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Scott Galloway
Founder; Host of The Prof G Pod; Co-host of Pivot and Prof G Markets, Prof G Media

Anne Applebaum and Fiona Hill: Are the Autocrats Winning?

📅 Jun 11, 2026 The Prof G Pod – Scott Galloway 61 MIN 297431 VIEWS 79 SEGMENTS · 3 SPEAKERS
For our 400th episode, Scott Galloway is joined by Anne Applebaum and Fiona Hill to discuss the wars in Ukraine and Iran, the future of global power, and what these conflicts reveal about America's role in the world. They explore whether Ukraine is changing the future of warfare, how Vladimir Putin's position has evolved over the last year, and what might come next for Iran. They also discuss the strengths and weaknesses of authoritarian regimes, the importance of alliances, and why soft power may matter more than military power in the years ahead. Timestamps 00:00 - In This Episode 00:41 -...

Questions asked in this interview

3
  1. 0:00I think it's a problem of why are we in this war?
  2. 0:51How do I emerge from this conflict as the winner?
  3. 20:35And I have to say, I mean, it's interesting if you — I've had this conversation recently with a lot of Europeans actually about would Europeans fight Russia?
Anne Applebaum 0:00 ↗
There's a big difference between wars that are existential and wars of choice. If you're America in Iran, why exactly are you fighting? You're fighting because Trump was angry that he didn't get rid of all the nuclear facilities in the bombing strike last year, I guess, you know, or you're fighting for Trump's need to make friends with Netanyahu or to show that he's on their side. I mean, who knows what it's — Trump has never made it really clear why he's fighting or why America's fighting there. So, I don't think it's a problem of democracy. I think it's a problem of why are we in this war?
Scott Galloway 0:42 ↗
And you wrote that Trump does not think strategically or historically. How do you assess his handling of this war thus far?
Anne Applebaum 0:51 ↗
He's not handling it strategically. He's handling it the way he handles everything. Namely, when he looks at the problem, he doesn't think how do I solve this in a way that's good for Americans, that's good for the people of the Middle East, that's good for the people of Iran. He thinks, how is this good for me? How do I emerge from this conflict as the winner? How do I make sure people don't say I'm just adopting Obama's deal or people don't say X or Y. He's not thinking about solving the problem on behalf of others. He's thinking entirely about himself. And I mean, I think that's why you get these strange zigzags, these strange claims that he's about to do a deal or not to do a deal. He's trying to create applause. He's not trying to solve the problem.
Scott Galloway 1:42 ↗
And Fiona, walk us through — or either of you can comment on this. Walk us through. It appears, I think, Americans, you know, barely have the time to understand domestic politics, much less international politics, and it feels as if there's not enough attention or understanding around how Lebanon has become a key point of tension between Israel, Iran, and the US. And you go first. What role — or describe the situation, and I'd like to get Fiona's reaction.
Anne Applebaum 2:13 ↗
So Lebanon is important to Israel because Lebanon is the home of Hezbollah, which is a really important Iranian proxy. Iran has tried to spread its revolution around the Middle East through the use of — through the creation of other groups who have Islamic ideologies and who work not necessarily exactly coordinated with Iran but in the same, you know, toward in the same direction. And Israel feels that it won't be safe until it has destroyed not only the regime in Iran, which I think is still its ultimate goal, but also all of these proxies. And so the war in Lebanon is not — from either from the Israeli or from the Iranian point of view, it's not a separate story. It's part of the same — it's part of the same picture. I'm not sure that Donald Trump understands that or that his team understands that. But for the Israelis, it's part of that — it's part of the story. And if the war isn't over there, if the Israelis haven't defeated Hezbollah there, which by the way, I should say is probably a generational task, then — then the war is not over.
Scott Galloway 3:21 ↗
Fiona, any thoughts?
Fiona Hill 3:23 ↗
Yes. So I think the problem, just as you scoped it out in the way that you framed the question, is that for the American public this is just too much. I mean, it's literally overkill. I mean, most people are not listening to your podcast. They're not reading the New York Times or the Atlantic and Anne's columns. You know, they're not tracking the complexity of all of this and all of the ties between and among all of the conflicts. I mean, not just is Lebanon, you know, tied into Iran through the prism of Israel and Israel's threat perceptions, but Ukraine is also tied into the conflicts in the Middle East as well, through all kinds of different ways. And for everyone to untangle this is really a bit much. And I think Anne is absolutely right. Trump doesn't understand all of this complexity. For him, it's all very simple. It's all about dealing with whoever it is on top. Negotiating with himself most of all to, you know, figure out where he is coming from on all of this. He's not listening to any kind of advice. And we now also see that he has a major rift with Netanyahu, which is going to make any kind of resolution of what's going on on the ground in Lebanon extraordinarily complicated too.
Scott Galloway 4:29 ↗
I want to put forward a thesis and have each of you respond to it. If you'll — Anne, you go first. The IRGC is a car dealership. Trump is a car purchaser browsing for cars, and Trump is trying to negotiate and has accidentally — or has let the car dealership know that he needs a car to get home, or that he's playing poker and his cards are turned upside down and he has a weak hand. I have — I can find no reason why the IRGC would negotiate at all. I just — it strikes me that we are negotiating with — we don't even have a hand, much less a weak hand. Fiona, your thoughts.
Fiona Hill 5:07 ↗
I think that's absolutely true, and I think, you know, the other part of your analogy here is that Trump also thinks that he's the seller, not just the buyer, and that is the problem because he's always telling the Iranians what he would do, and in real time he's laying out everything — everything that he's thinking. So of course there is no incentive whatsoever for them to make a deal on any kind of basis right now because they have no certainty, no assurances of what the outcome is going to be. So Trump every single day confounds his own ability to make any progress.
Anne Applebaum 5:38 ↗
Yeah, I think there are some things the Iranians want, actually. I mean, they want their frozen assets. They want — I mean, they say they want some kind of compensation for damage done. I mean, that seems pretty unlikely. They want lifting of sanctions. There are things that they want, and they think they might get them. And there actually have been moments over the last few weeks when it looked like Trump was willing to give them some of those things. But of course, then that gets us back to where we started with the first question, was that then that looked a lot like previous attempts, including the one led by Obama, to do a nuclear deal or a sanctions-lifting deal with Iran. And then as soon as he realizes that, he backtracks again. But the — but, you know, the things that they want are things that he doesn't want to give them because that makes him look bad, and so he keeps reverting to this language of, you know, they have to — there we need absolute surrender, or we need regime change, or we need, you know, some kind of — he needs some kind of maximum, maybe even just some show of genuflection or some, you know, some demonstration that he's the greatest leader in the world. Maybe that's what he wants from them. And of course, that's not what they're going to give him.
Scott Galloway 6:50 ↗
And what do you think the political landscape looks like inside of Iran right now?
Anne Applebaum 6:55 ↗
This is a really interesting question and one I've tried to pay attention to to the degree to which it's possible because Iran is pretty cut off. They cut the internet. I think some of it is back on now. And it's very hard to reach people or get any clear idea. Obviously, there's no polling. There's no public opinion. There's no national conversation. I have some Iranian friends who are part of the opposition who've been in touch with people there, and they report — they reported initially really enormous enthusiasm and happiness and joy that the leaders were destroyed. Actually, a friend of mine said to me, you know, I know what you think about this, but I just want you to know — this is on the day Ham was killed — I just want you to know this is the best day of my life, you know. So people were initially very enthusiastic. Obviously, there's been a change since then. There's a lot of disappointment with the way the war is being conducted. There's a lot of fear that the end of the war will give more legitimacy to the regime rather than less. That we've in essence given them a new — not nuclear weapon, but something like a nuclear weapon that they can use against the United States and against the Gulf states, which is control of the Strait of Hormuz, and that will give them extra power. There may be people inside Iran — and this here I'm just guessing, I don't have any evidence or proof — who are rallying around the regime, you know, because they're being attacked by the United States. And we certainly haven't seen the kinds of protests that we saw a few months ago in January. That there's a sense that the regime is still in charge. Now, it's not so much the religious leaders, it's the army and the military. And the — you know, and that, you know, that seems to have kind of — I'm sure there are divisions within that group, but it hasn't — it doesn't leave any room for other conversations, you know, about what kind of other regime we would like. But this is almost a — you know, the strange thing about this is it's almost a moot point. I mean, even whatever you think of the Iraq war, during the — during the invasion, after the invasion, there was a constant conversation about Iraqis and attempts to reach Iraqis and speak to Iraqis, and there was concern about giving the Iraqis agency so that they could run their own country someday. And there was a — nobody wanted to have a long-term occupation. That was never the point. And here there seems to be almost no conversation about the Iranians and what they want and how we could help them live better or make them a country that's better integrated with the Middle East. And that seems to be very odd. I mean, you know, you're asking that question, but almost nobody else does.
Scott Galloway 9:38 ↗
Fiona,
Fiona Hill 9:39 ↗
Yes, I agree. I think it's very strange indeed. And in fact, if we think back to the very beginning of the conflict, of course, President Trump himself tried to actually suggest that he was doing this on behalf of the Iranians and even exhorting them to take to the streets to further his attempts to decapitate the regime. But look, it's as Anne has suggested here, a fundamental misunderstanding of how Iran works. And you can be sure that President Trump hasn't consulted any of the Iran experts. We've got many colleagues who are out there who really know the situation, been following it for decades, who always would have said that Iran wasn't as hierarchical as it looked. The theocracy is on top of these other groups that Anne has already delineated — the IRGC, the military, you know, other groups that have penetrated the whole economy. And the Iranian people are separate from all of this. And it's those groups that are fighting for their survival, and how one activates then or actually tries to respond to the desires of the Iranian people to live better, to work with opposition that is not also seen in a hierarchical mode. I mean, the latching on at first to Pahlavi, to the son of the late Shah, that was just a kind of a classic of a US top-down approach that also wasn't going to get any traction. I think we are completely missing the perspective of Iran looking out into the future here, and that is going to also complicate any means of resolving this war because you are going to leave — even if Trump manages to make some kind of accommodation with all of these different groups that are at the top — you're going to leave Iran in a very perilous and powerless state and essentially as a very weak state in many respects, despite the strength of these groups on the top, that is going to be dysfunctional in such a critical region. And it's traditionally, of course, been a country that was heavily involved in creating a balance of power of sorts in the region. It was very important for Russia as well as for Turkey and all of the other bordering states, not just its interrelationships with Iraq and Israel, for example, and Afghanistan.
Scott Galloway 11:51 ↗
Most of the autocracies you both study are secular — Putin or Xi, kind of the autocracy-inc model. Iran adds a theological dimension. How does a religious autocracy differ, and does it change how this war is fought and how it ends? Fiona, you start.
Fiona Hill 12:10 ↗
Well, it's interesting because the Russians and perhaps the Turks might say to you there isn't really a religious theocracy in Iran. I mean, they see the mullahs and, you know, religion as a kind of an icing on top of a cake of an ancient civilization and, you know, kind of a country that they've dealt with for, in some cases, millennia and, you know, more recently for centuries. And they saw the theocracy as having its own role but not dominating in the way that we would all have seen this from the outside. Putin, for example, you know, found it quite easy to interact despite obviously the religious differences, and I think he saw it or still sees it as a group that want to remain in power by harnessing religion for their own purposes, which is frankly what he has done. And to some degree, that's also what Erdogan has done. And, you know, I'll defer to Anne on Hungary and, you know, others, but I mean, I think you can also see attempts — and we've got that in the United States — to harness religion for one's own purposes. And I think for those in the region, Iran was seen as the ultimate harnessing of religion. And obviously, this is sort of top-down, bottom-up movement there. But I think the Russians and Turks and others have always approached Iran as a kind of, as I said, a sort of theocracy-light, not really kind of buying in to the whole idea that this was now everything was motivated by religion.
Anne Applebaum 13:28 ↗
I think actually the religious — the religious aspect of theocracy in Iran did make a difference. I mean, if you believe that your power is justified by God and that you're part of an eternal — you know, an eternal movement that is legitimate and doesn't need to brook any conversation or debate or opposition because, you know, because the long range of history will demonstrate that you were right, you know, I think that gives you a different attitude to the world. And I think it gives you a different attitude maybe even to fighting. I mean, I think it's not an accident that the Iranians produced, you know, so many people who were inspired by suicide missions and, you know, visions of, you know, virgins in heaven who would make it all worthwhile. I mean, there's a — they have a — it can motivate people and it can give people a sense of certainty that others don't have. I mean, I suppose there are sort of secular religions like Marxism used to be that give people something similar, but I think the Iranian regime with its pretensions to universality — or at least the pretension to, you know, that sooner or later every Muslim would be part of a regime like this one — you know, that gave them the confidence to be involved in, you know, all over the Middle East. It's what motivates their proxies and so on. So I think it does matter. Although I think, you know, Scott, the fundamental basis of your question, which is, you know, what binds this group of autocracies to work together — and right now the most important ones are Russia, China, Iran, North Korea, you know, plus a handful of others — is really not religion, and obviously it's not any ideology. So, you know, ideology doesn't matter. I mean, the Chinese are communists and the Russians are nationalists and the Iranians have a theocracy. You know, what binds all of them is rather their dislike of and fear of the language of the liberal world. In other words, the language of rights, the language of rule of law, the language of separation of powers. You know, all of these are states that are seeking to create a kind of total environment where the regime or the leader or the ruling party controls all media, all conversation, makes all the decisions, controls the court system — which is why so many of them become so profoundly corrupt — controls the legal system. And what all of them are fighting against is the influence of liberalism, secular liberalism, democracy, whichever word you prefer to use, but the influence of other cultures where you have actual debate, where you have independent courts, where you have the rule of law. And I think that's what — that's what they have in common with the other regimes. Although, as I said, I think the religious nature of their regime gives them a particular fanatical edge that you might not find in Russia or China.
Scott Galloway 16:34 ↗
Yeah. Speaking of that edge, and I'll put forward another thesis, and that is it doesn't matter if you spend $1.4 trillion or are committed to your military and you have the most expensive, sophisticated platforms in the world if you have a glass jaw. Now, what do I mean by that? I don't mean to diminish the loss and the tragedy of the families who've lost 13 servicemen and servicewomen in the war in Iran, but Russia's willing to lose a thousand people a day. Iran will kill 30,000 of its own people and let their civilian infrastructure be destroyed and bombed. Americans freak out if they can't get their Netflix for five minutes. And that is regardless of how strong we are, do we ultimately maintain our interest overseas if we can deliver violence but we're not willing to take — absorb the losses? If Europe is never willing — you know, granted Europe's really stepped up in terms of economic support, but at the end of the day, aren't the autocrats going to win if we lose 13 people and say we're out? Don't we operate at a severe disadvantage that maybe, correctly, we just aren't willing to make the type of sacrifices these autocracies are? I'll let you go first, Fiona.
Fiona Hill 17:50 ↗
I think that there's a fundamental difference in the way that we see power and the exercising of power in the United States and in other countries as well, in Europe and also in Ukraine, by the way. And, you know, I don't disagree at all with anything that Anne has just said about the way that all of this group of autocracies look at things. I think she's absolutely right that, of course, there is an edge that was given to Iran and to its perspective from the religion, you know, that was — you know, something that I — you know, a point I didn't make at the very beginning, but I was trying to also explain that most of the countries around that don't really see Iran as being all about religion. But it's absolutely right that they all see themselves as very strong states and states in which societies, individuals, people have no role. And that is really the kind of the fundamental difference for now still with the United States and with European countries. I mean, we've got over time, particularly over the course of the 20th century, to a point where I believe that societies and our populations have more say in how power is exercised. And of course, that's a fundamental struggle going on right now in the United States as we try to move in a different direction. And if you see in the case of Ukraine, for example, Ukrainians have been willing to sacrifice large numbers of people. I mean, yes, it's extraordinarily difficult for them, but they've proven to be just as resilient as the Russians have, but for a very different reason. They have had to fight for their existence and for their survival. And I think that the way that Trump has presented this whole war in Iran — this is not about United States survival. It's not about the American people. This is a war of choice that he made. And that was also the backlash that we had in the United States and in other countries after Iraq and the invasion of Iraq. Afghanistan might have been a different matter given 9/11 and the attacks on the United States by bin Laden and that sort of sense that the United States was in peril at that time. But if you look back to the wars of the 20th century, to World War I and World War II, you know, particularly in the case of the United Kingdom and, you know, many other countries, there was a sense that the society also had to rise to the occasion. And remember that the deaths in World War II on the part of the UK and all of the then Commonwealth countries were as great as the worst battles in World War I. So people were willing to sacrifice where they saw themselves as individuals, as families, as groups, as people, and as their countries on the line. And I think that the difference here is that no one in the United States sees the United States being on the line in this particular conflict in Iran. And that's also the case with Ukraine. Now, Europeans are having a big debate about how much they are on the line now in Ukraine, but they certainly don't see themselves — they see their livelihoods on the line, but not themselves, their own existence on the line in what's happening in the Gulf, although, you know, perhaps that might shift as the economic and other problems become more acute.
Scott Galloway 20:32 ↗
And do we have a glass jaw?

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APA

Galloway, S. (2026, June 11). Anne Applebaum and Fiona Hill: Are the Autocrats Winning? [Interview transcript]. The Prof G Pod – Scott Galloway. CEOInterviews.AI. https://ceointerviews.ai/interview/3002647/

MLA

Scott Galloway. "Anne Applebaum and Fiona Hill: Are the Autocrats Winning?." The Prof G Pod – Scott Galloway, 11 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3002647/.

BibTeX
@misc{galloway2026_3002647,
  author       = {Scott Galloway},
  title        = {Anne Applebaum and Fiona Hill: Are the Autocrats Winning?},
  howpublished = {Interview transcript, The Prof G Pod – Scott Galloway. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/3002647/},
  note         = {Speaker-attributed transcript with timestamps}
}