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Dear Inklings,

Yesterday I voted. I have never done so with more ardor. And yesterday, in the culminating sequence of their sham, the Republicans smuggled Judge Amy Coney Barrett onto the Supreme Court. It may be their last best chance of holding onto power — using the courts they have packed to suppress and rig the vote.

A reelected Donald Trump, abetted by a 6-3 Supreme Court, is truly a terrifying prospect — very possibly the end of the American republic in any real sense. But we are not there yet. Where we are, in fact, is in the liminal space where it is still possible to achieve a different future.

This looming election may well be the last exit before autocracy.

That was one of the things I carried away from my conversation with the brilliant Masha Gessen, whose wisdom I’m so happy to be sharing with you today. This era has revealed its share of charlatans and criminals and fools. But it has also revealed genuine heroes — including intellectual ones. One of mine is Masha.

Masha is a journalist and writer and thinker who spent the first part of their career in Russia, writing about science, democracy, autocracy, and disease. Then they made a home in America, where it turned out that some understanding of science, democracy, autocracy, and disease would prove very handy.

Masha was made for this moment. To be clear, given their interests, you actually never want to be living in a time and place that Masha was made for, but here we are.

But before we get to Masha, a programming note: There will be no live chat today, because I’m saving up my energy for a very special event to which you’re all invited. Tonight at 7 p.m. ET, I will partake in a public discussion of the new proposed 28th Amendment to the Constitution, brought to you by the people and public library system of Brooklyn.

How to stave off autocracy: a conversation with Masha Gessen

ANAND: You've talked about this arc of the attempt at authoritarianism, the breakthrough, and the consolidation. Asking for a friend, where are we right now on that arc?

MASHA: First of all, I use the word autocracy intentionally, instead of authoritarianism, for two reasons. One is because I've spent so much of my life writing about totalitarianism that, in that context, authoritarianism is something distinct from totalitarianism. Authoritarianism is a kind of regime in which basically the ruler wants people to go home and tend to their private lives while they run the country. So nothing is political under authoritarianism; everything becomes private. Politics as such disappears.

Under totalitarianism, it's the opposite. The totalitarian leader wants people out in the public square at all times, demonstrating their support for him. Under totalitarianism, nothing is private; everything is political. It's the private that disappears.

So let's stick with autocracy. Where are we in the autocratic arc? I hope we're at the stage of the autocratic attempt. If there's a spectacular failure of this election, not a failure as in Donald Trump wins, but a failure as in, he doesn't leave office because he can abuse the courts, abuse the power of the courts and secure being able not to leave office that way, because he can create enough chaos to throw election results into enough doubt that he doesn't leave office — if there is an actual engineered failure of the election, then we have already passed the point of no return, the point of autocratic breakthrough. So I don't actually know the answer. I very much hope that we're at the point of an autocratic attempt, and that attempt will be reversed because we vote him out of office.

ANAND: So in November 2016 when you wrote your essay “Autocracy: Rules for Survival,” one of the reasons the New York Review of Books’ poor little website crashed was because a lot of people wanted to do a good job at surviving the times. People wanted to do their best. Those of us in the media earnestly felt like this is our moment as journalists to hold these people accountable. I think a lot of people in all walks of civic life wanted to do a good job. So I want you to tell us, Masha, how we did four years on.

Which people and institutions have surprised you in holding up to Trump, following some of the rules you laid out? Which have surprised you in their failure?

MASHA: Anand, I think you know me well enough to know that my favorite answer to every question is: I don't know.

So how well have we done? Well, I don't know, and there's a reason I don't know. Of course, you specified your question, but I don't know because I feel like I live in a kind of bubble. Now I don't subscribe to the sort of "There are two different and equal information bubbles in this country." That is not true, but I am sometimes amazed by how well we have done, what an extraordinary amount of thinking and writing and investigative journalism and analytic journalism we have produced that is certainly more than in any autocracy or any attempted autocracy in history.

ANAND: If you look at the prehistory of Russia's turn to Putinism that you covered and the pre-history of Trump, they're actually quite different. A lot of what you wrote about in "The Future is History" is the scarring of the Soviet period that allowed that consolidation to be possible. Here, it's a different set of factors. Many people have different theories of what made our body politic so weak that this could happen. I wonder as you look at those potential explanations — 40 years of neoliberal economic policy, demographic change, the loss of white power, male power, other explanations — what do you think are the principal factors that made us as a society vulnerable to the Trumpian turn?

MASHA: The best explanation is, I think, offered by Erich Fromm, the great German, later American, social psychologist, who suggested in his lovely book, "Escape From Freedom," that there are times of extreme anxiety when people cannot envision a future, because the future is just too terrifying, because they don't know who they're going to be or how they're going to be. That is so frightening that they want to give their agency over to somebody who will just tell them what to do, take control, and, in return for their handing over their agency, will give them predictability. Now, this is not the sort of the poor-disenfranchised-white-working-class theory of Trump. It's a much more generalized anxiety theory of Trump. It's a well-founded-sense-of-economic-and-social-instability theory of Trump. It's also, I think, 9/11. Again, it's that sense that we're in constant danger. And I think it's the unaddressed, unacknowledged psychic trauma of the financial crisis of 2008.

ANAND: I want to ask you, switching gears a little bit, about this question of Russian interference in American politics that has consumed this country, consumed investigative organs, given the left a few years of nightly Rachel Maddow hope, only to be dashed by Bob Mueller]. I wonder how you now view it, given everything we know: What was the Russian project, what was the Russian project not, and how serious was it in sober retrospect?

MASHA: I don't know what I would less like to talk about, the Russian interference or last week's Zoom call [after which New Yorker writer Jeffrey Toobin was suspended for exposing himself on camera]. It's really my least favorite topic. So let me try to dispense with it quickly. I think that for Americans, and for American journalists and very politicized Americans in particular, the story of Russian interference was a really damaging crutch for the imagination. It was something that allowed us to think about Trump as somebody from outer space, or at least from Russia as a kind of alien body, but also an alien body from which we're somehow miraculously going to be liberated. I think to a large extent, and certainly Dean Baquet, the executive editor of The New York Times said as much, a lot of resources were wasted, were committed to the story of Russian interference when they could have been committed to something else. I hate also the story of Russian interference because I hate all stories about secrets.

I hate all stories about conspiracies. It's not because they don't exist. Secrets exist and conspiracies exist. But I think it's so much more important at all times, everywhere, to talk about what's out in the open, when we can all see, what is an actual felt and experienced part of our shared reality, than it is to look for answers that are hidden from us. It is ultimately politically always more productive to talk about what's out in the open and there's so much in the open and there has always been. And so ignoring any part of that in favor of Russian interference, I think, has been extremely damaging.

That said, I think the Russian project was, is, continues to be just wreaking havoc. In that sense, Putin and Trump are working in concert, not because they have agreed to be agents of chaos, but because they are. The Kremlin has tried to undermine faith in American democratic institutions since the Soviet state came into existence. And it finally struck gold in 2016, but that tells us more about us than it does about the Kremlin.

ANAND: There has been some talk now about if Joe Biden wins and we're in a post-Trump era, what do we do about various types of people who are complicit in the Trump nightmare? There's one conversation about high officials, and there's the obvious temptation to banish them from society, which I sort of favor. There is the issue that de-Baathification in Iraq did not actually turn out to make that society more stable. And so there are questions about what happens when you banish huge numbers of people from a power structure, but then there's also the question of what you do about regular Trump voters. What do you do about people who've been kind of addicted to misinformation on Fox News for ten hours a day? How do you think about those questions of truth and reconciliation and deprogramming?

MASHA: We could talk for hours about this. So let me throw a couple of ideas out. Jill Lepore had a wonderful piece in The Washington Post over the weekend that I agree with wholeheartedly, which was an argument against truth and reconciliation. Because there are laws, there are courts in this country.

The problem with Nazi Germany, the problem with the Soviet Union, the problem with apartheid South Africa, was that the crimes committed under the auspices of those regimes or in those countries were legal. The actions that were taken were lawful. They could not be prosecuted in the courts because you cannot retroactively apply laws. So you have to find other ways of redressing those crimes. I think that the bulk of crimes committed by, in the name of, or in favor of the Trump administration are just crimes.

They're just illegal acts in this country that can be prosecuted by regular courts. What I think is essential is to pursue every possible case of that. I really hope, and I fear that this will not be the case, but I hope that the hypothetical Biden administration won’t be tempted to let sleeping dogs lie and be very restrained in seeking legal recourse. I think that would be a mistake, but I also think that truth and reconciliation commissions would be a mistake. Now, I think how we bridge realities is a different question and requires thinking about it from an entirely different angle. As long as we think about it in the framework of the existing media universe, we're not going to get anywhere. We're just going to feel more and more despairing about this, and rightly so.

I think that we have to face the problem of a lack of shared reality head-on and think about its actual roots, which is that we have lost the sense of political communities everywhere, that local media have disappeared, that the whole idea that you were part of a political community connected through media has vanished. Less than a generation ago, there were local papers in every town. The unspoken goal was to make sure that every person in the town was eventually in the paper. That's what the local paper is for. Less than a generation ago, everybody knew a local journalist personally.

Less than a generation ago, people actually learned about what was going on in their communities when they weren't looking. I think we forget about that because people like you and I exist in a vast political community where things going on in that community can be communicated to us by Twitter because that sense of community is so expansive.

ANAND: So let's play the bad news, good news game. The bad news is Donald Trump wins and steals a second term and remains in office. The good news is The New York Times realizes that its old mode of editing is not going to work for the times that are coming, and they hire you as the new editor of The New York Times, to build a new kind of New York Times for what you've referred to as the breakthrough moment of autocracy. How would you do it, if you had that kind of organ at your disposal? How would you start to cover this administration differently from what The New York Times is doing right now?

MASHA: For the record, if asked, I will not serve. But I think that I understand why The New York Times does what The New York Times does. All The New York Times has, ultimately, is being The New York Times. Giving up its institutional culture, giving up its basic ways of doing things, would be giving up on being The New York Times. That's a huge loss. It's easier for comparatively much, much smaller operations like the New Yorker to change course and act like we're living through a national emergency, which we are. And it's much harder for The New York Times. That said, I think that they don't have to be quite so married to it. I think there can be more urgency.

I think there can be explicit policies such as: We will use the word "lie," and we'll not continue raising the bar for just how blatant the lie has to be for us not to cover it in euphemisms. We will not use normalizing political vocabulary when describing this administration. We're not going to talk about its strategies. It doesn't have any strategies. We're not going to talk about its policy priorities because it doesn't have any policy priorities. We're actually going to have one vast editorial retreat at which we invent a new language and create a new glossary for words that we're never going to use to describe this administration for fear of normalizing it.

ANAND: So in this epically famous Zoom call that you don't want to talk about, understandably, you all were doing an election simulation about what would happen. Setting aside the actually quite fitting outcome of the courts [represented in the simulation by Toobin] not doing their job, what was the result of the election simulation you ran?

MASHA: “Am I sworn to secrecy about the election simulation results?” is a question that probably comes to mind last when thinking about that Zoom call. But considering that it is likely never to see the light of day…

So we actually ended up with a Biden victory. Our starting scenario was that Pennsylvania was still counting ballots and other states broke down exactly to 251. So it was all up to Pennsylvania, where this was before the Supreme Court terrifyingly tied in its decision about whether Pennsylvania would be able to count as it is currently expected to through November 6th. So our other assumption was that more people voted for Biden, but those were mail-in ballots.

We were at it for three and a half hours. But what became clear to me, though, was that there was a built-in bias in playing this game because at any point, first of all, I don't think that any of our imaginations is catastrophic enough, and I include myself in that. Second of all, the motivation is to continue playing, not to make a catastrophic move that would bring the whole thing tumbling down, which is distinct from Trump's motivation. His motivation is going to be to make a catastrophic move that will bring the whole thing tumbling down.

ANAND: You've one way or another graded different institutions' performance in this time. How do you think about the left? Very broadly defined, the left half of the country. How have you watched its internal arguments?

MASHA: Well, I certainly fall on the much farther left side of the spectrum than Biden. And I find the idea of aiming for the middle of the road in order to confront the extreme of the road to be fundamentally suspect. But if he wins, I'll be proven wrong.

The question is what happens next. If he, God willing, wins, I think that in some ways Biden can be a transformative president, because I think that there's a grand ambition there, that's become very clear, to invest in infrastructure, to create a new welfare state, to bring the country together in some really, I think, beautiful ways. What I don't expect a Biden presidency to do is a really essential job of reinventing actual democracy. I don't think Biden, who prides himself on being integrated into the political system, I don't think he is capable. I'd love to be surprised.

ANAND: One of the difficulties in processing Trump as an autocrat in this period for a lot of people that I talk to is that the level of sophistication and development of a country like the United States in the year 2020 is such, and the institutional quality is such, that a president who is kind of an imbecile and an idiot and an autocrat doesn't make the driver's license department stop.

There is a way in which life goes on in many, many walks of American life. Do we need to change our picture of what autocracy looks like in a very high-functioning society so that we're not waiting for something to happen that we've seen in movies, that is actually never going to be what it looks like here?

MASHA: That's a great question. I don't know that you actually need to adjust for the United States. I think it makes it more pronounced, because life can indeed be so normal for so long. But since I was a kid, literally, I've been obsessed with how we collapse time when we think about history. It's like we think that Hitler came to power and then the Holocaust happened and World War Two happened and then it was over. But there were years, years when normal life and a sense of politics and a sense of society was destroyed and eroded. It is always a process.

Along the way, this process grows familiar and a lot of things stay normal until they don't. I think that's going to be true anywhere. So I don't even know that the first-world adjustment is so necessary for Donald Trump. What I think is really necessary is a broader adjustment of just how fast we think things happen and how we always think of history as a series of events rather than processes.

ANAND: Can you talk about any alternatives that you see to liberal democracy as we practice it in the United States?

MASHA: There are lots of alternatives to liberal democracy as we practice it in the United States. We're a pretty unusual liberal democracy. I mean, even as liberal democracies go. The two-party system only exists in a couple of places. Most liberal democracies are parliamentary democracies. Hannah Arendt used to think that two-party systems were actually better protected against totalitarian tendencies because each party was always within reach of real power. So it had the awesome responsibility right there, and couldn't go off the deep end ideologically. But, of course, what we've ended up with is one party that does go off the deep end ideologically, and is pulling the other party along toward an imaginary center as this other party tries to maintain the awesome responsibility of governing. Which may be a sign that it's time to rethink the whole two-party structure. It's certainly high time to rethink the marriage of money and power, in which the United States is fully unique among more or less functioning democracies in the way that it allows corporate and private interests to control our politics, but you know a lot more about that than I do.

ANAND: What is the intersection between totalitarianism and plutocracy?

MASHA: I don't know that there has to be one, though there certainly is one in this country. I think we have legitimized the political power of money. We have legitimized the idea that political power accrues to money and money accrues to political power. That can be a precondition to totalitarianism because it is so blatantly anti-democratic.

So when we talk about other countries, usually in this situation, we talk about whose side the military is going to be on. It's a little bit more complicated in the United States, because the military is not the only factor. We have the weird entity that is the National Guard, which belongs to the states but can be federalized. We have the largest law enforcement force in the United States, which is actually Customs and Border Protection. So whose side are the armed uniformed services going to be on? And the answer to that question in traditional analysis is: it depends on perceived legitimacy, which basically means if Biden wins by an absolute landslide. If Trump fails to tie up results in recounts and court battles, then the uniformed armed services are going to be on the side of Biden, the winner. But if Trump succeeds in creating enough chaos, if legitimacy is in question, then I think there's a real danger that he'll remain the commander-in-chief.

ANAND: If the failure of the election will make us slide from the autocratic attempt to the point of no return, how can a mobilized public organize to prevent such a failure and an autocratic power grab?

MASHA: Well, the answer is that it gets so much more complicated. If it's not an electoral mechanism, the whole problem with autocratic breakthrough is that it is the point of no return. So the question is, What's the return from the point of no return? At some point, an autocratic regime can destroy itself only from the inside. We're seeing the absolute nightmare scenario in Belarus right now, where there has been a sustained mass protest for more than two months, tens of thousands of people in the streets every weekend, people protesting all over residential neighborhoods, small towns, the capital, every single day. And nothing happens because there's no connection between what the people do and what the dictator does.

You would think that by creating a large-scale strike, by creating this kind of protest, they would have paralyzed the economy and forced him to leave. No, nothing happens. So that's the nightmare. We're going to be years and years from that, even if Trump manages to maintain power and even if he manages to maintain power illegitimately. So I guess I'm avoiding being prescriptive, but I'm issuing a dire warning.

ANAND: I wonder how you view the Black Lives Matter protests this summer and the incredibly persuasive effect it had on public opinion, even compared to in recent years. Where does that fit into this autocratic attempt and the moment we're in?

MASHA: It reminds us that times of political crisis are also times of incredible political opportunity. When I say that, I mean something very, very specific, which is that a political opportunity is when ideas that are marginal can become mainstream and take hold and become central to legitimate political debate in a very short time. So we saw that actually happened twice this year already. We saw that happen when the pandemic hit the United States We saw ideas like universal healthcare and universal basic income travel from the margins to the center of political debate almost instantly, in the course of a couple of weeks.

ANAND: I want to expand a little bit on your dismissal of truth and reconciliation. A question that a lot of us are grappling with now is, How do we heal and resolve our relationships among each other as a citizenry? Of course, there's multiple ways of doing that. How would you think about that problem?

MASHA: That's a very different way of thinking about truth and reconciliation if I understand the question correctly. So it's not, How do we think about crimes, but, How do we actually reconcile? I think that is when art can become extraordinarily important and interesting and great because that's when we will be called upon to give up some of our certainties but by no means all of our certainties. Everything is not nuanced. Everything is not subtle. Some things are clear; some things are morally abhorrent and have no justification, and then other things are things that call for empathy. Some things are morally abhorrent but require strategic empathy because we still need to understand where they came from. That's where stories come in.

Maybe it's a time to think about whether leaving it to profit-making corporations entirely is a good way to come together. We don't have stories in this country, unless they're stories being told in the courts, that are not told in the public space for profit, and that probably has to change.

ANAND: What gives you hope?

MASHA: What gives me hope is distinct from the question of whether I'm optimistic. I can be incredibly pessimistic, but hope is a necessity of survival and a moral imperative. I hope because I have to, because a better future is possible. The foundational requirement for it is hope.

Masha Gessen is a staff writer for The New Yorker and author of eleven books, including their most recent title, “Surviving Autocracy.”

This interview was edited and condensed for clarity. It can be viewed in its entirety, courtesy of our hosts the Lannan Foundation and Haymarket Books, here.

Photo: Jens Schlueter/Stringer/Getty

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