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A
Hello everyone, this is JVL and Sarah Longwell. We're about to give you a preview of our secret podcast for you, our next level family. Sarah, say hi to the people.
B
It's just JBL and I know Tim and JBL and I, we agree on the fundamental tenets of democracy and then just about everything else we disagree on. And this is the show where we hammer some of those conversations out. It is, I think, where we wrestle with the biggest questions. And that is true of today as well.
A
Yeah, we're going to talk about the, this interview Cass Sunstein did with the New Yorker's Isaac Chotner, which is everybody in the discourse was fixated on because of stuff about Henry Kissinger which I think is, is actually sort of fun but silly, not important. There are some big important things that they talked about that we want to unpack. And then I, I posed this question at the end of tnl which was how do we fix all this? And we promised you we would talk about it and so we're going to do that and I'm going to explain why it can't be fixed and Sarah's going to explain how to fix it. Yeah, and you know, spoiler, that's how the show will go. So guys, come ride with us. Here's the show. Hello, everyone. This is JVL here with my best friend Sarah Longwell, publisher of the buarc.
B
Sarah, my guy.
A
No news. We're not going to talk about any news today. We're only going to talk about big, gigantic thought things. And the reason we're doing this is because we're taping on Thursday because you have to travel to Toronto.
B
We got a live show for a live show.
A
But I'm telling people, I just want you all to know we're still releasing it on Friday, which means you will get Rebecca, the most important piece.
B
The most important piece. Why don't you tell the people why you're not joining us in Toronto? Jvale, it's me, Tim and Sam.
A
Because I do a line. I'm just trying to think about how to, how to explain. So I am in my heart an actuary. Another thing that I could have done in life was I could have been an actuary.
B
You would have been a great actuary.
A
I think about risk all the time. All the time. And I try to balance it against reward.
B
JVL Actuary, you're going to die soon and you're going to die fast and it's going to be terrible.
A
Probably, probably. Anyway, I just, the. When you cross A border. You basically lose all of your rights in the administration at the physical place of a border. Even as a United States citizen, you have many less rights than you do at any other place in America. And I am not going to make myself hostile to assumptions that the Trump administration will adhere to the rule of law as it applies to my habeas corpus as I'm crossing a border. No fucking way.
B
Okay, jbl. Things are bad in America, but he's staying in America. No, we're going to Canada. It's gonna be great. Can't wait to see the Mounties. I've only been to Canada, like, one time in my life, and it was just a friend's cabin. And so this is my first time in Toronto, and I'm pumped about it.
A
Toronto's a great city.
B
Well, never been.
A
Toronto's a great city.
B
Sorry you won't be with me.
A
You know what? You'll see me. You'll see me for the other two lives.
B
That's good. I'll have my new best friend, Sam Stein.
A
Sam. Single white femaleing me. That's okay. I have my new best friend, Heather.
B
Deep, that nobody else even gets.
A
Okay, so we. We promised we were going to talk about how to fix things and why they can't be fixed. But first I wanted to talk about this interview that Isaac Chotner did in the New Yorker with Cass Sunstein. Cass Sunstein, for people who don't know, is an academic, a very, very mainstream neoliberal type. I have always thought incredibly smart, written tons of books, tons of scholarly articles, worked in the Reagan administration, worked in the Obama administration. Just. He's a political scientist. I think he's also a lawyer.
B
He is. He's married to Samantha Power.
A
Oh, yeah. Married to Samantha Power. Anyway, I. I just, I'm. I like him very much. And Isaac, he has a new book out which he almost called Big Tent Liberalism. And the. The idea behind it is that he is, in the face of the authoritarian attempt that is ongoing in America. He has been reevaluating all of the sides. And he, like I think myself and probably you, is no longer really interested in left versus right, but is interested in up versus down, with up being liberal and down being illiberal. And he makes the case that we ought to really expand our definitions of liberals, what liberal means. So, like, it does encompass everybody says from Martin Luther King to George Washington and Alexander Hamilton to JFK to Friedrich Hayek to Ronald Reagan to George W. Bush. He doesn't say George W. Bush, although maybe he does in the book, but makes the case basically, like, we've all basically been liberals all along, and it's time for us to recognize that because now there is an actual illiberal threat. Am I summing this up correctly?
B
Well, I think, I mean, both. Neither of us have read the book. We only read the interview. But one of the things that is made clear is that he either does not ever mention Trump or if he mentions him only very sparingly, doesn't talk a lot.
A
He talks in very big, broad philosophical terms, which I understand, I guess. And Chotner then begins picking away. So I would say here's my experience with reading the article. So I, I am there for Sunstein's argument like that. Like, I'm reading Sunstein's summation about big tent liberalism, and I'm like, yeah, get him. Go get him, buddy. Yeah, Cass. Because that's basically how I view the world. Sure. And Chotner starts trying to pick that apart, and he says, so, for instance, Hayek, I think it's Hayek I don't have in front of me, did support a coup in. I forget it was Peru, Argentina, Chile, or Argentina, somewhere in South America. He was, he was pro coup. This other guy, Murray Rothbard, who you say is a liberal. He wanted anarcho capitalism, or, you know, anarchic. He wanted to overthrow the U.S. nozick.
B
But Murray Rothbard was. Had some very, I think, bad opinions on race, I believe, yes.
A
Bad opinions on race. But I think was also wanted to, like, overthrow the government because he was such a libertarian. He wound up like, as a Lou Rockwell guy. And he points out Reagan, Reagan running for governor in California, talking about how businesses should be allowed to discriminate against black people if they want to. And I think that Isaac's point is. I think the point he's trying to make is that actually we're retconning. These guys weren't. Weren't really liberals. And I see what he's saying, but I also don't think I agree with it. And, and I just want to, like, I want to hear you go. And I was hoping we could hash it out because I don't really know what I fully think about this, but I think I know and I want to dialogue with you about it.
B
Okay. So I read it and I got to say what you described a little bit where I started the interview thinking, this is a book for me, Right. This is a book that talks about liberalism in the biggest, broadest context and allows us to see where the lines are. Right. And I Think my assumption going into it is that Trump, while not a discussed character, is like the thing that hovers over the entire book because one writes about what the contours actually are. And he also was going through his own sense of, hey, look, I used to regard people like Hayek and even Ronald Reagan as people who were not my political allies, but I realize now that actually they are my political allies because we all exist within this framework. And he kind of lays out, again, not in the book, but in the interview, that there is kind of a tent pole set of issues that make one committed to liberalism, and that is.
A
Freedom, the rule, free markets, plural.
B
Oh, it's actually, it's not free markets. It's pluralism. The rule of law and pluralism.
A
And free speech.
B
No, free speech. Yeah, like, so. And then. But it sounded like in the interview, he also threw in at other times, things like human rights and. But he, he was, he was critical. And I think one of the reasons he's talking about Hayek and von Mises and Nozick and Murray Rothbard, like, these are. A lot of these are. Are libertarians who push everybody. Kind of, let's assume that politics is on a linear spectrum, which it is not. But for the purposes of argument, further to the right or further to the place of, like, when you say anarcho capitalism, like, a lot of what we're talking about is just like, markets are everything. Like, they are. They are the thing that we sort of live and die by. Whereas, of course, I think modern conservatism, the one that we grew up in, is like, very free market forward, but not without some constraints. Like, and not without, you know, not without some idea that you need order, like anarcho capitalism. I always am like, so we don't have stoplights then, huh? Like, we don't have, like, the libertarian argument is one that's fun for all of us when we're 19. And then, like, we grow up and you go, you know, actually, society can't work that way. And so I, I myself went through my Ayn Rand, my. My Von Mises, you know, period of my life. I think there is a lot about Hayek to recommend itself. And I. But. And so I was like, kind of there for his. I have evolved on this to see that we're all. Because this is. This is where I think. Think we are right in the moment, is that's kind of the point of the Never Trumpers, to some degree, is actually because we believe in free speech, because we believe in liberal democracy, because we believe that Trump is illiberal. Right. That is why he cannot and should not be tolerated. It was always his threat to the liberal. And by liberal, I mean small L liberalism. Or do I mean big L liberalism?
A
Small.
B
Which one's the big and the small? The small L liberalism. And so Trump is like an inherently illiberal figure. And that is why never Trumpers happened where we didn't care that he just was like, yeah, I'm going to cut taxes and regulations. Like that wasn't enough to compensate for all the damage he was doing to the liberal order. So I was like, this is probably for me, maybe I'm going to go read this book. But then, then Chotner does start to. And here's the thing, Isaac Chotner, don't ever call me for an interview. I won't do it. You. You murder people in your interviews. You are a, A credibility destroyer for everyone who wanders into your zone. He just brutalizes Cass Sunstein in this interview in a way that it made it look like Sunstein had a thesis that he hadn't reckoned hard enough with. Because his defense of liberalism sort of said, okay, my big tent liberalism includes Justice Thomas and Alito because you don't ever see them put pen to paper to say Donald Trump is a king. And I was like, okay, but wait a minute. When you remove the guardrail so that Donald Trump.
A
Haven't put pen to paper to say that yet, Sarah.
B
But, but I don't know. I mean, it depends on how one interprets the decision to say that Donald Trump cannot be prosecuted or held accountable for any official acts in office. And so, like, I don't know, when you remove that level of accountability that allows him to be more effective in his authoritarian project. I found his defense of his own work deeply wanting. And I couldn't tell, and this is my general. I could not tell if I read the book, if I would find it compelling or because he's just making, you know, what I think is probably. I think he can. He can make a pretty defensible argument for his point. I think the question comes, if you draw the lines around what is liberalism? Then, you know, I think that the disagreement starts to be in Chotiner's disagreement with him is this. It's like, okay, well, who's in that? Who's. Who plays inside those lines and who plays outside those lines? And I think that Chotner's. Where he's playing Gotcha, I think quite effectively is he starts throwing people out as chum to be like, okay, in or out, your idea of liberalism. And Sunstein kept being like, oh, in. And he's like, but what about this thing where they, you know, were super duper racist or supported a coup or, you know, are Henry Kissinger. Right. And. And I thought that. I thought it raised a bunch of questions that actually made me want to see if casting was better in his book than he is in the interview. Because I actually came away from the interview thinking I thought that was a very poor defense of his thesis, not his best.
A
But this is why I. So I also would not participate in a phone interview with Isaac Chotner. I'd be happy to do an email interview or a text interview because I have tremendous respect for the power of mediums and for people who are really masters of their medium. And so there are, like, Bill O'Reilly. Whatever else you want to say about Bill O'Reilly, he understood how to do his show. And anybody who walked onto that set, it didn't matter how smart you were. Like, he knew how to make the show work and he could just embarrass you if he wanted to. And. And I think the same is true with Chotner. I am not actually comparing chotner to Bill O'Reilly. I'm just saying that he's really, really good at having very pointed interviews and catching people off guard. And I do not do that often in the same way. Like, I don't debate often. And so I would not participate in something like that. I'm really good at writing, though. And so if he ever wants to interview me over text, happy to do that. I feel like there aren't a whole lot of people who I fear in print.
B
Yeah, I was mainly making a joke, actually. Isaac Chotner interviewed me. I'll talk to you all day long. I don't care.
A
Yeah, I know you don't duck anyone, but here's what I'd say. So I want to grant Chotner's point because I think he's right in some sense, but I think in the larger sense, he's not. And I wind up with basically three things I would point out. The first is that whenever you're talking about any, there are very few people who, who are all the way in on liberalism. Right. Like, everybody is a little inconsistent. Right. Everybody has blind spots. Everybody has things where later in life, maybe they reconsider. Right. And what you're really talking about is the preponderance of evidence. Well, you're talking like, you know, on the whole, were they. Were they in support of liberalism or not? And the Second piece is that everybody is a product of their time and place. And I. This isn't an excuse, but it is an important to understand because we are all products of our time and place. And 100 years from now, if somebody were to pull up things that we've written, I don't know what it will be that will look offensive, but something will look benighted and stupid and it's just because this is the soup we swim in. And the third is that there is a. What's that line about pornography? Like the Supreme Court line?
B
I know it when I see it.
A
You know it when you see it. Right. And I think the three of those combine to make it a little. Yeah, I know it when I see it. And so I would view there's a.
B
Difference between pornography and art.
A
Right, right. So I, I absolutely disdain libertarians. Like I really, I have no use for them. But on the other hand, there's a difference between some 75 year old academic who's just jerking off in a book about abstract and somebody who is summoning an armed mob to the capitol and attempting to overthrow the government. They are, they are not both the same level of illiberal, you know, and, and so I could.
B
Yeah, but Sorry, who's your 75 year old? Is it like.
A
Okay, yeah, like, you know, or Hayek or somebody like that. I'm not saying that makes them all the way in, but just that there is a little bit of like, yeah, okay, so a guy who's always obeying the law, a guy who is never actually attempting to overthrow the government. A guy who is sort of in his daily life totally liberal, but he just makes these like, you know, jerking off motion like stupid abstract dorm room session BS arguments about why we should overthrow. I'm a little less.
B
Well, I don't know that. I mean again, sometimes I'm like, are we gonna, we're just gonna go off this interview and not actually read the book? That's a little bit of tough sledding. But I don't know if the coup.
A
That Hayek's worst in the Murray Rothbard books and like his blogs on lourothwell.org yes.
B
Although I think Hayek had better ideas than Murray Rothbard. So I don't know. Road to Serfdom was quite influential for me in a way that, but I. And also part of, part of what was tough for, for old Cassier is that Isaac Chotner had done his research and so he kept like hitting him with facts about the guys that he'd just written about that he was like, oh, I didn't know he did that, or I didn't know he said that. I didn't know he was wildly biased against Near Easterners, Indian.
A
But you see what I'm saying with like, the preponderance of like, I mean, this gets back to all the Founding Father. Right. Like, you know, they're almost all slave owners.
B
Yeah.
A
Right. And yet they believe in these Enlightenment ideas about liberalism. Like, there is a, you know, nobody's really all the way in or all the way out. Everybody is straddling. And so we're judging by, like, the preponderance of mixed with understandings about the place and time. And I think it's. When you see somebody who's truly a liberal, it's not a close call. You don't have to go and parse everything they ever said, you know, like, when you see the real liberals, it's just coming out of their pores. Yeah.
B
I guess, though, if you write a book endeavoring to sort of draw the lines, like that's the point of the book. And like, you're saying, no, actually here are the people who are in and I, I'm saying who's in so that I can contrast it with who's out. And then suddenly the people who are in actually have, like, big strokes against the fundamental tenants you lay out. I don't know. I. The thing is, is that maybe based on the interview, I thought he had a thesis with which I agree and a defense that I thought was, like, comedic.
A
Would you agree that Ronald Reagan is in?
B
Of course I would.
A
I would, too. This is what I'm saying. Right. I mean, I, I again, I just like, yeah. Have read the book. We do a lot of these.
B
But, like, the reason, I think the reason that the, the, the what's his name, Kissinger stuff really lands isn't because I think it betrayed in Sunstein a bit of a lightweightness around the argument. Because what he does is he says they were like, well, you're good friends with Henry Kissinger.
A
That was a rough. That's a rough. Please explain to the people how that goes.
B
I should grab it and read it because it's. But basically he says, okay, well, you, you and your wife are. We're good friends with Henry Kissinger, who I think a lot of liberals would say is a war criminal because of what he did in Vietnam and Cambodia. And I, I, this is where I will wander in. I so I'll just say up front, I have, I, I cannot, I do not Know enough. This is before my time. And I, I could go back and study it, but I haven't. Whether or not Henry Kissinger is a war criminal or just had some bad idea, whatever, I can't parse that on this podcast. But I certainly know that Henry Kissinger is reviled for some of the things that he did in Vietnam and then the bombings in Cambodia. And I think that the push. So he's pushing on this particular thing. He's like, you know, is he in or out? And Cass Sunstein says he's in, and then says, I can't really evaluate. Like, his, his level of evaluation of Kissinger rivals mine. Like, he couldn't tell you whether he is illiberal or not, but he can tell you that he once came to his book party about when he wrote his Star wars book, which, by the way, is when I was like, oh, this is why JBL wants to talk about this guy. Because this guy wrote a book about Star wars being, you know, not true. The not true. Okay. And so he's like, well, he's a very generous friend. You know, he didn't. He was a very busy man. He came to my book party and he said a nice thing to me. And the, the killer in the, in the interview. And this is where Isaac Chotner just, just opens your inside with a. With a saw. He go, He. He concludes the final line from Sunstein. He says he thanks him for the interview and then includes the line that Sunstein says right after he's been thanked where he says, maybe go light on the Kissinger stuff. It'll distract people from my main point.
A
And, you know, you don't include that unless you're knifing the guy.
B
Yeah.
A
And this is. I, Look, I. There's nothing wrong with knifing people in print. Is something I have done from time to time. It's something I imagine I will do in the future.
B
Doesn't sound like you.
A
You. The thing is, you always. If you're a professional, you never do it by accident. Right. You don't knife somebody accidentally. It's not like, oh, I hit him with an elbow while I did. Oh, so sorry. I didn't mean that. Right. Shotner knew what he was doing there. Oh, yeah. I.
B
But actually, I found that part kind of instructive and interesting. And can I tell you why.
A
I.
B
Was thinking about this? And I don't know whether or not it's worth me saying out loud in what context I was thinking about this, but I do think that you and I have had because we broke with many of our old friends who, I think there was a period of time where we thought they were normal people. And there are people that maybe we, we respected at a time or were our, our elders, as we were coming up in the conservative movement, who we watched get on an authoritarian train and just a bullet train and betray every value they ever taught to us and now are publicly poisoning the discourse and, or selling out in big and specific ways in order to get their own bag of cash, but at the expense of the country and an expense of the liberalism that they say that they defend. And I could say about a great many of those people, nice guy was at my wedding, gave me a nice present, send something to my kids when they were born. And I don't know that I think that, though, and this is. I think you and I do agree on this. Again, it's, this isn't about, like, it's not that I've cut these people out of my life or it's not that I. But I won't lie about the damage that they're doing. And I just think that this idea of like, well, it goes back to when you're kids, you're ever. When you're kids, and you were saying, you're saying to one of your friends, like, yeah, but that guy's such a jerk. And they're like, who's always nice to me? And you're like, what does that mean? Okay, but, but, but still, like bad in general. Right. And I, I sort of, it's just that. And so I guess I, I find that to be a, it's a little bit of a Washington failing, almost like it's kind of Washington brain to be like, why I know Mitch McConnell. And like, he's not a monster. And you're like, okay, like, probably he doesn't stab you with a knife when he sees you.
A
Because I think Mitch probably does stab people with knives when he sees them pick somebody up. Try Paul Ryan. Paul Ryan seems like a nice enough human boy human being, Mitch McConnell.
B
But I don't think Paul Ryan is a good one, actually, because Paul Ryan has, I would say his, his, his net contributions to the negativity have been so much less than the people I'm talking to or that I'm talking about. I'm talking about, you know, many of the people who I'm talking about, like Rich Lowry, you know, or, or worse than that. Much worse than that, you know, many people who, who work in the administration who are actively looking for ways to help Donald Trump, like, take this project and bring it forward contra everything they've ever said that they believed.
A
Yeah, I. Yeah, I, you know, I, I want to. I want to say something briefly about Kissinger because I think I'm gonna get Savage for this in the comments.
B
Oh, do you want to take it behind the paywall?
A
Okay, let's do that. I will. I will mount my quasi, kind of not really a defense, but a series of line drawings around Henry Kissinger behind the paywall. And then we're going to talk about why nothing can be fixed after this moment and how Sarah's going to fix it.
B
Okay. But I'll just say for those of you who get mad when we go behind the paywall, we have so few products that we pay well. Like if you want to go to daily. If you look at all the other products, they are paywalled within an inch of their lives. We make almost everything free. We have a couple things behind the paywall so that you will subscribe and ride with us. It is. We are mostly running an information charity, but not this part. So help support the work that we do and come listen to the other half of this convo.
A
Yeah. Help support me defending history's greatest monster, Henry Kissinger.
Overview
In this intellectually charged episode, hosts Jonathan V. Last (JVL) and Sarah Longwell (with Tim Miller absent) engage in a nuanced, sometimes combative, discussion about the boundaries of liberalism, sparked by Isaac Chotiner’s interview with Cass Sunstein in The New Yorker. They dissect Sunstein’s "big tent liberalism" thesis, reflect on the nature of ideological coalitions, and debate how—and whether—American democracy and political culture can be "fixed." The episode features trademark Bulwark banter and deeply reasoned disagreements, along with a frank critique of prominent figures, both contemporary and historical.
JVL and Sarah point out they're taking a break from the week's news to dive into "big, gigantic thought things" because Sarah is traveling to Toronto for a live show.
JVL humorously explains his absence from the live show: He distrusts border crossings due to the erosion of rights, especially under a potential Trump administration, and would rather not "make myself hostile to assumptions."
JVL introduces Sunstein as a respected academic and legal mind, lauding his career spanning the Reagan and Obama administrations.
Sunstein’s Core Thesis: In light of rising authoritarianism, Americans should expand the definition of "liberal" to include figures as wide-ranging as Martin Luther King, JFK, Hayek, Reagan, and perhaps even George W. Bush. The fight now is not left vs. right, but "liberal vs. illiberal."
Both hosts agree Sunstein’s thesis is appealing—at first.
Chotiner presses Sunstein on historical figures’ racist or anti-democratic actions (e.g., Hayek supporting a South American coup; Reagan defending business discrimination).
Sarah and JVL both note that everyone is inconsistent, shaped by time and context.
Sunstein’s “Tent Poles”: Free speech, rule of law, pluralism, and sometimes human rights.
Sarah draws on the Never Trump experience: The movement’s animating force is the defense of small-l liberal democracy against Trump’s illiberalism.
Chotiner is relentless; both hosts joke about refusing his interview requests out of self-preservation.
Chotiner exposed the vagueness of Sunstein's "big tent" by naming problematic "liberals" and watching Sunstein hem and haw on the inclusion of individuals with deeply anti-liberal actions or beliefs.
Preponderance of Evidence Standard: JVL advocates for weighing the dominant themes in a figure’s life, accounting for era and context, rather than demanding moral purity.
Acknowledgement of the Founding Fathers’ Contradictions: JVL brings up slaveholding founders as an example of necessary ambiguity.
Distinguishing Between Theoretical and Practical Illiberalism: JVL dismisses "dorm room" libertarianism as less dangerous than actual authoritarians.
Critique of DC’s “Nice Guy” Excuses: Sarah points out the fallacy of defending public figures based on private decency.
The interview’s most notorious section is Chotiner’s focus on Sunstein’s personal friendship with Henry Kissinger, whom many consider a war criminal.
JVL and Sarah agree this ending was a calculated, brutal journalistic move by Chotiner.
Sarah’s Reflection: She draws a parallel to current moral reckonings about former conservative friends who “betray every value they ever taught to us… publicly poisoning the discourse.”
On border-crossing and risk analysis:
"In my heart, I'm an actuary. I think about risk all the time... When you cross a border, you basically lose all of your rights... And I am not going to make myself hostile to assumptions that the Trump administration will adhere to the rule of law... No fucking way." —JVL [02:23–03:10]
On the tension between theory and danger:
"There's a difference between some 75-year-old academic who's just jerking off in a book about abstract... and somebody who is summoning an armed mob to the Capitol." —JVL [18:07]
On “just following orders” friends:
"Nice guy was at my wedding, gave me a nice present, sent something to my kids when they were born... but I won't lie about the damage that they're doing." —Sarah [25:20]
On journalistic technique:
"You always... if you're a professional, you never do it by accident. Right. You don't knife somebody accidentally... Shotner knew what he was doing there." —JVL [24:52]
Engaging, witty, and deeply skeptical, with a uniquely Bulwark blend of policy wonkery and personal candor. The conversation is both good-naturedly combative and intellectually rigorous, as JVL and Sarah push each other—and their audience—to move beyond "team" politics toward confronting real philosophical questions about the future of democracy.
Missed the second half? Subscribe to The Bulwark for more of this ongoing, essential conversation.