The Bulwark Podcast - Tim O'Brien: The Hollow Men

Episode Date: October 4, 2023

Kevin McCarthy aspired to the speakership for his resume, not because of legislative talents. In the end, he was a victim of hubris. And in NYC, Trump is acting like Yosemite Sam, shooting himself in the foot, and fearing the loss of Trump Tower. Tim O'Brien joins Charlie Sykes. show notes: https://www.bloomberg.com/opinion/articles/2023-10-02/new-york-says-trump-committed-fraud-now-comes-the-price-tag?srnd=undefined

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For the first time in American political history, a sitting speaker has been ousted by members of his own party. Actually, it was bipartisan. Eight Republicans joined with all Democrats to throw Kevin McCarthy out of office. This is the way it went down. This is the way it sounded. The yeas are 216. The nays are 210. The resolution is adopted. Without objection, the motion to reconsider is laid on the table. The office of Speaker of the House of the United States House of Representatives is hereby declared vacant. And so with that, Kevin McCarthy, who was once the future of the Republican Party, by the way, Tim O'Brien joins us from Bloomberg. Tim, do you remember that book, Young Guns? That might be the most cursed cover ever.

Paul Ryan. Yeah. Eric Cantor. Kevin McCarthy. I mean, Kevin McCarthy hung on the longest because he was willing to crawl the furthest, but it kind of caught up with him. It's like that. Remember that Time Magazine cover that had Alan Greenspan, Larry Summers, and Bob Rubin

on it, and they were the committee to save the world. And it came out about seven years before the financial crisis hit. It's one of those things. If you do a cover like that, you're going to doom yourself. That's right. It's sort of like being on the Sports Illustrated cover, but on steroids. All right. So Kevin McCarthy delivers his swan song last night. You know, this has moved so quickly that at the beginning of the day yesterday, it was not absolutely certain that he was going to lose his speakership, but there was still the possibility that the Democrats were going to bail him out. Democrats kind of took a look at Kevin McCarthy,

played a couple of videos of Kevin's greatest hits and said, drop dead, Kevin. So that didn't happen. Well, he also dumped on them over the weekend. Well, that's right. That was the video they played. Kevin's greatest hits are pretty extraordinary. We can get into that in a moment.

But I mean, there was still, even after he was ousted, there was a non-zero possibility that he could make a comeback because like who else, right? But he came out last night and said, no, he's pretty much done. So here's Kevin's post-defenestration swan song. You need two eight teams. Unfortunately, four percent of our conference can join all the Democrats and dictate who can be the Republican speaker in this house.

I don't think that rule is good for the institution, but apparently I'm the only one. I believe I can continue to fight maybe in a different manner. I will not run for Speaker again. I'll have the conference pick somebody else. I'll have the conference pick somebody else. And, of course, you had to take a shot at Matt Gaetz. I mean, at some point, the most despised member of the House of Representatives did get a scalp yesterday.

And Kevin McCarthy had to address the guy that made the motion the day before to vacate the chair, Matt Gaetz. You know, it was personal. It had nothing to do about spending. It had nothing to do about everything he accused somebody of he was doing. It all was about getting attention from you. I mean, we're getting email fundraisers from him as he's doing it. Join in quickly. That's not governing. That's not becoming of a member of Congress.

It is not becoming a member of Congress. And the thing about it is that Kevin McCarthy seems genuinely surprised to find out that there are people who are not interested in governing, that they actually are attention whores, that the incentive structure of Republican politics actually encourages people like Matt Gaetz. I mean, it's kind of interesting that it's taken this long for Kevin McCarthy to notice that, Tim. Well, I know I have, you know, the world's tiniest violin as I listen to his dulcet tones about his noble quest to retain his speakership and the fact that he- The institution. Yeah, but you know, he didn't bother counting votes apparently prior to Monday.

Counting votes used to be an age-old, you know, congressional practice that smart speakers like Sam Rayburn, going back in the day, made part and parcel of their armory. And then, of course, he defaulted to Gates got me. But Gates and that small clique of MAGA, you know, stalwarts had him from the beginning of his speakership. He cut a deal with them to become speaker that always left him beholden to them. And if he ever thought, you know, he could escape their clutches, simply by cutting a deal with him, he's either ignorant or naive, or maybe both. I don't think he's a deeply sophisticated man. You know, I think he aspired to the speakership

because it would look good on his resume, not because he bought any particular talent or legislative insight to the process. And so he's a victim of hubris at the end of the day, I think. You know, he wanted that speakership so badly. He wanted that portrait. He wanted that sign so badly that he was willing to, you know, make one humiliating concession after another. I hope that there's some part of him that has to ask, you know, was it worth it? Maybe it was, because now he is the shortest tenure of, you know, was it worth it? Maybe it was, because now he is, has the shortest tenure of, you know, as speaker since the guy who died of tuberculosis back in 1876. I mean, Kevin McCarthy, let's be honest about this. You know, I mean, he does his whole life. This is

what he wanted. And he's going to end up being kind of an asterisk, if that. So I guess part of the irony of all of this is that this was inevitable. He sowed the seeds of this during that 15 round vote, right? By making the concession, it was Kevin McCarthy that agreed to allow one member of the House to make the motion to vacate. I mean, he basically put the gun to his own head, loaded the bullets in himself, and is looking around going, this is really shocking. It's also interesting that he really did think that he could buy off the lunatic caucus. He really did think that if he gave them everything they wanted, if he gave them the seats on the rules committee, if he hugged Marjorie Taylor Greene, if he said, I will never abandon this

woman, if he launches the impeachment inquiry into Joe Biden that somehow this was going to buy him immunity from the fever swan. And it didn't work. And it's like, this is just shocking. This baby crocodile that I have been feeding all of this time, it just came out of the bathtub and it ate me. I wasn't expecting he would ever come after me. And now he's MAGA roadkill. He's MAGA roadkill. I mean, as I wrote this morning, it would be tragic if he's not so absolutely pathetic. You know, he turned himself into this hollow man, unloved, completely distrusted. So a couple of aspects of this. There are people who are suggesting today that, you know, the Democrats should have

been the adults in the room. They could have rescued him. And, you know, 24 hours ago, there was at least the prospect that maybe some Democrats wouldn't go along with this. They might vote present. But your thoughts about this, the Democrats were unanimous and unambiguous in saying, screw you, Kevin. Should they have bailed him out?

What do you bail him out for? What do they get from bailed him out? What do you bail him out for? What do they get from bailing him out? Now, I think one logical answer to that is they avoid Steve Scalise or Elise Stefanik stepping into the speakership. And arguably, both of them are just more sophisticated versions of the same Kevin McCarthy problem. They may be more intellectually adept. They may be more wily as legislators, but they're both shapeshifters, Stefanik in particular. I don't see either one of them being able to fend off the MAGA right that has held the speakership in captivity. I don't see anything else they gain

from protecting Kevin McCarthy. And if they wanted to just sort of talk to him and have sympathy, the fact that he then went on TV over the weekend and blamed the shutdown of the Democrats, when it was the GOP that was holding up negotiations, you know, that's part and parcel of the way that Kevin McCarthy rolls, by the way, he comes up with inane excuses for why everyone else is creating problems for him, when it's usually germinating from himself. You know, the other thing when I think about these things, when these politicos of either side are really grasping for office, there's that famous story of Lyndon Johnson when the Civil Rights Act and the Voting Rights Act

were being passed in the early 1960s. And one of his aides said to him, if we get behind these acts, the Democratic Party is going to lose the South forever. And according to Robert Caro, Johnson turned to his aide and said, then what's a presidency for? And I think you want some steel in your politicians, whether they're Republican or Democrat, for them to be in the mix, not simply to hang on to office, but to use the power they accrue in crucial moments to stand up and do the right thing. And Kevin McCarthy has never done that. He kowtowed to Trump.

You know, he condemned Trump for 30 seconds after January 6th and then went immediately back into the fold. He hasn't been able to govern his own caucus. And what have they put forward legislatively that would make the GOP look like something other than a bunch of rodeo clowns. Nothing. So he deserves to be left on the curb, I think. Well, I think this whole notion that the Democrats should have been in the adults in the room because whoever's coming might be worse, it's kind of a ludicrous argument, especially when

you look at what he's done. I mean, you run through the way that he's groveled in front of Donald Trump, the fact that he actually voted against the certification of the election after the mob attack January 6th. You know, for about five minutes, he did hold Donald Trump responsible, but then he ran down and really threw Donald Trump a lifeline. You know, when you think back over the last several years, Kevin McCarthy's decision to, you know, go on bended knee down to Mar-a-Lago was crucial, both for the Republican Party and for Donald Trump. Then the way he tried to kneecap the January 6th investigation,

how he... And that was a massive strategic error. Right, huge. On his part, by the way. Well, I remember he also lied. Remember, he had his guy negotiate the bipartisan commission, and then he reneged on it. And then he made the strategic error of not appointing anybody to it. But he undermined that again and again and again. I mean, the list of things that were really unforgivable sins from the point of view of the Democrats. I mean, cutting the deal with Biden and then walking away from it. You know, having this vote last week and then, as you point out, going on television and just this complete bullshit explanation. Well, the Democrats were the ones who wanted to shut down government. There was just no incentive for Democrats to clean up the mess. I feel like we've been here before, but the level of dysfunction and chaos,

it's kind of amazing. And all these Republicans looking around and saying, you know, to each other, like, geez, it's kind of shock that no nurturing and appeasing the lunatic fringe has led to this. I mean, who knew if only they had been warned about this, but how bad is it, Tim? And we're 44 days away from another government shutdown. This is not going to get fixed, you know? No, it feels to me like late stage Rome, you know, with, with sort of, you know, Trump is Caligula. Again, the processes of good governance and of civil society are getting really undermined amid the tragic comic kind of lunacy of events,

like what just happened to Kevin McCarthy, is I think a reminder that we're heading in 2024 to a very difficult place. I worry about violence, particularly in the swing states. You should be. I don't know where we get voters and the public to focus on the fact pattern and have disagreements about what to do with the facts, if you're conservative or liberal, but to at least acknowledge there's a common set of facts. I think we're surrounded by disinformation. And I think the GOP really, its energy is tied up in Trumpism. I don't think its voters are. I still believe, though, that the polling that has Donald Trump out in front is MAGA movement polling. I think there's a certain amount of that is informed by the most likely people to respond to polls, who are, I think, akin to the most passionate voters that come out in

primaries. And I think there's this, as there always is in US politics, this broad middle ground of voters, moderate Republicans, independents, conservative Democrats, who Trump pierced the veil on that group in 2016, enough to squeak by Hillary Clinton, but he never did again after that. He didn't in 2018, 2020, and 2022. He and his cohort in the GOP are not doing anything to court that group. Even voters who don't follow this stuff as closely as you and I do on a daily basis, they turn on television and they see this three-ring circus. They're not governing. You know, the putative leader of the GOP is in a courtroom attacking a clerk. The Speaker of the House is being guillotined

by his own members, and Biden passes drug price control measures. You know, so like, what do you want your government to do? Do you want it to try to do something, even if you may not disagree with the policy? Or do you want it to simply be a shambolic mess with a bunch of juvenile delinquents willing to burn the house down? And I think that's what a lot of where the Republicans are right now looks like to moderate voters. I want to get to the Trump trial, but it seems just unavoidable to not think about the way

that what's happening in Congress really is an outgrowth of the Trumpification of the party. Kevin McCarthy did everything imaginable to curry favor with Donald Trump to the point of even having, what was it, the jelly beans that he had in his office that were Donald Trump's favorite? I mean, it was just- Yeah. And then Trump called him my Kevin, my Kevin, as if he was a house pet. But at the moment when he's on the bubble, Donald Trump did not lift a tiny finger to save him. He was completely silent, which seems to me so on brand for the orange God King. He's such a mobster.

You know that Mike Kevin had to be on the phone at some point saying, you know, sir, sir, I'm, you know, I'm calling you with tears in my eyes. I know you're very, very busy with one indictment or lawsuit after another, but I could really use your help right now. And what did Trump let it go to voicemail? What, what happened there? You know, I was thinking of that moment in the Godfather at the end of the movie when Michael Corleone's brother-in-law comes in and they sit down and they have a little bit of brandy together. And Michael said, you know, I just need you to know, did you kill my brother, Sonny? Nothing will happen to you. I just need to know. And he said, yeah, yeah, I did it. He goes, okay, get out of my house. And then they put him in the car and they strangle him and he drives off dying. And I think about that. I have to imagine these conversations

with McCarthy and Trump were very similar with Trump saying, if you're here for me now, I'll be there when you need me. Just be here for me now. And then push comes to shove. He's like, sorry, I'm going to let these guys push you off the edge. Because that's how Donald Trump rolls. Loyalty is a one way street. And he will abandon people with the snap of a finger. I think he also had to see what was coming with McCarthy. I think he probably calculated that there was no way to rescue McCarthy. You are a long-term student of Donald Trump. And one of the things that I remember, I probably learned this from you, is that even though Trump demands this kind of slavish loyalty, he also despises the people who humiliate themselves.

There's a level at which the Lindsey Grahams of the world, he makes fun of them. He humiliates them in public. So is that part of this? That here's Kevin and thinking, he's going to like me. He's going to support me if I crawl on my belly. And Donald Trump is thinking, this guy's a loser. He's weak. You know, when I don He's weak. When I don't need him anymore, I won't need him anymore. I want you to suck up to me. But the second you suck up to me, I will despise you. Yes. Because it shows that it's so easy to bend you to my will. And I'm more intrigued by the people who joust with me. It's one of the reasons he's so fascinated with the media. He courts the media, but the second journalists,

you know, kiss up to him, he gets a little bit bored and he really actually is the most intrigued by the journalists who go to battle with him. You know, in his White House, in his first term, there were certainly, I would think of Mattis as a fairly good example. There weren't many of them, but Mattis never really kowtowed to Trump. And he ultimately walked. And I think that Trump respected Mattis. I don't know that he respected most of the other people in his cabinet. I think he respected Barr for a while, until he thought Barr turned on him. But Barr was strong minded and was his own person, even though he was also a Trump enabler. And so yeah, I think he had no respect for Kevin McCarthy. What will be interesting now is anybody who watched what just happened to McCarthy. You know, I think of somebody like Matt Gaetz, who in any other world in which social media

didn't exist, his political franchise wouldn't exist because he's entirely performative. And that's true, I think, of Marjorie Taylor Greene and Lone Bobart. You know, there's this group of people who just use video and social media to propagate themselves. If any of them think now, and I think Stefanik will be a very interesting case study, because she also, I think, has kowtowed in enormous ways to Trump and has turned her back on her own positions in order to do so. If they think that they're somehow different from McCarthy, they're going to have a lesson in store. Enjoy them for years with the Michelin X-Ice Snow Tire. Get a $50 prepaid MasterCard with select Michelin tires.

Find a Michelin TreadExperts dealer near you at TreadExperts.ca slash locations. From tires to auto repair, we're always there. TreadExperts.ca Okay, so there's a little bit of fan fiction out there. It's a quirk of the Constitution that you do not actually have to be a member of the House to be the Speaker of the House of representatives. And of course there's some buzz, let's make Donald Trump the speaker. And there are some reports, I don't know whether they're true or not, that Donald Trump is interested in it. Look, Tim, this is not going

to happen. I mean, there's not going to be 218 votes. Hannity, Hannity is pushing it. Is Hannity really pushing it? I miss that. Yeah, Hannity. Do it. This is what you want. This is what you deserve. You really do deserve this. Wow. What could go wrong? You know, when you asked earlier about like, why didn't the Dems play ball and preserve McCarthy? I think what Hakeem Jeffries did might be a sort of awakening on the part of Democrats that how many times are they going to come to the table to try to play ball when they're constantly slapped down by a party that

never plays ball? And imagine how delicious it would be actually if Donald Trump ended up speaker with a year to go to a general presidential election. I don't think that'll happen. I think, you know, but it's remarkable that it's even in the air. You know, this did seem like a departure for the Democratic caucus, because there's always been this asymmetry in the politics. The Republicans go, yeah, we're going to burn it down. We're going to blow it all up. And the Democrats, no, come on, let's find a deal and everything. And yesterday, it was like, no, we're going to do exactly what you guys would have done in this situation. So I mean, it is interesting that Hakeem Jeffries was able to hold together every single member of his caucus and they decided to go along

with ousting the speaker. I mean, this is kind of an escalation, wasn't it? I mean, this is a, is this like a new, new swagger for the Democrats? I think it's a new steeliness. I think the Democrats sometimes have been a little bit too much kumbaya on the American political landscape. And while the Republicans quietly chuckle, sure, sure, now we'll rip your face off. So I think there is an awakening around that. The other thing is, you know, they're going to get awesome campaign ads out of this, of the children in the garage with their matches, lighting them around the gas cans. I think they have to be aware of that too.

So one of the first things that the new acting speaker, Patrick McHenry, one of the first things that Patrick McHenry did as acting speaker, and of course he was chosen by Kevin McCarthy in this weird system we have here, was to send an email to Nancy Pelosi's staff saying, get out of the hideaway office in the Capitol. We're going to change the locks. I mean, that just seemed like, okay, what's the first thing you do? It's like you escalate the pettiness, but this is seemed to underline how absolutely bitter and personal they're going to get. So what was that about? Why go after Nancy Pelosi, who apparently was not even around? She was at Dianne Feinstein's memorial service and they decided to kick her out of her office.

I'm very curious about Pelosi's thinking in this. It's interesting to me. I don't know the answer to this. If she really wanted to come back to vote on this, I think she would have. And I think for her, there was a sense of decorum about it that transcended the politics of it, that she had been a speaker. She wasn't going to come by and participate in this process that defenestrated another speaker. I may be romanticizing that and ascribing things to her. She didn't think at all. But in that context, I wondered about that. And if you think about it that way, then it's okay, here's someone thinking about the institution and thinking about process and thinking about being an adult. And what's the first thing the romper room attendees do? They strip her of office space. It is so pathetic

and ridiculous. But it shows the new rules, right? That we're not going to recognize any decorum, any sort of civility. We're going to find the ways to hurt you at all, but humiliate you in ways like, I don't know, like, no, you're not going to get new stationery. No pens for you. We're not going to vacuum your offices anymore. And if you're, I mean, it's at that level. Okay.

So let's talk about the other big story because, look, you have been writing about Donald Trump for, we've talked about this every time. I keep losing decades, two decades. Since 1990. Oh my God. Since 1990. Okay, so let's talk about Trump's civil fraud trial and the way this is going. Yesterday was kind of dramatic, right? I mean, the New York judge presiding over this civil fraud trial orders Trump not to attack or comment on court staff after Trump posted on Truth Social about the

judge's principal clerk. So Trump is posting a photo of the clerk, woman named Alison Greenfield, who has apparently had a selfie with Chuck Schumer, claiming that she was his girlfriend and the case against him should be dismissed because it was a political attack. So what is going on here? Well, you know, I'm reminded of Ruby Freeman and Shea Moss, the two Georgia poll workers who got publicly put out as sacrificial lambs by Rudy back decades where Donald Trump, because he's a coward, a thug, and a bully all at once, doesn't hesitate to pick on small fry who lack his resources and presence to defend themselves. And he does it time and again because he enjoys it. He does it for sport. That's part of the reason. I think the second reason is the courtroom he's sitting now in Manhattan, the outcome was preordained. The

judge in that matter had already said he was guilty of fraud and that he was going to recommend that Trump's business licenses in New York get stripped and that he'd face a penalty. All that we're seeing in the courtroom now between now and Christmas, if it goes through its full court calendar, is a decision about how bad the penalties will be. So Trump's in there knowing that at best he can get a lower fine and may be able to hang on to some of his businesses at very best. So what does he do? What does an adult who's thinking strategically

about maintaining their business position in the great state of New York do? He comes flying off the wall like Yosemite Sam. And he's shooting himself in the foot. And he's blazing his guns around because he is so angry that he's cornered, that he lacks the emotional, intellectual self-discipline to stop himself from acting otherwise. So his bully comes out. his cornered baby comes out, and I've actually never seen him in a public setting repeat this kind of

activity this way. And I've thought about it. You know, he used to, when Atlantic City was burning down around him, his Atlantic City casino holdings, he used to do these hilarious press events where the press would talk back to him and he'd strut off in anger, you know, off the dais or there was famously he was getting interviewed in a restaurant at Trump Tower and he stripped the earphone out of his mouth and huffed off. But this is on an order of magnitude well beyond that. And I think he's worried. You know, it's about his money. It's about his family's legacy in New York.

It's about his business reputation. And this court case is putting all of that up for play like a ping pong ball. And I think it's torturing him. See, this is really interesting that you would say this because you've been watching him for years and it did seem as if the rage was more raw, that sense of humiliation. And it is interesting that this seems to bother him even more than the felony charges against him. I mean, you would think that, you know, the other perp walks, but this one, as you point out, you know, this is about his money. This is the, about his whole image of his business. So, I mean, he's going to lose this lawsuit, right? And so give me some sense of the

business damage this does. I mean, it's, it's obviously huge. $250 million, that's going to hurt. Even Donald Trump, it's going to hurt. But it's the loss of the business licenses, you know, putting the Trump Tower into the receivership. I mean, this is the most visceral humiliation. I mean, it feels like this is worse. Losing Trump Tower and losing his business licenses is worse than actually being convicted of a felony and going to prison for him at this point. Oh, completely. Really? Okay. Why? Why? You know, in the early nineties, when he almost went personally bankrupt, he was at the mercy of his creditors and the bankruptcy court sorting it out. And he basically went on his knees and he begged for three things not to be taken away from him. Mar-a-Lago, his jet, and his Trump Tower condo.

And he said, take everything else you want, but don't take those because those are, Trump Tower was the first deal he did entirely independently of his father. Every deal he had done before that, his father had to help arrange the financing and the zoning. So Trump Tower was his coming out story. And he was always haunted, by the way, by the Orson Welles story, that Orson Welles shot Citizen Kane, one of the greatest movies of all time, and never really equaled it. The Magnums and Ambersons is a great movie. But in the lore, it was that Welles never achieved that again. And Trump always worried that Trump Tower was going to be his last big thing. And it really was in certain ways

until the presidency came along. The presidency rescued him from the Orson Welles trap. So Trump Tower has loomed in his mind forever as like his coming out property. And then the jet, because he's a bozo and he loves flying around with his name emblazoned on the side of a jet landing places. He just loves that.

And then Mar-a-Lago is his next door to Palm Beach Society boy at the window pressing his nose up against class, which he also has enormous insecurities about. In practical matters, most of his wealth is tied up in a small handful of buildings in New York. I think the most lucrative property he owns in New York is actually 40 Wall Street. Trump Tower, remember, he long ago sold off the condominiums in that building, so he doesn't own those. He doesn't own the land under the building. He controls some commercial space and his condo. So he gets some management fees, and that's about it. So it's largely symbolic now in terms of his wealth. There are other

buildings that are way more valuable. But be that as it may, collectively, his footprint in New York is responsible for a significant part of his wealth. And with those properties, if they get put into receivership, and someone has to follow a court order and sell them off, it will be a fire sale, meaning he won't get top price for commercial properties that are already distressed because of COVID. Because all the urban centers around the United States, commercial properties everywhere have struggled to get their occupancy rates back up post COVID. So the valuations were already stressed. And then you're taking a property that has stress valuations. And then all the buyers know that ding dong just went into a courtroom and was Yosemite Sam. And they're not going to rush to pay any big price for those.

So he's not going to get top dollar for those things either. So it's a financial blow. And I'm curious, we talked about this over the years too, Charlie, you know, he hides a lot of his indebtedness. It's always been hard to figure out exactly how indebted he is. But he is a debt monster. He gorges on debt the way he gorges on cheeseburgers. And if he doesn't have enough liquidity, his debt becomes a problem. If he can't get a good

price for a building, the debt becomes a problem. And that'll be an interesting thing to sort out as well as the kind of financial stressors some of this liquidation might impose on them. Get a $50 prepaid MasterCard with select Michelin tires. Find a Michelin TreadExperts dealer near you at TreadExperts.ca slash locations. From tires to auto repair, we're always there. TreadExperts.ca Let's talk for a moment just about the merits of the lawsuit without getting too deeply into the weeds. The defense from Trump seems to be, okay, so I inflated the values of these various properties, but no harm, no foul. The banks didn't seem to complain about it. It was up to them to do the due diligence, plus there's a statute of limitations. Everybody does this in New York.

This is not that unusual. You know this world. And he's basically saying, look, nobody was supposed to believe these financials anyway. Don't I have like disclaimers? Plus I'm Donald Trump. And I added 10 stories to Trump Tower. Nobody was going to believe that. So who exactly was harmed by his fraud? I guess that's his point. Yeah. And it's a good issue to raise, frankly. And it would be a good issue to raise in front of a jury. So you could sort that question out unless you recruited your lawyers from a Saturday Night Live skit and they forgot to actually ask for a jury trial. Therefore, you never get a chance to road test your defense in front of a jury. It's only going to be road tested in front of a judge who you're attacking every day in the courtroom. That's genius legal

strategy. You know, he came out yesterday after in the middle of the court proceeding during press conference, he said, Look, this can't be a fraud, because it was up to the banks to figure it out themselves, which is kind of like a bank robber saying, I couldn't have committed a crime, because the teller should have recognized that I was a bank robber the second I walked into the bank. That's just not how the law works. If you go in intending to steal, it doesn't necessarily matter what your counterparty did. Let's put that issue to the side. The other issue is our damages.

Were the banks harmed? The case is built on the Martin Act. It's a 1920s New York Act that was designed during the high-flying 1920s to go after securities firms that were ripping off individual investors, leasing individual investors. And it gives the New York State Attorney General a lot of power to just go at them directly on the Attorney General's own bona fides. And that's what he's subject to here. And there's an argument to be made that the banks aren't like naive and vulnerable individual investors. They're sophisticated institutions. It was upon them to do their own due diligence. And I suspect, again, if you had put this out in front of a court populated with a jury,

you could have said, in fact, they weren't relying on these garbage statements of financial condition. They did their own due diligence to see what I was really worth. And the fact pattern supports that. When he and I litigated, he sued me for saying I lowballed his wealth. In the course of the litigation- Sounds familiar. Yeah, yeah. We got a document from Deutsche Bank where he went to them saying he was worth $3 billion. They did their own due diligence and they calculated he was actually worth $788 million because they did their own due diligence. I calculated he was actually worth $788 million because they did their own due diligence.

I think that is an issue in terms of determining damages and the banks as sophisticated counterparties. You could make a good argument that they weren't harmed and you could mitigate the assessment of the penalties against you if you were in that scenario. But guess what? He's not. So is this vulnerable on appeal? It seems that I was watching some of the trial and some of the speeches that the lawyers were making, which clearly were not going to have any effect with this particular judge. The best analysis that I heard is they're addressing this now to the appellate courts, trying to create some sort of an issue. Is that his main hope? Normally on these legal issues, I think that Donald Trump is appealing to the court of public opinion, is trying to do politically. This one, he obviously needs to win in the legal system. So talk to me about the possibility of appeal.

This judge seems to be, and again, you know, I'm willing to eat the popcorn, but the judge has been very, very aggressive. Does that make the rulings more vulnerable? I don't think so. Ultimately, I don't know. But every time he has tried to appeal to a higher court in New York State to adjudicate on his behalf, he wanted the judge removed. He wanted certain charges dropped. He's lost every one of those because I think the appellate courts are recognizing this

as a Martin Act prosecution. They've always given a lot of deference to the foundations of that act. You know, Eliot Spitzer used it to great effect when he was attorney general. And so I don't anticipate them successfully appealing the final result here, but I could be wrong. I sort of imagine the appellate court the same way I think about the people in the Kremlin when Trump got elected, that like Putin and his cronies are sitting around going, they just elected that fool. And they pop back a little shot of vodka. The appellate court is like, oh, here he comes again. He's appealing, but doesn't this guy understand how the world works? Okay, let's go back to this gag order, because you wrote yesterday that the gag order was a watershed moment. Talk to me about

that a little bit because this is the first really, you know, very pointed gag order, you know, with a real threat of jail. Kind of surprising because I think a lot of us were waiting for this from Judge Chutkin or maybe the judge down in Georgia, but we got it in this New York civil case. So why was it a watershed moment? Because I think the danger in the way that Donald Trump rolls is that institutions and the legal system and voters and the media and everyone we rely on in this fragile community we have right now holds him to account in the same way that any other person would be held to account. And that he shouldn't get special treatment because he's a former president. In fact, because he's a former president, the bar should be even higher, I think,

for being lenient. And he has been, in a number of these cases, attacking the prosecution, the judges, and possibly tainted other potential witnesses and the jury pool. And the court system has an interest, regardless of a defendant's ideology or station in life, to make sure the process keeps rolling along. And you mentioned Judge Chutkin. She's got the federal case with the January 6th case. I think she's warned him now four times that he can't post to social media and he can't talk to the media about his view of the process.

And she hasn't given him a gag order yet. She's given him repeated warnings. The next step will be a gag order. If he violates the gag order, the next step is jail. And I think there's people who argue you can't put a former president in jail. I disagree with that. I think there's good strategic reasons to say why you would not want to do that. It could poison the political process. It could make all of this look like a witch trial, which is what

Trump's calling it. But the law is what the law is. And I think finally, in the New York case, the judge had had enough, and he issued a gag order. And I think it is a watershed moment in that he's using the powers at his disposal to silence a defendant who's out of control and is damaging the court process, pure and simple. And Trump did take down the social media post. I mean, he did, interestingly enough. After like tens of millions of his followers disseminated it already. It does feel as if he's trying to goad the judges into doing it. I mean, is there some part of Trump that wants to be martyred,

that actually wants a judge to slap him in jail? Because he's behaving that way. For most people, that's irrational. I mean, who the hell wants to go to jail? But what do you think? You know the guy. I'm a victim. I'm a victim.

I know what it's like to be a victim. Look what they're doing to me. I know how you feel. I know how you working class Joe and Jane. Donald on the cross. Yeah. You're victims too. You've lost your station in the world.

All these immigrants are crawling into the country. The economy's not working for you. You're a victim. And guess what? I'm a victim too. And I'm the only thing that stands between you and the woke mob. And so, yeah, this fits right into that narrative. I think he could be miscalculating who, however, that narrative resonates with, because he doesn't

need to convince his cult anymore. Trump is a cult leader. He won't get elected at the national level as a cultist. And he needs to be courting moderates and nothing he's doing gets him there. So let's talk about this lawsuit. You've given some previews of all of this. We're going to get the defense witnesses, Eric Trump, Don Jr., all the people, the financial consigliere is going to show up. So what can we expect? This is going to be a hell of a show, right? I mean, this is going to be, Donald Trump, this is your fraudulent life. So what do we expect from the Trump family, from the Trump clan, when they're on the witness stand answering questions? Well, if prior behavior is predictive, you're going to see three buffoons, at least in the

Donald, Don Jr. and Eric realm. Ivanka will testify, but I think she's much more self-possessed than her brothers and father. You know, last Thursday, after the judge noted one of his rulings that Mar-a-Lago's valuation was inflated, for example, and that was one of the reasons he wanted to impose penalties, Eric took to social media to say it's worth a billion dollars, which it most certainly isn't, and do exactly what the court was censoring the family for doing. So I think the boys are going to take a cue from dad and go in there without a strategic sensibility of how they should conduct themselves in the witness stand. They will be easy for a prosecutor to inflame. And so that makes all three of them wild cards when they're on the stand. And they could end up, you know, doing more damage that extends beyond this case, I think.

So it occurs to me that, I mean, I remember when Jack Smith brought his case in Washington, DC, you know, the case in front of Judge Shutkin, that we were all saying, this is the case, this is the one. But in Donald Trump's mind, the civil case is the case, This is the one. But in Donald Trump's mind, the civil case is the case. This is the one. This is the one he cannot lose. This is why he is melting down. Now, is Donald Trump really going to testify in this case, Tim? I mean, is he really going to get on that stand? You know, I don't know. His lawyers are not restraining him. Because Donald Trump Trump is performing for the judge and his voters and his lawyers are in the courtroom performing for him. And no one's acting in a strategic or professional way. So I don't think they'll restrain him. So I think there is a high chance he'll be on the witness stand. And I think it will be a carnival. Wow. That will be incredible. That will be the show and kind of a bonus show since we were all expecting it was going to be the other trouser winning show. Tim O'Brien, thank you so much for joining me. Tim is senior executive editor of Bloomberg Opinion, host of the podcast Crash

Course, also a political analyst at MSNBC, a former editor and reporter of the New York Times, and author of the classic Trump Nation, The Art of Being the Donald, published in, checking my notes here, 2005, before he came down that golden escalator and New York's problem became the world's problem. Tim, thanks for joining me. Thank you for having me, Charlie. And thank you all for listening to today's Bulwark Podcast. I'm Charlie Sykes. We will be back tomorrow and we'll do this all over again. The Bulwark Podcast is produced by Katie Cooper and engineered and edited by Jason Brown. We'll see you next time. Enjoy them for years with the Michelin X-Ice Snow Tire. Get a $50 prepaid MasterCard with select Michelin tires.

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