Transcript: Timothy Snyder on Iran, Ukraine, and the Future of Freedom

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Transcript: Timothy Snyder on Iran, Ukraine, and the Future of Freedom

The Long Game with Jake Sullivan and Jon Finer

June 22, 2026

TEASER:

Jake Sullivan:

Welcome back to The Long Game. I’m Jake Sullivan.

Jon Finer:

And I’m Jon Finer. So we’re bringing you a different sort of conversation this week with the historian, Timothy Snyder, who joined us on Substack Live. Many of you will be familiar with Tim’s work. He’s obviously one of the most astute analysts of international affairs, including obviously the conflict in Ukraine, but also someone who’s spent a long time looking hard at American democracy, its decline and the potential slide towards authoritarianism.

Jake Sullivan:

So, as Jon said, rather than a typical episode where we bring a guest on for the hour, we did a shorter Substack live with Tim Snyder. We really enjoyed the conversation, so we thought we would share that on our regular podcast feed for all of you as our weekly episode this week. We covered a range of topics with him from international issues like Ukraine and Iran to things here on the home front, including where things stand in terms of Donald Trump’s push in the direction of authoritarianism. So onto the show.

Tim, I thought we’d start because we’re in the midst of these negotiations over this Iran MOU on the back of the ceasefire agreement. And you’ve been quite outspoken on this, quite critical of the president, as have we from the inception of this totally misbegotten and illegal war. But one of the points that you made and have made I think very articulately is that the Iran war is not primarily a story about Iran, but rather a story about American power. Talk to us about that observation, what you mean by that and where it leads you here 100+ days after this war started and now in the midst of negotiations?

Timothy Snyder:

Thanks for that. I mean, number one, I want to just stress before I answer that, I’m just now going to talk about power. So a lot of the things that I’ve written about this war and that the two of you have said about this war have to do with the ethics of it and the law of it, so I am quite deliberately bracketing that and just talking about power. So, I mean, I think it’s quite clear that the Iranians responded essentially as you’d expect a middle power with their capabilities to respond. They did the kinds of things they are capable of doing. The regime was put in what they understandably thought was an existential situation, and they responded I think quite predictably to that. The surprising thing I think for folks who haven’t been paying too much attention to this administration and maybe to some longer-term trends too is how weak the Americans were.

We’ve lost this war. I’ll just make that very clear. We lost this war, and we lost it a long time ago. Americans are very slow to realize we’ve lost wars, but that doesn’t mean we’re slow to lose them. We lost this one very quickly in my view. And the terms of this piece, even as they stand now, and I actually expect they’re going to get worse with time, but even as they stand now, they’re basically capitulation. I mean, promising $300 billion, unfreezing assets, allowing the Iranians to set tolls on the Strait. It’s just an astonishingly thorough defeat, and I think it goes to two issues of American power.

The first is how incompetent leadership can be, and the second is how you get yourself to a situation where radically incompetent leadership is possible. And it’s that second point which worries me that we’re in a kind of ... Now that we’re in a kind of cycle where it’s not just that the leadership is capable of starting and losing these wars of whimsy, but also that that’s just a symptom of the deeper problem that leadership is undermining the bases of American power in science and technology and education and right down the line. So that’s how I see the Iran war. It’s obviously incompetence, it’s obviously defeat, but we’ve gotten ourselves to a point where we can have such leadership, and then that leadership in turn is undermining the pillars of American power going forward.

Jon Finer:

I’d offer a third explanation for this that I’d love your reaction to, and that is a tendency among US administrations, and this is obviously not the first one to make this mistake, of overestimating what military force can accomplish strategically. We obviously have an incredible military that can perform heroic operational feats, tactical successes, including in this war, but strategic success has been much more elusive. And Donald Trump seemed like the kind of president, not to give him credit for anything, not really my inclination, who understood this on some level, who had expressed a degree of skepticism about war, about the use of military force and now has blundered down this same path. And I’m wondering if that has surprised you, if we never should have had confidence that he would avoid this sort of thing and whether you buy this theory that we just overestimate sometimes what we can do even with this incredible military tool that we have?

Timothy Snyder:

No. I appreciate your saying that because I agree with you that this is at some level an American problem that we think that if you ... You can sort of switch from everyday politics, which is messy and unsatisfying, and kind of push a button and apply violence and then everything changes. And that’s just not what the history of warfare teaches. The history of warfare teaches that the enemy has a vote, things are unpredictable, and very soon the reasons you went to war for you forget and you start talking about other things. And that’s not just true for us, it’s true for everybody. But I think you’re right, that we rather uniquely forget that kind of stuff and we start wars with these wildly optimistic interpretations. I think your question’s a good one too.

I just wrote a little essay about that on Substack a day or two ago, which I called Utopias of Violence, which is about how we toggled from this Trump skepticism, which you rightly note, to this really utopian idea, and I think the answer’s Venezuela. And I think when we get to these politics of small numbers where it’s just a few people making decisions and Congress is cut out and advisors are cut out and public opinion is cut out and expertise is cut out and everything else is cut out except for one guy and a few people around him ... I think that mood of elation after Venezuela is the answer, that call he made to Fox & Friends where he just seemed like he was high. I mean, he was just so elated. And that sentence he uttered, like, “We can do this over and over and nobody can stop us,” right? I think that’s where he switched.

Jon Finer:

By the way, and sorry to hog the mic, Jake, but in my-

Jake Sullivan:

[inaudible 00:06:20]-

Jon Finer:

... experience, probably yours too, it tends to be actually people who have experience with war or military who are a bit more skeptical sometimes of offering these grand military strategic solutions to problems. And people who have less, like many of the people in senior roles in this administration, who think it’s the solution to everything. So another aspect of this maybe.

Jake Sullivan:

Yeah. It’s funny. We’ve talked on our podcast about that Venezuela pivot, and I think it actually began even before that. It was the 12-day war last year where Iran didn’t really respond where President Trump felt he could have this beautiful military operation, as he described it, and essentially tie it off after 12 days. Then you get Venezuela, and he thinks two things. One, I can use my military whenever I want for whatever purpose I want, and two, Iran’s not going to respond because they didn’t respond last time. And despite all the warnings that when you actually go for regime change, when you make it existential for the leadership in Tehran that they were going to act in an existential way, including closing the Strait of Hormuz, he had decided, no, no, people said that and I bombed them last year and nothing happened. And people warned me about Maduro, and I went and grabbed him and nothing happened, and then you get this.

And I think we’re paying the wages for that sequence of events over the course of the past year in a way that’s ... As you’ve said, we lost the war, and now we’re paying for it. Actually quite literally paying for it. So, Tim, knowing that we don’t have you for that long and wanting to cover a wide range of ground, maybe we’ll shift to another war, and you’ve actually talked about these super losers, the United States and Russia, the war in Ukraine. You have been a great advocate and champion for Ukraine sovereignty and territorial integrity, for defending them against Russia’s brutal onslaught, and you’ve also obviously been a deep historian of Ukraine and of Eastern Europe. So we’re now more than four years on from Putin launching this full-scale invasion back at ‘22. Tell us how you see things in the war right now, and what are you looking at, and how do you assess where everything stands?

Timothy Snyder:

So I think there’s a pretty obvious pivot between the last question and this question, and that is that if the Trump people had been paying attention to the war in Ukraine, I think that too would’ve discouraged them from starting this war. I think they’re personally and emotionally committed to not paying attention to it for various reasons. And had they paid attention to it, it would maybe have taught some lessons about the difficulty of being on the offensive and also about the technological changes in war, which I think they have deliberately overlooked while they deliberately overlook the Ukraine war. The American military is set up with systems that are easy to deplete and very expensive, and under Trump, I think that lesson has been actively not learned with a focus instead on spending more money for fewer systems. The Trump-class battleship, which of course is a mixture of fiction and anachronism, being the extreme example.

So I think these things are actually connected. Like their lack of realism about Russia and the notion that Russia must win because Russia big. Not letting that logic be challenged I think also is behind their bad decisions in Iran. As for me, I think the Ukrainians have revolutionized war to an extent, which is not ... I mean, I realize you guys are on top of this, but it’s to an extent which is not fully appreciated in general. We’re at the point where coal miners from the Donbas are right now in Arab countries defending other people from drone attacks, and there’s a reason for that. They’re in a class of their own. The only one who’s close is the Russians when it comes to the current way of running war. And I think that leads to where we are, which is that there’s now a kill zone where it’s very hard for human beings to advance. And the Russians are still trying to, and they’re still losing huge amounts of people. They’re losing more than they can replace at this point.

And in May, they lost actually more territory than they were able to gain. And more than that, on the political side, I think Putin’s position is weaker now than Zelenskyy’s by a lot. And the fact that the Ukrainians are using medium, long-range drones against Russian logistics, but also against prestige targets like Moscow and economic targets like refineries and so on, that is new and that’s only going to get worse for the Russians. So I think we’re in the interesting position that people keep thinking of the Ukrainians as dependent on someone else, but even as they get less and less support, especially from us, they’re still winning as I see it. So you can’t really [inaudible 00:11:04] winning a war, but their position is stronger at this point than the Russian position is. And I think in a strange way, Trump has been bad for Putin because Trump de facto has helped the Russians, but he’s helped them to extend a war that they can’t win. In a way, by helping them, I think he’s made the damage for them greater. That’s how I see it right now.

Jon Finer:

Do you think that Russia can ever recover from this conflict? I mean, as bad as the Iran quagmire has been for the United States, we’ve lost 13 American service members killed, many more wounded, that’s a tragedy, every one of those, but we are talking about just an extraordinary magnitude of Russian loss, generations almost, in this conflict. To say nothing of their position in terms of standing in the world and their economy and everything else. Is Putin under more pressure, you seem to be suggesting he is, than is commonly appreciated? And can Russia ever recover under Putin from what they have done here?

Timothy Snyder:

I think the answer to your last question is no, not under Putin. And I don’t think it’s a matter of recovery. I think it would be a matter of transformation. And those of us who are students of Russian history, there’s just a commonplace that the times when Russia has tried to reform have been after the defeat in the Crimean War, after defeat in the Russo-Japanese War, after the defeat in Afghanistan with the Soviet Union. And so if you want Russia to have a chance, you have to help Ukraine win. And so there’s actually no tension between ... And people get anxious about Russia, but I think if you want Russia to have a chance to reform itself in some sense of a way, they have to lose the war, and so the best Russia policy becomes the strong Ukraine policy.

I think beyond that, it’s really hard to predict what will happen in Russia because even the regime changes. What happens after Putin? I think his position is quite weak at this point, but the way he loses power and the way someone replaces him is going to seem very strange to us. Just like the way Putin came to power was very strange with oligarchs around Yeltsin selecting somebody who they thought looked like a movie character, and then Putin managing to win a war and the Russian Secret Service is blowing things up inside Russia. That chain of events is very odd, and I think the next one will be very odd. And we’ll be thrown by it, but the Russians won’t be thrown by it.

Jake Sullivan:

Tim, it’s interesting, coming back to your point about the way that Ukraine has revolutionized drone warfare and how now it’s actually the rest of the world, including Gulf countries, but frankly, also including the United States of America that is learning from them, being supported by them rather than the other way around. One story that we have not really told I think effectively from the Biden administration that Jon and I are very proud of is that we spent years investing in Ukraine’s drone and missile industry, and we’re seeing some of those investments play out now with Ukrainian ingenuity, with Ukrainian iteration every day, every week, every month on the front line. And it really goes back to 2023 because during Ukraine’s counteroffensive in ‘23, we saw the limitations of conventional capabilities in the fight.

Their brigades basically ran headlong into Russian minefields and drone swarms, and so we became obsessed alongside a bunch of our Ukrainian counterparts about the idea that Ukraine needed a technological edge to win the war. So we can be in the Cabinet, in the Situation Room basically calling for a Ukraine technology sprint saying, “We got to get them funding, components and support for their drone and missile development.” Got a lot of pushback in our government, including from the Pentagon who really didn’t want to spend their money on Ukraine’s drone industry, but we kept at it and had a lot of great champions in Kyiv. And by the end of ‘24, the US had put $1.5 billion into Ukraine’s drone industry. And we thought, okay, hopefully this will seed something.

We could not have imagined what Ukraine could do with that two years later. We had a sense in our minds that this is where the fight was going, but we didn’t ... For a country under attack every day in little workshops spread all over the country to come up with these capabilities and also transform these capabilities has been genuinely astonishing for us to watch, and Russia has not been able to keep pace with this. So I guess the question from my end is, can this set of capabilities actually put Ukraine in a position to win, and how long will that take in your view? I mean, nobody has a crystal ball, but what’s your read on where this war goes say over the course of the next year?

Timothy Snyder:

It’s incredibly important that you did that. And I just want to repeat what you emphasized that there are thousands and thousands and thousands of Ukrainians in government, in the private sector, in the military, but mainly somewhere in between working on this stuff all the time. And so The way the drones get way out ahead of everybody else’s and their ground defenses is that they’re in this constant feedback loop where a little company makes something. It gets tested. The data comes back the same day from the battlefield, and they just keep going, going, going, going, which is why it’s hard to catch up from a position like ours actually. And so while we did a lot of good things to help at the beginning, we’re going to have a lot to learn at the end from all of this. The attitude that the current administration has that the Ukrainians are nothing, they don’t matter to us, et cetera.

At some future point, we’re going to have to accept that we have things to learn from people who can win wars and defend themselves. My sense is that the propaganda story in Russia involves advancing taking territory. And in Ukraine, they would like to get territory back, but they don’t have to get territory back to keep fighting, and so the Russian story can collapse in a way that the Ukrainian story can’t, right? And the things that Putin is having to do inside Russia, like try to shut down Telegram. As far as one can tell, those things are unpopular, but also they tend to make him seem out of touch. And then the other thing I already mentioned is the charismatic displays of Ukrainian power like attacking Moscow when Kyiv gets attacked. That’s only going to get worse. So it’s easy to be wrong about stuff like this, but I don’t think the Russians can do this for this full calendar year. I think by this time next year, something’s going to have changed.

Jon Finer:

So I want to make sure we end with a question or two about America, but maybe to help make that pivot I’ll just acknowledge I’ve been surprised by the degree to which support in the US has held up for this war. I think we’ve all observed even American military adventures that have enjoyed far less support from the American people, including the current one by the way, than this conflict involving a country pretty far away that Americans, I think to a large extent, didn’t have a ton of familiarity with before this happened, and yet here we are with strong levels of support showing up in polls. I guess I’m wondering whether you’re surprised by that, how you explain it, but also when you do encounter Americans or others who question the value of supporting Ukraine or what we get out of doing this, how you respond to that?

Timothy Snyder:

The way I think about it is like this, I’m sitting in a building, and I don’t remember every day to thank the walls in this ceiling, but that’s what Ukraine is doing. All this stuff we’re doing, like this nice conversation we’re having, all these chances that we have are in some way related to the fact that Ukraine didn’t surrender and Ukraine is defending themselves now. And if they had surrendered or if they weren’t defending themselves, we’d be just in such a different world, and it would be worse in every respect. And it’s hard to think about that, but I think I try to appreciate the everyday reality, the democracies that still function, the optimism we can still have because all of that has to do with Ukrainian decisions and Ukrainian armed forces. And but to make a list, the international order on non-aggression, the rule of law, non-proliferation, because if Ukraine gives up and Russia wins with nuclear blackmail, then other countries build nuclear weapons.

Freedom and decency, which seem like old-fashioned things and maybe a little conservative, but I believe in them. The Ukrainians really think that they’re ... And they’re right, that they’re defending one way of living from a different way of living where people can be themselves as opposed to people having to be told who they are. And getting to your question, I think that’s why a lot of Republicans and independents and Democrats are on the side of Ukraine because a lot of people that might disagree about a lot of things do have that basic gut sense that this is indecent and that it’s about freedom. And they’re right. They’re right about that, and that’s how I tend to talk to people about it. I find at this point you don’t convince a lot of people about Ukraine, but the basic thing that I say is something like that. We’re not helping them. They’re helping us. They’re helping us in a lot of big ways. And so if we can find some small ways to help them, then we probably should.

Jake Sullivan:

Tim, you said something I think deeply piercing that fundamentally this is about freedom, and that’s what Ukraine is teaching us and trying to help preserve for the rest of us. You have, as everyone watching and listening to this knows, written a book called On Freedom. By the way, my dad didn’t just give me a copy of it for Christmas. He gave me a copy and wrote a note, a four-page note explaining his reflections on the book, why this mattered, and then gave me three other books that he thought I should read having read your book that could deepen my understanding of freedom. So shout out to my dad, but also shout out to you for just a remarkable book.

In that book you write, “Freedom isn’t simply freedom from constraint, but freedom to create something together,” and we’re now just around the corner from the US marking its 250th anniversary. And I think we would love to just hear from you about what a positive vision of American freedom in particular looks like in this moment, which has its dark elements because of Trump and all of the alarms you have sounded, but also continues to have some sense of regenerative hope because of who we are as a people and what we’re capable of. And so can you just talk to us as you’ve written this book, we’re approaching this huge milestone here in the United States, how you look at this question of the positive vision of freedom that you write about so eloquently?

Timothy Snyder:

The way I see it is this, we have a tendency to think of freedom as something just negative, so I’m free of something or I’m free from something, and we treat freedom as, I don’t want to be irritated, I don’t want things to be in my way. And if you push that too far, it gets into that sentiment, which I think is quite dominant now, at least in the White House, that all that matters is my feelings and my preferences and government’s bad and we can wreck it. We can fire the civil servants. We can get rid of whole departments because it doesn’t matter. Government’s just something which is in your way. And that notion of freedom I think is just philosophically and practically wrong.

The reason why you don’t want things in your way is because you’re a person and you have positive desires and you have ethics and you have projects you want to realize in the world. And so sure, we don’t want to have barriers that hold us back, but we also more fundamentally want to have institutions and projects and forms of cooperation that allow us to do things and do things together. And in practice, what you realize is that to have freedom emotionally, you can’t just be against stuff. If you’re just against stuff that drives you into that kind of Trumpian world where we are now where suddenly it’s just one person just kind of destroying stuff. But just to really be free, you have to have the courage to be in favor of stuff.

You have to admit that some things are better than others, and you’re willing to risk things for the things you desire. And then you realize also that in order to get there, you have to work together. That in order to build freedom, you can’t just be against things, you can’t just want what you want. You have to accept that some things are good and that to get there, you have to work together with other people. I think that notion of freedom, that positive notion then becomes a justification for government because government, whether it’s by providing roads or public schools or ideally healthcare opportunity, government creates conditions in which we can then realize ourselves and become free. The right kind of government I mean.

Jake Sullivan:

For those who haven’t read it, please go read it because for this moment I think there’s no better argument for people to digest and then think about how they can put into practice.

Jon Finer:

Don’t know about you guys, but that seems like as good a place as any to leave this and with a lot of gratitude. Better to end on a question on freedom than, for example, one on tyranny, so we’ll save that for the next round.

Timothy Snyder:

All right. Okay.

Jon Finer:

But thanks, Tim, for spending some time with us and really enjoyed the conversation.

Timothy Snyder:

Yeah. It’s been a pleasure. Yeah. Look forward to doing it again.

Jon Finer:

Well, that’s all for today. We’ll be back next week with a new episode of The Long Game.

Jake Sullivan:

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