Bill Kristol: What a Bunch of Jackasses

Summary

The Bulwark Podcast: Bill Kristol – "What a Bunch of Jackasses"

Date: May 11, 2026
Host: Tim Miller
Guest: Bill Kristol

---

Episode Overview

This episode of The Bulwark Podcast, hosted by Tim Miller with guest Bill Kristol, explores the deteriorating geopolitical situation in the aftermath of the recent conflict with Iran. Prompted by Robert Kagan’s new article in The Atlantic, the conversation dissects the strategic defeat for the United States, the historical norms upended by the Trump administration, and the broader implications for America’s role in upholding the global order. The hosts discuss the repercussions for U.S. alliances, the principle of freedom of navigation, and what this might signal for the future international landscape. The episode is packed with insightful analysis, sharp critiques, and some banter about favorite comedians saved for the end.

---

Key Discussion Points & Insights

1. Kagan’s “Checkmate in Iran” and the Scope of U.S. Defeat

• Summary of Kagan’s Point:
  Bob Kagan’s Atlantic article contends that the United States cannot reverse or control the consequences of its strategic loss in Iran, and likens the defeat unfavorably even to Vietnam.
• Bill Kristol Reaction:
  • Kristol emphasizes that recent events vindicate Kagan’s long-held views, particularly the irreversible fact that Iran has successfully closed the Strait of Hormuz—a line no adversary had crossed for 40 years.

    “The one thing they've never done in the last 40 years... was closing the strait. Really kind of striking.” – Bill Kristol (02:55)

  • He notes the shift: rather than consolidate their gains and deescalate, Iran appears emboldened, refusing to “let Trump slither away.”
  • The closure of the strait sets a precedent:

    “That principle, they didn't want to challenge... of freedom of passage in international waters. And now they've established the principle they can do this. That's a huge defeat.” – Kristol (03:54)

2. Consequences for U.S. Alliances and the International Order

• Loss of Confidence Among Allies:
  • The Gulf states, initially hawkish, are now seeking an end to conflict—signaling they might have to arrange new deals with Iran or even China as the U.S. seems unreliable.
  • Direct quote highlighting the urgency:

    “Could you end this, please? This is just getting worse and worse and worse. I mean, so they are going to make their own deals with Iran and also their own deals with countries like China, which seem like maybe more reliable allies than us.” – Kristol (04:14)

• General Principles at Risk:
  • Miller draws parallels with other Trump-era norm breakings—presidential transitions, Supreme Court rulings—arguing that upending the norm of freedom of navigation is a seismic shift for the global system.

    “There are these, like, kind of general principles that just were things that existed since I was born... and the US... we've had, like, these freedom of the seas for commercial ships to travel globally. And, like, that is now in question.” – Tim Miller (05:15)

3. America First: From Principle to Policy

• Shifting Strategic Doctrine:
  • Kristol cites America First’s logical extension: the U.S. looks out only for its own interests, leaving international goods like open sea lanes to others.

    “It's America first and taken to its... logical conclusion, I guess. Yeah. Which is who needs all this upholding the international order... holding open straits that are thousands of miles away from us... Let others do it.” – Kristol (07:15)

• Risks and Historical Lessons:
  • Kristol warns that such isolationism led to the world wars. Letting the global system fragment could harm both global commerce and U.S. interests:

    “That's a recipe ultimately for... That's what kind of got us into two world wars. It's not a recipe. Eventually it'll come back to bite us.” – Kristol (08:10)

• Ripple Effects on Security and Trade:
  • As U.S. reliability is questioned, other nations will act unilaterally, potentially leading to arms races and regional conflicts—signaling the end of the post-WWII order.

    “Nations can't depend on us. They look to their own weapons, they make their own. They suddenly decide they have to arm themselves. You just get regional conflicts all over the place.” – Kristol (08:40)

---

Notable Quotes & Memorable Moments

• On the Irreversible Precedent Set by Iran:

  “The one thing they've never done in the last 40 years... was closing the strait. Really kind of striking.” – Bill Kristol (02:55)

• On Trump’s Indifference & U.S. Retreat:

  “If Iran decides to put a toll on the Strait, like, that's a problem for Asia, but not a problem for us... that's a major shift in kind of how the world has worked and one that decreases our power.” – Tim Miller (06:18)

• On the Global Consequences of U.S. Withdrawal:

  “It's America first... Let others do it. We've got our ports... But that is just a recipe ultimately for... That's what kind of got us into two world wars.” – Bill Kristol (07:15; 08:10)

• On the end of the postwar order:

  “The end of the post World War II order... this war in Iran really... been the exclamation point on that.” – Bill Kristol (09:16)

---

Timestamps for Key Segments

• 00:51 – 04:45: Discussion of Kagan’s article, Iran’s new power, and what this means for U.S. credibility
• 04:46 – 07:12: Shifts among U.S. allies, upending of postwar norms, and Trump’s ambivalence toward global responsibilities
• 07:13 – 09:20: America First doctrine in action, parallels to pre-World War eras, and warning about future instability

---

Tone and Language

• Analytical and direct, with sharp historical perspective and frequent references to concrete policy shifts
• Some sardonic humor (e.g., references to classic comedians and banter about aging), but always in service of serious points
• Clear frustration—particularly with the Trump approach—a recurring motif

---

Conclusion

This episode offers a sobering account of the unraveling global order and the dangers of U.S. retreat from its traditional role as a guarantor of international norms. Kristol and Miller use both historical analogy and current policy critique to underline the stakes, closing with the grim suggestion that recent events mark an unmistakable turning point in world affairs.

Transcript

[A]

Foreign.

[B]

Welcome to the Bulwark Podcast. I'm your host, Tim Miller. It is Monday, so we're here with editor at large Bill Kristol. And you know, last week was pretty heavy. It's pretty heavy. A lot of serious topics, a lot of serious guests. We appreciated all of them. And so I have saved a section at the end of the podcast for some laughs. I feel like we need some laughter and deserve some laughter, Bill. And so, you know, we'll kind of see. Where are you a stand? Do you have a favorite stand up comedian? Is there a, is there an old timer that you're into?

[A]

Yeah, no, that's a good question. I'll think about it and get back to you at the end of the show. You know, okay, I can tell some of my favorite, my favorite Henny Youngman jokes. That'll go over well. That'll, that'll, that'll date me. That'll date me back to 19, you know, 46 or something.

[B]

That's exactly what I was hoping for in the answer. So you work on that. We need to start, though, with serious matters abroad and domestically. And I want to really begin with our friend and colleague. Well, not really colleague, but your former colleague, my aspiring colleague, Bob Kagan, who is in the Atlantic yesterday with an article titled Checkmate in Iran. Washington can't reverse or control the consequences of losing this war. And it's really well argued and just basically a full accounting of how rough the situation is strategically and geopolitically right now for Trump. And he goes into a lot of themes that he went into a month ago when he was on this podcast because not a lot has changed since then. But I do think he kind of even broadens it out further as far as, like, why this is such a geo's political strategic defeat, even more so than Vietnam, etc. Because of like, what some of the implications are for us losing control of the Strait of Hormuz. So I was wondering what your, your thoughts were on his assessment.

[A]

Yeah, no, I think it's a very strong piece and he's been arguing this for a while, as you say, but I think he's being vindicated by events. I mean, Trump understandably does not want to escalate. He doesn't want to get in an even bigger war. And I think the conventionalism has been, well, it's not great for Trump, but he kind of, and I've had this view somewhat and he can slide out of it without too much damage to himself or I suppose to the U.S. iran's capabilities have been degraded. We've paid a price, the world economy's paid a price. But we could recover. I mean, Bob's. I still think it'd be pretty serious defeat. Bob is more struck by the severity of that defeat, also struck by the fact that Iran and he's been right about this for the last week or so, we've been talking about it on the phone a lot. Iran's not so eager to let Trump slither away. Right. I mean, that's really striking. Iran feels they have the upper hand. I kind of thought maybe they just a little warrior being pummeled again. And they just ended in a good situation. Pocket their winnings ended in a pretty good situation for them. But so far they haven't seemed to want to do that. And Trump has bellowed and threatened, but not done much. So we'll see what happens. Meanwhile, the strait is closed and the economy, the global economy pays more of a price. But I think what Bob's big contribution is seeing that what a defeat it is for us to allow Iran to have allowed Iran to establish the principle that they can close the strait. And that's established going forward. Whatever fake kind of agreement there is, Iran says, well, we'll open it. They're pretty much making clear that it's at their sufferance. 40 years. Trump likes to talk about 47 years. This nation's been plaguing the world. It has been plaguing the world and us and others for a lot for 47 years and is a very bad regime. The one thing they've never done in the last 40 years been intimidated from doing was closing the strait. Really kind of striking. Isn't all these wars going out in the region, including with Iran, and we hit Iran in 2020 and then again in June, Israel, the US hit Iran. They didn't close the STR Strait. That principle, they didn't want to challenge the principle that we upheld with many others of freedom of passage and international waters. And now they've established the principle they can do this. That's a huge defeat. And then the damage that's been done to our alliances in Europe and elsewhere, confidence in us by the Asians who depend much more on the strait for oil and for energy. I'd say the Gulf states now signaling who were hawkish near the beginning, they thought Trump might go in and take care of Iran, which not a nation, not a regime they like, get along with very well and are scared. By now, they seem to be telling Trump, could you end this, please? This is just getting Worse and worse and worse. I mean, so they are going to make their own deals with Iran and also their own deals with countries like China, which seem like maybe more reliable allies than us. So I think Bob has seen the big picture of the damage to the US Standing in the world.

[B]

And I think that those are the two things that struck me, just like the Arab states maybe feeling like they need to take deals with Iran now, which is just dramatic change from just a couple months ago, just for economic purposes. And, and then just this general principle. It's, you know, it's kind of a piece of a lot of the. From the Trump era. There are these, like, kind of general principles that just were things that existed since I was born. Like, you didn't really have to think about, right. The president leaves when an election is over. You know, that president follows a Supreme Court ruling. Right. You know, that we are going to, you know, maybe have disagreements, but, like, generally, you know, work in concert with our allies and the democratic nations of Europe and. Right. Like. Like, there are just all these general principles that Trump has upended. And this one of, like, freedom of navigation on the seas is something that just has been the norm in the post World War II era. And, and the US through, you know, sometimes through military power, but also just like, projection of strength and, you know, fear of. From other countries, of wanting to incur the WRATH of the U.S. you know, we've had, like, these freedom of the seas for commercial ships to travel globally. And, like, that is now in question. And if you listen to Trump in his interviews, he doesn't seem to really prioritize or care about returning to that. And you hear him say a lot like, well, we've got a lot of ports. We got ports in Alaska and Texas, and people are getting our oil from us now. I don't know. In some ways, Bibi was on 60 Minutes talking about how he talked to Trump, about how Trump wants to send in troops to go get the nuclear stuff. Who knows if that's true or not? That's what Bibi says. And so you have that kind of pushing for more aggressive action. But on the other hand, you have Trump, like, not seeming to really care that much that the Strait of, again, maybe it's bluster, but, like, and if he decides that, it doesn't really matter because we have our own ports and our own oil exports. And, you know, if Iran decides to put a toll on the Strait, like, that's a problem for Asia, but not a problem for us. Like, that's what he Decides that's a major shift and kind of how the world has worked and one that. That decreases our power.

[A]

Yeah, I mean it's America first and taken to its reasonable conclusion and not reasonable, but logical conclusion, I guess. Yeah. Which is who needs all this upholding the international order and providing a public good of free transit of the seas, holding open straits that are thousands of miles away from us and so forth. Let others do it. We've got our ports, maybe we'll take care of our immediate vicinity. And that's actually in their strategy document. Western hemisphere comes first. I mean the price we will pay for letting the whole rest of the world outside the Western Hemisphere, maybe somewhat in the Western Hemisphere too, but certainly outside the Western Hemisphere kind of just topple into or descend into, you know, man eats dog, everyone. Or dog eats man, whatever, which is that man eats dog. I can't remember anywhere. Everyone for himself. You know, countries just making their own arrangements. It could become. It could be sort of stable for a while. These countries will watch out for themselves and they'll act in their self interest. But that is just a recipe ultimately for. That's what kind of got us into two world wars. It's not a recipe. Eventually it'll come back to bite us. I mean it did in 1914, it did in 1939. And it's certainly going to do huge damage to all. As you say, a lot of things we've just taken for granted, this global trade and commerce. Everything that we just sort of assume happens that it gets interrupted by the pandemic. And that was terrible. But then it got back on course again and you know, we quibble about, argue about should try to be permitted to have these particular chips and all that. That's a national security question. Fine. But in general, the principle that we can all these goods will flow and I mean that that that ends. Nations can't depend on us. They look to their own weapons, they make their own. They suddenly decide they have to arm themselves. You just get regional conflicts all over the place. Regional accommodations to all over the place to various dictators. It's really. It is. No, it is the end. I mean it's what a lot of people have been writing about, we've been talking about. And it's been sort of on clearly beginning to happen for the last year and a half. The end of the post World War II order. But this war in Iran really has, I don't think, been the exclamation point on that.

[B]

On the end accelerant was sort of news but yeah, same thing. Yeah, same trajectory. So just to that point, and the latest on talks is the same as it's been, but should.