Trump: The Art of the Deal

“One thing led to another, and now I’m talking about building a large luxury hotel, across the street from the Kremlin, in partnership with the Soviet government. They have asked me to go to Moscow in July.”

Donald Trump emphasizes his capacity to see deals everywhere by breaking down the barriers of the Cold War. The Soviet Union in the late 1980s was considered decidedly anti-capitalist, but even the anti-capitalist Soviets could not help but be tempted by Donald Trump’s ability to make a deal, the book suggests. The book presents Donald Trump as such a skilled dealmaker that he can tempt even the most anti-capitalist politicians toward capitalism. This aligns with the theme of No Publicity Is Bad Publicity, as Trump’s willingness to engage with a high-profile, politically charged opportunity demonstrates his belief in leveraging international attention for business success.

“More than anything else, I think deal-making is an ability you’re born with. It’s in the genes.”

Donald Trump does not present The Art of the Deal as a guidebook. The book doesn’t codify the dealmaking process beyond vague allusions to advice or best practice principles. Rather, Trump views the skill of dealmaking as something innate. Either a person is born with the talent to make deals, he believes, or they are not. Some skills can be learned, but Trump considers himself one of the lucky few who have been born with the natural ability to make a deal in any circumstance.

“Not all of them liked the idea of the world’s tallest building. But the point is that we got a lot of attention, and that alone creates value.”

Throughout The Art of the Deal, Donald Trump returns to the importance of creating press interest around any project, reflecting the theme No Publicity Is Bad Publicity. Building the world’s tallest building will be an expensive endeavor and will likely be an inefficient use of his money. But the existence of the world’s tallest building—particularly if it is branded with the Trump name—has a value all of its own. The attention created by the project is difficult to quantify but impossible to overlook, Trump says.

“We had a relationship that was almost businesslike.”

Donald Trump recounts his relationship with his father, Fred Trump, in business terms. His account of his father’s life almost entirely focuses on Fred’s business achievements and how they differed from Donald’s business achievements. Their relationship, Donald says, was “almost businesslike” (71). The implied coldness of this father-son relationship hints at why Donald sough to establish himself on his own terms rather than follow in the footsteps of a father who was reticent to offer warmth or love. This highlights how personal relationships in the book are framed through the lens of business rather than emotion or sentimentality, and there is narrative distance between the present and his youth in particular.

“I can always tell a loser when I see someone with a car for sale that is filthy dirty. It’s so easy to make it look better.”

Occasionally, the business-like language of the book slips, and a less formal Trump emerges. The idea of cleaning a car before selling it seems so patently obvious to Trump that anyone who fails to think about this is “a loser” (84). This attitude toward those who do not follow his business ideals can be found throughout the book, as Trump reflects on his personal grievances amid the discussion of broader business topics. This moment suggests that perception and presentation are just as crucial to business as the substance of a deal itself.

“Before long New York was suffering from a crisis of confidence. People simply stopped believing in the city.”

The figure of Donald Trump as portrayed in The Art of the Deal is tied to New York City. He does business in Cincinnati or New Jersey but always returns to his home city. When the city itself begins to struggle, Trump views this almost as a personal slight. People have stopped believing in the city as he believes in it; since he will continue to believe in it no matter what, this occasional slip in the city is, for Trump, an opportunity. This reflects the No Publicity Is Bad Publicity, as Trump sees economic downturns as moments where visibility and bold action can create new opportunities.

“Realizing that the positive approach wasn’t working, we tried to play to their guilt and their fear and their sense of moral obligation. Forget us, we’d say; you owe it to New York.”

As a New York native, Donald Trump believes wholeheartedly in the potential of the city of New York. When he wants to make a deal, he trades on this emotional investment, trying to shame or guilt others to sacrifice their profits in the name of the city. Ironically, this sort of emotional investment would be unlikely to work on Trump himself, though he is willing to try it on others in the name of sealing a deal. This demonstrates Trump’s belief that persuasion is a key element of negotiation, and that deals often rely on emotional leverage rather than pure financial logic.

“I now have in my will a clause describing the importance of that restrictive covenant, just on the chance that one of my heirs happens not to be that sharp.”

The importance of the clause is such that Donald Trump has written about it in his will. His boast could be read as an admission that he lacks belief in his children to recognize the brilliance of his decisions. While he believes that he has exceeded his father’s achievements, he may not be sure that his own children will do the same to him.

“He was a man with impeccable manners, perfect white hair, beautifully tailored suits, and an imperial style. If you were casting a movie about the president of Tiffany, Walter Hoving would get the part.”

A person’s worth and importance, to Donald Trump, is measured as much by their appearance as their accomplishments. He praises Walter Hoving’s achievements in running Tiffany & Co., but he does so through the lens of Hoving’s appearance. He simply looks the part and this, to Trump, is just as important as actually sealing the deals.

“A guy named Arthur Drexler, from the Museum of Modern Art, put it very well when he said, ‘Skyscrapers are machines for making money.’ Drexler meant it as a criticism. I saw it as an incentive.”

Donald Trump relishes any opportunity to defy conventional wisdom, especially when it is espoused by individuals or groups who he believes have unfairly criticized him in the past. In this instance, he delights in confounding the critics who disparage his architecture. He quotes Drexler explicitly to show how much he believes the exact opposite to the critics’ opinions. In this way, Trump’s buildings become physical manifestations of his defiant attitude. This connects to Deals as an Art Form, as Trump frames his real estate projects not just as financial ventures but as statements of ambition, power, and success.

“I have an almost perverse attraction to complicated deals, partly because they tend to be more interesting, but also because it is more likely you can get a good price on a difficult deal.”

Trump delights in putting together complicated deals. Throughout the book, he relates the complexities of many of his deals. These complexities often involve exaggerating or blurring the truth, adding even further complexity to deals and delighting Trump. The added complexity only makes the deals more satisfying in retrospect, as Trump can boast about his talent in getting such a complicated deal over the line. This reflects the theme Business, Memoir, and the Making of a Persona, as it highlights Trump’s self-perception as someone who thrives in high-risk, high-reward environments that others might avoid.

“A few sons set out to outdo their fathers at the same game, and that may be the toughest thing of all, particularly when the father’s name is Conrad Hilton.”

Donald Trump’s comments about Barron Hilton hint at his own relationship with his father. Trump believes that he has succeeded where Barron failed, having outdone his father in the world of business. His successes in besting Barron in the business world, then, have the added effect of bolstering his own ego and illustrating how he succeeds where others cannot. This anecdote has a future twist, in that Trump would name his youngest son Barron.

“But Conrad believed very strongly that inherited wealth destroys moral character and motivation. I happen to agree that it often does.”

Donald Trump agrees with Conrad Hilton’s position on inherited wealth, though he inherited a large sum from his own father and—as stated elsewhere in the book—plans to leave similarly large amounts to his own children. Trump’s statements in The Art of the Deal do not always line up with his actual actions, suggesting that his narration may not be reliable.

 “But then, ‘modest’ isn’t my favorite word.”

Donald Trump’s narration throughout The Art of the Deal is self-aware. He knows about his reputation as a brash, materialistic, brazen figure. This is the Trump brand, the persona that he wishes to project into the world. Modesty is not a part of this persona, he knows, so he is more than willing to point out where he is not being modest.

“You don’t act on an impulse—even a charitable one—unless you’ve considered the downside.”

Reviewing his own deal, Trump warns against acting impulsively. In this instance, the downside to a possible act of charity is negative press. Trump illustrates just how much he values publicity by ranking it higher than any act of impulsive charity. Damage to his reputation is not worth any potential good that results from his impulsive act.

“Temperamentally, I just couldn’t accept the idea that the tenants were using harassment charges as a lever against me so that they could buy a building for less than market value.”

Trump does not present himself as a coldblooded businessman. He acts emotionally and pursues agendas and rivalries, often to his own detriment. This bolsters his idea of dealmaking as an artistic endeavor, in which his deals are his way of expressing emotions in the way that an artist might paint a painting. Temperament is a foundational part of Trump’s business mindset.

“They had attracted virtually no press attention and very few fans.”

Donald Trump’s criticism of the USFL neatly ties into his own view of how business should be done. Building a good product is not enough, he believes, if people are not talking about it. The football league failed to create any publicity, which Trump points to as the cause for its failure. When he comes aboard, his first instinct is to generate press in any way possible. This aligns with the No Publicity Is Bad Publicity, showing how Trump sees visibility as a vital component of any successful enterprise.

“You can probably guess how much stock I put in polls.”

Trump’s approach to business is very single-minded. He follows his instincts at all times, which makes him wary of consultants or polls in any form. This wariness with regards to polls strengthens the image of Trump as a natural dealmaker: He is an instinctive dealmaker, rather than an accountant, which is what turns his deals into art rather than mere business.

“I never had a master plan.”

Trump does not approach his business dealings with a “master plan” (301). He presents himself as an instinctive, naturalistic dealmaker, who responds to his gut feeling at any time. He reshapes the architectural landscape of New York in an emotional, instinctive manner, rather than as part of a grand plan to rebuild the city.

“What you have to understand about Ed Koch is that he’s a bully, pure and simple.”

Ed Koch emerges from The Art of the Deal as Donald Trump’s primary antagonist. Whereas Trump wants to make deals and help people, he castigates Koch as too corrupt and proud to do what is best for the people of New York. It is not enough for Koch to simply be corrupt, however, so Trump presents him as “a bully, pure and simple” (306). He claims that Koch is bullying innocent developers like himself who only want what is best for the city. This framing is designed to make Koch seem even more objectionable and, in contrast, to justify Trump’s dislike of the mayor. This aligns with No Publicity Is Bad Publicity, as Trump’s rivalry with Koch reinforces the idea that conflict—especially when played out in the media—can serve as a powerful tool for shaping public perception.

“I took the letter of intent out of a folder and tore it in two, in front of Macri.”

Trump’s instinctive approach to business comes to a head when he rips up his letter of intent in front of Macri. Earlier in the book, Trump has used such letters to manipulate deals. Yet here, he shows himself to be an honorable figure. He does the right thing, he says, out of loyalty and the kindness of his heart. This has the secondary effect of endearing himself to Macri, who later returns to Trump to make good on the letter. The gesture shows that Trump’s instinctive attitude toward business is paying off.

“Trump, who believes that excess can be a virtue, is as American as Manhattan’s skyline, which expresses the Republic’s erupting energies.”

Trump revels in criticism, so long as it is in the press. He gleefully cites George Will’s indictment of his materialism as an advert for his building projects. While Will might have intended the comment to be a criticism, Trump uses it to emphasize his public persona as the larger-than-life manifestation of New York in the 1980s.

“The one thing I know is that I’ll be doing business in New York City long after Ed Koch has moved out of Gracie Mansion.”

The last mention of Ed Koch in The Art of the Deal looks to the future, rather than the past. While Donald Trump’s antagonist may have frustrated him in the present, Trump suggests, his true victory will be his ability to endure. The people of New York will remove Koch, thereby validating Trump’s opposition to the Mayor. In a novel that dwells on Trump’s prior accomplishments, Trump feels certain enough to make a bold prediction about his inevitable victory over his old rival.