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Bill Kristol
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JVL
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 Kristol 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, 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. Very much a self made guy. Comes out of Wyoming, small state with no electoral importance and winds up as secretary of defense and the vice president and important actor in American politics.
Bill Kristol
Yeah. And actually, I mean as 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, finishes his degree elsewhere, studies 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 Lynne, professional 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 church junior staffer in the Nixon White House, ends up as chief of staff to gerald ford what, five, six years later. That would have been 1975, so that would have been when he was 34 years old. So the degree you actually understated in a 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. It's stunning the public eye. 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 and I guess was his patron early on, you could say. But it was. And then he went. But it was entirely due to a self made man in a way to great American story. You know, he leaves the White House after Ford loses and I remember that he said he goes back to Wyoming and people. I'm in grad school at the time I guess, but little bit in these circles and I hear he's going to run for Congress. It was the Dick Cheney. He's like a consummate inside operator, 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 having a time to fact check all these things since the death was just a couple hours ago, but were announced just a couple 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.
JVL
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, if you came of age during the Bush presidency, George W. Bush's presidenc, Dick Cheney is Darth Vader and he is this, this evil figure who, 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 is 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 of wunderkind. That's super interesting to me. Just so many acts in American public life. He had, you know, like most people get one or two acts. He had like four.
Bill Kristol
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 whom 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, really more of a persuade Cheney movement. He chose not to do it. And. 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.
JVL
I think I found the guy. I was looking in the mirror.
Bill Kristol
That's the joke. I don't know how much of it was his thinking and how much of it was Bush's 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 as I 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. Wyoming 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 and that would have been interesting if he'd stayed in the House. Probably. You 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 Shaney becomes Speaker of the house in the 90s and maybe everything looks different. So anyway, it is a remarkable career, as I say, 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 he 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, they say, was not a, 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 was gonna be a close race against Gore. And he, and I gotta say, to Bush's credit, I think he picked the person he thought would help him most to govern.
JVL
And you know, interestingly, that then sets off a, 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 Kaine is not picked as somebody who, if Hillary Clinton wins, can then run for president. Right. You, 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.
Bill Kristol
I think Biden was really the instance of that. And I think in Obama's mind, I mean, very different from Cheney in so many ways, but sort of like Cheney in the sense foreign policy experience, Washington years in Washington. Biden had almost as many years in Washington, 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.
JVL
I suppose it's very interesting to me that, well, I mean here, 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 president. Obama's really only figured American politics for about like 12 years. Right, right. And, 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 then just disappears. Like that's an interesting, just case study in how political legacies can be different and how political careers can be different. Yeah.
Bill Kristol
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, a Harry Truman or something. 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 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, 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 Ford person. And then later on I became close to McCain and that caused some tensions and with Cheney world was 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 really a little younger at all 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 on terror and so forth really misses what was so much of Chaney'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, in the. When I got to Washington in 85 for the next 15 years it got as I say, people really needed to. And I think that was. I think he always tried to behave that way. You know, he had very strong views about the war on terror and people are entitled to disagree with him. Maybe they let him a bit awry at times or astray at times. But I mean he was a public spirited public servant. You know, there was very little, very little, you know, calculations about popularity or self advancement or staying in good with this part of the. Of the party or the movement. Much more about what was right for the country.
JVL
Yeah. If you, if you are a Democrat or a liberal listening to this, I think the analog is think of Dick Cheney as like a conservative version of Leon Panetta. Would that work for you? Like.
Bill Kristol
Yeah.
JVL
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, they went like W has never said anything publicly, right, about Trump. And Bob Dole got on board, 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.
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Bill Kristol
Interesting point because Dole is an interesting comparison to Chaney, an admirable man who long, long career in public service, admirers across the aisle and, and the like. So, but yes, he, he was on board. Jim Baker, I don't think publicly said much, but was not willing to speak out against Trump by cut. Now, I mean the combination, 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 leadership and during Trump's first term and she was frankly pulling her punches. But she was a, 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, which she did eventually. But after January 6 or even after November 3 and after the run up to January 6, 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. And both so strong, such strong people that I don't want to ascribe any, you know, any. 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.
JVL
So one of the things that interests me is also here, I keep saying that because he was such a fascinating guy. The 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 shitposter. Very hard to. 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 labash back at the Weekly Standard did a series of profiles of Janie of 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 Chaney 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?
Bill Kristol
Yeah, I forgot about Matt's. I didn't forget about. But I know that you remind me for a minute I hadn't, hadn't. I'd forgotten about Matt's fantastic piece about Cheney and that's very much worth people's reading. I had a. I did one of the first conversations I did in that series that's now been going what, 10, 11 years was 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 Kristol. It's from 20, late 2014 in the pre. In the. In the. What do you call those? The pre times. The.
JVL
Yeah, the before times.
Bill Kristol
Before times, Yes. I can't make my mind's 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 wry 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 the. In private, I would say, than in public, though. He could be stern and somewhat withering in his judgments of other figures. I mean, he. 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 caricature. 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. By what he thought was right, that he. But he was aware of the complexities of life. And at times in politics, you got to make a decision, and he made it and a choice and thought it had to be carried out. And. 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 life. 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 loved doing things like fly fishing. Close to a lot of friends, especially some people who'd worked for him 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 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 that, 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 in a 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 Lyn'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, when he was in the, you know, in the first Bush administration, the SecDef, 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 in 2021, rallying the other secretaries 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 publicly obvious, you might say, in January 6th. I mean, that was a real service to the country. So. Yes, but 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, they loved the life. They, McCain's case, sports and Chaney's case maybe were fly, fly fishing, but, you know, reading fiction, reading history. I mean, really impressive human beings as well as impressive political figures.
JVL
Yeah. Such as you say, complicated. Been part of American life for 50 years. Was a, was a Gerald Ford guy, became Darth Vader in the American imagination. Was also a girl dad. And then was it never Trumper? I mean, I can't just, you know, whatever else you want to say about Dick Cheney, he meant it. Right? I mean, the, the guy was not positioning. He was not, it was not kayfabe 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, you know, but I don't know, isn't that all you have really asked for, for your public servants is that they mean it?
Bill Kristol
Yeah, they think about it and reflect on it and then make their choice and they mean it and. No, 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 Errol Ford's campaign in 1976. He was, you know, which was a pretty close race. Everyone's forgotten that in 76. And it did not occur to Dick 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.
JVL
So.
Bill Kristol
Really? Yes. The degree to which he meant it and the degree to which he. We use that term public servant all the time and it's. But, but he really was a public servant. I would say that. You know. And you know what, what he. This morning I wrote this little thing for morning shots and I only. I had 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. So maybe it was about 7am 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 was that Teddy Roosevelt, the famous Teddy Roosevelt passage from the 1910 speech about the man in the arena. It's a little bit cliched and it's not something I quoted that much or, you know, that'll sit around rereading it a lot. It's. It's so famous and 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.
JVL
Yeah. If you want to understand what Cheney was, think of J.D. vance. And everything goes the exact opposite. That 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 unserious 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, and who never believes anything and is always just positioning. Everything is positioning for him. And that is not what Cheney was absolutely right.
Bill Kristol
I hadn't thought of as the current Republican vice president. Yeah. Cheney to Pants to Vance, I guess. Right?
JVL
Yeah. Right? Yeah. That's the trajectory. Rest in peace, Dick Cheney. Bill Kristol, thanks for joining me. We'll be back with more. Good luck, America.
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Episode: Bill Kristol and JVL on Dick Cheney’s Legacy
Date: November 4, 2025
Host: The Bulwark (JVL, Bill Kristol)
This episode of Bulwark Takes is a timely reflection on the legacy of Dick Cheney, who has just passed away. JVL and Bill Kristol engage in a deep, candid conversation about Cheney’s extraordinary influence on American politics spanning five decades. The discussion critically examines Cheney’s career trajectory, his personal attributes, his political evolution, and his complicated public image—from consummate inside operator, to George W. Bush’s “Darth Vader,” to a voice of conscience during the Trump era. Both hosts reveal personal anecdotes and provide keen insights into Cheney’s substance, style, and the lessons that can be drawn from his long life in public service.
"Cheney sort of comes from a very different place... Very much a self made guy. Comes out of Wyoming, small state with no electoral importance..." (00:59)
"He is White House chief of staff at age 34 and ends up in his 80s being a major force as a Republican... So that's 50 years really right in the public eye." (01:52)
"If you came of age during the Bush presidency...Dick Cheney is Darth Vader...If you came of age during the Trump years, he is this voice of conscience..." (04:00)
"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..." (04:59)
"You can be on the fence as to whether or not you believe Cheney meant it all until the Trump Years...the Trump years prove that he, I mean, whereas many of the old guard...they went like W has never said anything publicly, right, about Trump. ...I think Cheney's the only one from that generation who really publicly came out against and said, no, this is dangerous." (12:12)
"...the idea of Dick Cheney tweeting is almost impossible to...or Dick Cheney is a shitposter. Very hard to...see any of that." (15:24)
"The guy was not positioning. He was not...it was not kayfabe for him. It wasn't team politics either...He was thinking seriously about America as a place and history as a thing that happens and making his best judgments." (20:49)
"He fought hard for what he believes he got in the arena. He took the blows, he behaved honorably and an impressive man." (22:17)
"If you want to understand what Cheney was, think of J.D. Vance. And everything goes the exact opposite. That that's what Dick Cheney was." (23:16) Cheney defined meaning and conviction; present figures, in their view, are often defined by posturing.
On being a self-made political figure:
Bill Kristol:
"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." (03:32)
On Cheney’s multifaceted legacy:
JVL:
"So if you came of age during the Bush presidency...Dick Cheney is Darth Vader and ...this evil figure...If you came of age during the Trump years, he is this voice of conscience..." (04:00)
On conviction and public service:
JVL:
"...whatever else you want to say about Dick Cheney, he meant it. Right? ...He wasn't just wearing the jersey. He was thinking seriously about America..." (20:49)
On Cheney during the Trump era:
JVL:
"I think Cheney's the only one from that generation who really publicly came out against and said, no, this is dangerous." (12:44)
On what separates Cheney from modern politicians:
JVL:
"If you want to understand what Cheney was, think of J.D. Vance. And everything goes the exact opposite." (23:16)
On public service:
Bill Kristol:
"We use that term public servant all the time…but he really was a public servant." (22:18)
The episode’s tone is reflective, respectful, and keenly analytical, occasionally wry but always serious about the weight of Cheney's career. Both hosts, despite differences with Cheney on policy, acknowledge his seriousness, substance, and underlying integrity—a foil for much of today’s political culture. The discussion insists that, for all his controversies, Cheney’s courage of conviction and stamina in serious public service deserve special recognition as his legacy comes to a close.