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Hey everybody, it's Tim Miller from the Bulwark reporting once again from my parents basement. The Iran war seems to be back on. At least we're not in a ceasefire. We're back into the decrease fire. Given all the pageantry and all the ceremony and all the self congratulation visiting Versailles to sign a document. It seems another pretty big failure of the Trump administration and their foreign adventurism. At first they thought they were going to get a big win in Iran. They're going to have regime chains, they're going to bring in their own Delsey Rodriguez and after that their goals diminished a little bit. They're just going to get rid of their weapons and their navy and their air force and their nuclear dust. And then it's kind of like, well, they can keep most of the nuclear, but we'll get the Strait of Hormuz back open and we'll sign a victory document in France, a surrender document marking that and then we can just move on to other things. And you know, when you decide to get into a war, the enemy also has a choice, as they say. The enemy gets to make some decisions. And in this case, Iran decided that they wanted to continue to push their advantage. They didn't like exactly how things were shaking out in Lebanon or otherwise in the negotiations. So I'm going to run you through the TikTok of the Iran war being back on at the end of this. I have a little dessert for you. If we can't point and laugh at Donald Trump, what's the point of being on the Bulwark YouTube page? So going to do give you the Iran war update then. Then we'll get a little giggle at the end. It's, it's the weekend after all. It's the freaking weekend. Okay, so Iranian drones attacked four ships in the Strait of Hormuz that began the recent back and forth. I think that it's, you know, we're still kind of waiting through the rationales coming from state media out of Iran and American state media and Trump's social media feed. You know, some of this is way to the back and forth vis a vis Oman. Marco Rubio is over there having discussions with the Gulf states. I think Iran has a certain view upon how things are going to go in the Strait going forward. That is different from what the Americans want, which is, you know, well, you don't sign the deal until it's, you have the same view. But. Okay. And other factors at play here. But that is what starts this out. There are four drones that Targeted ships in the Strait. Here was the President's kind of limp reply to that. I would say the Islamic Republic of Iran shot at least four one way attack drones at ships traversing the Strait of Hormuz. He wrote transversing. Transversing. Not sure that's a word. One of the drones solidly hit the upper deck of a large and very expensive cargo carrying ship. Damage was done, but the ship was able to proceed on its way. We knocked down three other drones. Obviously this is a foolish violation of our ceasefire agreement. Is it foolish? And that's, I mean, Donald Trump, ender of civilizations, that's the critique he offers. Foolish. He said meaner things about Mika Brzezinski. Doesn't seem like he's really, you know, getting bucked up for a fight. Anyway. I chuckled. The US does strike back. We hit some targets around the Strait of Hormuz. This is late Friday, our time here in America. Vance then puts out a statement. Following those attacks, those counterattacks, Iran signed a ceasefire agreement. We have honored it. If they have disagreements about how the MoU is being applied, they can pick up the phone. But violence will be met with violence. This, like, kind of smarmy, like millennial sarcasm. I just don't know if that hits in Iran. Like if, if you have disagreements, you can pick up the phone. Like this passive aggressive snark. I just. Okay. I mean, I don't know, I don't think that that's like how they're doing business over there. This is why we have professional diplomats handling this kind of stuff. You know, like you can do the. I guess JD is trying to apply the condescending snark he uses when he talks about liberal women and apply it to the mullahs. Well, it doesn't seem to be working so far. Then he tries to butch up a little bit. Violence will be met with violence. Okay, whatever. Iranians didn't seem to be scared by that. They retaliated. NASA's giving the news this morning, waking up Saturday morning here in America. Iran hit U.S. targets in Bahrain. And also an oil tanker was hit traversing the Strait of Hormuz on the Oman path. Like on the map, Oman is to the south and Iran is to the north. And it seems like some of the ships now are going up kind of the Iranian path and some the south, the Oman path. My understanding, based on, you know, what I've seen from experts and other reporting, is that there's still kind of concerns about some mines there in the heart of the Strait. And so that's how ships are going through right now. Again, you know, I think unclear a little bit exactly whether it was something particular about the ships, you know, kind of going on the other side of the strait that caused Iran to target them. Iran state media saying that the IRGC has targeted several locations of the US army deployment in the Middle east, which is what they're doing since the war had been starting, you know, going after US Bases in other countries. So that's what the IRGC says they're doing now. And they also said that any further attacks by the US Will draw a broader response. So that's interesting. Now you have JD Saying violence will be met with violence and the Iranian state media saying that further attacks will be met with a broader response. This is what you call the escalation ladder. This is how you get back into war. Someone has to eat it. Someone has to swallow it and say, okay, we'll just let you guys be the last one to hit so that we don't continue to escalate. Do you want to guess who I think that's going to be? I think that's going to be us and that's going to be the Americans that decide that we can't, we don't want to be in this war anymore because Donald Trump doesn't want to be. So we're just going to have to eat it. When the IRGC attacks our military in Bahrain or elsewhere. Pretty, it's pretty weak position to be in for the world superpower, but that's where we're at. I want to give you guys a quick flashback. Was not, not just a little under two weeks ago now, the president of these United States, the leader of the free world, the commander in chief, the most powerful man in the world, wrote this.
Episode: BREAKING: Trump’s Ceasefire May Already Be Dead
Host: Tim Miller
Date: June 27, 2026
This episode of The Bulwark, hosted solo by Tim Miller, delivers an urgent update on the rapidly deteriorating ceasefire between the U.S. (under Trump) and Iran. Miller analyzes tangled foreign policy moves, critiques Trump administration responses, and provides insight into the risks of renewed conflict in the Persian Gulf, all delivered with trademark Bulwark sarcasm and bluntness. The episode ultimately explores how diplomatic failings, communication missteps, and escalating tit-for-tat attacks have pushed the ceasefire to the brink of collapse.
On Trump’s Leadership Style:
“Donald Trump, ender of civilizations, that’s the critique he offers. Foolish.” – Tim Miller (03:52)
On J.D. Vance’s Diplomacy:
“I just don’t know if that hits in Iran... Like this passive-aggressive snark. Okay. I mean, I don’t know, I don’t think that’s like how they’re doing business over there.” – Tim Miller (04:36)
On Escalation Dynamics:
“This is what you call the escalation ladder. This is how you get back into war. Someone has to eat it. Someone has to swallow it and say, okay, we’ll just let you guys be the last one to hit so that we don’t continue to escalate.” – Tim Miller (07:07)
On U.S. Maneuvering:
“Pretty weak position to be in for the world superpower, but that’s where we’re at.” – Tim Miller (07:27)
Miller delivers the episode with dry humor, directness, and critical analysis—frequently mocking the Trump administration’s language and the unseriousness of their responses while explaining the real-world consequences and risks of military brinkmanship.
Listeners receive a clear, pointed rundown of the rapidly failing ceasefire and the perils of amateurish foreign policy, punctuated by humor and skepticism toward the motives and competence of Trump-era officials. Miller promises a “dessert” segment at the end, but the summary above focuses on the substantive war and diplomatic analysis.
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