The Best Books About the Trump Era, According to the Critic Who Read 150

From resistance literature to administration memoirs, Carlos Lozada read them all

So many books have been published on Trump, Trumpism, and the flurry of issues surrounding his time in office, you could never possibly make a dent in them. Unless you’re Carlos Lozada, Washington Post book critic, who read and wrote about 150 of them for his own book, What Were We Thinking: A Brief Intellectual History of the Trump Era.

If journalism is the first draft of history, What Were We Thinking is perhaps a third draft, a meta-analysis of the deep dives from Trump’s advisers and adversaries, the activists, philosophers, and sociologists of our era, and everyone else who thinks they have a way to explain this period in American history. GEN caught up with Lozada ahead of the book’s October 6 publication to talk about what he found.

GEN: Some of the books you cover, like Fire and Fury, are specifically about Trump, and others, like Hillbilly Elegy, less so. What is it that makes a book a Trump era book?

Carlos Lozada: There are the obvious books that are either about Donald Trump’s life, his career, or his time in the White House. A lot of those are very interesting, sold very well, and I certainly read a lot of them. But what I tried to do in my book is to read about the major debates that the Trump era in American politics has brought up for all of us. Books about immigration, books about truth in politics and truth in our culture, books about identity. To me, all of these can be Trump books.

Depending on the moment, books that aren’t really even about Trump at all end up getting wrapped up into debates over Trump. Hillbilly Elegy was one of those. J.D. Vance wrote it before Trump was a candidate; it was not a “Trump book,” but it became one. When we look back on this time, we will think of Hillbilly Elegy as a book that is part of this whole conversation about the white working class and where Trump’s support came from.

You write, “One of the ironies of our time is that a man who rarely reads… has propelled an onslaught of book-length writing about his presidency.” Why do you think that is?

Sometimes we turn to books for affirmation of what we already believe, and I think you’re seeing plenty of this. People gravitate toward books that may fulfill their views on the president, whether pro or con. But at the same time, I think there was a sense in which people were really surprised by Trump’s election. It certainly shocked the political establishment, but I think it also shocked the intellectuals, the activists, the writers, the insiders—people who responded to the rise of Trump the only way they knew how, by writing all of these books.

I think among audiences, also, there was a sense that maybe I didn’t understand our country’s politics or our country’s culture as clearly as I thought I did. So there’s a process of discernment these books are helping us go through.

Can you talk about the differences between books by the conservative never-Trumpers and the conservative Trump apologists?

The Trump apologists, their books, after a while, all start sounding the same. They even sound like Trump in some ways. They use Trump’s turns of phrase; everything is “the likes of which you have never seen,” which is something Trump loves to say. Whether they’re Fox News personalities or former campaign officials, they decided very quickly they were on board with the new reality and started making all sorts of justifications for it. Anything they didn’t particularly like about Trump, they avoided, ignored, explained away, or turned into a virtue.

The never-Trumpers, like Max Boot or Charles Sykes or Rick Wilson or Jeff Flake, laid out the opposition very early against the president. Now, they write these book-length breakup letters to the conservative movement and to their party, but they don’t really wrestle fully with the role they had.

All the things that happened that they’re so concerned about with Trump’s candidacy — the rise of politics that’s not based on truth, that has so much nativism and xenophobia wrapped up in it — say that all that happened, but somehow the Republican party had still managed to eke out one more traditional candidate, like Jeb Bush or Marco Rubio? None of these books would exist.

You also write about books from the left, and I would say you’re critical of some of the resistance books. Where did they go wrong?

Resistance books came out very early in the Trump presidency. I mean, right away. There were some even published in the weeks before the inauguration. One recurring thing I saw in them was a tendency to speak solely to the converted. There was enormous fear and concern over Trump’s America, but total uninterest, or maybe contempt, for Trump’s Americans. There is no sense in any way, of trying to reach out beyond traditional conventional constituencies. So this, to me, was a little disappointing.

There was also a very constant, enduring sense of utter righteousness in these books; the sense Trump’s moral compass is broken and we are the ones who have to lead the country in the right direction. Just because Trump’s moral compass is broken doesn’t mean that yours always points north.

There’s also a kind of exclusion in the resistance literature. A lot of it is about, who belongs, who’s really resistant, and who’s not. One of the authors, for instance, is very critical of the anonymous author of A Warning, saying “Oh, you say you’re part of a resistance inside the White House or inside the administration, but you’re there working for him. You don’t support progressive causes, and so you can’t really count as part of the resistance.” I assume there are political moderates and conservatives who are appalled by Donald Trump for all sorts of reasons, but they’re not invited to the party.

One of the topics of criticism of Trump books is of people like your colleague, Bob Woodward, who have pertinent information about the Trump administration that they are accused of sitting on for months until their books come out. What do you think about that debate?

I think it’s a totally legitimate debate to have. I would say it far transcends Trump books — this is something that happens in every administration. I think it’s important to note that those conversations between reporters and editors are often happening, and sometimes reporters do stop and tell those stories [in the publications they work for].

Woodward is constantly criticized for this sort of thing. Woodward can defend himself, he doesn’t need me to stick up for him. In this case, I can imagine him acquiring this information, leading to a conversation with an editor about whether or not he could have done a story. At the same time, I’m not convinced it would have been a transformative revelation in the Covid debate by the time he felt he had all the information he needed to tell the story correctly. When Donald Trump tells you he knows something or he believes something, you might have to wait 10 minutes and then ask him again, depending on whoever you talk to. So when he says something, does that reflect an overwhelming consensus of his advisers or intelligence agencies, or is that the latest thing that he’s thinking? It’s tricky to determine.

Also, I think the larger criticisms of Woodward—that he basically puts his sources in a favorable light and tells the story through their eyes, rather than with a lot of his own discernment—is the endless standard criticism of Bob Woodward that’s been around for a long time. Every time there’s a new book, people raise it like it’s a new thing, but it’s just the way he works. His books are best read with the belief he’s going to lay out this information. It’s up to you to decide how significant or meaningful particular moments are.

Of course, like I said, he’s a colleague, I would even consider him a friend, and so take everything I say with a grain of salt.

What are the most overrated and most underrated books of the Trump era?

Well, for instance, on the white working class, there were books that got a lot of attention, and deservedly so, books like Heartland by Sarah Smarsh, or Hillbilly Elegy by J.D. Vance, or White Trash by Nancy Isenberg. A book I especially did not like in this genre was Strangers in Their Own Land, by Arlie Russell Hochschild, which was a finalist for the National Book Award, so I suppose that means it was very highly rated. I found it to be a very condescending book. I felt that her assessments of the white working class in Louisiana felt very preconceived and oversimplified.

On that same subject, there was a book that kind of came and went that didn’t get the attention I thought it merited: We’re Still Here, by a sociologist named Jennifer Silva. It expanded my vision of who does or does not belong in the heartland, who is or is not part of these communities and this working class. It got beyond this internal debate, Oh, are these folks driven by their cultural prejudice or their economic anxiety? It showed me these things are inextricable, and also that the biggest concern here is not whether these personal struggles or prejudices lead them to one politician or another, but rather that it leads people to think there is no place for them in civic and political life at all.

It’s hard to say it’s underrated because the author is so famous, but Michael Lewis’s book The Fifth Risk was vital for me in understanding this period. When you think about the debates about the deep state, and whether there’s a resistance to Trump inside the bureaucracy, a book like The Fifth Risk puts a whole different light on all of this.

At the end of every administration, the outgoing administration is supposed to prepare a series of briefings for the incoming administration. By law, it’s required. The Obama team very diligently put together all these briefings for the Trump team. The Trump folks barely showed up, or sent the wrong people, or didn’t care about what these agencies had to tell them. So what Michael Lewis did is he went and spoke to a bunch of recently retired officials and basically got the briefings himself. It shows you how important it is to have a functioning government, and it shows you how the president’s particular traits of character and of interest were so ill-suited for the Covid crisis.

There’s a chapter in my book on all the literature of identity that has emerged in this period. So much of this debate is over group representation and group rights and group justice. But in these books, for instance, you see a constant cry for individual dignity. For instance, When They Call You a Terrorist, by Patrisse Cullors, one of the founders of Black Lives Matter, is a memoir of activism and of organization, but really, it’s just a story of her life, of her family, of what it was to have a brother and a father separated from you because they were incarcerated.

It’s interesting, we talked so much about family separation during this presidency, and it was always in the context of the border and of immigrants. But you read a book like When They Call You a Terrorist, and you see the family separation that happens everywhere, far, far, far from the border.

You finished the book with a list of 12 books you think sum up the era or give counterintuitive takes. It feels like a Trump studies syllabus. Do you think we’ll have Trump studies departments in the future?

I think you’re already seeing universities assign these books, whether it’s American studies or political science. I think we’re going to be thinking about this period for a long time.

The next thing that happens is we’re going to see a lot of memoirs by top officials or participants in the administration. I want to see a memoir by Don McGahn, the former White House counsel; I want to see a memoir by Kirstjen Nielsen, who ran Homeland Security during all the massive debates over family separation; Anthony Fauci — these are all memoirs I hope will someday come out. As new documents are declassified, as new insights on this period are developed, we will end up seeing those in books. Of course, the president himself is going to write one too.

This interview has been edited and condensed for clarity.

Director at Medium working with authors and books. Formerly a staff writer and editor at Time.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store