Pop culture obsessives writing for the pop culture obsessed.

Donald Trump’s The Art Of The Deal is an awful book about a terrible man

The Art Of The Deal cover

Silly Little Show-Biz Book Club is Nathan Rabin’s ongoing exploration of books involving show business, with a special emphasis on the very bad and the very sleazy.

The two books Donald Trump’s The Art Of The Deal remind me of most are Bret Easton Ellis’ American Psycho and O.J. Simpson’s If I Did It. One of these is a satirical novel about a man who does unspeakably awful things to women and their bodies, sometimes involving rodents, sometimes while discoursing windily on Huey Lewis And The News. The other is a strange confession/non-confession from a man who allegedly murdered the mother of his children in a fit of anger.


Compared to Patrick Bateman and O.J. Simpson, Trump is practically a mensch. He’s a reality-show villain who recently launched a stunt candidacy for president, not unlike Pat Paulsen or Vermin Supreme. In a bizarre, King Ralph-like turn of events, Trump’s presidential run appears to have an actual (although fortunately narrowing) chance of proving successful.

Trump is a businessman running for political office, but he’s really an entertainer. Trump’s presidential campaign has blurred the lines between politics and show business in ways even Ronald Reagan, an actual actor, never could have imagined. Whether he’s appearing in the supernatural sex-themed comedy Ghost Can’t Do It, hosting Saturday Night Live, or working as a pitchman for Pizza Hut, Trump’s presence in entertainment is a walking sight gag. But as a politician, he’s terrifying, less a joke that has worn out its welcome than a waking nightmare I pray to God we wake up from in November.


The Art Of The Deal particularly reminds me of American Psycho in early passages that drily and tediously document what a week in Trump’s life is like. As a fascinating and revelatory recent article about Trump’s Art Of The Deal ghostwriter Tony Schwartz in The New Yorker reveals, the book begins with a rundown of an unremarkable week in Trump’s remarkable life for a reason. When he tried to plumb his subject/co-author’s depths, Schwartz was chagrined to discover that Trump had no depths to plumb. Schwartz discovered that Trump is an empty shell of a human being, a man devoid of self-reflection, candor, vulnerability, humility, and perspective. He discovered in his subject a creature of pure ambition and calculation, a deal-maker uninterested in the sum of human activity, from small talk to the joys of family, and exclusively committed to making money.

Schwartz was asked to write a book with a man with an attention span so small and a sense of curiosity so nonexistent that it’s doubtful that Trump is capable of reading a book to completion, let alone writing one. So Schwartz soon realized that he wouldn’t necessarily be writing a book with Trump, but writing a book around him. Still, Trump continues to claim credit for The Art Of The Deal, even pimping it extensively in his campaign literature, despite its co-author publicly condemning Trump as a person, a politician, and an ostensible collaborator. Schwartz was not unlike the co-author of If I Did It, who similarly came to the project hating Simpson, believing him to be a murderer, and left the project with those convictions strengthened.


As Hitler advised, Trump begins with a big lie, opening his book with this whopper:

I don’t do it for the money… I’ve got enough, much more than I’ll ever need. I do it to do it. Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That’s how I get my kicks.


As Schwartz acknowledged much later on, this was an example of what he coins “truthful hyperbole,” but it’s actually untruthful hyperbole. It’s exaggerating feverishly, from a starting point of total dishonesty. Trump is pretending that he’s a true artist of capitalism whose purity borders on preternatural. Yet it’s clear that he actually likes deal-making because it affords him an opportunity to crush other people, to emerge from a deal the clear, uncontested winner, holding the bloody head of his opponent aloft for all the world to admire.

Trump’s book describes all the parties he’s invited to, all the media hounds desperate for his attention, celebrities who suck up to him, the organizations out to give him awards. Yet the only details that linger are the sentences that accidentally give a revealing, tragicomic glimpse into his true being, like when he writes about how lunch is a waste of time and energy (and also, you get the sense here that Trump doesn’t actually like people, individually or as a species) that he just has a can of tomato soup in the early afternoon while weaker souls compromise their judgment with three-martini lunches. Trump is a teetotaler, which makes me want to go back to drinking more than anything else has.


The Art Of The Deal also resembles American Psycho in passages like the following:

Even in elementary school, I was a very assertive, aggressive kid. In the second grade I actually gave a teacher a black eye—I punched my music teacher because I didn’t think he knew anything about music and I almost got expelled. I’m not proud of that, but it’s clear evidence that even early on I had a tendency to stand up and make my opinions known in a forceful way. The difference now is that I like to use my brain instead of my fists.


It’s telling that Trump has so many skeletons in his closet—at this point it’s more of an amphitheater than a closet—that the fact that he bragged about punching a teacher in the face so hard as a 7-year-old that he gave an adult a black eye hasn’t been a factor in the campaign. Of course, since this is Trump, there’s a good chance that he is lying, so in this case Trump’s famous dishonesty undercuts his equally famous predilection for bragging and queasy embrace of violence. What’s fascinating about this passage is how unrepentant Trump is; he says that he’s “not proud,” but you can easily imagine Trump winking mischievously over the idea that he’d be ashamed of anything, ever.

Then Trump begins giving actual business advice, but his nuggets of wisdom tend to be either bland aphorisms (“Think big,” “Fight back”), or simple common sense (“Maximize your options,” “Know your market,” “Get the word out”). The moral of many of Trump’s stories is to trust your gut, particularly if you’re Donald Trump, and your gut is never wrong. As a business guru, Trump belabors the obvious, as when he regales readers with the account of how he and his father bought Swifton Village, a run-down apartment development in Cincinnati, Ohio, for cheap, fixed it up nicely, then sold it for a considerable profit. Trump’s advice here is only slightly more sophisticated than the old admonition to “buy low, sell high.”


Throughout the early part of the book, it’s apparent that Trump was the same man then that he is now, and that in the decades since he has not evolved at all. The man who takes to Twitter to insult people in bizarrely personal ways talks proudly of how he writes angry letters denouncing the snobbish architectural critics who panned his buildings.


Trump writes dismissively of settling the lawsuits filed against his father for racial discrimination and his years as a protégé of Roy Cohn, one of the most reviled and unscrupulous figures in American law over the past century, as if both are merely matters of good, hard-nosed business and not clearcut evidence of a troubling lack of ethics.

It’s easy to draw a line from the man who spends much of The Art Of The Deal tediously seeking tax abatements to the man who stood onstage in the first debate and bragged that he didn’t pay taxes because he was smart. Trump is ultimately running for president on the Art Of The Deal platform: He’s selling himself as such an intuitively brilliant deal-maker that, if we make him the world’s most powerful person, he’ll make sweet-ass deals and cut us in on them. When Trump complains about former Mayor Ed Koch, as he does throughout The Art Of The Deal, particularly in the concluding chapters, the implication is that if only Trump were mayor, he’d do a much better job than Koch, and it’d be easier for him to realize his business dreams. A similar dynamic seems to be at play with his presidential run.


Trump ends the book by casting an eye to the future. He once again brags about how astonishingly rich and successful he’s been and vows to devote the future to giving back to society. That’s probably how Trump sees his presidential run: as a gift to the public, when in fact it feels more like an ominous threat I pray he does not make good on.

Trump’s saving grace is that he’s entertaining. You may love him, you may hate with a ferocity that scares you, but you probably find him good for a laugh or guilty chuckle. So it’s shocking how dull The Art Of The Deal is. Much of it is devoted to going over the dry, agonizing details of the deals that resulted in the various buildings that collectively make up the Trump mythology. If you’re fascinated by zoning and licensing and the intricacies of putting together a complex deal with many different parties, then The Art Of The Deal is for you! Trump exhaustively describes how he took buildings that were small and drab and made them huge, shiny, and, in his vulgar mind at least, classy. The book doubles as a brochure advertising the exquisiteness of all of Trump’s properties and the astonishing deals that made them happen.


The Art Of The Deal gets better as it goes along, or at least grows less egregious. A chapter on the United States Football League is surprisingly readable, if only because reading about a football team in a doomed league is more colorful and engaging than reading about zoning, financing, and taxes. Yet even here, Trump’s arrogance is staggering, even as he brags nonstop about his participation in one of the biggest sports failures of the past century. He states that he assembled the most exciting, dynamic, and huge football team ever, only to be brought down by the weakness of his fellow team owners. He’s even more audacious in proposing that the USFL won its antitrust case against the NFL, yet only received a one-dollar token reward because its case was too strong; its lawyer was too good; and Trump was such a convincing witness against the NFL, he made the jury feel sorry for the more established league. Trump simultaneously portrays the NFL as an evil monopoly and a ragtag bunch of losers who only were able to defeat the USFL out of misplaced pity.

Why was such a worthless book not only a bestseller, but the vessel that helped propel Trump to permanent fame? I suspect it’s because people like to feel like they’re learning something, whether they actually are or not. This explains the popularity of Dan Brown: People reading The Da Vinci Code get a bogus history lesson and a tedious potboiler in one unwieldy package. On a similar note, The Art Of The Deal professes to teach adults the foundation for understanding deal-making and business without ever throwing any ideas at them a 6-year-old couldn’t grasp. The Art Of The Deal made readers feel like they were learning about business from a top corporate mind when all they were receiving was a lot of self-congratulatory nonsense and hot air.


Another key to the book’s popularity: In all likelihood, no one read the damn thing. The Art Of The Deal, Stephen Hawking’s A Brief History Of Time, and Bret Easton Ellis’ American Psycho were all designed to be displayed rather than read. Leaving A Brief History Of Time around told visitors that you were smart. American Psycho said you were edgy, and displaying a copy of The Art Of The Deal on your living-room table told prospective sexual partners that you were interested in money. In the 1980s, that meant an awful lot.

The Art Of The Deal says something terrible about Trump and even worse about us. Just as Trump’s popularity says awful things about a culture that would deify such a vile human being, the popularity of The Art Of The Deal speaks to a deep strain of uncritical hero worship, greed, and unmerited reverence for the powerful that’s as troubling as it is enduring. Its resilience speaks volumes about the fools who made it a runaway bestseller and its subject a prime contender for a job that couldn’t be more important, and that he couldn’t be less qualified for.

Share This Story

Get our newsletter