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Bleak House
October 20 2025
Summary: The episode centers on what the hosts see as accelerating authoritarian abuse of government power, beginning with the indictments of John Bolton (and earlier targets like Comey and Tish James) and a debate over how classified-documents cases differ when deception and obstruction are involved. They discuss the political logic of using federal force and threats against cities like New York, arguing that governance is being shaped by loyalty tests and punitive pretexts. A major theme is the administration’s effort to sideline independent scrutiny, including the Pentagon press credential purge and a broader concern that major media and tech platforms are increasingly controlled by Trump-aligned owners or incentives. They then focus on the dangers of weaponizing the IRS and labeling opponents as “terrorists,” tying these moves to a breakdown of democratic norms and the citizen-government “compact.” The conversation ends with a darkly comic detour into JB Pritzker’s reported gambling winnings as brief relief from the episode’s broader anxiety about institutional erosion.
00:02 JVL Hello, everyone. 00:03 This is JVL here with my best friend, Sarah Longwell, publisher of The Bulwark. 00:08 Sarah. 00:09 Sarah Longwell My guy. 00:11 JVL John Bolton was indicted yesterday. 00:13 Sarah Longwell Sure was. 00:14 JVL That's pretty cool, I guess. 00:16 We now have Jim Comey and John Bolton indicted on what seemed to be bullshit charges. 00:22 An actual weaponization of the Justice Department. 00:26 I mean, it's not great, Bob. 00:31 Sarah Longwell It's real bad. 00:31 Here's my question. 00:32 And maybe you can help me out with it that I've been wondering and haven't had a full chance to run down. 00:40 This is a secret show. 00:41 And it is this. 00:44 I've seen a lot of people arguing that the Bolton case is sort of substantively different than the Comey-Tish James case. 00:58 It appears that for Comey and Tish James, and by appears, I mean these ones I have looked at pretty closely, and they are trumped-up nothings. 01:09 Those are 100% meant to just screw with these people, mess with their lives, and the likelihood, like, they barely got indictments, and they are very unlikely to almost no chance of getting convictions. 01:27 Anything can happen, but whatever. 01:29 The Bolton one, where he has kept documents that he shouldn't have, which is an interesting one from a, hey, there was a whole timeline in which Trump was keeping documents he shouldn't have in Mar-a-Lago. 01:43 Not only was he keeping them, he wouldn't give them back. 01:46 And if that case had gone to actual trial, if we'd been able to really move that one forward, everybody seemed to agree that was a pretty open and shut case. 01:54 Whereas, and then you got Mike Pence, right? 01:57 And Joe Biden. 01:59 Everybody's like, suddenly there was a documents bonanza. 02:01 Nobody was doing the correct thing with their documents. 02:04 Although, when they were asked for their documents back, they, of course, just apologized, gave them back. 02:09 It was sort of unclear why they had them other than their being president and vice president allowed them much more latitude with these kinds of documents. 02:20 And so, unlike... 02:23 other people where people get prosecuted for this stuff all the time because you are definitely not allowed to have them. 02:30 And so now we've got John Bolton doing it. 02:33 Now, 02:34 And this was also a case that started under the Biden administration about Bolton having these classified documents. 02:42 So I can't, I think both things can be true. 02:46 I think this can both be vindictive prosecution, which it clearly, clearly is against Bolton. 02:52 But what I don't know is just like with Trump, where you could say like, 02:58 Well, some of the cases brought against him, like the Stormy Daniels case or the one against, you know, Trump Inc., they weren't, like, great cases to bring, but, like, there was underlying criminal activity. 03:14 Now, it might not have been prosecuted in a different world, and I think that might be the case here, right, where it is both that maybe he did something wrong and it's vindictive prosecution. 03:25 Right. 03:25 Which is just different than Tish James and James Comey, which are just purely made up for the reasons of vindictive. 03:33 Or like, made up like, they're trying to get them on these real technicalities of something. 03:42 That it's not even clear they did. 03:44 So anyway, those are how I see them as being different, but what do you think? 03:49 JVL So we don't know. 03:49 And, you know, I don't want to prejudge it. 03:53 We will find out. 03:54 Um, I mean, I, my general view of classified documents mishandling is that, uh, 04:07 I mean, a lot of it is really circumstantial. 04:09 And like one of the reasons normies, right? 04:13 If you are just a line agent in the FBI or NSA or something, and you don't have access to all that many classified documents, which is why it's a big deal if you mishandle them. 04:25 Whereas at the upper echelons of government, where you're like deeply involved in record keeping about what you do, 04:34 There's, there's a, just a, a sea of documents. 04:39 Documents do tend to be overclassified. 04:41 Like we do classify too much stuff. 04:43 And, uh, 04:45 like innocent mistakes are the norm, not the, not the exception. 04:51 And like the, the law of this as practice is typically like it's self policing or, you know, uh, in cases where you don't like you find yourself, you yourself find classified documents are like, Oh crap. 05:06 Have your lawyer called a, 05:08 archives or the justice department to try to arrange a turn of them. 05:12 These just happens. 05:14 And what made the Trump prosecution notable wasn't that he had classified documents. 05:23 Like that is a totally, that's a non-story. 05:27 What made it notable was that he engaged in a prolonged period of lying and 05:36 to the department of justice about whether or not he had them. 05:41 And he refused to give them back and engaged in all sorts of criminal activity in order to avoid giving them back. 05:49 Like that is, that is different. 05:51 It's just a wholly different. 05:52 Now, maybe John. 05:53 Sarah Longwell I was clear that I also thought it was different, right? 05:56 I made that clear. 05:56 JVL No, no, I completely different. 05:59 Maybe, maybe Bolton did the same thing and we'll find out, but I will say this is one of the, cause we're going to get real dark. 06:06 One of the few things that I feel relatively good about over the next three years is the criminal justice system. 06:18 Because I think we have already seen that the Department of Justice is totally politicized and is going to prosecute people almost entirely based on politics. 06:33 But they still have to convince juries. 06:36 And that's one thing that MAGA can't fix, right? 06:40 Like they can't get into the jury room. 06:43 And, uh, what we've seen with grand juries already has been very encouraging. 06:49 And I, uh, 06:51 You know, I mean, you could see where they will try to bring these cases in friendlier venues. 06:58 Right. 06:58 Like, you know, oh, we'll see if we can find a way to try them in Texas. 07:01 Right. 07:01 But yeah, in general, I feel like a jury of 12 of your peers is like the closest to an uncorruptible place as there is. 07:13 So I feel pretty good about that. 07:14 Sarah Longwell Even with your low opinion of humans. 07:17 JVL Yeah, because one person in the jury room who is, like, not a mouth breather can just say no. 07:24 Right? 07:25 This is why. 07:25 You know, it only takes one of 12. 07:28 You know, what are the chances if you put 12 people together that one of them will have an IQ over 80? 07:33 I mean, it's not bad. 07:35 That's pretty good odds. 07:36 So that's bad. 07:38 But... 07:40 I want to move us into item two here because what I'm trying to do is layer. 07:44 This feels like it was a slow news week. 07:48 And yet I think there's so much that happened that just feels like authoritarianism run amok. 07:57 Andrew Cuomo said this week that if Momdani wins, quote, Trump will take over the city and it will be Mayor Trump who runs the city. 08:06 This is probably not true. 08:11 But on the other hand, it's not a ridiculous political attack, right? 08:20 The idea that if Mamdani wins and Donald Trump has made it clear he does not like Mamdani, then Donald Trump will attempt to punish the city of New York for electing a politician he does not like. 08:36 And that we're now at a place where that is just a totally acceptable. 08:41 Sure, of course. 08:42 Of course, he would do that. 08:44 Sarah Longwell Can I just quickly flag, though, how insane of an argument that is from Cuomo? 08:50 Elect me because the authoritarian likes me better than the other guy. 08:53 JVL I mean, it's it's not. 08:56 Sarah Longwell Shut up, Cuomo. 08:57 JVL It may be the best argument he has. 09:01 Sarah Longwell Uh, I don't know. 09:02 I, I just, I think it, I think it demonstrates just how cynical and nihilistic Cuomo is, uh, to try to, he's basically like threatening New Yorkers with Trump to get himself elected, even though he's Trump's preferred candidate. 09:21 Gross, gross, gross. 09:22 Okay. 09:22 Like we've been saying, I'm anti, anti-Mimdani. 09:25 and i'm i'm hard anti-cuomo uh that said i i do when we were in new york recently i was talking to someone in new york and i was asking them like i you know i'm surprised you guys have avoided the national guard so far like everywhere else they've been going in to every major uh liberal city or at least saber rattling about it so why not new york uh 09:54 Why do you think? 09:56 I suspect that would be in a way where you could sort of get away with Chicago because A... 10:10 whether it's true or not, the perception of Chicago as like very, very like a place of deep crime, I think is enough of a national story that they can sort of use the pretext of that. 10:22 It's also like the, and then DC is, 10:25 I was going to say, like, the media is here, but we also have home rule complications that make D.C. a little bit different. 10:34 You go to New York, you are full-on in the national media. 10:38 You are in the place where the finance and media live, and... 10:44 I wonder if there's something about New York that is causing him to not do that yet. 10:51 But maybe it's true that as soon as Momdani is in there, they will do the National Guard. 10:56 JVL I mean, I think it's as simple as Eric Adams is mayor and Eric Adams is a Trump ally. 11:01 Sarah Longwell Yeah. 11:02 JVL Right? 11:03 I think that's right, yeah. 11:05 The pretext, Trump wants pretexts, and so the pretext to move on New York would be, well, they elected a socialist. 11:13 and we got to stop socialism. 11:15 Look what this horrible socialist has done. 11:17 Right. 11:18 And then it'd be looked, everything was fine in New York when Eric Adams was, uh, Eric Adams, who I've just partnered or whatever, you know, uh, when he was, when he was in office, everything was fine, but it's all gone to hell since you elected this socialist. 11:31 And, uh, and then they'll go, I mean, that's just what I assume. 11:36 Um, also it could be, they can't eat two major cities at the same time. 11:42 I mean, Chicago is sucking up all of federal resources. 11:47 I don't think they can do Chicago and New York simultaneously. 11:50 I think they have to do these things in serial. 11:53 Sarah Longwell happens when there's like a real emergency. 11:56 Like the kind of thing the National Guard would do before it was planting trees in major cities. 12:01 JVL You mean like a no kings protest that they have to go break up? 12:04 Or do you mean something different? 12:06 A different kind of emergency? 12:06 What kind of emergency are you talking about? 12:08 A political emergency? 12:09 Or like an actual natural disaster? 12:11 Sarah Longwell I meant like a natural disaster. 12:12 JVL I can tell you exactly what will happen. 12:15 If the natural disaster is in a blue area, they won't show up. 12:20 And if it is in a red area, 12:22 They will show up belatedly and none of the voters there will blame them. 12:26 They will blame the Democrats somehow. 12:29 It'll be somehow it was AOC's fault that the National Guard didn't get to Asheville, North Carolina or something. 12:37 Because that's how those people are. 12:39 Sarah Longwell All right, keep going. 12:40 What are we getting? 12:41 We're getting progressively darker, you say? 12:43 JVL Yeah, we're going to get progressively darker. 12:47 Pentagon has purged the press corps. 12:50 There are only three American news outlets which are now credentialed at the Pentagon. 12:56 Sarah Longwell One of them's OAN. 12:58 JVL One of which I have written for. 12:59 Sarah Longwell Oh, The Federalist? 13:02 Did you write for The Federalist? 13:04 JVL I did. 13:04 Sarah Longwell What'd you write? 13:06 JVL I wrote a piece, a long piece, about how Prince Hans was not actually the bad guy in Frozen. 13:19 Sarah Longwell Are you serious? 13:20 Are you telling me the truth right now? 13:21 JVL Yeah. 13:26 Okay. 13:26 This is the piece I wrote for The Federalist. 13:28 Sarah Longwell Man, I got to tell you, we were living in a different world when you just had the time to sit there and opine on the frozen characters. 13:37 JVL My case for people listening is not that... 13:41 Of course, Prince Hans is the villain in the movie as we saw it. 13:45 But if you go deep in the early versions of the Frozen script, the reason Elsa has these powers is because she is cursed. 13:57 Like there's a prophecy. 14:00 And they did away with the idea of a prophecy. 14:03 And once there's no prophecy, which is powering her arc and all of the tragedy, they had to create a villain, right? 14:12 Because the prophecy was the villain. 14:15 And so that's why they took... 14:18 So Prince Hans, his character, he takes a turn that is basically totally unearned. 14:23 Like he is a genuinely like, Hey, Prince Hans is great. 14:25 And when he turns and goes bad, you're like, wait a minute, that feels out of left field. 14:30 The answer is it was out of left field. 14:32 It's because as he was originally written, he wasn't the villain. 14:35 Sarah Longwell Anyway, it does feel out of left field. 14:37 Now that you mention it. 14:38 JVL It's the only thing wrong with that movie. 14:40 It's a great movie. 14:41 Sarah Longwell Great, great music. 14:43 JVL Yeah. 14:43 Fantastic. 14:44 Um, anyway, that was the piece I wrote for the Federalist. 14:47 Again, it was a different time. 14:49 Uh, 14:51 So our American Pentagon press corps is the Federalist, the Epoch Times and OAN and six Turkish outlets, which are of various connections to a surprising number of Turkish outlets. 15:02 Is there twice as many Turkish members of the Pentagon press corps as American? 15:09 Sarah Longwell Well, we're all going to have to start reading the Turkish papers to find out what's going on at our Pentagon. 15:14 JVL So I don't know if you listened to Tim's Ann Applebaum show yesterday. 15:17 I assume you did. 15:19 She don't answer that. 15:21 Don't answer that. 15:23 She made a point, which I had not considered, which is that the Pentagon and the Trump administration knew full well that no American news outlets would agree to this. 15:38 And the whole point of it was to get them out of the building. 15:42 So that we now have official state-sanctioned media outlets. 15:48 Because that's what the Federalist and the Epoch Times and OAN are now. 15:52 They are people who, they will report only the administration-approved news. 16:01 No different than, you know, Jing Zhao or Pravda or anything like that. 16:05 So they've gone from being like, you know, obviously totally alive. 16:08 And maybe this is a distinction without a difference. 16:11 But from just ideological allies and political allies to wholly owned subsidiaries in terms of what they are allowed to report because they've signed a pledge. 16:24 I thought that was pretty sinister. 16:25 Sarah Longwell Well, it is sinister. 16:27 It's interesting, this idea that they wanted them out of the building on purpose. 16:31 Because I will tell you, I am surprised at how many people didn't sign it, including people like the Washington Examiner. 16:40 Um, and because we've, we've had a real problem. 16:44 I mean, Trump has been doing the thing where they kick out reporters who have been reporting stuff, right? 16:51 They're going after the wall street journal and the media has been 16:57 Has done nothing to defend themselves, their professional allies, right? 17:04 Their colleagues. 17:06 And I actually was genuinely viewed it as a positive, like a net positive. 17:12 JVL Oh, don't do that. 17:14 Sarah Longwell That they were unwilling to sign it. 17:17 JVL No, this wasn't principled. 17:19 I mean, what distinguishes Newsmax from OAN or The Federalist or The Epoch Times is that those three outlets which are on site are judgment-proof because they have no assets. 17:35 Like, those... 17:37 those are fly-by-night operations with nothing for anybody to ever come after. 17:41 Whereas if you are Fox or the Wall Street Journal or even Newsmax, Newsmax is a publicly traded company, um, 17:49 you can get yourself into legal trouble, right? 17:52 You sign on that pledge and you wind up breaking it somehow accidentally. 17:57 And now you are opening yourself up to legal action and you have assets. 18:02 That's what this is about for them. 18:04 They're like, no, no, we can't do that. 18:06 We'll still be friendly to the administration. 18:07 This isn't about principle, but like we do have to protect our assets. 18:12 And so they're, they're, they are not judgment proof and you know, OAN and the Epoch Times and the Federalist are. 18:20 Sarah Longwell Okay. 18:22 Well, all right, you've convinced me that that is deeply sinister. 18:26 And actually, the only thing I'm going to yes and on this is it does layer into what is to me, sometimes people ask the question, you know, what keeps you up at night? 18:37 What are you most worried about? 18:39 And for me, it is, and it's happening slowly, but it's happening really, really clearly. 18:46 The media legacy and independent and new is increasingly owned by Trump sympathetic allies, people who are trying to curry favor with Trump. 19:00 And that goes for Paramount and the Ellisons who are. 19:03 who have purchased Paramount, which owns CBS. 19:06 They are trying to buy Warner Brothers. 19:07 It goes for Elon Musk, who owns X, and Mark Zuckerberg, who owns Instagram and Threads and Facebook. 19:18 It goes for many of the people who are working on the AI slop that is coming our way. 19:24 TikTok was just sold to Trump's allies. 19:26 Like, 19:27 The extent to which the media ecosystem is becoming a wholly owned subsidiary of Trump and his allies cannot be overstated. 19:38 And that has the very long term ramifications. 19:44 And so this is another way in which the more they own the media or it is seeking Trump's approval, the more they feel emboldened to do things like this. 19:57 JVL Yeah. 19:59 All right. 19:59 I want to take you further down the hole, but we should do that behind the paywall. 20:05 So, I mean, what a great sell that is to people listening to the show. 20:10 If you would like to be even more depressed and hear even darker stuff, you should become a member of Bulwark Plus. 20:16 Sarah Longwell I will say, depending on what he's about to say, I may have an optimistic take, but I may not. 20:22 JVL Spoiler. 20:23 She's not going to be able to. 20:25 Okay. 20:27 Uh, last night news broke that Admiral Alvin Holsey, uh, the head of SOCOM was resigning his post one year into a three year term. 20:37 This is the guy who was, uh, overseeing the Venezuelan boat attacks, which there now have been six, which still nobody in the government has provided any legal justification for, uh, 20:53 On the one, the reporting so far, and it's very elliptical, is he raised questions about the legality of these operations. 21:03 And now he's not there anymore. 21:06 And I don't know. 21:09 Like, on the one hand, if he resigned out of principle because he thought that he was being asked to do things that were illegal, 21:21 That's good, I guess. 21:25 But what good is it if he doesn't say the reason I've resigned is because they were asking me to do illegal things? 21:34 Right. 21:35 I mean, to resign your office because you believe you are being asked to carry out illegal orders so that they can simply find somebody else who will do the illegal things? 21:47 What's the point of that? 21:51 No, I mean, like, I guess it's better than doing it because at least you make them try to find somebody else who will do it. 21:59 Maybe they aren't able to, but as we've seen, like, I remember, remember the, the, 22:07 the Republican MAGA lawyer who resigned, I think it was in, in New York, um, because she was being told to drop the Eric Adams case and email both came and they wound up firing like five people before he finally found somebody who would do it. 22:24 Like I did wonder like, well, the guy who eventually agreed to do it, who was a career, like why the fuck did he do that? 22:32 They should have made both fire everyone. 22:36 Sarah Longwell Yeah. 22:36 JVL and the idea that like people like there is a breaking point, like there really is a breaking point, you know, where people, you could have six people willing to stand up and get fired, but you will eventually find somebody weak enough that they come up with a rationalization for, well, you know, he's going to fire all 25 of us career attorneys. 22:56 And, uh, Jimmy just had a baby and Susie is, you know, would need it, has student loans and stuff. 23:04 Uh, 23:07 And the answer is she'll always, like, make them go all the way. 23:12 And in this case, like, I don't know, I feel reasonably confident they're going to find... 23:17 Another admiral who is not going to question legality of these things. 23:21 Maybe I'm wrong. 23:22 But there are a bunch of admirals. 23:25 Just like in any 12-member jury, you're going to find one person who's smart. 23:29 I'm sure there are at that 800-person meeting at Quantico with all the flag officers. 23:34 I'm sure you could have found 20 people there who would be happy to do anything Trump asked them to. 23:40 Sarah Longwell Yeah, I do think making them fire you. 23:42 This ends up being just sort of a... 23:45 Neither of them are great options, right? 23:48 Or you're going either way, right? 23:52 You know they're going to get rid of you if you don't do what they say. 23:55 The question you're asking is whether it's better to quit or resign in protest or make them fire you. 24:04 And I felt really strongly about this with, say, like Chris Wray. 24:07 I think Chris Wray should have made them fire him, not just get out of the way. 24:15 How it works in these military situations could be different. 24:19 I mean, sometimes people understand what signals they are sending to the community that really understands this, right? 24:28 Like the military community. 24:29 Is his stepping down? 24:31 Is that actually sending shockwaves through people because he is saying, I will resign rather than following this order? 24:39 Which, again, for the military maybe feels... 24:43 Like, it might be a more correct thing than just disobeying an order. 24:48 And that people who understand the dynamic there better than we do see that and say, oh, wow. 24:55 Because this was big news that this guy was resigning. 24:59 JVL Yeah, and I think you're right. 25:00 I think it'll play very differently within the military. 25:03 To be clear. 25:05 I think it's absolutely proper for the head of SOCOM to, if he believes he's being given an illegal order that he cannot carry out to resign his post. 25:15 Sarah Longwell Yeah, like I sort of want to say good on this guy before we criticize or before we do the tactical analysis of whether or not it's the right thing to do. 25:23 JVL But you very shortly then have to explain why you did it. 25:27 Because otherwise, if you do it in such a manner as to give them cover, which is what he's done, 25:33 Like, you know, he gave a very noncommittal thing. 25:37 Like, if he is not leaking to the press to explain why he did this, I mean, then just resigning and playing nice about it. 25:49 I'm not sure that there's any that really creates any difference in the world than just doing the illegal things. 25:56 Sarah Longwell So, well, I don't know about that. 25:58 I mean, that makes a difference to his conscience, which I think is fair. 26:02 And that means that he now has credibility if he chooses to criticize. 26:06 Although I got to say, this is a bigger problem. 26:09 And I do think it goes to how scared people are of Trump. 26:12 We've seen a ton of resignations at DOJ. 26:16 We've seen, you know, like when Comey's daughter resigned, like there's all these people who've resigned instead of, but we don't hear from them. 26:24 We heard from some of the lawyers early on who left some of the law firms, the big law firms that capitulated to Trump. 26:32 But there has been no real effort by people to sort of go public in a way. 26:39 And I think this is where people sometimes because, and this was the problem with the generals. 26:45 Norms. 26:46 JVL Their norms, they're clinging to our norms that we love so much. 26:49 Sarah Longwell They have their professional standards that dictate things. 26:52 And so they're trying to not violate their professional standards. 26:57 And this is where you just kind of get to the, don't you know what time it is? 27:01 JVL The authoritarians are counting on people adhering to their professional standards while they don't do theirs, right? 27:08 And it is not a case of like, oh, you have to sink to their level or anything like that. 27:17 But it is more of like somebody is trying to use norms against the system in order to reorder the systems that there will be no norms. 27:29 Sarah Longwell Yes. 27:30 JVL And you have to recognize that and be willing to attempt to counteract it. 27:36 Like, I just don't know. 27:38 Sarah Longwell I'm with you, bro. 27:39 We are we are on the same page so far. 27:42 JVL All right. 27:42 And then we have the IRS where Trump made clear that they're reordering the IRS. 27:48 They have drawn up an enemies list to target. 27:52 And it's all being done in public. 27:54 Like, that's the funny part is that it's not like they are that this is some super secret operation that then it was going to take ProPublica doing 12 months of investigation to tie all the pieces together and go, wait a minute. 28:07 It looks like they've actually been targeting all the drama. 28:11 It's like, yeah, and then we're going to go after all the people we don't like. 28:15 Sarah Longwell Okay, so this one I've got a lot of opinions on. 28:18 And this is a real, real step in a terrifying direction. 28:22 Let me tell you why. 28:23 Our country has always been very careful about weaponizing or utilizing the IRS. 28:34 Because the second that you start selectively going into your enemy's finances and businesses... 28:43 or shutting down nonprofits, taking away their 501c3 status, their 501c4 status. 28:52 In recent history, there was only one thing that I've seen where the IRS, the neutrality of the IRS is like, 28:59 as important as it gets to having a functional rule of law and democracy. 29:05 Like people think about the IRS. 29:07 JVL It is, it is like the state sanction for the use of violence, right? 29:12 And the way that I don't want to sound like a libertarian to say that taxation is theft, but, 29:18 Because it's not, but it is an exercise of force. 29:22 Taxation is an exercise of force by which the government is the only entity which is authorized to go and take things from people. 29:32 Sarah Longwell That's right. 29:33 That's right. 29:34 JVL Right. 29:35 Sarah Longwell That's exactly right. 29:36 And this is where, right, one of the reasons that, just if you want to go back, why conservatives, libertarians, the low taxation arguments is in part about the state being able to just decide what it takes from you. 29:50 It's why we oppose things like eminent domain, where the government can just be like, I'm taking your house because it's in this thing that we want to do something else with. 29:58 And 29:59 For me, part of why, when people are like, how, why were you a conservative? 30:03 It always mattered to me to limit the power of the state, right? 30:08 Even with things like criminal justice reform, which I was a supporter of in part, right? 30:13 One of the reasons that if you get me to really tell you, like if one of the things about the death penalty, the one thing, or the thing that I would say is my, if I had to argue against it, it would be that if the state has the power to take life, 30:29 It can only do it if it perfectly never, ever makes a mistake. 30:34 JVL And if it does perfectly ever- Anybody who's been to the DMV who also supports the death penalty, it's just like, I don't understand it. 30:42 Sarah Longwell Yeah, the DMV's getting better. 30:43 But point taken, point taken, the enormous power of the state is being used to take your money, okay, that you earn. 30:54 And this is the price we pay to live in a civilized society. 30:58 It is the kind of compact- 31:01 It is at the center of the compact between the government and the citizen. 31:07 And so you start messing with that compact, you are undermining just something at its core. 31:15 And for people who don't know this world of 501c3s and 501c4s and all this stuff, 31:22 There is a lot. 31:23 And you can have fights about it. 31:25 You can have fights about whether or not certain things should be anonymous, what should be public, whatever. 31:32 And we do. 31:34 There's lots of laws around what is public, what is private. 31:38 And people make decisions based on what the rules are, right? 31:42 And if... 31:45 Donald Trump starts to weaponize that. 31:47 And like what they are doing is they are bulking up, not the people who figure out how to like make sure taxes are paid and their refunds are given. 31:54 JVL They've cut that, right? 31:56 That stuff got doged. 31:58 Sarah Longwell It's the investigative part so that they can stick them on donors and organizations that oppose Trump. 32:06 They are trying to shut down the mechanism by which people, and let's say a 501c3, those are not political, right? 32:12 Those are public education. 32:14 But let's say there's lots of groups who do public education around, I don't know, the central tenets of democracy. 32:22 And so Trump is like, we don't want people explaining to the public why the rule of law matters, why pluralism matters, why freedom of speech matters, all while we're trying to shut those things down. 32:37 And so the level of chilling effect, right? 32:40 What they want is they want to send a signal to Democratic donors. 32:43 Crosstalk Right. 32:43 Sarah Longwell We'll know who you are. 32:44 Crosstalk That's what it's ultimately about. 32:45 Sarah Longwell We'll know who you are. 32:47 And so they don't give to the organism. 32:48 They are trying to shut down the mechanism by which people... 32:52 organize and develop a strategy to defeat Trump. 32:58 And so this is a story that should not fly under the radar. 33:02 This is as important as anything could be. 33:05 And I got to tell you, my team had it right away. 33:07 So back in the Obama years, when I was still a conservative, there was a story about Lois Lerner 33:14 I remember her. 33:16 She was the head of the IRS at the time. 33:18 There was allegations at the time that they were, and this was the allegation, that they were basically putting Tea Party groups or conservative groups through extra scrutiny to get what is called your 501c3 status, what is your charitable nonprofit status. 33:38 And at the end of the day, there was an investigation. 33:41 She had to go in front of Congress. 33:43 She had to do it. 33:44 And we were all mad at the idea that if you were a conservative group, you were getting this sort of extra scrutiny or they were slowing down how fast you could get your 501c3 status. 33:56 At the end of the day, they were found to have behaved sort of like the takeaway was they didn't break any laws. 34:04 It wasn't, you know, but it was a little, but it was kind of unprofessional. 34:09 And they had to do a public apology. 34:11 Like, that's right. 34:11 So they had to apologize for doing it. 34:13 Republicans lost their minds during that particular controversy. 34:18 And there are quotations. 34:20 out there from so many of the people who are still in office today, like Ted Cruz. 34:26 Ted Cruz is like, if somebody, a Republican, were to go after left-wing groups like this, I would be the loudest. 34:34 I would be the first to demand that that not happen. 34:40 Donald Trump himself, I would never weaponize the IRS. 34:44 JVL Kind of like you can't hold a vote on a Supreme Court nominee the year before presidential election. 34:50 Kind of like that? 34:52 Sarah Longwell Actually, I think this is much clearer. 34:53 J.D. 34:54 Vance. 34:55 J.D. 34:55 Vance is like, you do not have a country if you have a weaponized IRS. 34:59 They are all out there on this issue. 35:01 And now, I want to make it clear, because I'm going to get people are going to be like, Sarah Lois Lerner did nothing wrong or whatever. 35:09 I think that they, those were like, 35:12 some poor judgment calls. 35:13 There were poor judgment calls. 35:14 There were some like some unprofessional stuff where people are like, nah, they're pulling aside these groups and they're looking at them a little harder. 35:20 That is so different though, than what we're talking about here. 35:25 Like if you lost your mind about that as a conservative, just about, 35:29 JVL So prospectively, whether you'd be grant tax-exempt status, this is we're going to go after and try to destroy people and take their money from them. 35:38 Sarah Longwell Take their money. 35:39 But this is what they want to do. 35:41 They want to take Harvard's nonprofit status so that people cannot donate to Harvard for its educational whatever. 35:50 The extent to which this – and look, if you want to change the rules – 35:55 So that you can't talk about certain things using 501c3 because they are tax-exempt. 36:02 That's fine. 36:03 JVL Change the rules. 36:04 Sarah Longwell Change the rules. 36:06 Pass a law. 36:08 You do not just suddenly send in a weaponized tax force to go after Americans. 36:14 And this is where they're just going to start looking for anything they can find. 36:17 It's like what they're doing to Tish James. 36:19 where it's like they take a sort of common practice that, again, many people in Trump's cabinet have done, and they try to turn that into, and maybe that practice is not great. 36:36 Okay, well then, enforce that. 36:40 It's sort of like it's one of those things where nobody enforces that thing. 36:42 And so this is completely different. 36:46 JVL I want to underline the compact part because I've had people say to me like, oh, resistance people should just refuse to pay their taxes. 36:56 And I'm like, yeah, good luck with that. 37:00 But the compact is that you pay your taxes no matter who is in office or what that administration plans to do with those monies. 37:11 Because we recognize that, again, the taxation power is being applied fairly and is not being used as a form of punishment. 37:23 And that is the reason why we all pay taxes even when we don't like where the money is going to and we don't like the administration doing it, right? 37:30 That's the compact. 37:32 Once you blow that up and you blow it up, again, not even subtly, but openly, 37:40 Like, I don't know. 37:41 Well, how do you tell? 37:43 I mean, the only reason then that people should be willing to pay taxes is to avoid going to jail like that. 37:49 And I don't know how you walk back from that. 37:51 I mean, if this goes through and they're able to actually start doing what they say they would like to do. 38:00 Well, what is the answer? 38:03 Sarah Longwell I do not care for this particular thing that you do where you're like, how do you walk back from that? 38:09 Like, cause you end all of these like insane things with this idea of like that we can't, but of course you can, you, you, you explain to people what is happening and you say you like, this is where my, my great hope, 38:22 For Democrats who win in 2028 is that they roll back executive power. 38:25 They explain the abuses of power of the Trump administration and they restore. 38:28 And in some cases, you're going to have to codify norms into laws. 38:33 Like this is what they should have done during the Biden years. 38:36 Huge missed opportunity. 38:37 Like there are ways to walk it back and get back to the place where we just know now. 38:41 that you can't rely on the norms and you have to have laws that say the government can't do this. 38:45 But can I, just going back to this idea of the compact and how fundamental it is and why this one is something that people should take really seriously. 38:55 Do you remember how America started? 38:56 Do you know why we're here as a country today? 39:00 It is because people felt like we were being taxed without being properly represented because we were being taxed by the British while we were over here. 39:08 And so it was a taxation without representation, which is still what happens in DC, by the way, which is why we should be, which is why we should have our statehood. 39:17 But it's funny, but we make sort of an outlier joke about it. 39:21 It's on the license plates. 39:22 Taxation without representation is like on the DC license plate. 39:26 But the idea... 39:28 that you can start to mess with the taxation part. 39:30 Like this is for Americans. 39:33 We said no to this. 39:35 We fought a revolutionary war and built a country around the idea that if we were going to be taxed, it was going to be to the good of this place right here on rules we all agreed on, which is why weaponizing the IRS has been something that no matter how crappy most administrations have been, that like the biggest scandal you could get to 39:58 was, I don't know, we're going to look a little harder at some of these groups and make sure they are, because this is why they were looking at them. 40:08 I think that Republicans actually did overblow the Lois Lerner stuff, but it also was wrong. 40:13 I sort of want to say both those things. 40:14 They shouldn't have done it, but the reason they were looking harder at them is because the Tea Party was becoming a pretty explicit 40:20 uh, political group, right? 40:23 It was very political. 40:24 And so to say that they were just doing public education around, uh, why low taxes are good. 40:31 I do think like it is fair for the IRS to be like, well, is this a charitable organization that's just going to do education or, uh, are they an astroturf political organization? 40:43 JVL Yeah. 40:44 Sarah Longwell Yeah, although, to be fair, I still think that's, I want to say, I think that's garbage still. 40:49 Like, a lot of places, like, you get to do education around all kinds of issues. 40:54 I had somebody respond to me yesterday that's like, well, you can't, you shouldn't get tax-exempt status if your organization is fundamentally anti-taxes. 41:02 And I was like, well, that's a garbage position. 41:05 JVL Yeah, I don't think that agrees. 41:06 I don't agree with that. 41:07 Sarah Longwell course not that is it's like it's a perfectly legitimate um okay we our position is that uh that taxes are bad and we're gonna make a case for why taxes are bad and you know or or that we think the national debt is too high and so we are gonna make the educate the public about how high the debt is like all and all of those things can be tax exempt and educational they completely fall within squarely within the rules i just i want to make clear that like it was it was like 41:36 wrong-ish but also and overblown by republicans at the time but also shouldn't happen like it should be a sacred thing that you are very much like stay out of the tax the taxes part and that you would never let it get partisan the second that you don't have neutrality in the irs you really do the things really do start to crumble 41:59 JVL All right, two more things. 42:01 Two more things? 42:02 One the darkest and one something nice. 42:04 So a little cherry on top for the end. 42:06 I want to just take back to the Venezuelan boat attacks. 42:09 And so the administration's explanation for why they have done what they are doing is that the boats they are attacking and the people they are killing are narco-terrorists. 42:27 Therefore, they are allowed to target them with military force and kill them. 42:35 And they are not required to adhere to any laws surrounding the exercise of war or the arrest of people committing crimes. 42:48 They can simply summarily execute them. 42:51 The administration is also saying that the people who are going to show up to the No Kings protests this weekend are terrorists. 42:58 Because they call them Antifa and that they are pro-Hamas and Antifa is now a designated domestic terrorist organization. 43:08 Is it all concerning to you that the administration's position is we can kill terrorists anywhere we want? 43:17 And also you people over there with the nice gardening hats, you're terrorists. 43:21 Sarah Longwell Yeah. 43:22 JVL I mean, I assume they won't kill anybody this weekend, but. 43:28 Like, I don't know. 43:28 Am I being crazy alarmist JVL or. 43:31 Sarah Longwell No, I actually I don't have a lot to I'm not going to push back on this one. 43:35 This is the they're the them going from the Charlie Kirk murder talking about rhetoric. 43:43 And how we have to tone down the rhetoric and that the left did this by talking about fascism only for them to turn around and designate the No Kings protest as a hate rally filled with Hamas and other terrorists while they are using terrorism as the reason that they can illegally bomb things. 44:06 Like, no, you're 100% right on this one. 44:09 JVL Wow. 44:09 All right. 44:10 Well, then let's get to the good stuff. 44:12 I found your 2028 presidential candidate. 44:15 Sarah Longwell Okay, great. 44:16 JVL His name is JB Pritzker, and you are going to be all in on him all the way. 44:21 It does not matter what he says or does because he's reported $1.4 million in gambling winnings. 44:28 And if that doesn't get the Sarah Longwell seal of approval, I don't know what does. 44:34 Sarah Longwell I'm obsessed with this story. 44:36 I should be paying attention to other things, but the fact that JB Pritzker... 44:41 went to vegas and won 1.4 million dollars so i am just desperate for something what did he tell me what did he bet well that's my question but like what was he putting was he playing blackjack yeah he said he was playing blackjack he said he was playing blackjack and oh and there was an and something else baccarat no no um however 45:06 Do you know what you would have to... 45:07 Okay, so when you do... Is he betting... What's 1.4? 45:11 Is $700,000? 45:13 JVL Do you think he bets seven large on a single hand? 45:20 Sarah Longwell Because the balls of that would require... Do you know how hard it is to go up to that? 45:26 You can get hot cards, but was he betting... Just think about what you would have to bet to sort of double over the course of an evening. 45:32 Is it 20 grand a hand? 45:35 like 10 grand a hand. 45:37 JVL I play $10 a hand. 45:39 Have you ever been into the high roller lounge? 45:42 Sarah Longwell I mean, I've walked through it and been like, and I immediately get, um, like that. 45:50 I, I, if you let me, I think I'd have a gambling addiction. 45:54 Um, but I get, I get scared, right? 45:56 This is why it's good is that if you go in the high roller lounge and you see the stakes, the minimums, the table, what are the minimums like in a blackjack game? 46:05 JVL At a table in the high. 46:06 Sarah Longwell It might be like a thousand dollars. 46:11 JVL Right. 46:12 It seems like a lot. 46:15 Sarah Longwell It seems like a lot. 46:16 So like, let's say you sit down and you just do like $5,000 hands. 46:20 Let's say you are a billionaire. 46:22 And so what is $5 to you and I is 5,000 to them. 46:27 I don't think he could have even been betting that low because to win, to get to 1.4 million is, 46:35 you'd have to bet a lot. 46:36 And the thing about blackjack is like, you go up and down. 46:39 So like, I believe he could have gotten hot, but like usually that they, they take it facts. 46:44 Like what was he doing? 46:45 I want to know. 46:46 JVL All right. 46:47 So here's my question for you. 46:50 What is the answer to what was he gambling on that would make you like him the most? 46:57 So let's pretend we don't know it was blackjack, but what is the answer that you, that when, if you found out you would just go, that guy's awesome. 47:07 Sarah Longwell Uh, I think it is that he, so some people I think like, like the big stakes, like he took a 50-50 chance, right? 47:18 And he just like went big. 47:19 But for me, as somebody who likes to play blackjack in like 14 hour streaks, right? 47:25 it would be the idea. 47:28 JVL Like somebody's got Michael Jordan. 47:30 Sarah Longwell It's like my sister's behind me. 47:31 Uh, and suddenly I look up and she's like, where have you been? 47:35 And I'm like, what? 47:35 And she's like, it's four 30 in the morning. 47:37 What are you doing? 47:39 And I'm like, well, I'm here with my friend, John and me and John have been playing together for hours. 47:43 And you know, so it's like, 47:45 Where it really is, is like, did he sit there for such a long time? 47:50 Has he been drinking, right? 47:52 He's not drunk, but he's been drinking for 10 hours straight. 47:56 He's smoking several cigars. 47:58 The dealer's got to turn the fan into his face because he's sitting there in a cloud of smoke. 48:03 He's hunched over and he's like, we're going, we're going. 48:06 And does he, here's the thing. 48:07 Is he a table player, right? 48:09 Does he just sit there by himself playing with the dealer? 48:12 That is okay, but it doesn't make me like you better. 48:14 What makes me like you better is when you're a table player, you've got your people around you, you've all built a camaraderie, you're all playing against the dealer. 48:21 Yeah, that's right. 48:23 That's the best part about blackjack. 48:25 JVL So for me, the answer is that he would have done it on a crazy bet. 48:33 So he was playing craps and he put 50 grand on a heartache. 48:38 Or something like that. 48:40 That is the level of like, oh, I like that. 48:43 Oh, I like that a lot. 48:44 Sarah Longwell So I never play this. 48:45 So like mine, like when my blood really gets pumping, it would be he split his eights. 48:51 And then he got a couple more eights and like, he's having to double his bets and it just keeps getting bigger and bigger. 48:57 Right. 48:58 And like everybody's people from other tables are coming over. 49:01 Cause he's been splitting. 49:02 He's now been splitting his hands multiple times. 49:05 He's not, so he's got doubling down, splitting, doubling down, splitting, doubling down. 49:09 That's right. 49:10 Uh, and then he's asking for the cards down and then the dealer buss and the whole place goes bananas. 49:20 JVL Or the other thing is, if he was counting. 49:25 If he was counting cards, because he's secretly like an MIT-level genius who is running the math in his head so that he knows to alter his bets when the count is in his favor, so that he's betting small when the count is not great for him and then very large when the count gets good for him, that would also make me like him even more. 49:47 Sarah Longwell Interesting. 49:47 Yeah. 49:48 JVL I like that. 49:50 I like the people who are either completely cerebral mathematicians or just balls to the wall. 49:55 Yeah, let's put $50,000 on the number 17 on the roulette wheel. 50:00 Sarah Longwell Oh, 35 to one payout. 50:02 Here's the thing. 50:02 I will say as much as I like that, he's just he's a guy that plays cards. 50:07 There is something about being a billionaire that just makes it less fun. 50:11 For me, like there's, you gotta, that's why, that's why I get that feeling. 50:16 It might tell me when I go into the high stakes is because I'm like, do people lose this much money? 50:21 That's so frightening. 50:22 Do people bet this much money? 50:23 That's crazy. 50:26 It's fun when it's like, I won $400. 50:29 Can you believe it? 50:30 JVL So this is a very funny thing. 50:33 The most I ever won at a single time in a casino was actually I was playing craps and I went on a real heater of a run. 50:45 I was betting the $5 minimums, but there was a dude across the table from me who was throwing down like $100 a bet and was putting bets all over the place. 50:57 And I made him like $5,000 over the course of five minutes. 51:01 He'd take you to dinner? 51:03 He threw me $100 chip at the end. 51:06 And that was the most I've ever won. 51:08 I was like, oh, I'm done for the night. 51:11 Great. 51:11 I didn't even do it by winning. 51:12 I did it by helping somebody else make money. 51:15 That was great. 51:16 It was just a tip. 51:17 Sarah Longwell I'll tell you the best one that I did is I went to Vegas with my sister to go wedding dress shopping. 51:26 And I won like $1,100. 51:29 It was the most I ever won and went and bought a wedding dress with it. 51:33 JVL That's awesome. 51:35 Fantastic. 51:37 Well, I'm going to use that to keep me warm. 51:40 You know, the tanks roll in. 51:43 Sarah Longwell Yeah, where everybody's gambling on our democracy right now. 51:45 That is not fun. 51:47 JVL Rebecca, take us home. 51:49 Rebecca Black 7 a.m. Waking up in the morning. 51:51 Gotta be fresh. 51:52 Gotta go downstairs. 51:54 Gotta have my bowl. 51:55 Gotta have cereal. 51:56 Seeing everything. 51:57 The time is going. 51:58 Ticking on and on. 51:59 Everybody's rushing. 52:00 Gotta get down to the bus stop. 53:36 Yesterday was Thursday, Thursday. 53:41 Today is Friday, Friday. 53:45 We, we, we so excited. 53:48 We so excited. 53:51 We gonna have a ball today. 53:54 Tomorrow is Saturday and Sunday comes afterwards. 54:00 I don't want the sleeping today. 54:04 Soundbite GRB, Rebecca Black. 54:05 So chilling in the front seat. 54:07 I'm driving, cruising, past the lanes, switching lanes with a car by my side. 54:13 Passing by, it's a scooper in front of me. 55:12 Rebecca Black to the weekend.