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A Portrait of the Con Artist as a Young Man

Donald Trump’s The Art of the Deal is a guidebook for ruining lives.

Gage Skidmore

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.”

Thus opens Donald Trump’s The Art of the Deal. Of course, Tony Schwartz actually wrote it, and he told the New Yorker recently Trump himself wouldn’t be able to write that prose.

Trump’s literary merits, however, do not negate this book’s ideological significance to the real-estate mogul’s self-image. Schwartz may have been at the typewriter, but Trump inspired his words. Schwartz created a Frankenstein monster, but his account simply expressed what Trump could not: the self-consciousness of American capitalism’s most revolting features.

Schwartz now regrets taking the job, admitting, “I put lipstick on a pig.” But the lipstick, it turns out, was just as hideous as the pig.

Trump brags at rallies that The Art of the Deal is among the most important books of all time, second only to the Bible. It’s advertised as a self-help book that teaches readers how to achieve the American dream (if they have the right “genes” for it), a business manual that explains how to manipulate and dominate.

But when John Kenneth Galbraith reviewed it just after its publication, he described the book less as self-help and more as self-justification. Instead of offering explicit advice on successful deal-making, the book takes readers on a tour of Donald Trump’s vulgarity, power, and aggression.

The book begins by recounting a typical week in the life of the real-estate tycoon, interspersed with his personal thoughts about various business deals, celebrities, and his wife Ivana. Trump boasts about his success and mythologizes it: you are either born for success or you’re not. He is represented as the perfect embodiment of capitalist self-discipline, wasting not a minute on anything that won’t maximize his cash flow. Even popping out to the street for a quick bite is a waste, he says.

Time is everything for Trump, and he identifies with its domination over his life. In truth, he internalizes his own alienation, presenting the fact that business has turned him into a profit-making cog as a personal triumph over all competitors.

As a result, Trump comes to personify the sickness and dehumanization that is American capitalism: He cheats; he lies; he manipulates; and he seduces. Trump romanticizes the baseness of his activity, packaging it as business tips in what he calls “The Elements of the Deal.” Deal-making for Trump is mystified as being inherent in one’s genes though, and he warns that this alienated lifestyle demands an “obsessive,” “driven,” “single-minded,” and “almost maniacal” attachment to work.

He calls this a form of “controlled neurosis” that may not lead to a “happier life, or a better life, but it’s great when it comes to getting what you want.”

Trump promotes a form of competition more vicious than the traditional Protestant work ethic, which emphasizes humility and honesty. It’s not enough to work hard; one has to be tough and outmaneuver other interests.

Trump’s “truthful hyperbole” — i.e., basic manipulation — allows him to make deals and promote projects:

I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do . . . People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole.

Intimidation Strategy

Donald J. Trump was born in Queens, New York to Fred and Mary Anne Trump. Fred was a real-estate developer and a no-nonsense type who intimidated most people he came into contact with, including the tenants in his buildings. “You made it in my father’s business — rent-controlled and rent-stabilized buildings — by being very tough and very relentless.”

In contrast, Mary Anne was more interested in the finer things in life:

Looking back, I realize now that I got some of my sense of showmanship from my mother. She always had a flair for the dramatic and the grand. She was a very traditional housewife, but she also had a sense of the world beyond her . . . She was just enthralled by the pomp and circumstance, the whole idea of royalty and glamour.

Donald’s character synthesized his father’s brutal efficiency and his mother’s ostentatiousness.

Of his four brothers and sisters — Robert, Fred, Maryanne, and Elizabeth — Donald had the most aggressive personality. He illustrates this with a childhood anecdote about taking all of Robert’s blocks to make his own building, ignoring the deal he made to eventually give those blocks back.

This youthful aggressiveness isn’t limited to a typical sibling disagreement. Trump explains that Fred Jr could not handle the vicious and competitive nature of his father’s business, perhaps implying that his brother’s alcoholism and eventual suicide came from his relative lack of aggressiveness.

Trump provides a host of examples of his aggressive tendencies from a young age:

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.

The young Trump wanted to appear as a domineering leader and learned how to imitate and overcome other bully-like figures in his life. One such person was Theodore Dobias, Trump’s teacher at the New York Military Academy: “I learned how to play him . . . I respected his authority, {so} that he didn’t intimidate me.”

Trump’s instincts led him to surrender to Dobias’s authority in order to be respected: “If he sensed strength, and you didn’t try to undermine him, he treated you like a man. From the time I figured that out — and it was more an instinct than a conscious thought — we got along great.”

Trump uses these stories of stealing from siblings and intimidating teachers to equate aggression with superior leadership and business qualities. Trump’s strategy to intimidate competitors includes academic credentials, with his undergraduate degree from the Wharton School of Business in Pennsylvania. He does not consider his formal education all that important — instead, he thought it would make his peers see him as a better leader: “A lot of people I do business with take it [a business degree] very seriously, and it’s considered very prestigious. So all things considered, I’m glad I went to Wharton.”

Profiting From Disaster

Trump calls Swifton Village in Cincinnati his first “big deal.” He took advantage of Federal Housing Administration foreclosures to buy the property at a discount rate.

He describes the original tenants as “very poor,” and, at least according to him, “each family had seven to eight children.” As he systematically kicked these families out, Trump gentrified the development, replacing the original tenants with a “better element.”

He put together his own management staff, including one nefarious character the book calls Irving. While Irving was admittedly a womanizer, a liar, and a thief — he even stole from Swifton Village — Trump expresses admiration for his ruthlessness and skill as a “bullshit artist.”

Despite his unsavory characteristics, Irving serves as a “lion tamer” for unruly tenants. In a way, Irving is a slightly more vulgar projection of Trump’s own character: the pig behind the lipstick.

Trump sought to surpass his father’s accomplishments in Queens and Brooklyn, and aimed at something bigger and more luxurious in Manhattan. But before he could embark on these future real-estate projects, he needed to cultivate the right political connections. He joined the exclusive “Le Club,” a fancy nightspot for the rich and powerful, where he schmoozed and hobnobbed with the city’s bigwigs, including the infamous lawyer Roy Cohn — Joseph McCarthy’s right-hand man during the Red Scare.

Trump admired Cohn’s toughness, and he hired him as part of his defense team when the Department of Justice sued Trump for discrimination in renting to minorities.

In the mid 1970s, New York City faced bankruptcy. The city was loath to lend out money, and Trump fed off these crisis conditions by turning bad circumstances into his “biggest weapon.” He took the Commodore — a “loser hotel” — and convinced the banks and the city to give him money and tax abatements to create new construction, playing on “their guilt and their fear and their sense of moral obligation” as he lined his own pockets. As he put it in his cynical pitch to investors:

The city is in trouble, but it’s still a great city, and it’s our city, and if you don’t believe in it, if you won’t invest in it, how can you expect it to turn around? If you lend millions of dollars to Third World countries and suburban-shopping-mall magnates, don’t you also owe some obligation to your own city?

When a reporter later asked him why he got a forty-year tax abatement, Trump replied, “Because I didn’t ask for fifty.” As Trump puts it, “The worst of times often create the best opportunities to make good deals.”

Leonard Stern’s documentary “What’s the Deal?” aptly states that if the Commodore was Trump’s graduate term paper, then Trump Tower was his doctoral thesis. He wanted a building big enough to match his ego in the finest location in Manhattan: Fifth Avenue. “From the start, size was a top priority. With such a great location, the more apartments I could build, the better the return I could hope to get on my investment.” Critics charged that skyscrapers like Trump’s were “machines for making money,” but he took that as a compliment.

The tower epitomized Trump’s career, symbolizing his status as the ultimate alpha-male capitalist. The building is a fifty-eight-story phallic structure that penetrates the sky and alienates those below in its shadow. Trump, of course, occupies its tip.

He obtained permission to build the tower twenty stories higher by opening the main atrium to the public. This act of generosity, however, is undone by what Trump doesn’t mention: he used a small, super-exploited group of undocumented Polish workers to demolish the existing structure and build the tower.

Trump promised that the original building’s sculptures would be removed and donated to the Metropolitan Museum of Art, but — because of the cost and the possible ten-day construction delay — he had them destroyed instead. Trump claims that he wasn’t looking to be “the bad guy,” but also recognizes that, from a “bottom-line perspective, bad publicity is sometimes better than no publicity at all. Controversy, in short, sells.”

His desire to boost sales also influenced the tower’s design choices. He requested a very specific Italian marble for the atrium:

Invariably, people comment that the atrium — and the color of the marble particularly — is friendly and flattering, but also vibrant and energizing — all things you want people to feel when they shop: comfortable, but also pumped up to spend money.

Trump had even bigger super-skyscraper ambitions for a proposed “Television City” to house NBC in Riverside Park South. Slated to be the “world’s tallest building,” it failed to materialize after massive community opposition. At the time, George Will praised Trump for his excess as uniquely American. (Later, Trump called Will a “loser.”)

Rich Donald’s Almanac

Atlantic City had an equally glamorous but slightly different appeal than Manhattan. Gambling provided an almost constant cash flow. “People think I’m a gambler. I’ve never gambled in my life. To me, a gambler is someone who plays slot machines. I prefer to own slot machines. It’s a very good business being the house.”

But Trump was always more concerned with appearing successful than ensuring that his businesses were stable enterprises. This ultimately didn’t work out — his casinos went bankrupt.

Schwartz presents Trump as a mischievous schemer who used every trick in the book to project the image of success. For instance, he “rounded [up] every bulldozer and dump-truck” he could find for his vacant Boardwalk property to pretend he was busy with construction. He wanted to fool the Holiday Hotel board members into thinking it was “the most active construction site in the history of the world” so that they would invest.

Trump’s scheming was aimed not only at rival developers, but also at his own tenants. His Central Park South project revealed him as the nightmare landlord he is, but in The Art of the Deal, he tries to put a good spin on it. Trump was “sitting on gold” and wanted to demolish the building and replace it with his own. But the tenants resisted.

Ironically, Trump had no problem kicking out immigrant families in Cincinnati, or getting rid of the peddlers on the street in front of Trump Tower, but he describes himself as a humanitarian for recruiting homeless people to occupy Central Park South to harass and scare the tenants out.

Trump’s nose for business has actually been a nose for crisis: he understands when to use foreclosures and bankruptcies to his advantage at the expense of others. The Art of the Deal is pitched as a self-help book, but it is a political manifesto for the American ruling class in its most decadent phase.

Benjamin Franklin’s Poor Richard’s Almanac was the earliest iteration of the American dream, expressed in the language of hard work, decency, and virtue. If Franklin invented the ideology of the dream, then Trump perpetuates the illusion that masks the nightmare. The mystical shell of success hides the cynical kernel of exploitation.

This is a guidebook for ruining people’s lives.