“History is larger than people: this is one thing I don’t know if Trump understands, at a fundamental level.”

Ben Greenman has a restless mind. You can sense it in conversation with him: the way he makes connections, not simply across dimensions, but arrowing straight through them. He marries politics, literature, and pop culture with the enviable, subtle ease of an author capable of dissecting both the latest Congressional debacle and current Billboard charts. His body of work reflects this insatiable curiosity: on the Greenman side of the shelf, “adapted and celebritized” versions of Chekhov stories featuring contemporary VIPs jostle for space with his current-event musicals written for McSweeney’s, alongside collaborative works with musicians such as ?uestlove, Brian Wilson, and George Clinton.

Greenman’s latest offering, Don Quixotic, is a fictional portrait of Donald Trump, told via a series of close, personal vignettes. It is neither a lambasting nor a strict lampooning of the current president; Greenman believes that enough of these versions have been, and continue to be, launched daily in both the press and the public. Rather than villainize the man, Don Quixotic attempts to humanize him, or at least to understand what makes him human. The stories, each less than a page long, read alternately like press releases, Calvino-esque musings on how to reconcile views of the same thing from multiple angles, and bizarrely familiar fever-dreams of a nation in turmoil. It is a peculiar, delightful read. It does not seek to convert the skeptical or reassure the fervent; it offers neither the knee-jerk criticism nor the fawning equivocation that have so far characterized the Trump presidency. Rather, it provides the type of insights into Trump that have been glaringly absent in most discourse surrounding his presidency: insights into what drives him, what feeds him, and what he feeds upon.

I spoke with Greenman this summer, over FaceTime and across the International Date Line, about Don Quixotic, politics and people in the age of the Internet, and leaving a legacy for the history-readers of the future.

Stephanie Pushaw


THE BELIEVER: Don Quixotic gives us a side to Donald Trump we rarely see, albeit a fictionalized one; it’s an attempt to dig underneath the celebrity and get to the man. What spurred this approach towards considering his inner life?

BEN GREENMAN: I think as a culture, we tend to deny famous people emotional complexity. In a way, we force them to serve us. So when one of them actually does become a public servant, the wires inevitably cross. Trump ought to be be more transparent than he is: he’s supposed to be ascertaining the will of the people and acting in ways that represent us. But, obviously, celebrities are human beings—and Trump is a complicated and strange human being. The question is, regardless of whether he is a monster or a child, how to handle him within a literary context. And what I decided was, rather than going big and epic, to go the other direction—internal and comic—because I didn’t think there was any dividend to investigating or attacking him on the big stage, as that’s the stage where he feels the most comfortable. I wanted to shrink him down a little bit.

BLVR: I’d think that imagining the interior life of a real person necessitates at least some degree of predictability on his part. Do you think Trump’s statements and actions tend to be prethought, if not exactly predictable?

BG: I did start this project with the assumption that his actions are calculated, though what that means can get a bit knotty. I believe he thinks constantly about himself and others’ perceptions of him. This is why social media has become such a fertile breeding ground for his ideas and opinions—it’s all crosstalk and replies and retweets. And I imagine there’s a tremendous amount of lost sleep and obsession on his part about how he’s being perceived. In Don Quixotic, I was trying to think about the moments between the notes: in musical terms, the rests. I wanted to imagine the moments of repose that we don’t see.

BLVR: A large part of Trump’s appeal to those who lionize him (as well as a reliable fuel for his detractors) is his seemingly unfiltered approach to “meeting” the people through such ostensibly casual avenues as Twitter. How do you reconcile the self-conscious obsession you’ve mentioned—the degree to which you see Trump as preoccupied with others’ views of him—with his seemingly thoughtless or trivial outbursts on social media?

BG: The thin skin seems indisputable; I don’t think that’s an act. But I view his lack of filter as a technique which may have worked for him better in the past than it currently does. For example, his claim to have devised “Little Rocket Man” as a distasteful form of provocative rhetoric—a strategy to bring Kim to the table. Regardless of whether that’s true, that’s how he spun it. I assume the same will happen when he has to, inevitably, explain away all of this fulsome praise of Kim.

This is what’s philosophical about him: his fundamental disrespect, not for any individual incidents of truth, but for the whole idea of absolute truth. I don’t think he believes there’s any such thing. He thinks there are situational ethics, situational facts, situational virtues. And that’s the guesswork, in a literary sense—how to inhabit the mind of someone with that type of flexible personal philosophy. All of us are calculated to some degree. The stakes have just become so outsized for him that these strategies, which may have worked great the boardroom, are now tragicomic at the highest level.

BLVR: Regarding Trump as someone with a situational moral compass, it makes it easier to understand his current rhetorical model, a model which partially hinges on sheer informational assault—the contradictions and constant online bravado, both of which allowed many to originally dismiss his legitimacy as a candidate. You imply this in Don Quixotic: the possibility that Trump’s deluge of rhetoric, whether on Twitter or via media soundbites, can be used as a deflecting technique via which he can then retroactively pick out the pieces that align with current events.

BG: In a related way, I chose this literary form for Don Quixotic because it didn’t make sense to have just one linear narrative; that’s not how Trump appears to me. Instead, he appears like a very bright dotted line: one pulse, then some time, then another pulse. It could be Twitter, a speech, a schtick at a rally. Those rallies are a loosely connected series of these brightly articulated bullet points, but there’s no coherent narrative overall, other than the one he sets.

This form is, in some ways, an insane one—like probing a brain at intervals over time and then trying to determine a personality from the results. But in a linear narrative, we create the illusion that we are pulling a character or an intelligence through a finite period of time. This is not that. It’s very broadly organized: there’s a cluster at the beginning about his declaring candidacy, and a cluster at the end where he appears to die. Then in the middle, these narratives bounce around. I was trying to determine which form best approximates this kind of bullhorn insanity. It’s an inversion of the way people perceive themselves. He’s a weird guy: he doesn’t talk a lot in coherent ways about his own past. He doesn’t seem to plan; he’s a reactor, always in the present. Like you say, he can justify past actions as part of a plan, but at the time they seem to have just been outbursts. It’s like leaving breadcrumbs, going back and eating them, and then insisting you’re not lost.

BLVR: And the nonlinear format is also reflected in its timeline shift. I wondered about your approach to creating the childhood Trump.

BG: I noticed several consistencies in his interviews. His father was problematic, as were many at that time: he had policies which were legally determined to have been racist (such as denying equal housing), and he attended rallies for rightwing groups. We should be careful to look at these things within the context of their time: there were many extremist and nativist political movements earlier in the century that now seem overtly racist but were, at the time, not considered thus. In addition, Trump talks a lot about his father, and about his brother, who died of alcoholism; I rarely heard him talk about his mother. So you start to see this damaged, macho personality Trump has constructed. He’s super controlled, but he’s very accepting of certain kinds of vindictiveness and cruelty.


BLVR: How did you select the pieces for Don Quixotic?

BG: I’d written about five hundred pieces, and the publisher wanted to pick one hundred. Many of them were too specifically yoked to daily events—for example, the Taco Bowl photo. We erred on the side of the more philosophical and general.

BLVR: More universal illustrations of his interior state. But the media presents new incidents daily, which makes maintaining detachment all the more important. Did the ironic distance and fictional lens give you the liberty to view Trump more compassionately? Because the book is not an attack—it’s an attempt at humanization.

BG: Definitely. Though my political stance is obvious, I didn’t want to attack and demonize him. Certainly, his actions harm others: obviously, his immigration policy and tax policy have harmed families. But I’m neither a political scientist nor an economist; I’m a writer. I’m capable of contributing because I’ve had practice in seeing how certain utterances and behaviors shape the contours of a person’s idea of himself, and of other’s perceptions of him. With this project, there was no upside to screaming “he’s a monster,” because everybody’s already doing that all the time.

There have been multiple books written, at this point, to confirm people’s suspicions that Trump is a monster or idiot. There’s a lot of preaching to the converted in all of those books, and it’s been interesting to note where people found their limits. People called Comey petty for discussing Trump’s tanning, the circles around his eyes, the size of his hands. I thought it was interesting that liberals, in some cases, wanted to deride Comey for being petty when that’s what happens a million times a day. Everybody wants their little shots at him. De Niro at the Tonys saying “fuck Trump,” Samantha Bee going after Ivanka: none of this is new, but every three months the media needs to say: are we going too far?

But every time that cycle plays out, it’s not that interesting to me. For me to sustain my interest in this weirdo over the course of a book, I needed to make him more damaged and strange. And he is damaged and strange. It’s not just that he’s cruel, though that’s part of it; it’s that some of the choices he makes are genuinely weird. Like misspellings, or his punctuation in tweets, or the nicknaming he seems to think is funny or catchy. He’s weird, and he fits into this weird country in weird ways. A shade less than half the country obviously responded to him in some way. It doesn’t pay to demonize him, or call him a monster, or say there is no way to understand him, because a lot of people do understand him and are willing to cut him a lot of slack. I may not be among them, but part of the project was an attempt to figure out the ways in which he is, if not charming, at least engagingly odd.

BLVR: Although he isn’t our first president to inhabit the internet age, he’s definitely the one using it the most. I wonder, if previous presidents had been able to preside in this modern type of media sector, what kind of reverberations we might see.

BG: Trump has drastically changed the way we deal with our public officials. He’s using these media in ways that no one else dared to or could. But some of that audacity comes from the fact that he’s crass, or dumb, or has a bad temper, or is thin-skinned, or doesn’t care about facts.

Remember the raccoon in Minneapolis climbing the skyscraper? If I had tweeted out that that raccoon fell, although many people would know I was not telling the truth, some people would think I was—and some tiny little ripple would go around of that totally incorrect story. As a journalist, I couldn’t have done that before, because I did not have the unedited, unprocessed ability to. Trump’s is the highest level of that ability. It’s testament to the success of his method that I can’t remember all of his excuses since taking office. If I asked any person that’s followed this, chronologically, since the election, to list all of his absurd lies, none of us could.

But there’s a carnivalesque aspect to it that people like. It’s entertaining. The rhetoric is funny. There’s also a very serious, damaging part where all of these “funny” things hurt people. He figured out how to manipulate New York media: the tabloids, Howard Stern, The Apprentice. Then he figured out how to manipulate social media. He’s good at knowing that you shouldn’t have shame, because there is no point. Shame is not a thing that exists anymore, at least on social media. And if you have it, you’re one step back in evolution: holding onto this weird thing, like your appendix; this vestigial organ that no longer achieves anything. So he’s discarded it, and because of that, he’s able to move further than others can. I don’t know if Jimmy Carter or George W. Bush or Obama ever would have been this person.


BLVR: It’s a given at this point that Trump is fed by the public’s attention—that he can’t help himself. Sometimes it works in his favor. Often it backfires: people pull up contradictory statements he’s made—some from years ago—that directly contradict what he’s doing and saying today.

BG: People can have a change of heart… if they have a heart. There have been other presidents who were, in their own way, complicated monsters. The Robert Caro biography of Johnson makes LBJ sound like a nightmare. He belittled people, he schemed. But he also aged into a time in America where his skills as a politician and a lot of his deeply held beliefs were extremely important in moving the country forward.

History is larger than people: this is one thing I don’t know if Trump understands, at a fundamental level. He may yet achieve some things, whether by overconfidence or by virtue of this dumb buzzword “disruption” everybody uses. Because it’s true: by doing things differently, you may achieve something new. But I couldn’t possibly have the long view: the ten- or twenty-year-view, where we’re going to think: the least prepared person became President—and yet, achievements occurred on his watch, good and bad.

Kennedy remains an interesting president because I feel like he would have used Twitter. He was super charismatic, great at meeting people, great at the direct deal. And yet he benefited from an incredible privacy curtain. A lot of things just weren’t revealed because that wasn’t the way the media operated: there was no tabloid culture.

BLVR: Obviously the tabloid culture fetishizes scandal, particularly celebrity scandal. But so much of this information is difficult to verify, which contributes to the proliferation of apocryphal stories being spread as facts. Rumors multiplied by an errant hashtag, or speculation caused intentionally by trolls, or imposters, or misinformed but earnest observers.

BG: There’s a Norm McDonald joke where he says he has one picture of his great-grandfather, with a split beard, staring at the camera—the aperture open for five minutes—and he says, in the future, kids will say: “do you wanna see a hundred thousand pictures of my great-grandfather?” We’ve just been documented to death. In the past, without all this access to information, we’d build our idea of public figures from five or six anecdotes. Kennedy, Lincoln… there are the stories and the myths most people know about them. The question is: what will be the five or six things people know about Trump, fifty years from now? The summit? Stormy Daniels? The Russian investigations? Indictment? Impeachment?

BLVR: Yet the approach you’ve taken in Don Quixotic of selecting the more timeless pieces, rather than the cheap laughs or small anecdotes, has ensured that this book will remain a portrait, rather than a collection of arbitrary moments.

BG: Right. The hope is that, in five hundred years, some kid will be at whatever a bookstore is then and they find a copy and they think: I know this isn’t a history, but this gives me one person’s insight into what he thought was happening. And that, to me, is more valuable. When I find books like that from a hundred years ago, that’s what is interesting to me. The kinds of history textbooks I read as a high schooler—I’m not sure they even exist anymore. There have been so many upheavals about how to tell the untold story, the historiographies, how best to incorporate narrative and image. A psychological portrait, for better or for worse, has legs; that’s sort of what I was going for. I won’t be alive in five hundred years, but I’ll die with optimism.

BLVR: The impulse towards narrativizing our own lives, I think, naturally leads us to narrativize the lives of others, and this is a quality which inherently improves the retelling of history.

BG: Right. While working in the ‘60s, historian Hayden White began worrying that the study of history was being harmed relative to that of other disciplines because it wasn’t moving fast enough. He believed there was a fake continuity in history books between the old and new worlds, whereas other disciplines were willing to admit that sometimes there are abrupt jumps forward; for example, we should acknowledge inventions which rapidly advance history.

He did a lot of work on how historical narratives should operate, regarding metahistory and historiography. I ran across one of his essays while working on this book. I thought through a lot of those questions, because, not to be too grandiose, Don Quixotic is a work of history. At the very least, it documents how one person who followed the news a lot, and wrote a lot, saw the internal evolution of this weird leader. So in that sense it’s a document like anything.

It’s like the letters from the soldiers that Ken Burns finds and puts in documentaries hundreds of years later. The letter the guy wrote home from the front in the Civil War, filled with typos and misunderstandings, nonetheless gives you a very clear sense of the terror they have, or a ringside seat to amputations we wouldn’t otherwise have, because all we’d had before was the line in the textbook that said, many soldiers lost limbs. Which is fine, I can repeat that to you—but it doesn’t tell you that he was vomiting all night after he was amputated. So this is an attempt to add a piece to the puzzle. That’s how the mosaic ultimately comes about.

BLVR: Let’s say you were to add a story to Celebrity Chekhov with Trump at its helm. Who would be his literary counterpart? Does he have one?

BG: I think he does. These stories are largely about vanity, social cues, and the way others perceive you. There’s one where, in the original version, it’s a soldier and a general; in my version it’s Conan sitting behind Larry King at a Lakers game. Conan sneezes on him, and he feels so guilty, and so worried that Larry King is mad at him, and everybody tells him, you’re making too much of it. But it turns out Larry King is mad at him and won’t accept an apology, and Conan is just torn up about it. And, mimicking the Chekhov story, eventually he just goes home, lays down on his couch and dies.

There are a lot of these stories, with fits of transitory self-awareness, wherein people are consumed by the idea that they’ve been misunderstood, or they come back to the village where they grew up just to let everybody know they’ve changed. There are Chekhov stories, I’m sure, where you could find cases where someone pretends to be a good husband or wife bc they’re getting social advancement, or their personality changes as their spouses change. So I’m sure there’s a counterpart, because there’s just so much vanity, social climbing and status. These are stories that would fit Trump. He doesn’t seem to have fully formulated relationships with other human beings.

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