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A
All right, we're live Saturday, 5:40pm on the east Coast. Tim's out west, and we got breaking news. Unlike the last fits and starts, it does appear, Tim, that we are on the verge of an actual Iran deal. You can call it a extension of the ceasefire, a memorandum of understanding, but some sort of negotiated temporary settlement is close. Trump tweeted about it this afternoon. It's a lot of words. I don't need to read them all. Maybe we could put it up on the screen so folks can see it. But it was just a summarization. He talked to a lot of leaders in the Middle East. He made it clear that they're near the final aspects of a deal. They're currently in discussion, really just kind of down to the wordage he did say, and we'll get to this in a little bit, that the Strait of Hormuz will be opened. Now, there's some questions about how true that is.
B
But.
A
But I have my takeaways on this. But, Tim, I know you wanted to. You had a few thoughts here about sort of what's happening.
B
Yeah, I mean, look, I guess it is important to just say, certainly preferable, that Trump humiliates himself and surrenders and does a deal worse than the Obama deal as opposed to, you know, ending the Iranian civilization or unending escalation. So that's worth noting. I think that. And we can get into kind of the. The details of what's happening to the extent that we know. But just looking at this from a political perspective, just a total unmitigated disaster for him. If you created a Venn diagram of people who thought the war was a good idea and think that this deal is a good idea. It's like literally people on his payroll. It's Trump and Wyckoff and I guess I'm sure Scott Jennings and CNN just pays him to say whatever Trump wants right now.
A
Accounts are loving it. They think he's brought peace to earth. But other than that.
B
Right. Yeah. I'm the Trump fanboys who. Anything Trump could. But. But like the core group which of people that wanted this, you know, the more hawkish wing of. Of his administration and his movement. You know, the Lindsey Grahams, the Mark Levins, the fdd, Mark Dubowitz and that crowd. And they're all trashing this right now on social media.
A
Livid. They are livid. Hair on fire. Livid.
B
Right.
A
I think it's important to explain why. So what, again, everything is so tenuous. We don't really know what's real. But the Sort of outlines from all the contemporary. All the reporting that's happening are this. There will be a cessation of hostilities. There will be some form of sanctions relief over time for the Iranians. There might be some sort of check on their missiles, I guess, but there will be. According to the Wall Street Journal, the deal will not. The main goal will not prevent Iran from ever acquiring a nuclear weapon, which was Trump's main goal. It would prevent the restart of war in the Middle east that the Middle Eastern countries didn't want to have. It would alleviate a global economic crisis by spurred by the closure of the Strait of Hormuz. But it's not clear if the Strait of Hormuz will be open or if there will be a toll attached to ships going through the Strait. So those are the details that we know. And yeah, if you, if you held it up against the Obama nuclear deal, it looks comparable or worse.
B
Yeah, I mean, significantly worse. And, and this is the thing, like, part the. The original sin of this war was that there was no rationale or strategic purpose for it originally. Right. Like, it was not clear what it was. Right. Like, at first it's worth saying that he demanded unconditional surrender. That was the first. That was. That was what he was saying. The initial bombing, that was the standard Trump set, that we're going to not stop until Iran gave us unconditional surrender. We're extremely far from that around that same time. The other thing that he was talking about was it was important that the. You wanted overthrow of the regime and freedom for the Iranian people. Freedom for the Iranian people was part of the original pitch for this regime change. Was part of the original pitch for this.
A
None of that.
B
None of that. We're not even in the ballpark of all the opposite. Right. Like, the regime is stronger. Trump is the one that is offering close to, like, surrender. So not like he's achieved none of that original goals. Then after the war started, and it was clear immediately he was not going to achieve any of those goals. They pivoted to, like, a new set of. Of objectives. Right. Which was, we're going to limit Iran's power to, you know, ability to project power in the region. We're going to get rid of all.
A
Worse than that.
B
Yeah, we're to get rid of all the nuclear material.
A
Not happening.
B
It doesn't. Yeah, none of that is happening. So none of the goals that they set, which were changing and moving and kind of opaque, but any. The ones that they said over the course of the last three months, none of that has come to pass and Iran is in a stronger strategic position. And so it's not surprising that you have the people that were supporting the war because they believed in whichever one of those series of objectives were important, being the people who are unhappy today because he's not achieving any of the objectives that they thought that they were going to get. Now they were stupid to get into a deal with Trump. They should have known they weren't going to get any of those deals. But, you know, I, I, so I do, I do, I kind of want to spend the day just like dunking on Mark Dubowitz and, and my friends and commentary and all the, like John Potterettes. I do kind of want to spend the day dunking on all them because it was pretty obvious from, like, the first second of the war that this was not going to happen. But anyway.
A
But the alternative is what? Him wiping out civilization and taking out the power plants?
B
I'm saying, can I not make fun of them? Can I not make fun of them for being stupid?
A
But we, we have, we have a special guest. We smuggled him into Tehran under the dark of night, and he's there from an undisclosed location. Andrew Egger, what's it like on the streets?
C
Pandemonium. No, I, I am in, I'm in Alexandria, Virginia, about as far from Tehran as it's possible to be on this earth, basically. Yeah, yeah, I don't know. I, I, I, I came in late, I was eating dinner when I saw you guys were going live. So what do you want me to talk about? You can't just throw to me.
A
Well, well, we're, I guess our, our, we're, we're trying to sort of assess how, how to process this because, I mean, on the one hand, it's not continuous war for unstated purposes in like an escalation, as far as we can tell. And then the other hand, it's like a, you know, it achieves, like, none of the objectives that Trump wanted to set out. I guess I'll, I'll toss it to you because we could put up the Lindsey Graham tweet this morning because Tim kind of references. How about how bad some of the Trump supporters are freaking out. This is Lindsey Graham. It's relatively muted for Lindsey, but he writes, if it is perceived in the region that a deal with Iran allows the regime to survive and become more powerful over time, we'll have poured gasoline on the conflicts in Lebanon and Iraq. A deal that is perceived to allow Iran to survive and possess the ability to control the strait in the future will put Hezbollah in Lebanon and the Shia militias in Iraq on steroids. This is one of a couple tweets that he put up today. Roger Ricker was another one who's worried about this war. I mean, yeah, they're not like, I don't think he's particularly wrong, but what did you expect? What's the alternative?
C
Right, Yeah, I mean, these guys are, for the record, completely correct on the, on the factual merits of this. Like, it is just, it's true that having gone to war with Iran and like thrown everything we could at them and realized, well, we didn't throw everything
A
we could at them. We, we could have gone crazy. Like, we, we didn't.
C
We did about as much as we could do in terms of like aerial bombardment alone, right? With, without, without dipping into, like, just tipping over into completely unambiguous war criming behavior. We hit every military target we could hit without sort of supplementing with boots on the ground or doing the sort of like genocide adjacent power plant day thing that Trump had threatened before, right? So like enormous amount of aerial bombardment that leaves. But if the regime sort of is able to hold together, which they did, eventually they realize that, you know, the US realizes that Iran is not gonna be so easily dislodged and we leave them alone. And this does especially, like he says there, I mean, like, there's two tracks here. There's the military track, right. Of just sort of everybody needing to start respecting Iran as a regional hegemon. At this point, not a hegemon, but a real, real, real significant, strong regional player that cannot be bullied. And that's, you know, obviously got all of these foreign policy hawks in a tizzy for not bad reasons, for good reasons. But at the same time he only just kind of half gestures at the Strait of Hormuz situation there. And that's what I think we have. Unless I'm wrong, unless you guys have seen stuff that I haven't seen yet, that's the stuff we have the least detail about, right?
A
So what we know about that now is Trump says it's going to be open. The far as news agencies reporting, we could put that up. Iran Fars News denies Trump's claim that the share of Hormuz will be, will return to its pre war status, saying any possibility would leave Iran in control of passage routes, timing and permits, while only allowing traffic volume to return to previous levels. So Trump's, Trump's post is ambiguous on this.
C
And this is, and this is to be clear, basically Exactly. What we have seen repeatedly already in this conflict is you get this sort of ceasefire agreement, Donald Trump is like, good news, everybody. The strait is open for business, sail on through. And then it turns out over and over again that that's not the case. Not, not in any significant way. Neither of those things are going to be 100% accurate, to be clear. Like, it's obviously not true that, that, you know, we're just, we're just going back to the status quo ante. What, what Trump would like to be true, what everybody should like to be true, that people are allowed to just sail through the strait, that's not happening. But this business about allow Iran allowing traffic to return to pre war volumes, if it's true that they're going to be trying to implement this toll booth situation, that's not going to happen either. They don't have the capacity. Talk to a lot of people who basically say, like, you cannot have like the equivalent of the previous free traffic through that entire strait. If Iran is continuing to route all this traffic through, you know, past, past their shore, there's just not the bandwidth for traffic to like, continue to make this happen. So, so nobody knows. I think it's fair to say still right now what this is actually going to look like in practice, other than that it is a significant movement in favor of Iran from the previous status quo.
B
Yeah, a couple of thoughts on that. Just first on the straight and then I'll get back to old lady Lindsay and I think obviously there will be some easing of pressure on energy prices. Just like the sense that, okay, we're not going to have an indefinite shortage will cause some easing of prices, but the structural problems that were already going to happen months down the road, those are only going to continue to be exacerbated for a while. Right, because it's not like you can just as Andrew was saying, like snap your fingers and have the straight, go back to the pre war status quo ante. I mean, there's insurance companies. Are they worried about the mines in the straits? Is that going to cost more to ensure the ships? Are they going to let Israel flagged boats through? We should come back to Israel. You know what I mean? Like, there's, there are a lot of, I think, questions. So I think you'll probably see an initial dip both in energy prices and in, you know, kind of the bond yield and borrowing rates. But they still have major problems ahead on the economic side. I want to just put on my hawk hat for a second going back to the Lindsay TWEET. My former Hawke hat like the ins. You know, part of the argument in that second line always for like part of the critique that I think was fair about some of the ways that the Obama administration handled like the growing ISIS and other terrorist regimes in the region was like, and this, you can, you can equate this to the border, right? Like one of the criticisms of Biden on the border is that like you create an incentive structure where people feel, you know, people feel like they can continue to do bad things because there won't be consequences. Right. And, and I think that that notion, like now there's, now the question is how do you do that in a way that is strategically smart, Right. How do you do that in a way that is appropriate? There are a lot of then questions but that incentive question is real. And if you are one of the Iranian proxies right now, if you're one of these militias in Iraq, if you are China, there are a bunch of different people that they're like, oh wait, we can just go after non military targets, we can just go after energy targets. And these guys don't have the gumption to fight us over it. I think Iran has, there's been an emboldening, I think, of people that want to come after.
Episode Title: BREAKING: Trump Nears Iran Deal—Pleasing No One
Date: May 23, 2026
Hosts: The Bulwark team (Tim, Sarah, et al.)
Guest: Andrew Egger
This emergency episode dissects the breaking news of a “deal” being brokered by President Trump to end the current hostilities with Iran. The hosts analyze the preliminary details, how the deal measures up to past agreements, its likely fallout both politically and geopolitically, and the reactions from Trump’s supporters and opponents. The consensus: the deal is not what Trump promised, pleases almost no one, and leaves major questions unresolved, especially concerning the Strait of Hormuz.
[00:02-03:20]
Notable Quote:
“If you held it up against the Obama nuclear deal, it looks comparable or worse.” – Host A [02:11]
[01:01-04:31]
Notable Quote:
“If you created a Venn diagram of people who thought the war was a good idea and think that this deal is a good idea, it's literally people on [Trump’s] payroll.” – Tim [01:22]
Host context: The hosts openly share their schadenfreude at pro-war pundits being disappointed.
[05:23-08:25]
Notable Quote:
“A real, real, real significant, strong regional player that cannot be bullied. And that's, you know, obviously got all of these foreign policy hawks in a tizzy—for not bad reasons, for good reasons.” – Andrew Egger [07:32]
[08:25-09:58]
Notable Quote:
“What Trump would like to be true, what everybody should like to be true, that people are allowed to just sail through the strait, that's not happening.” – Andrew Egger [08:46]
[09:58- ]
Notable Quote:
“Now the question is how do you do that in a way that is strategically smart. How do you do that in a way that is appropriate? ...That incentive question is real.” – Tim [10:32]
This podcast episode provides a detailed, skeptical breakdown of the developing Iran deal under President Trump. The hosts and their guest agree that the deal fails to deliver on any of Trump’s original strategic promises and has left both pro-war hawks and isolationist doves dissatisfied. Iran appears to have come out of the conflict in a better position, having weathered military pressure and maintained key leverage (especially over the Strait of Hormuz). Meanwhile, political costs for Trump are high—his coalition is split, and there are legitimate concerns that adversaries worldwide will draw lessons from this episode about US resolve and credibility. The deal itself is seen as a hasty grab for “anything but war,” with long-term consequences still unclear.