Chapter 1: What are the potential outcomes of the Iran War after Khamenei's death?
When it comes to the bombing of Iran, the killing of Supreme Leader Khamenei and Iranian top brass, the unspooling of regional war and the prospect of a prolonged conflict, it is very easy for me to distinguish between what I hope and what I fear. What I hope is that the Islamic Republic just rolls over and gives up.
That a nation brutalized by this horrific regime emerges from this episode as a richer and freer society whose stability extends peace across the Middle East. That is, I hope this moment represents a break from history. What I fear is that history is repeating itself. Donald Trump has bombed Iran and killed its leadership without a plan.
It sometimes even seems without even the pretense of a plan or a timeline. And in this sense, this feels to me like a bit of an eerie echo of a very American tendency. Go back to the 1960s when President Lyndon B. Johnson and his top advisors claimed that, quote, limited pressure and modest escalation would stabilize Vietnam.
Instead, what happened is we tiptoed into the catastrophe of war, which ended up spilling over into a regional calamity that killed millions of people.
Chapter 2: What are the hopes and fears regarding Iran's regime change?
In the Gulf War of 1991, George H.W. Bush bombed Iraq and sent aircraft to drop leaflets on citizens and troops, telling them to rise up and topple their leader. Instead, Hussein remained in power and massacred tens of thousands of his own people. In Somalia, the Bush and Clinton administrations attempted regime change on the cheap again,
only to watch that end with Blackhawk down in Mogadishu, leading to a rapid U.S. pullback. And then in Afghanistan, George W. Bush tried to break al-Qaeda and topple the Taliban with overwhelming military force, only for the U.S. to be drawn into a democracy-building enterprise that lasted for decades, overseeing that infamous rebuild effort.
Then in Iraq, Bush and Defense Secretary Donald Rumsfeld claimed that the U.S. could topple Saddam with a lean force, only for that war to require surge after infamous surge.
Chapter 3: How has historical U.S. intervention influenced the current situation in Iran?
In Libya, Barack Obama presented a coalition-led intervention as a brief operation. But after the killing of Gaddafi, that state fell into crisis. Over and over and over again, it seems, history doesn't repeat itself, but it rhymes. And in the case of U.S. intervention on the cheap, that rhyme scheme is not particularly subtle. Donald Trump is a unique historical figure.
But this blueprint is not unique. This is what we do. It is no defense of the Islamic Republic to point out that the U.S. keeps getting seduced by the prospect of cheap intervention, keeps bargain shopping for the cheapest way to topple our adversaries, only to find quite frequently that lasting change is hard or bloody or just not worth the effort.
You know that meme from Arrested Development where Tobias is telling his wife, Lindsay, it never works for people, but they keep deluding themselves to believe it might work for them. And, oh, it also might work for us. That kind of feels like he was talking about America's belief that cheap regime change is a button that we can just press. And then even after all of that, there's still my hope.
I still feel like this isn't the 1960s. Iran isn't being backstopped by a communist empire. Maybe this will work. This isn't the 1990s. Iran's leader has actually, in this case, been taken out, unlike Saddam Hussein. Maybe this can work.
Chapter 4: What miscalculations did Trump and Khamenei make in their strategies?
Iran isn't Somalia. It's a resource-blessed country that in another timeline might be one of the richer countries in the world. Maybe this can work. So that's my big question for today. Which way does the future go? Today's guest is Karim Sajjadpour, an American policy analyst at the Carnegie Endowment for International Peace.
Karim provides necessary context to understand why the US and Israel might have launched this attack. And we propose several ways this war might end, from complete regime change to moderate regime evolution, to a bloody and calamitous regional war,
And then finally, we consider the prospect that, as so often happens in history, a great amount of fire and fury fails to change the status quo, and that for all of this moment's chaos and carnage, the state of affairs at the end of 2026 might look, tragically, a lot like the state of affairs at the end of 2025. I'm Derek Thompson. This is Plain English.
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Chapter 5: What military actions were taken against Iran and what were their objectives?
Kareem Sajjadpour, welcome to the podcast. Thank you, Derek. Great to be with you. You have written that to understand why Trump attacked Iran, we have to understand the miscalculations of both Trump and Khamenei. Why did each man miscalculate?
So if we start with President Trump, I think that what he wanted to do in Iran was what he managed to do in Venezuela, which was he subjected Venezuela to significant economic pressure, significant military threats as a prelude to essentially a political decapitation. Maduro was captured from Venezuela, taken to New York City, and within a very quick period of time,
The Trump administration managed to do a deal with his successor, Delcy Rodriguez. I think that was what he had been hoping for in Iran. And so we saw over the last six weeks this remarkable military escalation in the region. And Steve Witkoff, Trump's special envoy, even alluded to the fact that they were surprised that Iran hadn't yet capitulated.
And so that essentially, in my view, was kind of the broad sense Trump's miscalculation. He thought that with enough economic and military pressure, he could have a Venezuela-style outcome in Iran. And I think he actually, when you listen to his public statements, he's still somehow hoping for that outcome. In the case of Ayatollah Khamenei,
He's really had one big idea over the last four decades, and that's resistance against the United States. And he's actually continuously miscalculated vis-a-vis Trump. I think that they had oftentimes not taken Trump seriously, thinking he was merely bluffing. There's a few good examples of this. The most notable one perhaps is in 2020, January of 2020,
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Chapter 6: How might Iran retaliate and what could trigger regional conflict?
when Iran did a number of provocative acts against the United States and US allies in the Middle East, and Khamenei was publicly taunting Trump, And a few days after that public taunting, Trump chose to assassinate Iran's top military commander, Qasem Soleimani. Last summer was Operation Midnight Hammer.
Iran thought it was in the midst of negotiations with the United States, and the United States wasn't possibly going to attack. They thought Trump wanted to do—he's a dealmaker. He wanted to do a deal. That was another miscalculation. And so this time around, Ayatollah Khamenei paid for that miscalculation with his life. Turning to the strike itself, can you walk us through what the U.S.
actually did here? What was targeted? What was at least the stated military objective? And what distinguishes this from previous U.S. military actions in the Middle East? So we're still early days. I don't think it's even been 72 hours. And the administration hasn't been terribly forthcoming on the specifics of the operation. And I should note, Derek, that it's not only a U.S. operation.
It's a joint U.S.-Israeli military option.
Chapter 7: What are the four pathways that could emerge from the current conflict?
It seems that the division of labor is that the United States is focused on military targets, degrading Iran's missile capacities, perhaps some of the nuclear facilities, perhaps the command and control of the Revolutionary Guards. It seems the Israelis are the ones that are more focused on the targeted targets. political assassinations.
And so I think it's still unclear to us whether it was American missiles or Israeli missiles that actually killed Iran's supreme leader. There's been some reporting that it was U.S. intelligence which led to his killing. So when President Trump has been making public statements about his endgame, he says contradictory things.
First, he's repeated the fact that he aspires for the Venezuela model in Iran, He said that he knows who the new leaders of Iran are, and he's prepared to do a deal with them. He's also said that he's willing to keep these hostilities for another five weeks, and his goal is to essentially implode the regime.
This style in which it's almost like a regime changed by jazz improvisation is really unsettling if you're the Iranian regime. Obviously, this is an existential moment for the regime.
remainder of iran's leadership a lot of its top leadership has been wiped out and in part it's it's a period of tremendous it's the fog of war you know do they do they believe that they can save themselves by escalating or do they believe that they can save themselves by de-escalating and trying to compromise and and you know we can talk about the arguments for both
I love your observation that this is regime change by jazz because it helps me to frame something that's confused me in the last 48 hours. What I'm used to seeing is America engage in war after the president makes clear to the American people what we're doing and why.
And instead of that, what you have is the president seeming to call various reporters at The Atlantic, Axios, The New York Times, and giving them entirely different interpretations of why we're fighting this war and what we should expect. He will, for example, tell The Atlantic that we're ready to talk and the Iranians are ready to hop on the phone.
And then he'll tell The New York Times or Axios, no, we're willing to extend this war for days or even weeks,
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Chapter 8: What leadership changes could occur in Iran following the conflict?
which suggests that there's no counterparty that's ready to pick up the phone on the other end. This seems to me like a very strange, unusual way of operating a military engagement with another country. How unique is this as an American strategy? Well, Derek, I think of Donald Trump as the Jackson Pollock of grand strategy. To his supporters, it's the art of the deal.
And there's all a method to the madness. And to many or perhaps most others, it's someone violently throwing paint on canvas and seeing what happens. I think that the statements, on one hand, you could argue that someone who makes these types of contradictory statements, you keep adversaries on their toes, and obviously you also keep allies on your toes with this kind of conduct.
And I'm always reminded of something that one of Trump's first-term senior cabinet officials said. He said when Richard Nixon was president, Henry Kissinger, who was then Secretary of State, went around the world and tried to convince foreign adversaries that Nixon was a madman. And he said when he was in Trump's first term, he didn't need to convince anyone.
All they needed to do was watch CNN, and they could kind of figure out that this president is very erratic. And so I don't think that there is... I mean, I'm hard-pressed to... to understand what is the point of offering so many contradictory statements to so many journalists, because in this current context, if you've chosen to take this path of war
you want to signal a resolve to the adversary that we're prepared to fulfill our objectives and see this through. The challenge also here, Derek, is that it's not totally clear what those objectives are. He's moved the goalposts on several different occasions. And so in some context, you could argue this is useful to keep an adversary on their toes, but
In this situation where we're literally talking about war and peace, the other side is not quite clear for them, as I was alluding to earlier. Are they better off compromising, believing that if they de-escalate, there is a way out in which they can save themselves? Because ultimately, the paramount goal of the Iranian regime is to stay in power.
Or if they feel that any type of compromise will project weakness and further embolden their adversary, then they will continue to escalate. And so I think this is a risky strategy. And I think the word strategy conveys a little too much. Let me... No, hold on that. That's exactly where I want to go next. So I do think it's important to say that there's two layers of uncertainty here.
One layer of uncertainty is what exactly is the game plan? The other layer of uncertainty is who exactly are we negotiating with? I mean, the U.S. government didn't just assassinate Khomeini, it assassinated many of the top leaders of Iran. And so who's even at the top of that PEZ dispenser seems to me to be a big open question. But going to strategy specifically, Trump...
Trump and Vance ran explicitly on a no wars, no regime ticket of peace message. They called themselves the peace ticket. They said Iraq and Afghanistan discredited American interventionism. This is a point that has been made a hundred million times on the internet in order to accuse the administration of hypocrisy.
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