The Biggest Baby: A Conversation About Donald Trump with Ben Greenman

THE NEW YORKER‘S Ben Greenman has never been one to go easy on a tough subject. His profiles for the Miami New Times were legendarily sharp and The New York Times described has described his prose as “fluid and commanding.” Greenman’s stories aren’t just a carefully strung assortment of words, but they also tend to forcefully pierce the veils that we’re forced to endure every day. One of the latest subjects to perturb him is Donald J. Trump. His latest book is Don Quixotic, a collection of satirical pieces about the president.

In January, Greenman reflected on the 2016 presidential election, the first anniversary of Trump’s inauguration, and what he learned about his country in writing Don Quixotic. The following is an abridged version of that conversation. In sum: In a time when brash talk and braggadocious behavior seems to be lauded incessantly, subtlety may be what — in the end — reigns supreme.


JONATHAN KENDALL: Do you feel after a year of having Donald Trump as president that the public understands him now or do you think he’s still elusive to many?

BEN GREENMAN: We all understood things about Trump all along the way, even before he was president, when he was a celebrity in New York City or when he was a television personality. He was always a self-centered boor, a kind of clumsy self-promoter. He always had an inflated idea of himself and didn’t seem particularly smart in some ways. All those things were in place.

But then came the push to the presidency. What did that mean for him, and for the way that we saw him? You could argue — as my book does, and as other books have — that he didn’t expect to win, that he just thought he’d get a bunch of publicity for The Apprentice. You know: run a populist campaign, lose, go back to NBC with huge leverage for his contact. Possibly he won accidently — I don’t know — but I didn’t see anything in the campaign that suggested to me that he was especially serious about it. Which is why the electorate’s response to him was very confusing. I still don’t know what people saw. And that’s one of the engines of the book. I think I understand him pretty well, but I don’t know that I understand people who keep supporting him very well. It’s a very confusing set of linkages — I don’t know why people across the country, who are hard workers, who work jobs, who are living check to check, why they think they identify with this person who is a New York real estate billionaire. For that matter, I don’t know why evangelicals, people who profess that moral living, that Godly living, is at the forefront of their concerns, I don’t know why they think they identify with this — I mean, I’m not particularly judgmental about it — but why they identity with this repeat adulterer/crypto-racist/corrupt buffoon.

Do you think that maybe his position on the NBC show, which showed him as a boss to the households of millions, encouraged many Americans to see him as someone that perhaps could make high-paying jobs or something?

I think that was one of the strategies, certainly, that he was positioning himself as the CEO of America, “I will be your CEO. I’m a great negotiator. We’ve gotten bad deals from the Chinese. We’ve gotten bad deals from NAFTA. I’ll fix it. I’ll be the one who will come in and be smart. They’ve ripped us off. Obama was foolish, stupid, shortsighted — I see how things really work!” Now, in truth, that hasn’t happened. I mean, you know, again — I’m not primarily a political analyst, and as I followed the news, if I’m completely objective about the news, there are probably some things on the business side that are good and some things that are bad, as there would be for any administration.


But the optics of it, and also the priorities of it, don’t scan. Take this whole idea about deregulation being good. Obviously, in some cases, regulations can choke out entrepreneurship and can choke out business innovation, but in a lot of cases, regulations and restrictions are there because they protect the long-term. They’re protecting the environment, they’re protecting workers, those kinds of things. The electorate, to some degree, wanted to see Trump as a strong, decisive character. He could make fun of Jeb Bush, he could make fun of John Kasich, he could make fun of Marco Rubio, and Ted Cruz, and Carly Fiorina — even though some of those people were more proven leaders, either in business or in politics.

So how do you get to the core of this person?

Well, down inside all that other stuff, though, there just seems to a big baby who seems to be only worried if people are nice to him, and if people are loyal, and if people see him as smart, and see him as handsome, and see him as rich, and the decades-long pattern of inflating his own value is psychologically kind of interesting. It’s inherently comic — I mean, a lot of what’s he’s doing is tragic because it affects people — but that persona of the buffoon and the self-aggrandizing clown is inherently comic, and I think for a lot of I think for a lot of people that’s the contradiction.

The book uses a strange method to explore that contradiction.

The pieces in my book attempt snapshots of his mind and psychological state. They fall somewhere in the vicinity of stories, but they’re not particularly narrative because they’re so short. Taken as a set they kind of add up to a portrait. It’s like a kind of much more frightening, much less rewarding version of Thirty Two Short Films About Glenn Gould or something, where I’m trying to get all these different angles on him, in a bunch of different styles, to try to take a guess at him, a creative guess, an artistic guess, how a person like that sees the world. They’re all written from inside his head. For example, there’s one where he’s watching an awards show on TV — and he constantly through the campaign, and through his life, would complain about awards being rigged when he didn’t win. When The Apprentice didn’t win Emmys, the awards were “rigged.” So, in this story, he’s watching an awards show and every time they call out a name he says his own name out loud when he’s in the house. Because that is the only way he can endure it, is to imagine that he is the winner of everything. And then at one point he stands up to accept one of these imaginary awards and he bumps his head on the TV because he doesn’t realize he’s at home — he’s sort of lost in this reverie of winning everything. And that kind of clownishness, which I see in him — I mean, I think a lot of people do. He’s frightening to them because he’s in charge, but he’s effectively a clown. You can speculate, and I’m not a diagnostician, so the best way to do it was to make these little fictional scenes and let him, him the character, play his way through them.

What about the cases when he wasn’t comic, where his behavior was truly destructive?

That’s an interesting point. As we were finishing up, Charlottesville happened. My editor picked all the pieces, we were ready to go, and there was a whole conversation all over again around normalizing Trump post-Charlottesville. It was an old conversation. When he was elected, David Remnick went on Sunday shows and said something like, “I think we really are in danger of normalizing. Just because someone wins, and now he’s the president, let’s not start to think that the things he’s saying are acceptable or normal. These are dangerous attitudes and they are potentially destructive to our republic, and to our country. Let’s not do this.” So we’re putting the book together, Charlottesville happens, and my editor called me and he was distressed, and he said, “This is one case where he seems to really be openly courting some of the ugliest elements of our culture, and of our society. Does it change our idea of putting out a book that’s kind comic, in some ways gentle, because it allows him to have his own foibles and to work through them?” This book sees him as human. I’m not a big fan of demonizing people, him or anybody, because I don’t feel it’s productive.

And people are a mixture. Everyone has their demons and everyone has their virtues.

Yeah. I think the current culture is very hate-immersed, on all sides. We say that we’re protecting the idea of humanity, but if we sacrifice the idea of humanity to do so, are we working against our own aims?

I’m happy that you’ve written this because it’s not a demonization of Trump; it’s a very strong critique of him.

And it’s an attempt to understand. So when Charlottesville happened, we discussed it. And I ended up writing a new introduction, and the new introduction had been written in the wake of sadness shock over what had happened in Charlottesville, and the way he failed in my mind — and many people’s mind — to bring the country together, to deal with the injury, to identify the problem.

But as you say, it was a person making those errors.

With Trump it’s not that I empathize with him as a person, I find him to be reprehensible, but the exercise of forcing myself to believe, “Well, this is a human being,” I don’t think he wakes of every day and says, “I’m going to go do evil.” I think he probably thinks, “I’m a human being. I want to be noticed for what I do. I want credit. I want to do some good things. I want my family to love me. I want to seen as successful.” His methods are ridiculous. I could be wrong, history will tell, but I don’t think it’s like a demon. And the thing about a demon is the only way to get a demon out is to exorcise them. You can’t understand them. There’s nothing to understand about a demon. They’re just an instrument of evil. And I don’t know for me if that’s an especially useful way to think about Trump. It might be if you’re a policymaker. If you’re protecting a national landmark, and he comes in to reduce the size of the landmark by 60 percent, then you probably demonize him for that campaign. But as a fiction writer, and in trying to understand him as a human, demonization isn’t a useful tactic, for me at least.

What does Donald Trump’s swiftness in his own self-justifications tell you about internal processes?

The easy answer is that there’s insecurity. I mean, a person doesn’t come right out to justify their own actions unless they’re either insecure or there are elements of paranoia, where he’s hearing as he does things, he’s hearing in his own head, a critique of them. Like if I say to you, “I’m going to the store to buy a sandwich,” and you don’t say anything, and I say, “I’m going now. It’s the best store. It’s the best sandwich. You know turkey sandwiches are best sandwich,” and you haven’t said anything to me, I’ve heard your criticism without you saying it, which is paranoia. So I imagine that he has some very, very fundamental built-in need to justify his behaviors, and to promote himself. I mean, look at what he did before where he’d invent publicists — the “John Miller” and “John Barron” publicists who would go and call magazines on his behalf, but it was really him calling.

Sometimes there’s good in losing. I don’t think Donald Trump would be able to understand that.

And one of the things during the campaign that we always heard was “doubling down.” Either he would say something that was unfortunate and unkind, or he would make a simple error. Everyone can misspeak. But then when you insist that it’s true when the record shows otherwise, when the facts show otherwise, and then at some point it’s a lie. But a lot of people, when I’d watch the news, his supporters liked when he didn’t back down. So this notion that you should always insist that you’re right … if you admit you’re wrong, who knows where it ends. Once you admit you’re wrong once, you can be wrong about everything.

Did you learn anything about yourself in writing this?

I thought a lot of about what kind of fictional form makes sense of this kind of person, for me. And I didn’t think a big epic novel would do it because in some ways it monumentalizes him, again. And that’s sort of the problem. As a writer, I liked writing these short pieces. I like finding forms that fit what I think the topic is. And often they’re the exact opposite of what the dominant form is. So, whereas the dominant treatment of him are these big gestures, very broad comedy, and very rhetorically overheated articles, I felt very strongly that it was important to go entirely the other way, into something approaching subtly and kind of gentler comedy because I think people need to — I can’t tell them what to do — but I feel they need to occupy that space because the other space is kind of already scorched earth. If you go into the area of overheated rhetoric, and giant gestures, and Godzilla, he’s already won that ground. Because his shamelessness, and these things, allow him to. If you go into subtlety, and if you go into interiority, then you’re able to do battle with him in interesting ways, you’re able to pry him apart in interesting ways. And I don’t think he has any weapons on that ground.


Jonathan Kendall is part of the editorial crew at the Southern California arts and culture magazine LALA. His writing appears in Vogue, Cultured, Atlas Obscura, The Hairpin, and Miami New Times. He enjoys collecting first-edition books and spending time with Taylor, his goldendoodle.

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