BREAKING: Trump’s Ceasefire May Already Be Dead

Summary

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Bulwark Takes – “BREAKING: Trump’s Ceasefire May Already Be Dead”

Podcast: Bulwark Takes
Episode Theme: The apparent collapse of Donald Trump’s much-vaunted ceasefire agreement with Iran, escalating hostilities in the Strait of Hormuz and the broader Middle East, and a sharp take on Trump’s presentation of the situation.
Date: June 27, 2026
Host: Tim Miller

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Episode Overview

This episode, hosted solo by Tim Miller, provides a rapid-fire update and pointed analysis on the unraveling of the Trump administration’s ceasefire deal with Iran in the wake of renewed hostilities. Miller deconstructs both the sequence of events and the embarrassing disconnect between Trump’s public triumphalism and the escalatory reality on the ground. The episode also cuts into the administration’s apparent ineptitudes, especially as showcased in a bizarre, self-promoting Trump “commemorative passport” post—which Miller lampoons—to close out.

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Key Discussion Points & Insights

1. The Ceasefire Unravels (01:00–07:52)

• Renewed Conflict:
  • Iranian drones attacked four ships in the Strait of Hormuz, reigniting open hostilities [02:28].
  • Conflicting narratives between Iranian and American state media, and Trump’s own social postings.
• Escalation Cycle:
  • The U.S. responds with strikes on targets around the Strait of Hormuz.
  • Iran retaliates, hitting U.S. targets in Bahrain and another oil ship, intensifying the “escalation ladder.”
• Diplomatic Breakdown:
  • Commentary on the quality and tone of the Trump administration’s communications—Miller lampoons their “passive aggressive snark” for being out of place in high-stakes diplomatic negotiations:

    “This like kind of smarmy, like millennial sarcasm. I just don’t know if that, if that hits in Iran... This is why we have professional diplomats handling this kind of stuff.” (04:10, Tim Miller)

  • Critique of the administration for treating international crisis management like a Twitter feud, with special digs at JD Vance.
• Strategic Weakness:
  • Miller predicts the U.S. will be the one to "eat it"—begrudgingly accepting the latest Iranian attacks in order to avoid further escalation, painting it as a humiliating comedown for a supposed superpower [07:40].

2. Revisiting Trump’s Premature Victory Lap (08:51–10:32)

• Trump's Boastful Declaration:
  • Just two weeks prior, Trump claimed:

    “The deal with the Islamic Republic of Iran is now complete. Congratulations to all. I hereby authorize the toll free opening of the Strait of Hormuz and simultaneously herewith authorize the immediate removal of the United States naval blockade. Ships of the world, start your engines. Let the oil flow.” (09:03, quoting Trump’s social media)

  • Miller mocks the pageantry and delusional aspect of Trump’s messaging:

    “I guess that was Oprah voice, not Donald Trump voice.” (09:26)

• Reality Check:
  • The strait never actually “reopened” to pre-war levels. Insurance and safety concerns linger, and ships were recently attacked, demonstrating the hollowness of the White House’s claim.
  • The episode highlights how Trump’s administration is out of touch with on-the-ground developments.

3. Regional Ripple Effects: Lebanon and Israel (10:32–11:15)

• Expanding Theaters of Violence:
  • Israel strikes southern Lebanon over perceived threats to troops.
  • Miller keeps the focus on how Lebanon is pivotal in Iran’s regional calculus—the MoU’s first point mentions Lebanon three times:

    “Iran was very clear that Lebanon is part of this deal for them. And that kind of theater, of this decrease fire, also activated today.” (10:59)

4. Trump’s Passport Farce: Symbolism and Cluelessness (11:15–15:07)

• Lampooning Presidential Self-Obsession:
  • Trump reveals a “commemorative passport” featuring his own photo, accompanied by the message “Welcome, but be good.”
  • Miller eviscerates both the narcissistic symbolism and its fundamental misunderstanding of what a passport is for:

    “Does Donald Trump know what a passport is for? Does the President of the United States understand who gets the passports and what they are used for?” (11:42)

  • Critique that the passport “welcome” message—intended for Americans—is nonsensical; typically, signage would be for foreigners at customs, not citizens with passports.
  • Sarcastic summation:

    “You don’t even know what the fuck’s going on. You don’t know what you’re doing. You don’t know anything. It’s pretty concerning that the President of the United States... either is so stupid that he doesn’t know what a passport is, or... his mentals are declining at such a rate that he’s forgotten.” (13:21)

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Notable Quotes & Memorable Moments

• On Trump’s “limp reply” to escalation:

  “Donald Trump, ender of civilizations, that’s the critique he offers: ‘Foolish’... He said meaner things about Mika Brzezinski.” (03:22)

• On the administration’s posturing:

  “If you have disagreements, you can pick up the phone... I don’t think that’s how they’re doing business over there.” (04:19)

• Escalation logic:

  “This is what you call the escalation ladder. This is how you get back into war. Someone has to eat it... I think that’s going to be us.” (06:31)

• On the commemorative passport:

  “You would think that a very wealthy man who rose to the office of President of the United States would understand what a passport is and how one uses it and who gets it.” (12:10) “Welcome, but be good. Be good. Unless you’re a star and they let you do it. But the passport... gets given to us. We don’t need to be welcome. We’re here. We’re Americans. We’re already in the house.” (13:00–13:20)

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Key Timestamps

• Iranian drone attack recap: 01:00–03:30
• US military response and escalation analysis: 03:30–07:52
• Trump’s previous “victory” post and reality check: 08:51–10:32
• Lebanon/Israel flare-up and its importance: 10:32–11:15
• Trump’s commemorative passport: mockery and significance: 11:15–15:07

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Takeaway

Tim Miller delivers an acerbic, detail-packed recap of how Trump’s self-declared Iran ceasefire is unraveling, highlighting both the policy ineptitude and the farcical pageantry with which the administration approaches foreign affairs. The episode is sharp, irreverent, and underscored by a theme of exasperation: “Is this our world?... I guess this is real life. We’re here.”

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Transcript

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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. 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 change, 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 we're 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 we're still kind of wading through the rationales coming from state media out of Iran and American state media and Trump's social media feed. 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 you know, other, 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 transvers. 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 counter attacks, 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, 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. And, 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 T 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. 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.

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I want to give you guys a quick flashback was 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. The deal with the Islamic Republic of Iran is now complete. Congratulations to all. I hereby authorize the toll free opening of the Strait of Hormuz and simultaneously herewith authorize the immediate removal of the United States naval blockade. Ships of the world, start your engines. Let the oil flow. I guess that was Oprah voice, not Donald Trump voice. But. Looking back on that now, a little under two weeks later, it doesn't seem like Donald Trump was the person who could authorize the 12 free opening of the strait. Ships of the world and their insurance and reinsurance companies maybe need to continue to be concerned because a couple of them got snaked in the last 24 hours. And that is not a kind of let the oil flow situation. We've had a situation for a little while now where the number of ships going through the strait is not, it's not really anywhere near the pre war numbers. So there is some movement to the strait, but below not completely open like Donald Trump promised. And as of today, as of Saturday, a couple of ships have gotten hit by Iran and we'll see what the United States does next. Just before I get to the little dessert, I should also mention that Israel also struck southern Lebanon this morning

[A]

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[B]

that there was threat to their troops that are in southern Lebanon, not in Israel that they had to deal with. And so that kind of element of this MOU and this negotiation, remember the word Lebanon is in the first point of the MoU three times. So Iran was very clear that Lebanon is part of this deal for them. And that kind of theater, of this decrease fire also activated today. So we're going to keep an eye on all of that. The dessert. Donald Trump posted this picture of the new commemorative passport with a photo of himself. We're a third world country now. The leader puts his photo on everything. You can't go anywhere without seeing the eyes of the leader watching you, saying, don't do anything wrong, grimacing at you. We have a tin pot dictator who can't even keep the reflecting pool clean running the country. Anywho, he updated the passport with this message. He says that this is the message that the passport sends to people. Welcome, but be good. Welcome, but be good. Now this raises the question, does Donald Trump know what a passport is for? Does the President of the United States understand who gets the passports and what they are used for? Welcome to who? The US Passport is for Americans. We use it to go other places. Okay, I know Donald Trump wasn't a big world traveler before he became the president. Know that he, you know, he did go to Russia the one time. We don't know if there was picture in the hotel, but he did go to, you know, want to hang out with some fancy models. Besides that, he just mostly liked to stay on his own golf courses. And so he's not exactly a worldly person. He's not a lot of person that has experienced other cultures as we know that. You would think that a very wealthy man who rose to the office of President of the United States would understand what, what a passport is and how one uses it and who gets it. Welcome, but be good. And this would be like a childish kindergarten level sign to put up on customs for people coming into the country, foreign people landing at our airports, coming in. Donald Trump wants to put his hideous ass, fucking burnt orange bronzer ass face up on the pillars at security at customs so he can glower at foreigners before they come here. That would be a pretty good representation of the Trump administration, I think, and the MAGA movement. And he could put up a sign that you would again put up for like 6 year olds. Welcome, but be good. Be good, be good. Unless you're a star and they let you do it. But the passport, the passport gets given to us. Okay? We don't need to be welcome. We're here. We're Americans. We're already in the house. So, like, you don't, you don't even know what the fuck's going on. You don't know what you're doing. You don't know anything. It's pretty concerning that the President of the United States either is so stupid that he doesn't know what a passport is, or that his mentals are declining at such a rate that he's forgotten. But that's where we're at. A glowering president reminding Americans, welcome in your own house, in your own country, but be good. I've been indicted several times. I don't know. It's. It's. Is this our world? How is this? Is this. This is it. I guess this is real life. We're here. There's your news update for Saturday morning. We will be back as more things develop over the course of the weekend. I'll be back on Monday with the Borg podcast, of course. Subscribe to the feed where else are you getting material like this? Subscribe to the feed Please tell your friends. We'll see you all soon. Peace.

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