Read a Book, Why Don't You?

The Art of the Deal by Donald Trump

The Art of the Deal came out in 1987 when Donald Trump was still a member in good standing of the Manhattan billionaire boys’ club and married to Ivana. The book shot to the top of the New York Times best-seller list when it was released and hung around for about 40 weeks. Trump wrote it together with a ghostwriter, Tony Schwartz, which is the normal course for celebrity books. Schwartz ironically has since developed Trump Derangement Syndrome and now says that if he ghosted a Trump book today, he would title it The Sociopath.

Ghostwriting is how celebrities and even some non-celebrity experts write books. Most people have a story to tell but they lack the skills at organizing it and nearly everyone but professional writers lack the ability to create 200 or more readable pages that don’t break continuity and are properly formatted. Ghostwriting is what is called in financial terms “work for hire,” meaning the ghost gets paid to write something. He is not necessarily paid to love the person he is working for. He is not paid to write his own ideas or inject himself into the story. Ghostwriters are paid to craft the other person’s story in a readable, engaging format. Reviews of the book at the time were good overall, although sometimes mixed with comments that Trump was brash and boastful. Some said he exaggerated his wealth and deal-making prowess. He bragged too much. Others said he was a little bit in love with himself.

While the bitter ghostwriter of the book claims Trump had nothing to do with the book, those critiques sure sound like Trump to me. The book is a series of brags and hyperbole and humor along with some interesting tidbits about how real estate deals actually are made. It’s kind of like reading the transcript of a Trump rally if the rally was about real estate and not politics.

At the time, the New York Times said, “Trump makes one believe for a moment in the American dream again.” Sure sounds a little bit like Trump had something to do with the contents.

The Art of the Deal is not very autobiographical although there are a few details here and there; this is not the book to read if you want to know how he met Ivana or when his kids were born or his adventures in military school. They’re missing. Details about his life only turn up as they relate to this or that major business deal. Despite its self-help-type title, this is not a how-to book in the classic sense; you won’t get tips on how to make your first million in real estate. But what Trump does provide is a glimpse into his gold-plated world during the razzle-dazzle 1980s.

Early on, the book provides narrative snapshots of a week in the life of Donald Trump. It paints a picture of a busy guy who manages multiple complicated projects simultaneously without dropping the ball or getting mixed up. It describes a man who uses the phone relentlessly, but hates to spend more than a minute or two on any one given call. It shows a guy who can keep a thousand details in his head and who is fast and spontaneous in his responses to questions. In addition to his busy business day, Trump also found time to attend parties, raise a family, and make appearances at various charity events. Exaggeration? I find it quite believable that Trump juggled dozens of deals simultaneously, had lots of rapid-fire phone calls that were surprisingly on point and effective, and went to random parties and meetings in the evenings. You get a sense that this is a guy who can run a big business or a government—he jumps fluidly from one arena to the next, from one problem to the next, always remembering names and keeping the details straight.

Then the book describes a series of projects, like Trump Tower or the ill-fated Atlantic City casinos. I learned from this book that in New York, real estate is a devilishly complicated business. In one deal, Trump had to negotiate rights to a building (one business entity), rights to the ground on which the building was built (another person owned the property separately), and “air rights” or rights to the space above the building (another business entity). What are “air rights”? The book explains that if you want to build a tony store on the street level, you may want to purchase air rights to prevent another store on the floor above from putting up a neon Everything Must Go Sale! logo above your posh store. Or worse, maybe one of those Girls! Girls! Girls! places with a big neon sign of a buxom female inviting patrons in. These various deals had to be negotiated separately, sometimes in secret (since if people knew Trump was interested in the building, then suddenly the price of the land or other components would double or triple over night). The deals have to be synchronized so that all deals came to fruition around the same time. Losing one piece of the puzzle could jeopardize a whole deal. On top of that, financing had to be arranged on the side, so that after the negotiations were finished, Trump could write the checks. Trump is very blunt in this book about financing, saying that he hated to use his own money—although sometimes he had to.

Getting a casino license in New Jersey was another daunting task, but Trump managed to do that where even some seasoned veterans failed. You would think a process like this would not take more than a year—but it does. It is interesting that Trump committed to building a casino before the license was secured, a calculated risk that he was willing to take.

One of his favorite achievements is the famous Trump Tower on ritzy 5th Avenue in Midtown Manhattan. The Trumps reside in a three-story penthouse on the top when they are in town. The photos show the two sides of Trump tower. The angles in the left image (below) were an architectural touch to distinguish the building and make it aesthetically appealing—but it also made Trump money. By structuring the building this way, most of the apartments had views and commanded higher rentals. (Trump sold apartments here as condominiums and refused to go the co-op route, since co-ops could impose their own rules on tenants and even vote to keep specific tenants out of buildings without citing reasons. Trump has said that co-ops allowed certain tony apartments in New York to camouflage their racism by having their boards secretly vote out “undesirables.” Trump stated in the book, he sold Trump Tower condominiums to anyone who had the money.) And they sold like hot cakes, despite the price tag—95% were sold in the first four months after Trump Tower opened. By the way, prices at Trump Tower are about $4,600 per square foot; penthouses go for $11,400 per square foot. Despite a shaky luxury real estate market in Manhattan, they’re still expensive and the address is still a status symbol.

Reading this book in 2024, it is easy to align Trump’s deal-making skills with his ability in foreign policy, the ability to negotiate with multiple people (sometimes in secret) at the same time and synchronize results and funding. Trump sometimes had to work out his deals with cheaters, liars, bureaucrats, stupid people, and people who did not like him. That was pretty much the demographics of the people Trump engaged with back then, and they map onto politics pretty exactly. Yet Trump never hated these people, although he sometimes called them names and played rough. But in the book, you get the impression that being nice is not in the deal-makers’ toolkit and bullying behavior is part of how things get done in this country.

Trump was boastful, yes, when he succeeded, and he wrote a few times about how deals fell apart. While success is always better than failure, the book does not make any pretense that failure was a stranger to his business. It was part of the game. Reading the book, I got the impression that no failure was ever wasted on Trump; he learned and moved forward. Of course, this is Trump telling the story, so he tends to describe himself in glowing terms.

The book is exuberant. It was interesting, engaging, and at times quite funny. If you hate Trump, do not read it, since anything dealing with Trump will upset you, but if you want to see why this guy might be good at politics, it’s quite insightful.

And the book had reverberations.

One guy who read the book was a man named Mark Burnett who was scraping out a living selling T-shirts on Venice Beach in Los Angeles. He read the book and got inspired. This launched what later became his TV career, where he started to put together his own deals to produce major TV shows. One of his projects was Survivor. And later on, Burnett thought he’d produce a show with the man himself: The Apprentice. The Apprentice, which later morphed in The Celebrity Apprentice, ran for 13 seasons and tried to morph out into other lesser brands (like Celebrity Apprentice with Martha Stewart). It nabbed Trump a star on the Hollywood Walk of Fame and was a landmark reality show presentation. It was very popular and highly rated at the time. E. Jean Carroll (Trump’s nemesis in the New York civil rape case) said once on social media she never missed an episode. Trump reportedly earned over $200M over the life of the series, until he was fired by NBC because they didn’t like something he said about immigration; this announcement was not made on the show but occurred in his announcement that he was running for President. Chances are if NBC hadn’t fired Trump when they did, he would have quit to pursue his political campaign anyway.

And it is easy to see how Trump—with no political connections to speak of—parlayed first his flamboyant real estate career and later his reality show ratings to get the name recognition needed to run a Presidential campaign. It may not be the best way to do politics, but it was effective. Trump is arguably today the most famous man in the world—love him or hate him, he is that rare man who needs no introduction.

The Art of the Deal is airport-type reading; it’s amusing and the kind of book you can put down and pick up again without missing much. If there’s one thing Trump can do, it’s tell an engaging story.  I think the ghostwriter gives himself too much credit; it sure sounds like Trump talking.