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Richard Engel
Hello, I'm Richard Engel in Israel, and welcome to the World podcast.
Ken Pollack
They told Trump very categorically not to attack Iran. We didn't change the regime, we changed the leadership. And this is a much worse version. They can take the amount of pain they're suffering right now longer than President Trump is willing to take the pain he is suffering.
Richard Engel
Yalda is off this week, taking a break, but we'll be back together next week as usual. So no deal between the United States and Iran. Waiting for Godot with bombs. Both sides are still trading drones and missiles. And Israel is once again ramping up its campaign in Lebanon, triggering Iran to suspend negotiations with Washington. Today we'll be talking all things Iran, Lebanon, the wars in the Middle East. And one question I'll be asking is how did the Trump administration not see any of this coming? And the person I'll be asking that and where it's all going is my guest for today, Ken Pollack. He is the vice president at the Middle East Institute, author of 10 books on the Middle east, and a former senior analyst at the CIA. And as always, please subscribe and you can Watch us on YouTube. And joining us now at long last is Ken Pollack. It is a great pleasure to speak to you. I can't remember a time when I haven't known your name. I've read many of your books. I've read your analysis. It's a great pleasure to finally be be speaking directly to you.
Ken Pollack
Thanks so much for having me on, Richard. I am a great fan of your work as well, and so I'm delighted to be doing this with you.
Richard Engel
So why don't we start a little big picture, because people ask me this question all the time. Is the US Winning? Is Israel winning? What are they hoping to accomplish? Where is this going? I mean, I know that was like eight questions in one, but it really is one question. And the question is what the hell is going on?
Ken Pollack
Sure. So I'm gonna start in the Middle Because I got a phrase that I've been using that you kind of alluded to there, which is that we're winning, but I'm not sure we're going to win. Right. And I think that's the great problem. And we should recognize we got into this with a set of ideas. And let's also recognize the United States and Israel had different incentives to get into this. Our interests are not identical on the American side. Very clear. President Trump was hoping to overturn the Iranian regime, think, thought that there was an opportunity to do so, decided to take the shot, maybe get another Venezuela.
Richard Engel
He thought it'd be quick and easy. You agree with that assessment?
Ken Pollack
Yep, absolutely. Quick, cheap, easy. And let's recognize that's what President Trump's foreign policy structure has looked like mostly in his second term. He's looking for quick, cheap, easy wins for the United States. It was, let's try to get rid of this regime if we could, because that'd be fabulous if we could. Big win for President Trump and frankly, big win for the United States, big win for the Middle East, Israel, the world. Right. Rid of this odious regime in Tehran. But that was always going to be a long shot. And there clearly was a sense that, okay, even if we didn't get that, we'd fall back on, well, we would destroy a lot of the Iranians ballistic missile capability, their navy, their air force, do a whole bunch of other things in the expectation that we could walk away. Right? That we could walk away whenever we wanted to do so. So whatever damage we did to the Iranians was a win. Right? It was going to be a win. That was Trump's perspective on it.
Richard Engel
And who do you think convinced Trump that this was how it would play out? Do you think it was Netanyahu? Do you think it was Hegseth? Is this Trump himself? Is he advisable?
Ken Pollack
So these are all great questions, Richard. Of course, none of us really knows the answer. My sense is that, yes, Netanyahu was a part of it, did convince him at the very least that it was going to be possible to kill Ayatollah Khamenei, the Supreme Leader of Iran and much of its leadership, and that this could bring down the regime and that even if it didn't, that it would accomplish all these other goals. But again, let's recognize at the end of the day, it was Trump who was the principal mover here. He is the one who believed this. He is the one who made all this happen. It's worth pointing out Bibi has more or less been singing this same song to every American president since George W. Bush, Right? He's been saying the same thing for 25 years. The variable here is not Bibi, it's Trump.
Richard Engel
So if this is something, and I asked Prime Minister Netanyahu about this, I threw a question at him anyway. You've been pushing for this for so long. He finally got it. Is this the parable? And this is not how I asked the prime minister, but I said, is this the parable that the dog that finally catches the train, you know, the old expression, you're chasing the dog, chases the train, and then finally he catches it and gets run over? Is that what happened here? He finally got the war that he wanted, and now he's stuck with it.
Ken Pollack
So I think from the Israeli perspective, and again, let's recognize they had a different perspective, they certainly wanted regime change. And recognize for them, any regime change is good. Right. For the United States, overthrowing this regime, getting you could, you know, chaos, civil war, that'd be worse for the United States or just as bad, that'd be fine for the Israelis. And for the Israelis, any damage to the Iranian military, ballistic missiles, that's all good for them, and they get to.
Richard Engel
Do you think that's the case? I mean, you worked in the CIA for many years, analyzed the Middle east, written, as I said extensively about it, Any regime change from Israel's perspective is better than what they had, even chaos and nuclear material around and a more hardline regime or civil war or et cetera, et cetera, that's potentially better.
Ken Pollack
I think that's what they believed. I'm not going to agree with that, because I think you're right that there are, you know, there always worse. It's the Middle east, right? One of our expressions for people among the work on the Middle east is don't assume that they've scraped the bottom of the barrel. They can always scrape deeper. Right. There's always another bottom. There's always worse out there. But I do think that that's what Netanyahu believe. That's why he got into it. Right. But again, a somewhat different set of motives than Trump's. And, you know, right now, where are we? Well, we've got a really big problem. And, you know, give me a second here to unpack some stuff because it's important, please. Iran always had the capability to interfere with traffic in the Strait of Hormuz, right? They never actually tried to shut it down. They never did because they were always terrified that if they did, the United States would come for regime change. We would decide this regime is beyond the pale. We have got to get rid of them. Cuz what they're doing is interfering with the global economy. So we got to take out the regime. And for that reason, they would never touch the Strait of Hormuz. Think about what Trump did. He kills Ayatollah Khamenei. He kills most of the military and internal security leadership. The first night he proclaims regime change. He says, we want a new regime. He says, I'm going to be the one choosing the new Supreme Leader of Iran.
Richard Engel
Remember he said that we don't want regime change, but the regime has changed, I think is how he phrased it.
Ken Pollack
All kinds of stuff. But he's makes it very, very clear that he is coming for regime change. So the Iranians then flip to their contingency. Their contingency is if the Americans ever do try to change the regime, then we close down the Strait of Hormuz. And at that moment, what they learn is that shutting down the Strait of Hormuz is not going to cause the United States to try to overthrow the regime. It's going to cause the United States to back off from trying to change the regime. Trump is not talking about regime change at all. He has no interest in it. Right. That's the signal he has sent to the Iranian leadership. And we should also recognize this is a much worse version of this regime. We didn't change the regime, we changed the leadership. And this is a much worse version.
Richard Engel
And why would you say it's worse? Because it's more hardline, less inclined to democracy or all of the above?
Ken Pollack
This is, this is the hardest of the hardliners. And again, there clearly is some dissonance there. It's Iran. There's factions. There's always factions in Iran. These are the people who always wanted a nuclear weapon. These are people who really don't care very much about Iran's economy and certainly don't care very much about the Iranian people. They're going to be much more difficult to deal with.
Richard Engel
Would you say that this was a war, though of misconception that Israel thought it would be easier? Trump thought it would be easier that these two personalities came together and got into an adventure that they can't get out of? Or do you think it's more corrupt, more dirty than that? Is it about money? Is it about backroom deals? He's been convicted as an international war criminal. He's facing trials at home. You have Trump, who's a unique brand of American leader. He's running his businesses openly. Tremendous investments in the Gulf nations. It seems much murkier and less clean. And I think that's the politest way I can put it. What do you think about that?
Ken Pollack
What I can say is, look, first, we should recognize the Iranian regime has defined the United States and Israel as its enemies for 47 years. Right? There's no reason for this. Every American president since Jimmy Carter has tried to reconcile with the. With the Iranian regime. We've done all kinds of things. You know, I worked for Bill Clinton. I was his Persian Gulf director. We did all kinds of things to try to bring about a rapprochement. The Iranians were not interested. They did everything in their power to hurt us. They've killed at least 1,000Americans over the years. So this is not a good regime. And, you know, there has always been kind of an argument out there that going to war with Iran would pay dividends, would be beneficial to the United States, was something that was worth doing, that needed to happen under the right circumstances. As to corruption, you know, honestly, Richard, I'm just a dumb Middle east analyst. You know, I can also, as an American, look at the way that President Trump has handled his time and office, especially in the second term. I, too, have all kinds of questions about things going on there, but I try to stick to my area of expertise when I'm getting interviewed in public, and I just can't speak to any of that stuff. It certainly could happen. It's the Middle East. But I think the more important points are there was always a bottom, you know, an underlying foundation of strategic logic of some kind of a war against Iran under the right circumstances. But I do think that really what you had here was a real misunderstand understanding of what those circumstances were at this moment.
Richard Engel
And before we get to this very interesting war game that really predicted a lot of what we're seeing right now that you were involved in. Just to be very clear, do you think that Iran was building a nuclear weapon?
Ken Pollack
Iran's nuclear program was always a nuclear weapons program. However, in 2015, when they signed the original nuclear agreement with Iran, President Obama, as a number of other people have pointed out, they were complying with the agreement, and they were, in fact, much farther away from having a nuclear weapon in 2018, when Trump pulled us out of the deal, than they were either in 2015 when Obama signed it, or in 2025 when the U.S. and Israel began bombing Iran. Right. So pulling the U.S. out of the 2015 nuclear deal, that was the Thing that really brought Iran close to having kind of a nuclear capability. And even then, they were enriching uranium. There was no evidence that they were really making tremendous progress to getting the bomb. Right. Remember, you got to have both the fissile material and the working bomb to actually have a nuclear weapon.
Richard Engel
So they only need a detonator, which is not an easy thing to build and which they didn't have. And you need a way to deliver that bomb that is an intercontinental ballistic missile, which they also didn't have.
Ken Pollack
Right. So, yes, they were. They. You know, and especially after the strikes In June of 2025, what President Trump calls the 12 day war, I had seen nothing to indicate. And in fact, President Trump used to say that their nuclear material was buried deep. Right. In fact, that's one of the problems we have now, is people have talked about we need to get that material. They've talked about commando operations to go in and retrieve the highly enriched terrain. Well, those are impossible. They're ridiculous, because it's all buried deep underground, these super penetrator munitions that we use to destroy the sites. And again, there was no evidence that the Iranians were excavating those sites, were trying to reach that material. This was always something I worried about, but there was no evidence of that. So before this war began in February, February 28, there was no indication that the Iranians were anywhere near close to having a nuclear weapon.
Richard Engel
So how do you think Trump got pushed over the line? Was it personal? Was this Prime Minister Netanyahu being particularly persuasive? You are an expert in the Gulf, and the Gulf is a big part of this. There are huge rivalries between Qatar, Saudi Arabia, the United Arab Emirates, there's the Abraham Accords floating around. There's data centers. There's billions and billions of that have been invested in this and are on stake. The entire oil market. There's. There's a lot of money behind this conflict, no question.
Ken Pollack
All right, let's start there, though, because I think this is an important point that has been badly misunderstood. There's been some really bad media coverage of this. The Saudis, the Emiratis, the Kuwaitis, the Qataris did not want this war. And they told Trump very categorically not to attack Iran. Some may remember, even before the war began, they told the United States they would not allow us to use their basis for attacks against Iran. They did not want this to happen because they were afraid of something just like this happening. So point number one, they did not want this war. What might have pushed Trump into it. What. Probably, as best I can tell, I do think that it was this combination of. He always wanted to do something about the Iranian nuclear program. Remember, as I said, he. He pulls us out of the 2015 nuclear deal because he promises to get a better deal, but he hadn't gotten a better deal. The Iranians absolutely refused to agree to a better deal, in large part because, as I said before, their hardliners felt like the original 2015 deal was too generous to the United States of America. So he hadn't been able to deliver on that. I think he was hoping that this war would help him deliver on that, would force the Iranians to come to a better deal. And because I think it's very clear, and here, I think that the media reporting has been good, that he did believe that with Israel's help, the US could take down this regime and that it would be another big win, just like Venezuela. And that's what he was looking for.
Richard Engel
So some. Some hubris in there, which is an old lesson of war and life. So let's get to this. Let's get to this war game, which I've teased enough, so if you could tell people a little bit about what. What that means and which side did you play? What was the war game? And. And how. How did it play out?
Ken Pollack
Sure. So I actually ran the war game. This is back when I was at the Brookings Institution, and we used to kind of regularly do these war games looking at different aspects of conflict with Iran. We actually played out an Israeli strike on Iran any number of times as well in this game. The game started with the Israelis continuing to assassinate Iranian nuclear scientists. This is before the. The 2015 nuclear deal. And the Iranians retaliate, and they decide to retaliate against both the Israelis and the Americans. And the strike against the American goes wrong. It's a. It's a attack with a bomb.
Richard Engel
So it goes wrong. In which. What is. What does that mean?
Ken Pollack
It goes wrong because the Iranians kill far more people than they had meant to. They really just were trying to kill this one American nuclear scientist to retaliate.
Richard Engel
So suddenly, things escalate in your scenario dramatically, right?
Ken Pollack
Exactly. And what happens from there is the United States decides to. And it's an interesting. It was an interesting dynamic because the American team was actually initially very cautious and conservative and decided to do something that the United States thought was not a big deal, which was lob a bunch of cruise missiles at the Iranian Revolutionary Guard headquarters in Tehran. The Iranians look at this and say, they just hit on Iranian territory. We can't let that stand. Right. And so what they do is they decide to try to signal to the United States. And this is a really important thing to think about. They're going to try to signal to the United States. We really don't like the fact that you hit a target in Iran. We want you to stop doing that. So we're going to sink some ships in the Strait of Hormuz. And again, they think they're just. The Americans think they're signaling, the Iranians think they're signaling, the Iranians sink these ships in the Strait of Hormuz and the American team goes nuts and says, we cannot allow any kind of a threat to the Strait of Hormuz and we escalate to all out war with the Iranians. And again, what was so interesting about it was how impossible it was for these two groups of people to signal to each other across a war, even though it was nothing but a simulation, nothing but a war game with two groups of people in separate rooms divided by what, a 12 inch wall? And again, people who understood each other much better than the US Government actually understands the Iranian government, or vice versa.
Richard Engel
So how long did it take these two teams to arrive at a war in the Strait of Hormuz? How long did it take for the tit, for tat and the back and forth to happen before suddenly the Strait of Hormuz is in the conflict? Was it day one, day two, day five?
Ken Pollack
So, I mean, in real time it was a matter of hours. I think in game time it was about a week where these things played out, but it got very fast.
Richard Engel
So what do you make of the assessment that President Trump said numerous times that no one could possibly imagine that or could have predicted that Iran was going to move to the Strait of Hormuz when you and your experts did it and immediately came to the conclusion that that's how it would play out.
Ken Pollack
So there is literally nothing that has happened in this war on the Iranian side, Richard, that I wouldn't have predicted that a thousand other experts on Iran would have predicted. The first time I participated in a war game that was about the Iranians closing the Strait of Hormuz, I think was in 1992. And the US government does it over and over and over again. We plan, we prepare. The US Military is all over this. They've thought it through in every possible respect. What the Iranians did was not unexpected at all. It was completely expected. It's what the United States did that was completely Unexpected.
Richard Engel
Well, when you said the United States, you mean President Trump particularly. Do you think there's any way, shape or form that your former colleagues at the CIA missed this one?
Ken Pollack
No, I cannot imagine that they did. And the little bits of reports that we're getting is that they had, in fact predicted this. As said, all the evidence is that this is whatever the opposite of an intelligence failure is. This is that right. This was every single step was called at every step of the way. But again, you had a president who believed what he wanted to believe, which was that regime change was easy, cheap, and eminently doable, likely to happen. But again, the US government. Forget about my war game. The US government has been studying this for 30 years, right? Over 30 years, understood this, completely understood exactly what was going to happen. I was able to predict everything that happened because I had been part of that community, and I know that other folks had as well. That was not the variable here. That was not the unknown here.
Richard Engel
I did reports on television that said the Iranians were going to close the Strait of Hormuzid. This was hardly hidden information on network news. Big, big audience, not, not secret intelligence reports that may or may not have been been read. So let's use your, your analytical brain. Where do you think this is going? What do you think their next steps are? And I know that's hard because there's a lot of wild factors, but I'm asking, you know, hard is good. So I'm asking you a hard question.
Ken Pollack
Yes, and we analysts like to be given hard questions, but, you know, recognize hard questions rarely admit for easy answers. So right now, there is some kind of a debate within Iran. But the group that seems to be winning are the hardest of the hardliners who seem to believe that they are winning the war with the United States and that if they can hold on, they will force Trump to make all kinds of concessions to them regarding money and their control over the Strait of Hormuz. And we should recognize that that is enormously valuable to them. Again, because that lesson that I pointed out beforehand, that their control of the Strait of Hormuz not only brings monetary value to them, but it also will cause the United States to refrain from changing, trying to change the regime that's actually probably more useful to them than a nuclear weapon. Right. That's another one of the things that's most dangerous right now is they may actually be willing to make some concessions on the nuclear front because they've now seen suddenly got something that's more useful to them. And just as important in guaranteeing the perseverance of the regime. They are taking damage. They are hurting economically from this. But as I said before, this is a group that tends not to care very much about the economy. They tend to believe that they can kill themselves into power, remain in power, simply by killing as many people as they need to do. So. I think they probably are nervous that if the war were to restart, the US Might and Israel might be able to kill some of them. There probably is some element of self preservation there. But again, what we're seeing from them is a willingness to kind of stick this out based on the assumption that they can take the amount of pain they're suffering right now longer than President Trump is willing to take the pain he is suffering.
Richard Engel
So it sounds like you're saying with great tragic irony, that among the biggest losers are the people on the streets of Tehran who President Trump claimed he was going to be helping, the people who went out to demand change, to demand more rights, to demand democracy. They were met by the besieged forces and a terrible crackdown. President Trump said, help is coming. We're doing this in your name. If the new government is more powerful, more emboldened, and more entrenched, it seems like the people who were hoping for a Tehran spring ultimately get caught holding the back.
Ken Pollack
So certainly in the short term, I think that exactly what you described is the most likely outcome for the Iranian people. And I agree with you. I think that that is an absolute tragedy. We can all be hopeful in the long term. I think that the conduct of this war, the outcome of this war, and the callousness of this version of the regime are going to further antagonize the Iranian people against their leadership. And perhaps at some point in the future, they will be able, they will be in a position to once again revolt against it. I mean, again, I know you know this because I know you've covered this any number of occasions, but pretty much every two or three years, the Iranian people tries to rise up and overthrow its government. And that's been going on for almost 20 years now, arguably for 30 years now. Perhaps at some point in the future that will change. But yeah, in the short term, I think that they once again are going to get the short end of the stick.
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Richard Engel
I would love to change subjects a little bit. Although it's not a new subject because as Iran has made abundantly clear, it sees them as absolutely linked. In fact, Iran has suspended negotiations with the United States because of the ongoing war in Lebanon. Where do you think this war is going? There are some in Israel who I've spoken to believes that this could be another Vietnam for Israel. You know, this is not a Gaza situation. Israel doesn't have Lebanon completely surrounded. Hezbollah has weapons, it has terrain, it has access to foreign borders. In Syria, they have lengthy experience fighting against Israel. And already the Israelis are suffering many more casualties in Lebanon than they ever did in Gaza or any of these other conflicts. So how do you see this war expanding? Was this another miscalculation? And I recognize there were multiple questions in that.
Ken Pollack
Yeah, there's a lot of.
Richard Engel
Sorry about that.
Ken Pollack
It's okay. So here's where I'd like to start. Where I'd like to start is to say there is an incredible opportunity in Lebanon. And this is another one where I find myself frustrated with the Trump administration because, boy, if you were looking for a win, I'd be looking for it in Lebanon. That's the place. You now have a circumstance where Hezbollah was badly weakened by the Israeli attacks of 2024. The Lebanese population has turned dramatically against Hezbollah, including large segments of Lebanon's Shia community.
Richard Engel
Right.
Ken Pollack
I mean, always hard to come by numbers, but it looks like about 80% of the Lebanese population now wants to see Hezbollah disarmed. You've got a president, a prime minister, a chief staff, all of whom are committed to disarming Hezbollah. The Lebanese parliament has demanded that Hezbollah disarm, has said that its milit illegal. I mean, this is incredible. But Israel cannot help Lebanon achieve that or take advantage of that opportunity. Only the United States can. Right. And leaving it to the Israelis, it will not solve this problem. Right. To me, again, it is so frustrating. The United States will not recognize. We need to provide the assistance to the Lebanese government and the Lebanese armed forces. And if we do, if we ramp up our support, there is every indication that the Lebanese themselves will disarm Hezbollah and transform Lebanon. You leave it to the Israelis, and what we are seeing happen is inevitably going to happen because Israel can't transform things. They can't help the Lebanese armed forces because they are still seen by the vast majority of Lebanese as the enemy. Right. They don't want them there.
Richard Engel
How are your former colleagues in the intelligence community feeling? Are they feeling excluded, not listened to? Are they pulling their hair out? Are they quitting? What's the mood over there?
Ken Pollack
Yeah. So obviously, I haven't done a survey of everyone, but my own contacts, my conversations with former colleagues. There's a lot of frustration. I recognize people in the US Intelligence community tend to be really patriotic Americans. They want their country, whether they're Democrat, Republican, liberal, conservative, whatever. They tend to be very patriotic. They want the United States of America to do well, and they bring their expertise. That's what they have to offer the country is their expertise. We all know they sometimes get it wrong, much less than people actually think, but when they do, it can be pretty spectacular. But this is another one of those instances where they actually know the right answers and. And they just wish that the administration were listening to them again. I know very, very few people, the administration, sorry, in the Intelligence Committee, who, you know, want to spite this president somehow. They all want this president to do well because at the end of the day, he is the commander in chief of the United States of America. They want him to do well for that reason. And they're just very frustrated that they don't get listened to.
Richard Engel
So if you're saying they're not planning a deep state overthrow, as President Trump has somehow suggested, or as at times suggested, quite, quite directly, aside from their frustration, what are they doing? Are they being more vocal, resigning? What can you do? If you're at the top levels of an American intelligence agency, the CIA, and the boss isn't listening.
Ken Pollack
Yeah. So it's very difficult. First, remember, I know, you know, some of these stories, you try to find ways to get the boss to listen. I mean, famously right. With President Reagan, the CIA adopted comics as a way of kind of, you know, delivering messages to him because they knew he would read them. That's a little bit of an extreme, but, you know, you do what you can.
Richard Engel
Tell me more about this comics. So they made this was during the Cold War. So they would have what, cartoon version
Ken Pollack
of Gorbachev, effectively, President's Daily Brief, that they would, you know, insert comics in there that they knew that the president would want to read and that would get him to read their analysis along with it. So they weren't literally drawing comics for Reagan, but they would include comics in it because they knew that Reagan was taken with the comics. And once he was reading the comics, he'd read the rest of the piece that they wrote as well. But so, again, you're looking for ways to get a president interested. And again, I know with President Trump, they've been trying hard to think about, okay, well, what would catch this president's imagination? Right. What does he glom onto? What interests Tim? And, you know, can we structure the way that we report in ways that are going to catch his imagination? Some who get the most frustrated. Yeah. Are leaving, and there certainly are people who are resigning. Very hard to know what the numbers are. But, you know, I know of some people who, friends of mine, longtime analysts, who just decided that, you know, they were too frustrated, they parted ways. You know, others more or less kind of suffer in silence. They, you know, they look for the opportunity. They hope that at some point the administration will realize that what it's doing isn't working. And therefore, maybe we should see what the experts have to say, because maybe what the experts will say will actually work, given that what they're doing isn't.
Richard Engel
Are they using flattery? You know, I assume you saw that analysis in the New York Times that went through all of the public cabinet meetings, and they found that one out of every six sentences was either a direct compliment or an indirect compliment, insulting the Biden administration, insulting his predecessor and saying how much. How much better he was. And are they using flattery? And if so, is that helpful? You know, okay, slipping a cartoon because, you know, it'll catch Reagan's eye is one thing, but using that much obsequiousness, is that effective? Could that backfire? How are they doing it? How are they trying to appeal to him?
Ken Pollack
So I have to plead ignorance on that one. I literally just, I've never had someone say to me, you know, yeah, we fly to the president to get him to pay attention. Again, what my understanding is that what they're trying to do is trying to show him that they are on his team, that they're there to support him. They are absolutely not his adversaries. Quite the opposite. That they want him to do well, and that what they're trying to do is to explain to him what they believe would be in his best interest, in the country's best interest, would allow him to get wins. Right. And look, you know, again, that's a perfectly reasonable way of approaching the subject, assuming that is what they're doing. But that's mostly what we've heard from. What I've heard from them is this frustration that we try to make it clear to him that this is the way to get what you want to get right. We're here to help you, sir. And sometimes he doesn't listen, even then.
Richard Engel
Yeah, I was going to say it doesn't sound like it's working. Going back to all that we've been talking about, we could talk all day, all night. I look forward to more conversations. But one more impossible question while I've got you. How do you see this ending? Are they going to get a deal? It feels like a mirage. You see it there. We know what it looks like. But the closer you get to recedes further into the distance and may not even be there at all. So is this a mirage? Is there a real deal? How is this going to end, do you think?
Ken Pollack
So this is lovely because it lets us come full circle to my very first answer to you, which is that we're winning. But I don't think. But I'm very concerned that we're not going to win. I mean, we're winning in the sense of we have done a lot of damage to Iran, and if somehow you could just end this and tote up the military scorecard, we've done a heck of a lot more damage to them than they have done to us, or they've not done no damage to us. But the problem is the Strait of Hormuz, and the problem is the way that the Iranians have also. We haven't really talked about this, but we need to put this on the table the way that the Iranians have also demonstrated to all of our allies in the Gulf that they can threaten them whenever they choose to do so. And while it's certainly true, I mean, the Gulf states, with our help, of doing a remarkable job, shooting down Iranian drones and missiles, you know, the, the, the Gulf built itself as this paradise, right, for money and people and goods. And, you know, no one is going to want to invest in the Gulf. No one is going to want to trade in the Gulf. No one's going to want to take vacations in the Gulf. If, you know, every other day an Iranian drone comes over a ballistic missile, even if it's shot down, that's not exactly the kind of place where you want to bet your life, bet your fortune, right? So all of this has me very concerned that when this ends, we're going to wind up making significant concessions to the Iranians, paying them a lot of money, either directly or indirectly. And we should remember the Iranians are already going to our Gulf allies and saying, we can do this to you whenever we want to. The Americans have demonstrated they can't stop us. So if you want us to not do it, you're going to pay us and you're going to pay us tens of billions of dollars, which of course the Gulf can afford. They won't like it. But imagine this Iranian regime, right? This version of the Iranian regime, the worst, the hardest of the hardliners, with access to additional hundreds of billions of dollars. That is not going to be a good Middle East. And my fear is that's where we're headed.
Richard Engel
Well, it has been a great pleasure talking to you. I understand you have a new book coming out. Anything you can tell us about that that won't be too revealing and get your publisher sending you nasty emails?
Ken Pollack
Sure. It's not out for a while yet. It'll be out in February of next year. And it is, God help me. It is a history of the United States and Iraq, the whole relationship, you know, going back really to 1979, but going through the Persian Gulf war and the invasion of Iraq and the civil war and the surge and the ISIS war. It's telling the whole story in one volume.
Richard Engel
Well, I look forward to reading it. And most people forget that the United States was close allies with Saddam Hussein, gave Saddam Hussein a lot of weapons in order to fight against Iran. So to land the plane and bring it all the way full circle. We'll look forward to that coming. What's it called? Do you have a working title?
Ken Pollack
It's called the Iraq Wars.
Richard Engel
The Iraq Wars. All right. Well, we look forward to having you back on when that comes out. And thank you so much for spending some time with us.
Ken Pollack
It was my pleasure. Thanks so much for having me on, Richard.
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The World with Richard Engel and Yalda Hakim – Sky News
Date: June 3, 2026
Host: Richard Engel
Guest: Ken Pollack (Vice President, Middle East Institute; Former CIA Senior Analyst)
This episode dissects the U.S.-Iranian conflict and the wider Middle East crises, focusing on why the Trump administration was caught unprepared by events that seasoned analysts, like guest Ken Pollack, foresaw years ago. Pollack, a veteran Middle East expert and former CIA analyst, provides deep context on U.S. and Israeli strategies, Iran’s hardline turn, policy missteps, and the intelligence failures (or lack thereof) that led to the current crisis. The conversation spans the role of major regional players, decision-making failures in Washington and Jerusalem, the situation in Lebanon, and the prospects for some sort of diplomatic settlement.
The conversation is frank, analytical, and deeply knowledgeable, infused with a sense of both exasperation at missed opportunities and alarm over the human and geopolitical cost of leadership failures. Pollack offers no easy answers, stressing both the tragic irony for the Iranian people and the dire implications for the region if the current trajectory continues.
Summary by [Podcast Summarizer AI, June 2026]