Bulwark Takes - Bill Kristol and JVL on Dick Cheney’s Legacy

Episode Date: November 4, 2025

JVL and Bill Kristol reflect on the life and legacy of Dick Cheney—a man who defined a certain strain of Republican politics for half a century, from Ford’s White House to the Trump resistance. They discuss how Cheney went from “Darth Vader” to one of the last serious conservatives, and what his death says about the end of the old GOP.

Hey, everyone. Dick Cheney has passed away, former vice president, a guy who unlikely, as it is, wound up being a major force in American politics for, I don't know, 20, 30 years, 40 years. I'm JVL from the Bulwark here with Bill Crystal to talk about Dick Cheney and his life and his legacy and all of that. And Bill, I guess it's interesting in a way that we're now in a world of dynastic politics with like the Bushes and the Clintons and the Trumps. And Cheney sort of comes from a very different place, right? You're very much a self-made guy. It comes out of Wyoming, a small state with no electoral importance, and winds up as a secretary of defense and the vice president and an important actor in American politics. Yeah, and actually, I mean, has this meteoric rise as a very young man,

comes to the White House in 1989. He went to Yale. I guess he drops out, if I'm not mistaken, if I'm not mistaken, finishes his degree elsewhere. Studies in political science in grad school for a year or two. I don't think he got his degree, but he knew a lot, actually, of surprising about political science, and certainly American history and obviously his wife, Lynn,

a general historian. But anyway, he comes to Washington, and I heard about him at the time really through my father's circles, I would say, and just through the newspaper. And he's a junior staff from the Nixon White House, ends up as Chief of Staff to Gerald Ford, what, five, six years later. That would have been in 1975. So that would have been when he was 34 years old.

So you actually understated in the way his, I mean, he is White House Chief of Staff at age 34 and ends up in his 80s being a major force as a Republican and conservative, genuinely conservative critic of Donald Trump. So that's 50 years, really, right, in the public eye. It's stunning. really, and really, as you say, due to his talents. There was no, he had no, you know, I mean, Rumsfeld was his boss in the White House, I guess was his patron early on, you could say.

But it was, but it was entirely due to a self-made man in a way, had a great American story. You know, he leaves the White House after Ford loses. And I remember that he goes back to Wyoming and people, I'm in grad school at the time, I guess, but it's a little bit in these circles. And I hear he's going to run for Congress. There was Dick Cheney. He's like a consummate inside operator.

Right. Serious, sober guy, not Mr. Charisma, not Mr. Popular demagogue at all. This is the late 70s. He was a Ford guy, and Reagan is in the ascendancy in the Republican Party, runs for Congress, Wyoming becomes obviously a very, and then very quickly becomes, I think, number three in the House leadership. I mean, I think literally within two terms or something of being elected to Congress. So I've been a time to fact check all these things since the death was just a couple hours ago,

who were announced just a couple of hours ago. But anyway, it is really a remarkable career. One shouldn't lose sight of that, just that side of things. In addition to everything else, he then did substantively in his different positions. Yeah, so it strikes me that if, no matter how old you are right now, Dick Cheney was a feature of American politics during a period of time, which was formative to you. And, you know, so if you came of age during the Bush president, George W. Bush's presidency, Dick Cheney is Darth Vader, and he is this evil figure who was responsible for all sorts of, you know, not actually responsible, but in the public imagination was this bad guy. If you came of age during the Trump years, he is this voice of conscience who was standing up to Trump. If you came of age, as you said during Nixon, he is like, oh, he was this, you know, guy who was an inside operator who was a wonderful.

That's super interesting to me. So many acts in American public life. He had, you know, like most people get one or two acts. He had like four. Yeah, I was thinking about this. I mean, there's this category of people who never became president, but who are extremely important in American history. And it goes all the way back to Henry Clay.

I think it's maybe the person about when this was originally said, most important man not to be president, you know, in his era. And John McCain and many others, they ran for, most of those ran for the presidency. Dick Cheney chose not to he could have. In 1996, he had been extremely impressive and successful Secretary of Defense under George H.W. Bush, and there was a bit of a draft Cheney movement. I was a tiny bit on the fringes of that. Well, he wore of a persuade Cheney movement.

He chose not to do it. And then, of course, Bush taps him in 2000 to run the vice presidential search. And he discovers that, yeah, well, actually, he might be the best. I think I found the guy. Bush just got me. That's the joke. I don't know how much of it was his thinking and how much of it was Bush is. own decision or whatnot.

But, yeah, so no, but anyway, yes, the 50-year span of being a major, major figure in American politics, but to say, without being president or even running for president, I don't know how many other people one could say that of, you know, and it is striking and, you know, very striking and a very, very impressive. I mean, as you sort of said at the very beginning, just to reiterate this point, this was not because people had to be nice to him or do favors for him. It was not an important state. He has to say, had been a Nixon Ford person, wasn't really the place to be in the Republican Party later.

He wasn't originally selected. People forget this by George H.W. Bush to be Secretary of Defense. He was number three in the House leadership. Might have moved up there. That would have been interesting if he'd stayed in the House. Probably don't get Newt Gingrich becoming leader. You get Dick Cheney as leader in the 90s. How does that change everything?

He becomes Secretary of Defense when John Tower is defeated, Bush's original pick. And then Bush turns to Cheney. again, it's funny how much you and I have discussed this before in other contexts, how much political history is based on contingent things that no one planned and that needn't have happened that way, John Tower could have been confirmed. And then as I say, if Dick Cheney becomes Speaker of the House and the NIDs and maybe everything looks different. So anyway, it is a remarkable career.

But really on his merits, I think that's even true of the Bush vice presidential pick, George W. Bush, where I do think he just thought, Look, I am, I don't know how much you would have said this to himself even, but certainly not publicly, but I need help. You know, I need guidance in Washington. I need a sound hand and someone who understands how the federal government works. He hadn't been a major figure W when his father was president. He hung around a little bit in the White House, but he really wanted that serious guidance. And I think he picked him for that reason.

Certainly it wasn't electoral, you know, Chinese, as I say, it was not a vote. I remember at the time being sort of in 2000, thinking maybe you should have picked someone who would get him a big state or it would be a close race against Gore. And I got to say to Bush's credit, I think he picked the right person he thought would help him most to govern. And, you know, interestingly, that then sets off a string of presidential, vice presidential picks who are not intended to be successors, right? And so you, you know, you get after Cheney, you get people who are really low, like Tim Cain is not picked as somebody who, if Hillary Clinton wins, can then run for president, right? You are picking people who don't have their own independent power bases, but who are much more likely to help the president as, as that presidential candidate sees it, I think. Biden was really the instance of that. And I think in Obama's minds, I mean, very different from Cheney in so many ways, but sort of like Cheney.

in the sense, foreign policy experience, Washington years and Washington, Biden had almost many years in what I think about that. Dick Cheney, I guess Biden gets here in 72 as a senator, Dick Cheney at that point is moving up in the White House to have. So they are about the same age and, you know, both two of the longest lived public figures in modern times or ever, I suppose. It's very interesting to me that, well, I mean, here's there's so many interesting things here. One of which is, let's just contrast that with Barack Obama. So this, you know, so Cheney is a figure in American politics for 50 years, never becomes resident. Obama's really only a figure in American politics for about like 12 years.

Right. Right. And then it's almost like the inverse, like a guy who comes out of nowhere, gets the brass ring, does two terms of president. And it just disappears. Yeah. Like, that's an interesting just case study in how political legacies can be different and how political careers can be different. Yeah, and I guess, I mean, don't you think, if you think of other presidents, like Obama, they're very different from Obama individually, but, you know, by Harry Truman or something, they become, they have their terms as president. They do great or they don't do so great at different cases.

And then they, I guess Obama's unusual and not having more of a pre-career, so to speak, you know, like LBJ or something like that or Nixon. But Cheney, again, the other extreme. And, you know, he was someone, I've got to say this, I was mostly on, I didn't know him that well, but I knew him well, got to know him better, mostly on his side in most of these fights, but not in every respect, more of a Reagan person, ironically, than he was back in the 70s. He was a Ford Nixon, a Ford person.

And then later on, I became close to McCain, and that caused some tensions. And with Cheney World, as they were big fights then on the Guantanamo and issues and so forth. But so, but he was always respect. I mean, the degree to which he was, the modern, the view of your age are really a little younger, younger, I guess, and all you remember is the Bush years

and the W. Bush years and the controversies about the war and the treatment of the people in Guantanamo and the war and terror and so forth. That's really misses what was so much of Cheney's life and legacy, which, I mean, the degree to which he was respected by everyone and taken seriously by everyone and not thought to be a sort of self-promoter or going for cheap shots or all that sort of stuff, that was really striking to me in the, when I got to Washington 85 for the next 15 years, it got, as I say, people really need to, should have, and I think that was, I think

he always tried to behave that way. You know, he had very strong views about the war and terror and people who are entitled to disagree with them. Maybe they let him a bit awry at times, Australia at times. But, I mean, he was a public-spirited public servant, you know. It was very little, very little, you know, calculations about popularity or self-advancement or staying in good with this part of the party or the movement, much more about what was right for the country. Yeah. If you are a Democrat or liberal listening to this, I think the analog is, think of Dick Cheney is like a conservative version of Leon Panetta. Would that work for you?

Yeah. So, and here's the other thing. Like, Cheney meant it all, right? And this is, I think the, you can, you can be on the fence as to whether or not you believe Cheney meant it all until the Trump years. And the Trump year's proof that he, I mean, whereas many of the old, old guard, even if like W, they privately detested Trump. Trump. They, you know, like, W has never said anything publicly, right, about Trump. And Bob Dole got on board.

Like, you know, another guy from that generation, like, nobody was asking him to. Bob Dole could have, could have just kept his mouth shut, but he got on board with Trumpism. I think Cheney's the only one from that generation who really publicly came out against and said, no, this is dangerous. You know, that's really an interesting point. is M dole is an interesting comparison to Cheney, an admirable man who long, long career in public service and many admirers across the island and the like. So, but yes, he was on board, Jim Baker, I don't think publicly said much, but was not willing to speak out against Trump by kind. Now, I mean, the commentate, the question of what Liz Cheney, the Liz Cheney, Dick Cheney question is interesting because, you know, I think Dick pulled his punches a little bit about Trump when Liz was in the House leader.

and during Trump's first term, and she was frankly pulling her punches, but she thought she could do more good by being in the leadership and being in, you know, staying there. And she knew that if she took on Trump, she risked losing that, what she did eventually. But after January 6th, or even after November 3rd and after the run up to January 6th, she couldn't do that anymore. And he, I don't know how much, honestly, Dick encouraged Liz. Liz encouraged Dick. They were so close. and both so strong, such strong people that I don't want to describe any, you know, they both made up their minds, but they were also in constant communication with each other. I was in touch with Liz, much much more in those late years than Dick.

So one of the things that interests me is also here, I keep saying that because he was such a fascinating guy, extent to which Cheney never became a caricature of himself, which is kind of unthinkable in a social media age. Like the idea of Dick Cheney tweeting is almost impossible to, you know, or Dick Cheney is a shit poster. Very hard to see any of that. And so he, so he was never really a character of himself, but he was always kind of self-aware. Our colleague Matt Laybash back at the Weekly Standard did a series of profiles of Cheney at which he went fly fishing with him. In fact, that became the title of one of Matt's books, fly fishing with Darth Vader, where, you know, he and Cheney went out into the wilderness in Wyoming to like the Robert Redford movie.

Like, it's a river run through it, just standing out in streams and fly fishing. I don't know. What was he like as a person? I never met the guy. I try not to meet politicians. What was he like? Yeah, I forgot about Matt's.

I didn't forget about it. But now that you remind me, for a minute, I hadn't forgotten about Matt's fantastic piece about Cheney, and that's very much worth people's reading. I did one of the first conversations I did in that series that's not been going, 10 or 11 years just with Dick Cheney and it's a little more on the personal side but people might want to take a look at that

in conversations with Bill Crystal it's from late 2014 in the pre, what do we call those? The pre-times, the, yeah, the before times. Before times, yes, I can't make my mind going. Before times, yeah. And yes, discussing our comfort with American conservatism

and I guess generally with the Republican Party at the time. No, he was, I mean, he had a very rye and dry and wry sense of humor. He was aware of what people were saying about him at different times, and he was aware of the, you know, complexities of political life.

So I think he was, you know, there was a much less stern in private, I would say, that in public, though he could be stern and somewhat withering in his judgments of other figures. I mean, he was kind of what you'd expect, but, I mean, very intelligent, of course. And very, yeah, the image

of him, you said, the character Of course, there was one of him, though, was, I guess, almost what, sort of, you know, unaware of his surroundings, kind of, I don't know, you know, such, so determined by what he thought was right that he, but he was aware of the complexities of life. And at times in politics, you've got to make a decision, and he made it and a choice and thought it had to be carried out. And that was where he was publicly, and where he was privately, too. But as I say, I would say a couple of things about his private, he was very, very close to. his family, obviously to his wife, Lynn, and to Liz and Mary, and really a genuine family man, and love doing things like Five Fish, and close to a lot of friends, especially some people who worked for years, for decades, very loyal to them. I was not in that inner circle by any means.

And that was a well, that was a real circle, real inner circle, but one in which there was great, I think, candor and loyalty and really love, I would say. I mean, our colleague Eric Edelman, And worked for Cheney in the White House and then stayed very close to him in the W Bush administration, then went to the Defense Department, but stayed very close to him in the years after. And I'm going to try to, maybe I'll try to do a conversation with Eric later today, but here for the bulwark. But, yeah, I mean, Eric saw a side of him, even more than I did, of candor and reflection about the country, its history. And I do think that's what led him to break with Trump. way that his peers didn't, you know, Bush and Baker and all these people. He really, and this was influenced by his wife, I think, by Lynn's history, historical work, he understood what was at

stake. He understood what free government is. He understood how difficult it is to maintain. And he had put up with a lot of things in his many years in life and people who weren't entirely admirable were allies when he was in the House and when he was in the first Bush administration, a sect and then when he was in the Bush White House, but this was a bridge too far, and he saw that clearly, Liz saw it clearly, and what he did in helping, standing up to Trump, especially behind the scenes in those two months after Election Day before January 6th and 2021, rallying the other Secretary of Defense to sign that joint letters explaining what Trump was trying to do at the Defense Department and how dangerous it was, before that became political.

publicly obvious, you might say, in January 6th. I mean, that was a real service to the country. So, yes, but a really an interesting and complicated man, a guy who read, I mean, he read history, he read fiction. You know, I remember him talking to me about books he really American literature that he really loved. I mean, he and McCain were at a complicated relationship, I think it's fair to say. But they were similar in that way, you know, that they were not one-dimensional figures.

And they loved the life. They, McCain's case, sports and the Chinese case, maybe more fly fishing, but, you know, reading fiction, reading history. I mean, really impressive human beings as well as impressive political figures. Yeah, such, as you say, complicated. Been part of American life for 50 years, was a Gerald Ford guy, became Darth Vader in the American imagination, was also a girl dad. And then was it never Trump? I mean, it's just, you know, whatever else you want to say about Dick Cheney, he meant it, right? I mean, the guy was not positioning.

He was not, it was not K-Fabe for him. It wasn't team politics either. He wasn't just wearing the jersey. He was thinking seriously about America as a place and history as a thing that happens and making his best judgments, which were. sometimes correct, sometimes incorrect. But I don't know, like, isn't that all you have really asked for for your public servants, is that they mean it? Yeah, they think about it and reflect on it and then make their choice and they mean it. And now absolutely, and fought hard, but of course, it never would have occurred to him to deny an election result either.

So, you know, he was willing to lose, and he did lose. He ran George Gerald Ford's campaign in 1976, which was a pretty close phrase. Everyone's forgotten that in 76, and it did not occur in a addiction. Cheney that you were supposed to contest the results, and he, you know, and he supported Jimmy Carter when he thought he was right, incidentally, and wasn't that often, but there were some issues. I think especially late when Carter became more hawkish on foreign policy, and he was, and Dick was already in the house. Yeah, so really, yes, the degree to which he meant it, and the degree to which he was in general, we used that term public servant all the time,

and it's, but he really was a public servant, I would say that, you know, and, you know, what he this morning I wrote this little thing for morning shots and I only I learned he died I guess whatever else did but I missed I was busy reading other stuff so I missed the first 20 minutes or so maybe it was 7 a a.m. So I just wrote a very short thing. But I say in that in the little piece I wrote that the thing that first came to mind is it was that Teddy Roosevelt, the famous Teddy Roosevelt passage from the 1910 speech about the man in the arena. It's a little bit cliche and it's not something I quoted that much or you know that I don't sit around. We reading it a lot. It's so famous, as I say, almost a cliche. But it really applies to Cheney.

You know, he fought hard for what he believes. He got in the arena. He took the blows. He behaved honorably. And an impressive man. Yeah. If you want to understand what Tch Cheney was, think of J.D. Vance and everything goes the exact opposite. That's what Dick Cheney was, right? J.D. Vance, also sort of a humble beginnings kind of guy, rose to vice president, but a guy who seems to have never met any of it, who is an unsurious character of himself, who is a Twitter shit poster, and who just loves bloviating on podcasts with right-wing guys who love being cuckolded and whatnot, and who never believes anything and is always just positioning. Everything is positioning for him. And that is not what Cheney was.

Absolutely right. I hadn't thought of Vance, the current Republican vice president. Yeah, Cheney to Pence to Vance, I guess, right? Yeah, right. Yeah. That's the, that's the trajectory. Rest and peace, Dick Cheney, Bill Crystal, thanks for joining me. We'll be back with more. Good luck, America.