Trump Just Hung Scott Jennings Out to Dry

Summary

Podcast Summary: The Bulwark

Episode: Trump Just Hung Scott Jennings Out to Dry
Release Date: June 22, 2026
Hosts: Tim Miller (“A”) & JVL (“B”); special clips from Ben Shapiro (“C”)
Main Theme:
A post-mortem on conservative hawks’ shifting narratives about Trump’s Iran war, the collapse of early triumphalism, and the rapid rationalization of a disappointing outcome. Tim Miller and JVL revisit what major right-wing voices—specifically Scott Jennings, Hugh Hewitt, Ben Shapiro—said both as the Iran war began and after the unsatisfying memorandum of understanding (MoU) that ended it.

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Episode Overview

This episode delivers a scathing (and darkly funny) look at the reaction of prominent conservative personalities to Trump’s Iran war. The hosts revisit bold, optimistic takes that were quickly reversed once the scope and outcome of the conflict disappointed initial cheerleaders. Through a collage of past commentary and hindsight, the episode reveals how quickly many in the "Iran hawk" camp rationalized dramatic flip-flops in their assessments and loyalty.

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Key Discussion Points & Insights

1. Recap: Pro-War Euphoria vs. Reality

• Setup: The episode kicks off by setting the table for a “tour” through the archives — showcasing how right-wing media and pundits like Ben Shapiro and Scott Jennings were initially euphoric, even triumphalist, about the war in Iran.
• Purpose: The hosts juxtapose the war’s rocky, disappointing outcome with the chest-thumping optimism from those early days.
• JVL’s Friday newsletter: Immediate reaction to the emerging MoU was “coping”—either outright denial or threats of some vague, future accountability for Trump if he “surrendered.”
  • “There was a lot of coping... ‘Donald Trump would not do that. Don’t worry. That thing isn’t going to happen.’” (B, 01:18)
  • Those who promised to “stand on principle” mostly folded almost instantly: “It took literally 48 hours. And they almost all... have come up with rationalizations for why actually everything is great.” (B, 01:45)

2. The Memorandum of Understanding: Instant Rationalizations

• Hugh Hewitt’s take: “Trump is just buying time so that after the Republicans hold the Senate in the House... we will have rearmed and then we can really go to war against Iran.”
  • JVL jokes: “A punt for field position is what he called it.” (B, 02:57; A, 02:57)
  • Tim is deeply skeptical: “Well, I’m sure that’s going to happen.” (A, 02:59)
• Hosts note the absurdity of believing in a “bigger, better war next time” after a failed first round.

3. Rewind: The Ben Shapiro Montage

• Early Bravado: Ben Shapiro clip on day three of the war:

  "It’s the most courageous military decision of my lifetime and we are kicking ass. The United States military, the Israeli military working in tandem, kicking the hell out of the Iranian government..." (C, 04:35)

• Tim and JVL skewer Shapiro’s hyperbole:
  • “America. Fuck. Yeah.” (A, 05:10)
  • “There’s a dramatic pause before he said smartly about Trump. You almost... There’s like a little internal tick...” (A, 05:10)
  • They contrast Shapiro’s “most courageous ever” claim with real presidential courage (e.g., Reagan, George W. Bush’s AIDS campaign, bin Laden raid).
• Later Contradictions: Shapiro confidently predicts the worst outcome is extremely unlikely:

  “The only truly terrible outcome here would be a strengthened Ayatollah regiment, which seems at this point to be literally the most unlikely actual outcome.” (C, 06:31)

  • Tim: “The least likely and most truly terrible outcome is exactly what we got.” (A, 06:58)
  • JVL: “This is a defensible position for about 72 hours into the war. After that, it is not defensible at all.” (B, 07:06)

4. The Reality Sets In

• The Ayatollah regime not only survived, it was strengthened, and sanctions were lifted.

  “The outcome we got is... the Iranians traded from an aging leader... to like, they’ve got clearly a leadership team now... They are allowed to sell oil on the global market without sanctions for the first time in bazillion years.” (B, 09:04)

  • Tim: “Americans can buy [Iranian oil] now.” (A, 09:33)
  • “You fill up your Ford F150 Raptor with good old Ayatollah oil... and it’s Pride Month.” (B&A, 09:34-09:44)

5. Humorous Jabs and End Zone Dances

• The hosts point out the wild expectations about the war’s impact, with Tim referencing “football spiking” and “end zone dancing” (A, 02:57).
• Fantastical alternate histories are mocked, such as the idea the Shah’s descendants would ride back into Iran, or that the Kurds would “sweep down from the north.” (A&B, 08:37-08:51)

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Notable Quotes & Memorable Moments

• On speed of partisan reversal:

  “They’ll get onside so fast your head will spin... It took, literally, 48 hours.” (B, 01:45)

• Ben Shapiro’s bravado:

  “It’s the most courageous military decision of my lifetime and we are kicking ass.” (C, 04:35)
  “The only truly terrible outcome here would be a strengthened Ayatollah regiment, which seems at this point to be literally the most unlikely actual outcome.” (C, 06:31)

• Hosts’ sarcasm on exposed hypocrisy:

  “The least likely and most truly terrible outcome is exactly what we got.” (A, 06:58)
  “A punt for field position is what he called it. That’s exactly... I’m sure that’s going to happen.” (B&A, 02:57-02:59)

• Dark punchline to the episode:

  “You fill up your Ford F150 Raptor with good old Ayatollah oil... and it’s Pride Month.” (B, 09:34-09:44)

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Timestamps for Key Segments

• [01:12] - How the conservative hawks started coping as the MoU emerged
• [02:57] - Hugh Hewitt’s “punt for field position” rationalization
• [04:35] - Ben Shapiro’s real-time “courageous” celebration
• [06:31] - Shapiro predicts worst-case scenario is “most unlikely”
• [07:06-08:00] - Hosts break down how obviously wrong that became
• [09:04-09:44] - U.S. gets lifted sanctions, buys Iranian oil—hosts’ acerbic coda

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Takeaways

• The Bulwark hosts dissect not only how easily the conservative “Iran hawk” crowd shifted its stance, but also how post-hoc rationalizations replaced the prior jingoism, often within just days of Trump’s de facto surrender to a strengthened Iranian regime.
• The episode’s tone alternates between exasperated, biting, and darkly funny as Tim and JVL relish exposing the hollowness of MAGA-era “principles” when placed against the reality of failed foreign policy adventures.
• For those who missed the episode: This is both a chronicle and a critique of how quickly media narratives collapse when exposed to reality—illustrated with expert curation and memorable, acerbic commentary.

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Transcript

[A]

Hey, everybody, it's Tim Moore from the Bulwark here with my buddy jvl. When we did our dramatic reading of JD Vance's awful book Communion, we told you, we promised you that we're gonna have a little dessert, a little treat for you over the weekend. Didn't make it around to it for the weekend, but we're still cashing in on this. We're cashing in on our promise. We do follow through a little late, so you get it today. And jbl, what I want to do for people is just take a quick little tour through what the Iran haw world was saying about the Iran war back in March. Just go meet some of our favorite. Yeah, meet some of our friends, you know, whether it be Scott Jennings or Ben Shapiro or many other friends who are just huge cheerleaders for the Iran war. Let's just take a revisit to see what they were saying back then. I thought that'd be fun for everybody. Before we do that, though, your newsletter on Friday was about what that crowd is saying now. Hugh Hewitt, conservative hawk radio host, and some others. So why don't you just, just to kind of prepare us for, for what they were, you know, saying was happening in the war in March. Why don't you want to give us a sense for, for how they're feeling now?

[B]

So what's, what's interesting is that as the details of the memorandum of understanding were beginning to slowly emerge, there was a lot of coping. And so that coping came in two, two ways. First was, this can't possibly be true. This is, don't, this is not. Donald Trump would not do that. Don't worry. That thing isn't going to happen. And the other form came in, some of these folks trying to butch up and warn the Trump administration that if, if they were to do the surrendering of the scale that the, the memorandum of understanding suggested they, they were planning on doing, that they would have a very sternly worded letter to send to them. They might even ask for the manager. And, and what I said to people was, I said, look, you have to understand that all of these people will get onside. They'll get onside so fast your head will spin. And it turned out, I had said in my newsletter on Friday, I said, you know, it might take two weeks, it might take two months. It might take, it took 48 hours. It took literally 48 hours. And they almost all, not all of them, there have been some, some notable exceptions who have stood on principle, but almost all of them have Come up with rationalizations for why actually everything is great. And the, the, these rationalizations go from, hey, the deal is good, to actually, don't worry, this isn't a deal at all. This is just my favorite. This is Hugh Hewitt. Trump is just buying time so that after the Republicans hold the Senate in the House in the midterm elections, we will have rearmed and then we can really go to war against Iran.

[A]

I love that it was a punt for field position is what he called it. That's. That's exactly. Well, I'm sure that's going to happen. That seems really sure with how this one went. And I do think if we really went to war next time it would go a lot better. I think it's important to now go back to watch these march videos to appreciate though, like the degree of, like to extend the football metaphor, end zone dancing and football spiking that was happening like in the first few days of the war. Like the idea that this MoU and punting for time and, you know, weakening their navy was going to be acceptable, like, is belied by their, the view at the beginning, which was total domination, total domination. Who does Freedom for the Iranian people was at hand. Okay, so we're going to go through some of our faves. We're going to start here, shout out to our guy, Brendan Dansley and Jasmine, who are going through all of this. So we're going to go in order, selected by them. I think probably we put Ben Shapiro first because on last week's tnl, we were talking about how we want. I was talking about how I wanted a mug of his tears. And you're like, it might just be a shot glass for Ben Shapiro because it's hard, hard to film.

[B]

That was your joke, not mine, but that's okay.

[A]

I think you said the shotgun. Was it me? Was I just complimenting myself?

[B]

I just want to give you credit, that's all.

[A]

That'd be pretty bad if I was complimenting myself. Okay, whatever. I do make funny jokes sometimes. Let's watch Ben Shapiro in the early days of the war talking about how courageous the President was.

[C]

Well, we are in day three of President Trump's military operation in Iran. It's the most courageous military decision of my lifetime and we are kicking ass. The United States military, the Israeli military working in tandem, kicking the hell out of the Iranian government. President of the United States, spot on again. What he is doing right now is the most courageous thing I have ever seen a president do. He is stepping into the breach. He is Smartly recognizing opportunity when it arises. And he is taking strong steps to protect America's future. And not only the future of our allies, but the future of the globe.

[A]

America. Fuck. Yeah. We got the planes going in. I'd like to venture there's a dramatic pause before he said smartly about Trump. You almost. There's like a little internal tech that he had. I'm about to call Donald Trump smart right now. Well, there you go, kicking the hell out of the Iranian government.

[B]

The most courageous thing ever.

[A]

The U.S. president, okay?

[B]

I mean, Reagan said, tear down this wall. George W. Bush went and did this thing where he staked billions of dollars on a global campaign to eliminate aids, knowing that a bunch of conservatives were gonna make fun of him for it. I don't know. I can think of other courageous things that American presidents have done.

[A]

Went and stood on the road.

[B]

George Ribio's going to stay on the right. Yeah, you know, whatever. Look, teach his own.

[A]

Sending people to kill Osama bin Laden, who is being held by our new friends, the Pakistanis, who are the ones JD Vance says are doing such a good job.

[B]

Subjective judgment, Tim, Reasonable permission.

[A]

Do we think Donald Trump is still acting courageously right now as he cowers?

[C]

No.

[A]

Okay. After he showed courage, Ben Shapiro made a pretty bold claim about how things are going to look following the war in Iran. Let's take a look at that.

[C]

But the worst thing here is not chaos. It's not. The worst thing here is a re. Enshrinement of the ayatollahs. It is also the most unlikely thing here. The only truly terrible outcome here would be a strengthened Ayatollah regiment, which seems at this point to be literally the most unlikely actual outcome. So what is likely to happen next in Iran? Well, the least likely outcome is the one that we actually fear the most. The ayatollahs lasting and rebuilding and somehow becoming stronger than they were.

[A]

The least likely and most truly terrible outcome is exactly what we got.

[B]

I gotta say, this is a defensible position for about 72 hours into the war. After that, it is not defensible at all. Because by about 72 hours in, it became clear that, like, oh, actually, the regime is held.

[A]

Right.

[B]

You know, they've. They clearly were. The mosaic strategy that they've been planning for 35 years actually worked. They have command and control. They retain the ability to strike targets overseas. And that's when also became clear that the American government seems to have paid no attention to the reinsurance industry and Lloyd's of London and had no plan to help guarantee insurance for shipping in the Strait. And so, I mean, I don't want to, like, pat myself on the back here, Tim.

[A]

Okay.

[B]

But it does seem to me that the state of affairs we are in became the most likely outcome really fast. Maybe not by the end of the first week, but by the end of week two, it was pretty clear that actually this is where we were heading.

[A]

Yeah. I appreciate your generosity of spirit, but I don't even think in day three, the current outcome was the most unlikely actual outcome, which is what he said

[B]

if we had to actually diagram this out. And the most unlikely probably would have been the Shah coming back.

[A]

There were people talking about Razak, the descendants of the Shah returning from the West. Or how about another thing that Ben Shapiro was pushing back then on most unlikely outcomes? That we could arm the Kurds and that.

[B]

Oh, and the Kurds would sweep down from the north. Yeah. Also seems pretty unlikely from the very beginning.

[C]

Yeah.

[A]

I just love, though, that the only truly terrible outcome is the outcome we got. And.

[B]

But also, like, I mean, that is laying down a marker, right? I mean, the. That that is the outcome. The outcome we got is we, the Iranians traded from an aging leader who they had a succession drama about to like, they've got clearly a leadership team now. They, as of right now, as we sit down to tape, they are allowed to sell oil on the global market without sanctions for the first time in bazillion years. And we can buy them.

[A]

Americans can buy them now.

[B]

We can now get Iranian oil in our cars. And you fill up your Ford F150 Raptor with good old Ayatollah oil

[A]

and it's Pride Month. It's the game.