the way it went down shows some common sense smarts along with the usual nastiness (“I can always tell a loser when I see someone with a car for sale that is filthy dirty.”) And nobody expects him a sociological analysis or apology for his family wealth. But there’s no sense that all this was possible because Trump had millions to play with before he’d collected his diploma.

His beginning on third base and thinking he’d hit a triple – to borrow the phrase applied to George W. Bush – robs the book of any kind of arc or drama: Despite superficial similarities, it’s no “Wall Street” — or even “Wolf of Wall Street.” There are some individual enemies here, but no big obstacle to overcome. There’s a kind of obliviousness when he says things like, “When I graduated from college, I had a net worth of perhaps $200,000, and most of it was tied up in buildings in Brooklyn and Queens.” Despite its up-from-the-bootstraps tone, the book describes a rich-boy Horatio Alger.

Trump talks about the roots of his famous belligerence, writing about punching a music teacher in second grade (“I didn’t think he knew anything about music”) and his taste for trouble-making as an adolescent. (“I’d throw water balloons, shoot spitballs, and make a ruckus in the schoolyard and at birthday parties. It wasn’t malicious so much as it was aggressive.”) But while he talks about his admiration for loathsome attorney Roy Cohn, and occasionally tosses out an insult, and boasts a lot (the president of a social club was worried Trump would steal members’ wives “because I was young and good-looking”), this is mostly not the mean-spirited Trump we know now.

And two things we hear very little about in “The Art of the Deal” – from a man now running for president who has called the Bible his “favorite book” – are religion or politics. (More on one of those in a future post.)

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We also learn that he hates market research, dislikes postmodern architecture, and learned a long time ago that controversy, even bad press, sells.

Trump is full of himself at times, entirely unreflective, and seemingly allergic to empathy for others. But he’s never as obnoxious or narcissistic as we’ve seen on television or on the campaign trail.

The back jacket of the paperback bears a blurb from Mike Wallace, who calls this early Trump “vainglorious” and “combative.” But compared to what Trump’s turned into, he seems almost laid-back and likable.

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It shows how much more sensitive we were to personal arrogance back then -- and how much more tolerant of it we've become since -- that this milder Trump was seen as a swaggering ego at the time. You almost want to affix a cautionary preface to the book. Be warned, if you keep paying attention to this guy, his self-regard and aggressiveness will balloon beyond limit. The Trump in “The Art of the Deal” is at times brash and combative, sure, but clearly he was just getting started.

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Scott Timberg

Scott Timberg is a former staff writer for Salon, focusing on culture. A longtime arts reporter in Los Angeles who has contributed to the New York Times, he runs the blog Culture Crash. He's the author of the book, "Culture Crash: The Killing of the Creative Class."

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