The Art of the Art of the Deal


I read the first half of Donald Trump’s 1987 business-advice book cum memoir Art of the Dealer last weekend. A fun read, actually. The prose are simple and concise. The stories are amusing and replete with dropped names and power plays. The book spent 51 weeks on the best seller list in the late 80’s and I can see why. It gives the common person a window into the life of a very rich and powerful man. The first chapter is just an hour by hour recounting of a week in Donald Trump’s life. We hear about the phone calls he makes, the deals he’s considering, the charity benefits he goes to, the “work” he does at his office in Trump Tower in Manhattan. I think for a long time people appreciated it for the narrative voice. The book is written in the first person, presumably by Trump, though the book’s co-author Tony Schwartz has come out in the last year as saying that he wrote the entire thing himself with little to no input from Trump. If this is the case—and it probably is, in all honesty—then Schwartz does a magnificent job of matching Trump’s signature cadence and diction. I think it’s in line too with how people would expect an impatient and aggressive businessman to speak: short sentences with few subordinate clauses, uncomplicated ideas left largely unsupported, unfailing confidence in the truth of what’s expressed, a complete absence of anxiety. The Donald Trump of Art of the Deal, whether contrived or genuine, is very much a “don’t sweat the small stuff” kind of guy. He is shown to have an innate ability to reduce complicated matters to their most basic and essential components. He rejects doubt and counter-argument as mere distraction. A true pragmatist, Trump seems to care only about what that which prompts him to act, or the alternative, to wait it out and “keep your options open.”

One imagines the initial intent of the author and the publisher was for Art of the Deal to be an advice book brimming with useful negotiating tactics and investment tips and only a chapter or two of Donal Trump aggrandizement, just enough to establish his authority on the subject matter. Instead that formula was reversed: just one chapter of Art of the Deal is devoted to actual dealmaking; the rest is shallow memoir with a few insights thrown in about the lessons Trump learns from different episodes in his life. Reading the advice chapter, one discovers quite quickly that there just isn’t that much to the report when it comes to the Trump philosophy for doing business. The chapter even begins, “My style of deal-making is quite simple and straight forward.” Trump uses no theories of negotiation or of rhetorical persuasion. He has no special sense of how markets behave or where to find undervalued assets. He simply “aims high” and keeps “pushing” until he gets what he wants. And if you’re already playing from a position of advantage, that apparently is all you need.

Trump does have a handful of strategies for leading and dealmaking, which are referred to in the book as “Trump Cards.” Perhaps it could be worthwhile to consider a few of these individually:


Think Big

“If you’re going to be thinking anyway, you might as well think big.”
I can imagine Tony Schwartz writing that line with some relish. The thinking big mentality here means simply placing larger bets to reap larger rewards. Of course, to bet high you have to have some money to begin with, and you have to be far enough ahead that you can absorb the loss and live to bet again. One has to wonder for whom this advice is intended. It assumes the actor commands some degree of advantage already and that that advantage can be leveraged for still greater opportunities. I think the point of including it here has less to do with effective business strategy and more with motivational encouragement to seek—and expect—better returns. It tracks with a lot of prosperity gospel nonsense that tells people what they want to hear and not what they can come to expect. It also conveys a lot of what makes Trump appealing to people, that being the swagger and bravado of a winner.


Protect the Downside and the Upside Will Take Care of Itself

“It’s a very good business being the house.”

This one seems to have been thrown in to balance out the bullishness of the Think Big section. Here Trump tells us to minimize our exposure and take the easy money when you find it. I actually think the two ideas taken together constitute something that might approximate a coherent business strategy. When you are able to raise the kind of capital that Trump can, your business dealings start to transcend basic commerce. You come into the ownership of things that are so big that they are not simply properties and assets; they are things that compose the greater apparatus of society and the economy. Such investments are sure to pay, so long as society—or the part of the society that’s being laid claim to—remains solvent. Skyscrapers in Manhattan remain profitable if people keep doing business in New York. Casinos generate revenue so long as people go on vacation. The likelihood of any of these capital goods diminishing in value is comparable to the likelihood of there being some kind of social revolution that changes the way people on earth go about their daily lives. It goes without saying that the risk of losing under such conditions is quite low.


Maximize Your Options

“I keep a lot of balls in the air, because most deals fall out, no matter how promising they seem at first.”

All he’s doing here is telling us to hedge our bets. It’s such a banal insight that I hesitate to even lend it any thought. Though I do think it could strike an average person with average finances as novel that the more money you have to invest in things, the more options one is given for investment. Again, this advice is really only practicable if you literally have more money than you know what to do with.


Know the Market

“…I don’t hire a lot of number-crunchers, and I don’t trust fancy marketing surveys. I do my own surveys and draw my own conclusions.”

It has taken us all a very long to time to admit it, but Trump does know his customer. He has an instinct for seeing what people want most and a willingness to deliver. He doesn’t say it anywhere in the book, but if you look at the sort of businesses Trump runs and the message he reflects back to the consumer, you can unmistakably see what he thinks people want—and he isn’t wrong. People want to feel like they’re winners. They want to feel like they’re prospering and doing well in life. They want to think that they’ve been blessed with intelligence, prowess, and good luck. In the beginning of his career Trump sold newer, slightly nicer apartments to middle income people, and these apartments gave them the feeling of upward mobility. Then he moved on to Manhattan and began selling to a nouveau riche, people who actually were winning at capitalism and wanted material affirmation of their success. He bought casinos knowing that that brief and fleeting sense of victory the gambler gets from the occasional win will always keep the people coming back. Seeing professional sports as yet another delivery mechanism for getting the consumer his fix of vicariously experienced victory, he bought a football team. And of course now he is running for President of the United States on a one plank platform of making people feel as though America is winning again.

Understand, I see nothing wrong with people wanting to feel like they are doing well in life. It makes perfect sense that we should want to succeed as individuals in a world dominated and defined by market competition. There is no shame in demanding one’s dignity and wanting to be acknowledged and admired. I take issue with the man who presumes to sell our dignity to us to us as a fungible commodity. The scam here is that Trump is not offering a means for obtaining victory in life. He’s only offering the feeling of having won. There’s no guarantee that the feeling will signify real accomplishment, or that it will persist, or that there will be any truth to it at all.


There are about a half dozen other Trump Cards in the “Elements of the Deal” chapter, all of them having to do with consumer manipulation, managing exposure, and exerting leverage from a position of power. None of these lessons are actionable for normal person, and I don’t think they were ever intended to be. Art of the Deal does not teach you how to get rich. It teaches you what it’s like to be rich. It lets you sniff the bankroll without giving you any of the bills. And sadly, for a lot of people, having tickets to the show of someone else’s life is good enough. I suppose luxuriating in fantasies of another’s luxury rather than putting something on the line to realize your own is a way of minimizing exposure.

Fish on Academic Inquiry


Students at most American universities began returning to school these last few weeks. And with them has come a renewed discussion over intellectual freedom in the classroom. This year’s incoming freshman class at the University of Chicago was sent this letter from the Dean of Students in which the Dean, apparently responding to some perceived challenge, affirmed the university’s commitment to academic freedom and the administrators’ refusal to support “trigger warning” requirements and intellectual “safe spaces.” The tone of the letter is weirdly antagonistic though it names no adversary. In the absence of an organized argument to join, it seems the University of Chicago has resolved to create its own. In the last week, a new debate has arisen in academia and throughout the broader internet over free expression, inclusiveness, the role of the teacher in relation to the student, and the meaning of liberal values in the university enterprise. Here I’m using the classical meaning of liberalism advanced by John Locke, James Madison, John Stewart Mill and many many others, which rests on the free exchange of ideas, the impartial contestation of those ideas, and equity of power between contestants. In the modern university, Liberalism provides the rules and structure by which debate and inquiry are to be carried out with the aim of producing a reliable and credible result. To question Liberalism’s rule is a radical gesture and potentially very destructive. And yet Liberalism, when practiced correctly, demands that we regard it with some skepticism. For when Liberalism defeats its skeptics, it renews its reign and emerges ever more resilient and unassailable. We must always scrutinize Liberalism for flaws, because it does have some. I think the recent arguments over inclusion versus expression in universities emanates from the classic tension in Liberalism between freedom and equality.

There have been plenty of other attacks against the sacrosanct institution of liberalism, in the last few years, in the last few decades, in the last few centuries. One of the more interesting excursions into liberal disputation that I’ve found recently is this essay by Stanley Fish which ran in the Chronicle of Higher Education a few weeks ago. Fish comes to the defense of the old totems of academic persuasive writing: impartial analysis, exhibition of supporting evidence, citation of accepted authority, involvement with related counter arguments, and so on and so forth. He contrasts this grand old method of patient, plodding inquiry with a more activist approach–work that has an interest in some other agenda beyond the cold, mechanical pursuit of truth. He cites a student with whom he came to loggerheads over whether it is acceptable to submit work which betrays an obvious political bias and which proceeds from an unproven ideological proposition, rather applying the more orthodox method of starting from a posture of neutrality and building proof toward whatever conclusion the facts lead. It may seem like Fish is setting up straw men, but I’ve encountered people at my own university who do work this way and see nothing wrong with doing so. I know post-structuralists who reject any attempt at objectivity on the grounds that it is an imaginary precept and impossible to achieve. I know critical theorists whose explorations into identity politics are so wound up in their own narcissistic experience of themselves that they are utterly blinded to the ideas and arguments offered by others. I know social scientists who not only “study” subaltern populations but they also carry water for them politically and who would be the first ones at the barricades fighting for them when the revolution breaks out. And Fish is correct: challenge any of these activist types about the validity of their work as persuasive scholarship and their first response is to question the validity of an academy that fails to see the validity of their work. Yes, I’ve know plenty like this. I found it more than a little heartening to see them put in their place by one of the old masters.


Regrettably, the Fish essay is behind the Chronicle’s paywall. Here’s a rough summary:

Paragraphs 1 to 3: Fish complains about the uncredited appropriation of his interpretive community idea by other scholars. Defines interpretive community as being “made up of those who, by virtue of training, experience, and practice, have internalized the norms of some purposive enterprise—law, eduction, politics, plumbing—to the point where they see with its eyes and walk in its ways without having to think about it.”

Paragraphs 4 and 5: Proposes that this episode demonstrates the value of originality in academic discourse.

Paragraphs 6 to 9: Cites critics of the originality value, those who question the possibility of originality given the supposed spuriousness of authorship. Observes that such critics, in spite of themselves, still sign their work and take proprietorship over their ideas.

Paragraphs 10 to 12: How to make good academic arguments. Fish discusses the imperative in academic writing of contextualizing ones work by citing the work of others and with addressing opposing viewpoints. Uses example of student’s non-persuasive polemic.

Paragraphs 13 to 15: The problem with academic programs that give admission to non-academic writing, that is, writing that is not rigorously argued using the traditional framework of persuasive writing.

Paragraphs 16 to 21: Challenge to professional norms is perfectly legitimate, but it must be made within the boundaries of liberal inquiry. “An academic discipline can tolerate any challenge so long as the challenge is conducted within its precincts. Supposedly subversive arguments are absorbed into the very intellectual structures they claim to overthrow.”

Paragraphs 22 to 30: Formation of acceptable norms of argumentation and what counts as a worthy argument. Example: Holocaust denial.

Paragraphs 31 to 36: Effects of academic arguments. Academic arguments are made to produce a better understanding of the world in their listener. This is in contrast to activist messages which are intended to inspire people to action. Because academic arguments can be purely speculative, it is possible to achieve a certain degree of objectivity. This is the utility of academic discourse—that participants may inquire into a topic without having an interest in the outcome. This utility must be preserved. “[Academic arguments] are weightless, that is, without weight in the give and take of political strife unless they are appropriated for political purposes. But their weightlessness is their glory, and that is why they are different from domestic arguments, political arguments, and legal arguments. Like virtue, the making of them is their own reward. Other rewards are left to time and heaven.”

Reading this essay for now the third or forth time, I’m led to ask what I find so compelling in it. The argument isn’t particularly original; it’s just a version of Adorno’s theory and praxis dialectic decontextualized to the cloister of academic disputation. Fish’s language has a remarkable clarity, but the structure of the piece is a bit diffuse and he seems to begin to lose focus by the end. The Holocaust denial example is not fully explicated, I think. In spite of its shortcomings, the essay is still an interesting and even exciting piece of writing to read. I think it demonstrates exactly what good academic writing is supposed to do and what bad “non-professional” writing fails to accomplish. It arouses curiosity and intrigue. It weaves taught, marvelous ideas for the reader and then immediately calls them into question. It puts forth a proposition that offers the reader a means of making meaning of the ideas that are presented. It offers credible evidence to support that proposition. It persuades the reader to its side but also shows her the merits of the other side and what of interest can be found there. I find this to be a much more effective and worthwhile mode of writing than the dreck it inveighs against, because it seems to be at its very core motivated by honest curiosity. It is a path of thought beaten by an inquisitive spirit. And of all the motivations that propel humans forward, I think that is the best.


The Sin of Idle Sport


Today another September starts. As evidenced by my complete neglect of the Golden Assay I had a very enjoyable good summer. I wasted it all in games, sports, outdoor pursuits; all the things one ought to do with good weather. But one can indulge too much in leisure and become ashamed of his idleness. I am reminded here of John Bunyan’s “conversion” on the Elstow village green. As roads to Damascus go, his was wonderfully banal. Bunyan, of course, was an obedient Christian his entire life, but he enjoyed sport and bell-ringing on Sabbath days and apparently considered himself a spiritual delinquent for doing so. I think he was hard on himself. The wretch worked six days a week as an itinerant tinker, and understandably, needed a day off from time to time and a little diversion to go with it. But the Creator won’t even give us that, sadly, for one Sunday, while he was playing Tip-Cat with the other sinners, a numinous voice from the heavens admonished him to find shame in fun-having and quit sports. The line at the time was that Christ disapproved of sport because it was wasted effort and an idler’s refuge. A pious Christian works six days and spends the seventh in prayer. Any deviation from a rigid schedule of industry and devotion is depravity. I think this had to do with the Calvinist position of determinism and their equating sin with rejection of God’s plan. If you spend your life in work and worship, you are carrying out the destiny God intends for you and are therefore a righteous being, a saint even. Idle pastimes, observance of leisure, general amusement, are not evils in and of themselves; it’s simply that they divert people from more meaningful activity. Bunyan’s sin was not that he was playing Tip-Cat; it was what he was not doing while playing with his friends.

This animosity towards sport has almost completely vanished in the minds of modern people. Today sport is considered a noble pursuit. The exercise one gets from sports is understood to be essential to physiological health. The signs of regular exercise on the body are considered attractive. In a complete reversal of previous opinion, the practice of sport is now thought to be an indication of personal discipline and integrity. We even use athletics as a method of instilling discipline among young people in school. It is hard to imagine how totally different our conception of sports is in the protestant Christian world from the view of past generations. It feels like it has been with us forever, but it’s actually only recently that people began having even a positive view of exercise. Before the Industrial Revolution, physical activity was associated with manual labor and low social status. Sport encompassed hunting and riding and had nothing to do with physical exertion. Beginning in the late 19th century, the inchoate science of modern medicine demonstrated physiological benefits from vigorous exercise and proper diet. This led to the growth of a spa culture among the new leisure classes and a practice of new sports like aquatics, gymnastics, tennis, etc., the performance of which was done not just for diversion but for health.


Of course, there had always been a custom of physical conditioning and training in martial life. Within the context of military service a young man was encouraged to develop his physique through exercise and perfect his combat technique with regular drills so that he might become a more effective soldier. This tradition of militarism, of cultivating virility and strength, of meeting the adversary and besting him in an honorable contest, informs the formation of modern athletics as much, if not more, than the institution and normalization of exercise and the desire for good-health.

It is surprising how many of our sports today are abstracted pantomimes of warfare; not modern war but antiquated, non-mechanized warfare. One of my favorite sports from this past summer’s Olympics was the pentathlon, a multi-event competition comprising five extremely varied disciplines: swimming, running, fencing, riding, and shooting. It only narrowly made it into the games. Though held continually in every Olympiad since 1912, many have questioned its relevance in modern athletics. First devised by Baron Peirre de Cobertin, founder of the modern Olympic Games, the pentathlon was intended to model the skill-set of a 19th century cavalry soldier caught behind enemy lines: he must ride an unfamiliar horse, face the enemy with sword and pistol, swim in lake or river, and run great distances to return to his encampment. What I appreciate most about de Cobertin’s introduction of the pentathlon into the 1912 games is that these skills would have already been obsolete by the onset of the 20th century, and any doubt of this would have been completely erased with the Great War just a few years later. And yet the sport is still practiced. 72 men and women representing nations around the globe competed in the pentathlon last month, executing antiquated maneuvers of warriors from centuries ago. And lest we think our other sports are free of such influence, remember that our modern pentathlon itself is an updating of the classic contest from the ancient Olympiad. In the pentathlon of 500 BC the events were running, jumping, throwing, and wrestling. What sport does not include at least one of these most basic movements of the human body? What is athletics if not the practice of an old ritual of physical urgency? A solemn and determined preparation for the unforeseen contest to come.