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We've planned for the plot twists, so
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support is always available. The Because a great trip starts with peace of mind. 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 Straight of Hormuz will be opened. Now, there's some questions about how true that is, but the. 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.
A
Yeah, I mean, look, I guess it's. 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 details of what's happening to the extent that we know. But just looking at this from a political perspective, 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
B
right now counts are loving it. They think he's brought peace to. But other than that.
A
Right. Right. Yeah. I mean the Trump fanboys who just will say anything. Trump could but like the core group which of people that wanted this, you know, the more hawkish wing of his administration and his movement, you know, The Lindsey Grahams, the Mark Levins, the fdd, Mark Dubovitz and that crowd. And they're all trashing this right now on social media.
B
Oh, they're livid. They are livid. Hair on fire. Livid.
A
Right.
B
I think it's important to explain why. Why? So, 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 he held it up against the Obama nuclear deal, it looks comparable or worse.
A
Yeah, I mean, significantly worse. And this is the thing. The original sin of this war was that there was no rationale or strategic purpose for it originally. It was not clear what it was at first. It's worth saying that he demanded unconditional surrender. That was the first. 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 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.
B
None of that. None of that.
A
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 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 objectives. Right. Which was, we're going to limit Iran's power, ability to project power in the region. We're going to get rid of all the worsens that, yeah, we're going to get rid of all the nuclear material.
B
Not happening.
A
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 of 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, 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 this was not going to happen. But anyway.
B
But the alternative is what? Him wiping out civilization and taking out the power.
A
I'm saying, can I not make fun of them? Can I not make fun of them for being stupid?
B
But we, 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.
B
Basically.
C
Yeah, Yeah, I don't know. 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.
B
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 referenced this. 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 straight 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 Wicker 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? Right.
C
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
B
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 going to 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 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?
B
So what we know about that now is Trump says it's gon. The Fars News Agency is 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.
A
Yeah, a couple of thoughts on that. Just first on the straight and then I'm going back to old lady Lindsay and I think obviously there will be some easing of pressure on energy prices. Just like this 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 because it's not like you can just as Andrew was saying, snap your fingers and have the strait 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? There are a lot of, I think, questions. So I think you'll probably see an initial dip both in energy prices and in 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. 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 notion, 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? There are a lot of 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. 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 US And Western interests using these asymmetric, you know, types of attacks that, that I, I, well, you hate to handle. Like, I think that second point is, is right.
B
Yeah, well, let's pick on that because it looks like to me, some of the reasons we have a deal today is not because maybe, well, Trump obviously was yearning for this. We'd been a while, it's been a while now that we know he's wanted an off ramp and just has been unable to find it. But it looks like a lot of the Middle Eastern countries were the ones who are like, please, like, figure this out, get this over with. And also there were some reports that the Iranians were preparing to do strikes on other global energy targets in the region. So they were probably worried about this too. So regionally, this is kind of interesting because you have the Middle Eastern countries who don't want this to continue, and then you have one prominent Middle Eastern country that really desperately wants it to continue, and that's Israel. And from everything we've seen right now, Bibi is like, not happy with this. Now, that might just be posturing. I don't know, maybe he gets to play bad cop and Trump gets to play good cop. But it does feel like Bibi. And there's some reporting that Andrew Flagan slack that he's convening an urgent meeting on a, quote, very bad interim Iran deal being weighed by Trump. But, you know, I find this part to be the most interesting of the, of the sort of geopolitical relations here is, is whether Trump just basically screwed over Bibby and said enough.
C
The biggest problem for Israel here, again, it has to do with the Strait. It is this. It's the fact that Iran is coming out of this conflict with this giant economic weapon to wield against anybody it wants to wield against in the region in perpetuity. I mean, like, the whole, the whole sort of foreign policy focus of Israel and of America as Israel's ally for the past number of years has been, you know, getting Israel to these normalized relations with all these other countries where all these other countries in the region are more comfortable going with Israel than going with Iran. And they're, they're all comfortable kind of like isolating Iran and like, and that's a big shift from, from, you know, the, the way that Israel used to be very, very isolated in that region. The problem now is that there is very suddenly a gigantic economic disincentive for all of these companies, or, I'm sorry, for all these countries to be seen as very close to Israel. Because if you're like a really, really close ally of Israel in the region, Iran is going to be able to keep you out of the Strait of Hormuz and just not let you use that, not any of your ships use that very important waterway. So it's a gigantic shakeup as far as Israel is concerned of just like regional geopolitics. And it is not at all surprising that Netanyahu is fuming over this.
A
Yeah, I mean, I think it's worth spending a second on just the hubris of Bibi and MBS and NBC in the UA in uae, who I think all thought like, hey, this is our moment. We've got wildcat Trump on our side. We can finally get rid of the Ayatollah. You know, we can, you know, gain power in the region, protect, you know, do things that, that make us feel safer. And it's just like, you know, I mean, it's just like all of the business Trump partners Trump had over the years, you know, I bet the guys that went in with him on the casino in Atlantic City thought they were, you know, it's just like it's well, yeah. Why, how do these people keep thinking that, like you're going to sign up with Trump and like you're going to come out of, come out the other side looking like roses. And so yeah, I think that obviously all the reports are true that the Qatar and UAE and Saudi have been trying to stop this because of the pain that they had caused was far greater than any benefit that they had from, you know, moving from one harmony to another. And Israel's situation is a little different because they have like continuing ongoing security concerns. Right. Like if this war is over, you know, Saudi is not going to get bombed by anybody. Almost certainly Israel's got to worry about Hezbollah. Israel's got to worry about who knows, like what else other, other potential forces in the region. So they have more acute security concerns. And I just, it just feels like they, you know, decided that the right way to deal with their security concerns was just maximum offense, you know, all gas, no brakes at every possible opportunity. And like you just see it backfiring against them in multiple places right now, like both strategically with Iran but in their popularity throughout the world. And this is, it feels a little bit like obviously there's the real human like element of it but just like talking about it geopolitically, just a backfire,
B
all time backfire, all time backfire. They burned every bridge possible with Democrats. This is the Netanyahu administration I'm talking about, about burned every rich possible. He, he came to Congress to deliver a speech before the joint sessions about how bad the Iran nuclear deal or the Obama nuclear deal was. Okay, just keep that in back of mind. Then spend a couple years just absolutely torching, siding up with Trump and torching Biden more or less. Even though Biden, even though Biden was next to him in Gaza, then he did this and then he's going to get screwed over by Trump in the end and they'll end up in a place that's very much the same as the Obama nuclear deal. It's an all time fuck up and it's just remarkable that, well, whatever.
A
And just one more thing on this. And so they're going to supposedly Lebanon's part of this deal but the notion that that's going to hold feels crazy to me. So who knows what Israel will do. A temporary ceasefire and then on top of that we should just mention and you mentioned on the list, but I think it's worth just sitting for a second on the pallets of cash. The report is 6 billion in unfriendly funds.
B
Where'd you get that?
A
That's the report 6.
B
Bill, isn't that more than JCPOA?
A
Yeah, I'm looking at one of the. Don't you. I love it. I follow now these anonymous OSINT accounts.
B
Yeah.
A
This is where, you know, you feel like. I feel like. I feel like I'm a marker. Like, stand up because I'm following those.
B
The JCPO, just so you know, JCPO had a 1.7 billion dollar settlement around the implementation. And that was a 4. It was a.
A
This is Al Jazeera. They're getting it from Al Jazeera. Who know? I don't know. Who knows.
B
Again, the JCPO also unlocked about 50 billion in restricted foreign exchange reserves. That's different from the settlement. So again, devil's in details here, but it's the same structure. It is what? It's the same thing. And I think the big thing, though is that Trump made all these promises about ram, will never get a nuclear weapon, and we're going to get rid of the enriched uranium, the strait will be reopened, and it appears none of that is going to be. And end up being true. I want to have a couple more minutes here. But real quick, do you guys think,
C
do you guys think that Trump will have enough shame to stop making the, like, pallets full of cash to Iran? Like a baseline part? Like, he does that, that, like, shtick all the time when he's speaking about how awful it was that Barack Obama loaded up all this money and he cleared. He cleaned out every bank in the.
B
Yeah, every bank in Virginia, Maryland.
C
But, like, I mean, this is worse. Like if, if maybe he quietly lets that one die to not open up the, the obvious rejoinder. Or maybe he just, maybe he just like, doesn't care at all and just keeps, keeps, keeps talking about it. But it is, it's amazing.
B
No, he's got no shame. He'll definitely use again. I just want to read the Steve Chung tweet if we can, because this gives you sense. It's 4pm this is Trump's top comms guy. It's 4pm on a Saturday, and Trump has been working hard at the White House since early this morning. Man is focused and determined. I'm sorry, you don't get, you don't get points for working on a Saturday when you're the President to 4:00pm Here
A
we are, we're streaming on a Saturday.
B
Fucking.
C
We do get points for it, though.
A
Yeah. Yeah. Look, I just, I don't think that he will have shame. I get it's so important to him psychologically that this deal will be better than the Obama deal, that I actually think it'll be the opposite. He's going to just go over the top and trying to claim how much better the deal is. The question is, where do you get the COVID from it? You know, and I do think that this is where you see the. We can overstate it sometimes, but, like, there's somewhat fractioning of maga. You know, there are some people within the coalition. Like, everybody wasn't really that excited about the one big beautiful bill, frankly. Like, there were a lot of. There were a lot of factional concerns about it within the MAGA faction. There were a lot of concerns about it. But at the end of the day, it was like it was a tax cut. Nobody's going to burn their cred by going out there and criticizing it. So Trump had an echo chamber about why it was big and beautiful. I don't think that's going to happen this time because the Iran hawks have legitimate differences with this policy and the Tucker, Megyn Kelly, the critics of this war are going to feel vindicated by how bad this deal is. So they're going to want to do a victory lap on that. And so I think he's going to have significantly less air cover from the propaganda wing of MAGA than he usually does on this one, but he'll try.
B
I might disagree with you on that one. They're always, they always find a way to get back in line. I already see Benny Johnson celebrating how great this is.
A
Oh, well, Benny. Oh, well, there you go making fun
B
of Lindsey Graham for holding his little wand at. At Disneyland, saying you should never follow this guy's advice.
A
I feel like somehow that little Disney wand bottom has more YouTube subscribers to us than us. If you're watching this right now and are not subscrib feed, please subscribe. This is. This is unbearable. It's.
B
I agree with that. I'll just. Can. I want to end on this one. I'm going to read. I don't know why I'm doing this because I'm petty and I do this, but I'm going to read a comment from the comments from Hawk nest vision at 6:01pm this one's been really grading me for a couple minutes. I can't believe you 3 believe this BS you got online for this question mark. Pathetic. Crying emoji. Crying emoji. Crying emoji. You know what? Hawk Nest Vision, you responded to us getting online. Okay? So you're more pathetic than we are. Okay, stop It.
A
Sam is feisty. Sam's doing the Nick Fuentes yelling at the fans right now, yelling at the fucking.
B
Get out of here.
A
The question about believe, right, is, is I think I'm going to take this feedback at face value. What does that mean? Right? Like, this question is like, is this all kayfabe? Is it fake? It's not a real deal, right? Like, bb, as you mentioned, Bibi and Trump playing good cop, bad cop. Like, yeah, I mean, I don't, I don't think any. I don't think that there's anybody.
B
None of us are taking it at face value.
C
None of us think straight up Hormuz is actually reopening.
A
I don't think it is reopening. And I don't know that this means that this war is over either, by the way. And I think that there's gonna be a lot of incentives for Bibi to do things that might restart it. And I think that the deal in the end is gonna look worse than it does on Donald Trump's bleat. And so he's going to have pressure to get back in. And so, you know, I think that this, that what we know now is that it's a pretty humiliating walk down from Donald Trump's original demand that we have unconditional surrender. And it's a. It's humiliating and it's utter strategic failure. So that's where we're at right now.
B
All right, I gotta go. I got some dinner I gotta deal with. I know Tim's in a hotel. And Andrew, so much for coming out of your secret bunker in Tehran to do this and give us on the ground reporting. I appreciate that. Very kind of you. Hey, folks, if you like what you saw, subscribe to the feed. Tim's right. We need to catch up with Benny. To surpass Benny, destroy Benny. Hit that subscribe button. Take care. See you guys.
D
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Episode: BREAKING: Trump Nears Iran Deal—Pleasing No One
Date: May 23, 2026
Host(s): The Bulwark Team (Tim, Sam, Andrew Egger)
Theme: Analysis and reaction to breaking news that the Trump administration is close to finalizing a new deal with Iran—a deal that seems to satisfy almost no one, including hawks, allies, and even some supporters.
This episode features immediate analysis of breaking news: Donald Trump is on the verge of brokering a new, temporary deal with Iran—likely more an extension of a ceasefire than a grand peace agreement. The Bulwark team breaks down the geopolitics, domestic political ramifications, and why virtually every interested party is unsatisfied with the outcome. The conversation covers comparison to the Obama administration’s Iran deal, hawkish backlash, regional reactions, implications for Israel, and the strategic blunders in the Trump team’s approach.
“They’re currently in discussion, really just kind of down to the wordage… Trump did say… the Strait of Hormuz will be opened. Now, there’s some questions about how true that is...”
— Host B ([00:24])
“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.”
— Tim ([01:29])
“The original sin of this war was that there was no rationale or strategic purpose for it originally… He demanded unconditional surrender...We're extremely far from that.”
— Tim ([03:48])
“If you held it up against the Obama nuclear deal, it looks comparable or worse.”
— Host B ([03:48])
“The problem now is that there is very suddenly a gigantic economic disincentive for all of these...countries to be seen as very close to Israel. Because… Iran is going to be able to keep you out of the Strait of Hormuz…”
— Andrew Egger ([14:19])
“It's a pretty humiliating walk down from Donald Trump's original demand that we have unconditional surrender. And it's a... humiliating and it's utter strategic failure.”
— Tim ([23:16])
“Oh, they’re livid. They are livid. Hair on fire. Livid.”
— Sam ([02:39])
“All time backfire. All time backfire. They burned every bridge possible with Democrats… then he’s going to get screwed over by Trump in the end...”
— Sam ([17:29])
“It’s just like all of the business Trump partners… How do these people keep thinking that… you’re going to come out the other side looking like roses?”
— Tim ([15:34])
| Time | Topic | |------------|------------------------------------------------------| | 00:24 | Introduction to breaking Iran deal and ambiguity | | 01:29 | Political disaster & Trump coalition schism | | 02:39 | Hawkish backlash | | 03:48 | Comparison to Obama deal; original war goals | | 05:51 | Strategic failures, shifting war objectives | | 07:28 | Lindsey Graham tweet; military reality vs. claims | | 08:54 | Strait of Hormuz ambiguity; Iranian position | | 10:26 | Effect on energy markets & insurance concerns | | 14:19 | Israel’s new strategic problems | | 17:29 | Israel’s “all time backfire” and US alliance shift | | 18:31 | $6 billion sanction relief figure discussion | | 19:33 | Trump’s likely shamelessness about deal flaws | | 21:48 | MAGA propaganda split over the Iran deal | | 22:45 | Funny listener comment; hosts discuss deal’s reality | | 23:16 | Strategic humiliation conclusion |
The near-finalized Trump Iran deal is lambasted as a comprehensive failure: it achieves no stated US goals, emboldens Iran, alienates key US allies (especially Israel), angers hawks, and is politically toxic at home. The only clear “win” is averting further kinetic escalation. The episode concludes with the Bulwark hosts expressing deep skepticism that this deal will hold, seeing it as a humiliating strategic retreat for Trump. Meanwhile, regional power dynamics have shifted—with Iran newly empowered and allies like Israel left out in the cold.
“What we know now is that it's a pretty humiliating walk down from Donald Trump's original demand that we have unconditional surrender. And it's a... humiliating and it's utter strategic failure.”
— Tim ([23:16])
For anyone seeking a sharp, candid breakdown of today’s seismic foreign policy shift—full of expert insight, lively banter, and unapologetic verdicts—this is the definitive quick-take.