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Bill Kristol
Seems to be a piece with many other lame pseudo jokes that went over horribly.
John Heilman
I think that even his biggest fans, they watched it honestly would be sort of like he seems to have lost not just his fastball, but his curveball, his slider and his knuckleball. Hey, everyone. Welcome to the Bulwark Podcast. I'm John Heilman. I have the great extraordinary honor, really, it's like the thrill of a lifetime in a lot of ways to be able to sit and in the chair normally occupied. I mean, not literally the chair, metaphorical chair build, normally occupied by Tim Miller, who's off, you know, gallivanting around Europe having all kinds of fun and leaving this, leaving us basically here. We're like home alone here. It's a little bit like we're the Culkin. We're the Culkin brothers here. I'll be Macaulay, you can be Kieran, and we'll have fun here on the show today. Dolby, by the way, Tim will be back next week. So for all of you who are like, kind of sick of the replacements, the fill ins, the subs, the red shirt team here, he's back next week, so everyone can get excited about that. But Bill, I was delighted when I there when I was asked by Tim to fill in for him. I was like, I want to do a Monday because Mondays are Bill Crystal Day. And so here we are. Good to see you.
Bill Kristol
It's nice of you to say. I wanted to do Monday when I heard you were pinch hitting for Tim. It's a big upgrade. You know, I'm going to tell Tim that also next week. Next week, you know, we'll see if our, we'll see if Tim's loyal fans out there before I get now 72,000, you know, text messages, emails and posts on social media. How could you be so disrespectful of Tim? He goes away for one week and here you guys are jumping on him. No, it's great to have you, John. And you can fill Tim's shoes.
John Heilman
They're big shoes, but I'll do my best. And, and I gotta say, it was an eventful weekend. I also like the notion that it's a Monday. Podcast is basically kind of do a little bit of looking backward because we never, we don't have quiet weekends anymore in our politics. Bill, used to be back in the day when you and I were, were younger men, we used to spend weekends in D.C. padding around the title basement, taking a bike ride now and then, you know, switching off. But every Weekend now is another cavalcade of horrors. Before we jump into all this stuff is what's, what's like as the at the end of this weekend and we head in this week, what's like the very kind of like, here's your the biggest thing you were fixated on over the weekend, what was like really most front and center in your mind.
Bill Kristol
I mean, one of the bad things about Trump era is when instead of being fixated on whatever your favorite baseball team is not doing too well, or thinking back still to Spain's fine victory in the World cup, you do get fixated on the things that have to do with Trump. So I guess the military stuff, I guess we'll talk about this, but I mean, the degree to which one knows that Hagseth is a very bad secretary of Defense, I'm now worried that he's doing much more damage to our military than I previously had thought. Which, you know, that's one of the institutions you think holds up best under adverse circumstances. And it has many, many times. And I had talked with a couple of people who've served in the military, just sort of randomly ran it, saw them or talked to over the weekend. And I they did not disabuse me of my fears. Right.
John Heilman
You know, so we headed into the weekend after, I would say all of last week, the question of there's war plans now in front of Trump. He's backed into a corner and nothing he's doing is working. And might he under those circumstances just decide to finally go forward and do the things been threatening to do basically for the last like five months, essentially, which is like rain hellfire down on, on Iran and escalate the war in a really dramatic way. And the news of the weekend was he was presented with those plans. There was a thoroughgoing debate and he decided no, he was not going to do that, although the reasons for it, to the extent the reporting is, suggest that the reasons are basically, we don't have enough bombs anymore. The munitions stockpile is so low that General Kaine was basically like, I don't think this is a great idea. Talk a little bit about that and how we've managed to find ourselves. You were just talking about Hegseth. There's a lot of things to criticize Pete Hegseth, but one of them, it would seem to me, is if it's the case that we've left ourselves in a situation now where we basically can't fight a major war, we used to need to want to fight two major wars in two different theaters at the same time. We can't even really fight one now, given the state of the munitions, according to a lot of this reporting.
Bill Kristol
Yeah, no, it really was striking and I was, I guess, a little rattled by that. I mean, one knew obviously that Donald Trump is not a great strategist or a strategist at all, that he's doing this based on a kind of hubris and a whim and it's very foolish and we were going to pay a price for it. But the degree to which it's not just him being a bad commander in chief, but drawing down our stockpiles, I think especially of the things we use to shoot down incoming stuff. And that's presumably why people were killed a week ago. Not presumably, that is how people were killed. Those are the casualties that Trump doesn't want to acknowledge. The Trump Defense Department doesn't believe a part of the war in Iran even. I mean, really unbelievable, right? That thing, actually, that thing was on my mind. I should have mentioned that. I guess I wrote about it last Friday morning. I was so furious when I read that Thursday night. Right. That they'd removed those four army soldiers killed in action from the, from the website. But, but that turns out to be, I mean, that's terrible. But then it turns out to be, I won't say the tip of the iceberg, but a kind of indication of something much bigger, which is the military is kind of complicit, I would say, in the COVID up of how bad things have gotten in terms of our, as you say, our munitions, especially anti drone, anti, anti missile, anti aircraft, maybe anti aircraft as well, munitions in the region. Then over the weekend, there were stories, weren't there, about the appointment of the new chief of naval operations for the Navy and how incredibly politicized that was. You put that together with all the firings we've seen, obviously. So we have hirings and firings, politicized stories about West Point and the lack of free speech anymore, of teaching at the military academy. There is sort of one thing after another that just made you think it's not just that Trump is a bad commander in chief. It's not just that Hegseth is really kind of repulsive. I'd say as secretary of defense, it's that they really are doing some real damage now to this one institution that has held up so well over the most over recent decades through thick and thin. And I had thought, I do think still is probably holding up better than most our institutions in the federal government against the Trump and Trumpist onslaught. But it turns out you can do a lot of damage. You know, when you've got a secretary of defense and people willing to go along with him, and he removes the people who might have stood up to him and he's got the backing of the White House. And he, I guess, wanted to show Trump that everything was going great. So he just, they just, I can't believe the military thought this was wise. They know how many interceptors they have, right. And they don't think it's a good idea to shoot the wall off in the first two or three weeks. But Hegseth must have been insisting on it, and sadly, people in command seem to have gone along with it. What do you think about that? I mean, you've covered this stuff for a long time. I mean.
John Heilman
Well, I, I think that the, to, to your, your broadest point, CQ Brown, who was the, the chairman of the Joint Chiefs when Trump came back for Trump 2.0, he was an African American gentleman. He. And the argument was it was the beginning of hegsa's kind of war on dei. Right? And Bill, I think that to your point about the way in which the damage has been done to the culture of the military, that was the first thing. Because the thing that you and I both know, and I'm not a Pentagon reporter, but I've been around for a long time and talked to a lot of people who have been in the military at the highest levels and all the way down, is that the military is the most meritocratic institution in America. It's a life and death thing, right? You don't get to be chairman of the Joint Chiefs on the basis of dei. They have no time for dei. And it's one of the wonders of the military is that it's been this meritocratic institution that has also proved to be, because of that, one of the great mechanisms of social mobility in America, where extraordinary figures from various parts of the American gorgeous mosaic have been able to rise up to the tops. Colin Powell, the most notable, the CQ Brown thing was like they're starting to wage war on a culture of DEI that doesn't even exist. And I think that you've seen that now play out over the course of the last 16 months, not just the DEI thing, but the ways in which all of these things have become politicized. And I don't think there's literally an American institution that one should have more reverence for than the military for those reasons. Not to say that everything that everything the Pentagon's ever done has been great. But that the institution itself, the damage that's been done, I think is I don't think we've yet counted the cost to it and I don't think we yet have our arms around it. And I do think it's one of those things that when we get to the other side of Donald Trump, that is going to need a significant amount of repair and serious repair. When we think about, like what damage has been done to American democracy by Donald Trump over the last 10 years, this is one of those institutions where whoever decides that they're going to be in charge of leading the democratic restoration America, the first place, one of the first places they're going to have to start is on the military and counting the actual cost and then doing that repair work. Sorry to go on at length about that, but I feel, I think it's like one of the things that most upsets me, even though I am not a veteran, but I've come over time to really appreciate the value of this institution, American life, and to see it degraded the way it's been degraded over the last 16 months is really upsetting.
Bill Kristol
No, absolutely. And I mean, I've been a critic of the military. I'm not a veteran and I don't presume to have great knowledge of military affairs. But I remember when I was a critic of Rumsfeld and Casey's original strategy In Iraq in 2003, 2004, I was following John McCain's lead, the late Lindsey Graham, actually, and people who knew a heck of a lot more about it than I did. And actual people who'd served and were serving and quietly were talking to us about the lack of a counterinsurgency strategy and so forth. And it wasn't going as well as Ron Swells Pentagon was saying. Even there they made mistakes, I think. But you know, there were the mistakes that get made in an institution, in a bureaucracy, by individuals, by systems and ultimately they got fixed a little too late. Unfortunately, in Iraq, the surge worked, but it was too late to really save the overall enterprise and probably shouldn't have done it if it was going to be mismanaged the way it was. But having said all that, it was still a very well functioning institution and people respected it and people respected people coming out of it as they should have. And the way I was speaking to someone over the weekend actually was talking about this was, you know, he said, well, you've been a critic of the military. Yeah, there are times when I thought their leadership was B or Even C or C plus as opposed to A or A minus. But that's just life, right? I mean, that's different from taking a wrecking ball to it. And that's really what we have now. We don't know how many people have left. How many people. I just talked to someone today, this morning, actually, weirdly, as a relative in the military. Not weirdly, but I'm just talking about this person up for promotion, not at the general officer level, but not too far below that. Uncertain what's going to happen, uncertain whether he or she should stay in just the degree to which people have left. People have requested assignments to get them out of Washington. I talked to someone for whom this was the case recently and again, it's probably not good for this person's career. It's less of a fast track, but couldn't stand really being in the Pentagon and the kinds of things that were happening and worried that at some point this person was worried that he or she would have to make a real decision that would be unethical or, you know, contrary to what they thought was right. There's a story in the Washington Post this morning. I think it's in the Post about these drug boat hits, which I think you and I have both been very unhappy about and very dubious legality and sort of seem like murder on the high seas.
Episode: Bill Kristol and John Heilemann: Taking a Wrecking Ball to the Military
Date: July 27, 2026
Host: John Heilemann (for Tim Miller)
Guest: Bill Kristol
In this episode, John Heilemann sits in for Tim Miller and is joined by Bill Kristol for a deep dive into the alarming developments within the U.S. military under the Trump administration. The conversation centers on the politicization and degradation of the military, depletion of munitions stockpiles, a culture war against DEI (Diversity, Equity, Inclusion), and the broader implications for American democracy and institutional resilience. Drawing from personal conversations with military insiders, reporting, and past experience, Kristol and Heilemann unpack their profound anxiety over an institution long viewed as the backbone of meritocracy and stability in American life.
Heilemann asserts that the military has been America’s most successful meritocracy and a true mechanism of social advancement.
Both worry that the politicization threatens not just operational readiness, but the core values that have sustained the military as a national institution.
Bill Kristol:
John Heilemann:
The episode’s through line is one of concern, frustration, and a call to vigilance about the state of the U.S. military under Trump and Secretary Hegseth. Both Kristol and Heilemann—often with a tone of personal alarm—detail how undermining readiness, morale, and meritocratic values in the military signals a broader threat to the spirit of American democracy. Instead of natural mistakes, the recent period is characterized as a deliberate assault—a "wrecking ball"—that, in their view, will require significant toil and institutional renewal once this era ends.