What Donald Trump’s Books Say About Winning

Thirty years ago with The Art of the Deal, the president broke with a long tradition of American success writing by separating self-improvement from morality.

The cover of Donald Trump's 'The Art of the Deal' with a cutout of Trump raising his fists
Wikimedia / Shutterstock / The Atlantic

Donald Trump appeared in many guises—billionaire real-estate tycoon, golf-course mogul, beauty-pageant impresario, reality-television star—before his blindsiding rise to the presidency of the United States last year. One of his least recognized roles is also one of the most revealing: success writer. Thirty years ago, in 1987, Trump’s The Art of the Deal leapt onto the bestseller list as a rollicking account of his business triumphs that, according to a glowing New York Times review, “makes one believe for a moment in the American dream again.” A string of advice tracts followed over the next two decades, among them 2008’s Think Big: Make It Happen in Business and Life and 2004’s Trump: How to Get Rich.

These books present the Trump formula for upward mobility, what he describes in Think Big as “a recipe for success that the top 2 percent live by and that you too can follow to be successful.” Although ghostwritten, they also epitomize Trump’s sentiments and sensibility. In language alternately disarming and appalling, they explain his view of the world, and the values that drive him.

Trump’s books fall into one of the oldest, most influential genres in American popular culture: the success tract, or literature on how to get ahead in life. In the early republic, Benjamin Franklin advocated “virtue” as the pathway for aspiring individuals unshackled from aristocratic tradition. In the 1800s, Horatio Alger offered hard work and “character” as habits that would produce prosperity in a competitive market society. For a 20th-century society dominated by bureaucracies, Dale Carnegie urged strivers to cultivate human relations and an attractive “personality.”

But Trump’s writing has destroyed many of this tradition’s essential elements. To be sure, he borrows certain tried-and-true elements from Franklin, Alger, and Carnegie—unstinting labor, positive thinking, careful delineation of goals, mental focus. But he also peddles directives that ignore what these writers perceived as their obligation to shape good people and a good society. Instead, Trump’s injunctions look inward to promote a relentless self-aggrandizement, and outward to manipulate a world of facile images. These qualities, and their appeal to a popular audience, have reshaped America’s success tradition. They have jettisoned its moral ethos for one of bristling self-regard.

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The notion of making it—achieving a higher social status, earning more money, gaining respectability—is almost embedded in the genetic code of Americans. From their earliest arrival on the Atlantic seaboard, New World settlers displacing the land’s original inhabitants combined a rough embrace of personal advancement with different beliefs about religious, political, and social freedom. Whether chasing trade profits in tobacco or establishing representative assemblies, colonial Americans idealized the individual released from traditional restraints. Franklin, America’s first great success writer, voiced such aspirations in Poor Richard’s Almanack (“A penny saved is two pence dear,” “He that waits upon Fortune is never sure of a dinner”) and then offered more extensive praise for prudential and virtuous habits in his famous Autobiography.

The American socioeconomic landscape burgeoned in the early 1800s, due to the explosive growth of steamboats and railroads, factories and commercial farming, geographic expansion and trade networks. Reflecting on this new fluid society, success writers extolled individual opportunity in a market society. Alger, the most influential of them, published a series of mass-market novels from mid- to late-century with titles such as Struggling Upward and Ragged Dick. They romanticized the self-made man who rose from modest circumstances through hard work, emotional self-control, and upstanding moral character. Readers devoured these books. As literature, the Alger tales were trainwrecks with their fanciful plots and sentimental language. But as cultural documents they brilliantly captured the desires of an attainment-minded age.

By the early 20th century, the U.S. had entered an era defined by consumer capitalism, large-scale social and economic institutions, and corporate liberalism with its notion of regulated competition. A fittingly revamped success ideology emerged. In 1936, Carnegie’s How to Win Friends and Influence People burst onto the cultural scene, attracting millions of readers with a message that emphasized the importance of a winning personality and skilled human relations for standing out in a bureaucratic milieu. Carnegie argued that the success seeker must “make the other person feel important,” “avoid arguments,” and “keep your human contacts smooth and pleasant.”

Decades later came Trump, who followed this well-worn path with his own formula for success. First, his books stress that defeating (or crushing, if possible) your opponents is the key to upward mobility. Economic and social life is an arena for survival where the soft perish and the alpha male prevails. “The world is a vicious and brutal place,” Trump writes in Think Big. “They want your job, they want your house, they want your money, they want your wife, and they even want your dog. Those are your friends; your enemies are even worse!”

In this Hobbesian world where life is “nasty, brutish, and short,” Trump insists, the successful individual must cultivate hard-nosed traits to prosper. Trump’s father, himself an accomplished real-estate entrepreneur, taught his son to be forceful and dogged. Young Donald took to this naturally. He relates in The Art of the Deal an episode in the second grade where “I punched my music teacher because I didn’t think he knew anything about music and I almost got expelled.” An adolescent stint in military school taught him to remain assertive while channeling his aggression into achievement. Trump drew a clear conclusion: “You can’t be scared. You do your thing, you hold your ground, you stand up tall, and whatever happens, happens.”

The successful person, according to Trump, must strike back at anyone who crosses him.  “My motto is: Always get even,” he writes in Think Big. “When somebody screws you, screw them back in spades.” He recounts how a real-estate competitor, for example, once hoodwinked him in a complicated deal, initiated a lawsuit, and then offered to settle for a life-time membership in one of his golf clubs. Trump accepted, but then publicly humiliated the man at every opportunity. He admits, “I love getting even. I get screwed all the time. I go after people, and you know what? People do not play around with me as much as they do with others.” Trump also advocates ruthlessly pursuing goals, exploiting any advantage over a competitor, and maintaining flexibility when maneuvering against opponents. But he forbids retreating. “If you admit defeat, then you will be defeated,” he declares in Think Big.

While some of Trump’s lessons may sound commonplace, more unique is his advice to generate publicity by manipulating the media, a dictum that would have dumfounded his success-writing forebears. Early on in his career in the New York real-estate market, Trump learned to capture the public imagination by playing the media. “One thing I’ve learned about the press is that they’re always hungry for a good story, and the more sensational the better,” he says in The Art of the Deal. When razing a landmark building to prepare for Trump Tower, he suffered a torrent of negative stories but pointed out that most of them described how the demolition made way for “one of the world’s most luxurious buildings.” Trump’s conclusion: “Bad publicity is sometimes better than no publicity at all. Controversy, in short, sells.”

At the heart of the Trump formula for winning, however, lies the larger-than-life persona. His architecture of the self rejects earlier models in the American success tradition—Franklin’s “virtue” and Alger’s “character” and Carnegie’s “personality”—to focus on creating a Titan image, a persona that doesn’t earn respect or kindle affection, but that radiates power and inspires awe. Trump’s Titan first appears in The Art of the Deal, frequenting establishments such as the exclusive Le Club because “its membership included some of the most successful men and the most beautiful women in the world.” To become a Titan, one must go “first class all the way. ... Let everything you do and own convey an image of importance. Own a first-class car, carry first-class luggage, go to first-class restaurants, and shop in first-class stores.” The Trump persona specializes in, above all, the art of the gasconade. He notes shrewdly, “I play to people’s fantasies. ... People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole.”

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With its pragmatism and disregard for questions of morality, Trump’s approach to success makes no attempt to link an oversized personal image to a deeper notion of personal growth. Readers get no sense of how Trump’s vision helps create good people, either individually or collectively, as in Franklin’s virtuous republic, Alger’s bourgeois utopia, or Carnegie’s well-adjusted bureaucratic society. Trump’s reflections on family say little about love or even personal happiness, instead stressing no-nonsense issues of trust and support. While Trump values loyalty and recommends hiring and rewarding individuals who will stick by you, ultimately the success seeker can only depend on blood ties: “You can trust family in a way you can never trust anyone else,” he asserts in The Art of the Deal.

Similarly, Trump’s thoughts on women seldom address their humanity, talents, or role in the achievement of love and happiness. In The Art of the Deal, he dutifully claims, “I’ve hired a lot of women for top jobs, and they’ve been among my best people.” But in the commentary that follows, he depicts women primarily as status symbols for successful men. He describes the clubs he joined in New York as places where you’d likely see “a wealthy 75-year-old guy walk in with three blondes from Sweden.” Trump ventures into pop-anthropology analysis in Think Big, arguing that modern success-seeking is a male-dominated endeavor “only a short step out of the jungle. In primitive times, women clung to the strongest males for protection. …  High-status males displayed their prowess through their kick-ass attitudes.” For proof, Trump offers his own record of sexual conquest:

The women I have dated over the years could have any man they want; they are the top models and the most beautiful women in the world. I have been able to date (screw) them all because I have something that many men do not have. I don’t know what it is but women have always liked it. … Beautiful, famous, successful, married—I’ve had them all, secretly, the world’s biggest names.

Finally, the moral vacuum surrounding Trump’s success advice appears in the reward he holds out. The payoff for following his formula is wealth, and the flashier the better. His books are replete with paeans to gold-spangled display. From renovating glitzy hotels in Manhattan to building a lavish casino in Atlantic City, Trump relishes glamorous business projects. His crowning achievement was the 1983 completion of Trump Tower in the heart of New York, which demonstrated “how big a building I can legally build,” he describes in The Art of the Deal. These creations, along with his opulent penthouse apartment in New York and spectacular residence in Palm Beach, Mar-a-Lago, comprise the hard-earned fruits of success. “I know people are responding to my passion for beauty and style, which is reflected in my work,” he confesses in Think Big. Build it bigger and they will come.

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Franklin, Alger, and Carnegie tapped into many of Americans’ deepest needs and desires fueled by the standards and structures of their respective ages.  So what does Trump’s writing reveal about the author and the contemporary culture that has proved so receptive to his message? The Art of the Deal, after all, gained more than a million readers while his other books have sold briskly. Clearly, his approach guided his victorious presidential campaign: Denigrate any opposition, employ bravado, manipulate the media, elevate personal image over substance, eschew structured organization, and depend on your family. But Trump’s books also cut deeper to illuminate several modern American values and characteristics.

The appeal of his extravagant level of wealth reveals the deep hold of consumerism in modern American life. In a society where religious guidelines, loyalty to social institutions, and standards of bourgeois morality have waned over the last century, material accumulation has emerged as one reliable measure of value and achievement. Trump’s message also reflects the postmodern quality of American culture in its tendency to create reality through publicity and media. “Brand yourself and toot your horn,” he instructs in How to Get Rich, and this injunction stands as a centerpiece of his success creed. Lastly, Trump’s image signals the allure of celebrity for Americans. Indeed, his habitual use of “truthful hyperbole” to shape an attention-grabbing public persona is the essence of fame. No wonder he created a reality-television show called—what else?—The Celebrity Apprentice.

Despite Trump’s complaint in Think Big that young people have been spoiled by the “instant gratification ethic of the ‘me generation,’” Trump’s oeuvre can be easily read as one long tribute to himself. Franklin’s ruminations on virtue, Alger’s sentimental renderings of the character ethic, and Carnegie’s admonitions on the need for skilled human relations fall to the wayside before Trump’s imagined, inflated self. Unlike his predecessors, Trump offers a particularly empty sketch of American attainment. Readers get the sense that success-seeking is an addictive, even amusing compulsion, but not a very meaningful one.

Dimly aware of this problem, Trump turns to a set of banal rationalizations. Unable to attach any larger significance to the pursuit of social advancement and multiplying wealth, he admits in The Art of the Deal, “If you ask me exactly what the deals I’m about to describe all add up to in the end, I’m not sure I have a very good answer. Except that I’ve had a very good time making them.” In Think Big, he suggests that winning is its own reward: “I love to make the big score and to make the big deal. I love to crush the other side and take the benefits. Why? Because there is nothing greater.”

Trump’s portrait of modern success perhaps conjures the final scenes of Orson Welles’s Citizen Kane, where a brooding and angry Charles Foster Kane sits alone in the great hall of his immense mansion, Xanadu, surrounded by opulence but abandoned by loved ones. One wonders if Trump watched the film all the way through before claiming it as his favorite movie. It is, after all, a tale of an entrepreneur who rises to fortune and fame through media manipulation, develops an enormous ego, enters politics as a populist celebrity before falling into disgrace, spends much of his life bullying others until they desert him, and dies without grasping the meaning of his life. Citizen Kane offers an American vision of personal improvement and social advancement that has shrunk to the vanishing point. It has much in common with The Art of the Deal and its ilk, works that put forth a grandiose portrait of winning where big, bigger, biggest actually materializes as small, smaller, smallest.