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Ben Wittes
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Host of To The Contrary Podcast
Foreign Sykes welcome back to the to the Contrary podcast, joined today by our good friend Ben Wittes, editor in chief of Lawfare. Love the hat, Ben. You want me to ask, right? You're baiting me down.
Ben Wittes
I am dating you, man.
Host of To The Contrary Podcast
No. No clue. No idea. Sorry.
Ben Wittes
It stands for who is the administrator of doge. And because Before. Before Anna Bauer was, you know, a recipient of rage texts from U.S. attorney Lindsey Halligan. She was on a quest, a kind of one woman deranged campaign to figure out who the administrator of Doge was. And she wrote a long and wonderful and somewhat hilarious story about it for lawfare. And we actually printed up hats in response to it. And I, of course, ordered the bright red and white one.
Host of To The Contrary Podcast
Of course, of course.
Ben Wittes
Because, you know, that's the kind of guy I am.
Host of To The Contrary Podcast
Well, do we know. Do we know who the administrator of Doge. Do we know what Doge is anymore?
Ben Wittes
No. So I do refer everybody back to Anna's. Anna's piece on this. No, I think at this point, it is not clear whether Doge meaningfully still exists or if so, who the administrator was is. There's an interesting question whether we know at any point who the administrator ever was. And there are some legal questions that arise from that. But Anna did spend more time on this question than any other collection of human beings amalgamated. And. And there is a wonderful long lawfare article about the Doge Chronicles and strongly urge people. The Witoed Chronicles.
Host of To The Contrary Podcast
The Witoed Chronicles. Okay, so I was planning on starting this off by saying, ben, I don't know whether you saw this, but South Korea actually gave Donald Trump a fucking crown.
Ben Wittes
No, I did not see that.
Host of To The Contrary Podcast
I cannot tell you how many times now I've had this experience where I see something and I go, okay, that must be AI or that must be a spoof or a troll or something. And no, they were so anxious to suck up to him, to treat him, and, like, they actually gave him a gold crown.
Ben Wittes
So that is not a monarchy.
Host of To The Contrary Podcast
Well, maybe we're all a monarchy. So there's so many things I want to talk about. I mean, you know, my. What were your best memories when we actually had a congress that would show up? Is Trump really going to be able to give himself $230 million from the taxpayers? What's going on with the courts? I'm having a hard time keeping up with all of this. The President continues to. And I feel like we've become numb to this. That's why I want to bounce this off. The President continues to openly and publicly order the prosecution of his political enemies. Last Friday, you know, in ancient times, in the before times, right before the weekend, he's talking about going after now, going after Merrick Garland and Christopher Wray, his own FBI director. And it's like everybody's like, you know, okay, you know, this is what Trump does. On again, off again. Trade wars. He fired two prosecutors, that they fired two prosecutors who dared to call the January 6 attacks riots. I mean, if you ever were wondering what a one man government would look like, we're living through it right now. I mean, is there any part of the government that he doesn't have, except for the courts, complete control over?
Ben Wittes
Well, so, you know, by whim, by, by petulance, I, I mean, on the one hand, for those who, you know, kind of believe in originalism, right. This is, you know, a sort of Jacksonian era vision of the executive branch, right, where, you know, the spoils system was basically that, you know, which of course came from the phrase to the victor go the spoils. But the idea that the ability to appoint your people to government and that this is a kind of personalist executive branch, we moved away from in a very decisive way in the aftermath of the Civil War with the creation of the civil service. And the idea was that below a certain level, we should certainly have certain, we should simply have professional government. Above a certain level, the president is very much in charge and everybody reports to the president, can be fired by the president, can be replaced by the President. But below a certain level, you know, you have professional rules and, and that come with a certain, certain tenure protections. It comes with the idea that you can't be removed for simply political reasons, for not being loyal, for believing certain things. And this is very much something that Trump does not believe in. And I think one thing that we're seeing is a war on the sort of 1870s era idea that, I mean, it really comes to fruition in the period, you know, surrounding the Grant administration and the Chester Arthur and Garfield presidencies. Right. This is an old idea, I believe. I didn't know we were going to be talking about this today, but I believe the civil service is kind of the creation of Attorney General Horatio Hoare. H o ar one of. Thank you for one of the great, really innovators in, in the way we organize government. And I think that is something that Trump is really trying to dismantle.
Host of To The Contrary Podcast
Yeah, okay. Well, he's trying to dismantle. He's dismantling so many other things. You used the word originalism before. And you know, in, in my mind, when you talk about originalism, we go back to the Constitution and the founding fathers and their original intent was no kings. Right. I mean, that was the orig. Create a government that will be able to resist the concentration of power in the hands of a tyrant. And if you're originalist, you will take Note of the fact that Article 1 of the Constitution vests tremendous power in the Congress, which no one has seen now. I mean, it's like a milk carton thing. Mike Johnson shows up and says something stupid every other day. But we are in a moment now where the House of Representatives is just not around and even some Republicans are going, this is kind of embarrassing. You know, government shut down. We're still getting our checks. We're not even doing it. So we're at a moment now of max, you know, yes, on the civil service, but maximum executive power at the same time. We have this really historic abdication of power by Congress in a way that the founding Fathers, I think, thought that they had developed a system. They thought they understood human nature enough that this would not happen.
Ben Wittes
Well, to be.
Host of To The Contrary Podcast
There's nothing originalist about this.
Ben Wittes
To be. No, and I was, to be clear, I was being mildly sardonic in my invocation of originalism. But look, I think to, to be fair to the serious originalist thinkers, you know, Justice Scalia once said, and I think he said it in my presence, like I was in the audience when he said it. So I'm not sure it's written anywhere that in our system, all the power is actually in the hands of Congress. It just has to want to use it. And so the, the executive is unitary, meaning it's easy to get to decide even in the, I'm saying unitary there in the uncontroversial sense of a unitary executive. Right. It's easy to get the executive branch to act because it's one guy directing people and, and a kind of vertical integration underneath that. But the power is actually pretty limited. Congress has immense power, but the power is diffused. And so if Congress can get his act together to actually do things, it has all the power. Now, the point that you're making is that I don't think either Justice Scalia or the Founders imagined a situation. Justice Scalia, of course, is much more recent. And so he had glimpses of this that the Founders didn't give. How readily people would be walking away from their own power. And, and why that is happening is, I think, one of the central questions of our age. Right. Why is it that. That members of Congress of a Republican persuasion are so much less courageous than people in inflatable dinosaur costumes? Right. Why is it that, you know, Mike Johnson cannot trouble himself. Why would you run for offices with this power if you never meant to use it? Right. What, what, what's like. And I think some of that question doesn't It's a mystery. Ultimately. It doesn't sound in, in political theory, it sounds in psychology.
Host of To The Contrary Podcast
Yes. Right.
Ben Wittes
Because it's not like the American system doesn't have a theoretical answer to this problem. The theoretical answer to this problem is Mike Johnson is supposed to represent an independent act, a branch of government, and he's supposed to want to maximize his own power, not minimize his own power. He's supposed to be an independent mind and he's supposed to have his own coalition of people who will vote as he wants them to in, by way of maximizing his own power. And of course, he's not doing any of those things. And the interesting question is what in our psychology, our political psychology has changed such that the founding era presumption is wrong and that the Scalia presumption, which is that the, the, the challenge is not merely to organize a non unitary branch of government, but it's to organize people who don't want to be organized to exercise power that they don't want to exercise. And that, by the way, you, the leader, also don't want to exercise it because you've willing intentionally enslaved yourself. And I have no, I don't have the, even the beginnings of an answer to that question.
Host of To The Contrary Podcast
So one of the questions I asked earlier this week was, you know, maybe we've been asking the wrong question when we say, you know, what can Trump do? What will Trump do? When really the question is, well, who's going to stop him? Who's going to exercise power? Because Trump is, you know, he's walking down the corridor, you know, trying to see whether all the door handles will work, whether or not they are locked or unlocked. You know, the classic burglar. So let's just start with a couple of these things, okay? Can, can the, can Donald Trump order $230 million of taxpayer money to be put into his pocket? People probably know the story now. He's filed a claim against the government. The claim will be adjudicated by his own lackeys in the Department of Justice. In theory, this is, this is in, in response to his argument that he was so unfairly and egregiously prosecuted last year, so he made up the number of $230 million. Just give me, walk me through somewhat briefly, what does the law say about this? Under normal circumstances, this would be laughed out of the Department of Justice or it would be laughed out of a court. But the way things work right now, I mean, this, the guy just knocked down the east wing of the White House. Why are they just going to cut him a check and say, hey, you know, good, good, good luck, America, getting that back.
Ben Wittes
Okay, so it's going to happen a couple. First of all, the present and the past are hard enough. I don't do the future predictions of what they're going to do. I just, I'm out of that game. But let's talk about what the rules are. And so normally when you are indicted for a crime, there is no presumption that you get compensated for the inconvenience of investigation or indictment. And by the way, indictments can be. And investigations and prosecutions can be ruinously expensive, including to wealthy people, you know, millions. Millions and millions of dollars. Yeah. So that's. Now there are exceptions to that. There are situations in which the government errs, grievously acknowledges that it has aired grievously and settles and provides compensation either on what's called an expratio basis, like I'm sorry, we up, please accept this as as or on a different basis, which is that they know they have vulnerability to a lawsuit and so you reach a settlement before litigation is filed. Now, there is a process inside the Justice Department for considering such claims. And what happened is that Trump filed a claim in this process. And normally when somebody files a claim in this process, they, they are actually, they were mistreated in some respect because you don't go through this process or.
Host of To The Contrary Podcast
There was some kind of misconduct. Bad faith.
Ben Wittes
Exactly right. Normally you don't go through this process if you are in fact guilty of the crimes in question. And the government did not do anything egregiously impro. I think of this process as like, do you remember at the time of 9 11, the anthrax attacks and the government, the FBI really egregiously aired and went after a guy named Stephen Hatfill who had a second act, by the way. He as a Trumpist medical advisor and recently was fired from, I think the White House where he was being an anti vax guy. But at the time, Stephen Hatfill was at Fort Detrick and was the leading suspect in the anthrax attacks. And the FBI handed hounded him for a long time. Turned out he was completely innocent. And you know, after, I think this is the process by which he got compromised, compensated. And there was a. I don't know if there was ever litigation in that or there was just threatened litigation. Okay, so now you're the president. By the way, Stephen Hatfield's lawyers were not the attorney General and the Deputy Attorney General of the United States. So in, in this case, the President has a number of advantages. One is that he can, of course, the, just he can instruct the Justice Department to settle a case with him. The second you could order them to.
Host of To The Contrary Podcast
Say, give me the money, basically he can say just like, cut me the check.
Ben Wittes
Well, he can. And they could refuse to do it and then he would have to decide whether to fire them. Right, that's. But, yeah, that's the thing about the unitary executive is if the President wants to interfere in the business of the Justice Department, he kind of can do that.
Host of To The Contrary Podcast
Where we've learned this.
Ben Wittes
Yeah. And that it's really a matter of civic virtue, that presidents don't do that. And then if you, you replace the civic virtue people with the clown with the flamethrower people, you get a different set of outcomes. So then the, the, the second thing is that somebody at the Justice Department actually has to do this, has to approve this. And I think where they may run into some trouble is that. But they may not. Right. He may just do it. She. So, Todd Blanche, I think it would be highly, highly unethical and a matter that could be raised with a state bar. If your client, as a lawyer, your personal client, is demanding state funds and you are approving it. Right. Who is your obligation as a lawyer to here? And so I think in normal conflict of interest language, that is a, A, an unwaveable conflict of interest and you need to recuse. And the problem is, of course, that Trump doesn't like it when people recuse. See Jeff Sessions, who also had a bit of a ethical requirement that he recused. And so I think the question here is, first of all, does the Attorney general either refuse to do it or recuse? Number two, does the deputy Attorney general either refuse to do it or recuse? And, and number three, does the head of the civil division, who, who is a. I don't think he has ever had Trump as a lawyer, as a client, but he has had some of Trump's co defendants. He was Walt Nada's lawyer. He's represented a whole bunch of people. And you know, does he, is he willing to do it? And so if I think that's the parameters of the question.
Host of To The Contrary Podcast
Is there any recourse, though? I mean, I'm listening to this going, they're going to do it because this is okay, because I'm a cynic. So is there any recourse for anyone if they do do it, if they write him the check and he cashes the check, is there anyone who is standing to go to Court, is there any procedure to say, no, this is an improper, improper hijacking of American taxpayer dollars?
Ben Wittes
So I would.
Host of To The Contrary Podcast
Or is that just a done deal, like the east wing?
Ben Wittes
I think it is probably, if they are willing to do it, a done deal like. Like, just like, if you're willing to give me some money, who's going to stop you? Right. And by the way, I run. I run a nonprofit organization, lawfare. Yeah, right. I. If I. And just to be clear, I don't do this, but if I authorize lawfare to write myself a check.
Host of To The Contrary Podcast
Yeah.
Ben Wittes
What's the mechanism by which any. Now, somebody might say, hey, that was unethical, you're going to get fired, or you're going to be prosecuted for fraud. But I'm not sure there's a mechanism to stop it, which is, of course, federal government. In the federal government, the Attorney General is authorized to make disbursements. The. And so I. I assume that the only thing that would stop it would be a concern on the part of the three principles that they would have, that they would get disbarred if they did it. And just as my fear in dispersing money to myself from lawfare would be that I would get in trouble after the fact. But I don't think it's a. I don't think there's a. A mechanism that stops it from happening. I think it's, you know, fear of God and the law. And of course, unlike me, I am subject to the law if I steal money from Lawfare. Donald Trump is, of course not subject to criminal prosecution for authorizing payments to himself presumptively. And so. So I. I do think there's much less to prevent it from happening than there is.
Host of To The Contrary Podcast
That's what I was afraid.
Ben Wittes
A reminder that this is unethical conduct as a lawyer, and there are bar discipline proceedings available.
Host of To The Contrary Podcast
Okay, so speaking of clowns with flamethrowers and the Department of Justice, I want to go back to. We were talking about Anna Bauer before, and the. Her. Her text messaging back and forth with, I don't know, is she acting Attorney general.
Ben Wittes
Interim attorney, a U.S. attorney? Although Lindsay Howard, the web website of the Eastern District of Virginia, the last time I checked, just calls her the U.S. attorney for the Eastern District of Virginia. So, you know, you know, acting interim. And of course, both Jim Comey and Letitia James regard her as not even in office at all because they think her appointment was illegal. So I think you can. You can really call her the U.S. attorney. The interim U.S. attorney. The acting U.S. attorney or a private citizen, if you like.
Host of To The Contrary Podcast
Yeah. So. But this. This seems to be where all of a lot of these lines come together. The president orders the. The prosecution of James Comey and of Letitia James. She. You know, everyone who basically says there's. There's no law, there's no facts, gets fired. They move in. You know, former beauty contestant Lindsay Halligan, who is. Her experience, I think, consists of basically being an insurance lawyer down in. In. In Florida and appearing on the.
Ben Wittes
The aired reality show Florida Toe. Which or south beach toe. I forget. If you haven't seen the clips of. Of it, don't miss them. They're. They're Chef's Kiss.
Eddie (Person in Distress)
What you gonna do? Touch me again? Find out what I'm gonna do. You, man.
Ben Wittes
You, man.
Eddie (Person in Distress)
What you wanna do, man?
Ben Wittes
What you wanna do, huh?
Eddie (Person in Distress)
Told you not to touch my ass. Y' all up now, man. Just wait till I get back here, man. I'm gonna get my goons, man. Come back, man. I'm right here. I'm gonna be right here.
Ben Wittes
You just wait.
Eddie (Person in Distress)
You want, man, you wait. It ain't like I can go anywhere. Ass up, man.
Ben Wittes
Go ahead.
Eddie (Person in Distress)
Just wait right there, homie.
Host of To The Contrary Podcast
Are you okay?
Eddie (Person in Distress)
Can you please pass my phone?
Ben Wittes
Yeah.
Eddie (Person in Distress)
Appreciate that. It's broken, bro. Do me a favor. Go to the truck, grab the mic, call Bernice and tell her to please bring me some bolt cutters. Tell them I'm 16 in Michigan.
Ben Wittes
All right?
Eddie (Person in Distress)
Now hurry up, please. There's some guys coming back.
Ben Wittes
Okay.
Eddie (Person in Distress)
Tell her Eddie's in trouble.
Ben Wittes
I got some bitch down here from Tremont Towing. Hello?
Host of To The Contrary Podcast
Bernice, are you there?
Eddie (Person in Distress)
What the is this?
Host of To The Contrary Podcast
Hey, you don't know me, but your friend Eddie's handcuffed.
Eddie (Person in Distress)
Tell her Eddie's in trouble.
Host of To The Contrary Podcast
He's handcuffed to a fence, and he wanted me to call Bernice.
Eddie (Person in Distress)
You gotta be kidding me, right?
Host of To The Contrary Podcast
I don't really know what happened, but.
Ben Wittes
We'Re on 16th in Michigan, and you need to get here, like, immediately.
Eddie (Person in Distress)
You're not going anywhere. Tell Eddie I'll be there as soon as I'm done with this.
Host of To The Contrary Podcast
She was, of course, third runner up for Miss Colorado. But. But you one of your senior reporters. We're talking about her before. Anna Bauer is covering the indictments, including Letitia James. And one night she opens up her phone and Lindsay. It's like, hey, it's Lindsay. And she starts texting Anna Bower from Lawfare. So, Ben, tell me about what. What that. How unusual that is. And. And make it very, very clear. The Justice Department has confirmed the authenticity of these texts. She never said, this is off the record. And she goes on, what a texting bender with one of your people, Correct? What happened here? Tell me about it.
Ben Wittes
So I will just. I mean, Anna does not have a real relationship with Lindsay Halligan. They. They didn't. They had met once before for about 15 minutes following one of the hearings in. In Eileen Cannon's courtroom. And. And. But Lindsay Halligan apparently thought that she knew Anna well enough to text her. Apropos of nothing on signal using disappearing messages to complain to Anna about Anna's tweets, summarizing New York Times articles about the Lindsay. About the Letitia James grand jury, and when. I mean, to make a quite long story short, when we first became aware that Halligan was texting Anna, we. We really didn't believe it was really her. It. It seemed like it was much more likely to be some kind of troll or a disinformation operation. But the. The first sign that this was really her was that when Anna gave her a sort of identity challenge, as in, where do we know each other from? She immediately named the restaurant and the hotel at which. The restaurant at which they had met and who she was with at the time. And so it relatively quickly became clear that this really was Lindsay Halligan. And our later efforts to authenticate the texts were unambiguous on the subject. We. We were able to authenticate them absolutely. And when we confronted the Justice Department with them, the Justice Department confirmed their authenticity. So there's no doubt that this really is Lindsay Halligan. We then published the text exchange in its entirety. And so Lindsey Halligan was upset at Anna about Anna's characterization of the New York Times's coverage of this. It wasn't even about something that Anna had written herself. It was really about a story in the New York Times that Anna had shared on. On Twitter. And exactly what Halligan thought was wrong with Anna's tweets has never become clear to us because she was never specific enough in order for us to assess.
Host of To The Contrary Podcast
Whether she's paying attention.
Ben Wittes
She was clearly paying attention, and she was very upset at Anna for the substance of these tweets, and she clearly felt entitled to bring that to Anna's attention, which is fine. And. And, by the way, at no time went off the record. And so we simply published the entire exchange along with an account of our own efforts to, you know, engage her in further conversation.
Host of To The Contrary Podcast
I'll post a link to that with this for those of you listening to that. It'll be on. It'll be on my site, post a link to what she wrote about all of that. Another indication, though, that she was paying attention. She's thin skinned. She's in way over her head. Is it also an indication that she kind of realizes that she's kind of twisting in the wind on all of this because these cases are not aging well in the sun, let's put it that way. Neither the James case nor the Comey case.
Ben Wittes
Right. So look, I don't want to speculate about what's in her head. I only know what she wrote. And she, it is fair to say that she was upset at Anna for Anna's characterization of some of the material the New York Times had published as exculpatory evidence. She was upset that the New York Times had disclosed material that was grand jury information, though there is no rule against the New York Times doing so. There, there is a rule against prosecutors talking about grand jury information, but it's not inappropriate for, say, defense lawyers or witnesses to disclose to reporters or reporters to publish what went on in front of a grand jury. And so, you know, what she was trying to accomplish is not clear to me, honestly. I, and what her grievance was precisely against Anna was, is very opaque. And I think, and we spent a lot of time trying to get her to isolate. What it is that you think the New York Times got wrong, what it is that is wrong in the tweet that Anna tweets that Anna sent out. And, but she wouldn't tell us, give us any specificity. And by the way, she has not raised the same issue with the New York Times. So the, the very interesting. Which is an interesting thing.
Host of To The Contrary Podcast
Well, this is part of the problem when you have U.S. attorneys that spend too much time on Twitter. Okay, so I want to talk about a couple of these court cases and I have to say that, that I, you have to help me with this because as, as a non lawyer, as a, as somebody on the outside, this is the way it sort of looks. It looks like there is a law, you know, a lawsuit against something the administration is doing, particularly with ice. The lower courts, the district courts, the circuit courts come up with some pretty strong, you know, language stopping the administration from deploying troops. I mentioned circuit courts. And then sometimes the circuit court will step in and stay that everybody knows it doesn't matter until it gets to the Supreme Court. So, so the pattern out there is, at a certain point, I have to admit that I pay less attention to the rulings by the district courts, but it's like, get Back to me in five minutes whether we're here. And again, as a non lawyer, let me ask about what happened with the ninth Circuit, because the local judge, the federal judge, blocked the administration from deploying troops in Portland. The ninth Circuit, which used to be very, very liberal, stayed that ruling, but now it turns out. Are you familiar with what I'm talking about? Absolutely. The Trump administration has now come in and basically said, yeah, hey, really, really sorry about that. We gave you all kinds of bad information. We deeply regret this. It was false and erroneous and apparently this information was relied upon by some of the appellate court judges. So where are we at? Because that sounds like a massive fuck up to me.
Ben Wittes
Yeah, so there are a few things going on here. And let me, let me zoom out for a second before zooming back in. The first is that, you know, when we assess the conduct behavior of the judiciary in this environment is really important to understand that the, the pressure and difficulty in which the district judges are operating. And you know, this is an enormous volume of cases. They are, some of them are extremely complicated. And the appellate environment caused by the Supreme Court keeps changing. And so there's a, there's a sense in which, you know, you must step on this rug because there's precedent that says that you have to, whoops, I'm pulling the rug out from under you. Right. You know, now you have to step on this rug. Whoops, you know, and there's a lot of that going on. So I moderated a panel the other day with three former federal judges, former appellate judge Mike Ludig, and two former district judges, Paul Grimm and, and Nancy Gertner of diverse ideology. And it was interesting, the four of us all agreed that the aggregate performance of the district courts across the last nine months has been majestic. Yes, that's my sense. And so, and you know, that said, there have been a lot of reversals and there have been a lot of reversals, both because judges make mistakes. It's very hard what they're doing, and because there is this game of Calvin Ball going on and you know, which Katanji Brown Jackson has called out at the level at the Supreme Court. And, and so you're definitely seeing that. Oh, and then there's this other factor which this case implicates, which is that the government's been lying and it's been lying about a whole bunch of things in a bunch of different cases. And one thing that judges are not culturally used to is the federal government, which is the ultimate repeat player in litigation. Right. It's credibility in front of the courts really matters. Simply lying. And this has taken a process of the government, of the courts getting used to. And you see this in a big way in Maryland where, you know, the Abrego Garcia case happened. You see it in the District of Columbia where poor Judge Boasberg has been really abused by the executive branch and others. But it has not been. It's much more acute at the district court level where they deal with facts, than at the appellate court level where they have a pretty scrubbed, refined record by the time things get to them. And I think what you're seeing in California now is that a bunch of appellate court judges who were, you know, much less inclined to get down and dirty with the facts because that's not what appellate courts do. They're not fact finding institutions are suddenly realizing, holy shit, these guys are lying to us. And that, that has changed the relationship between the U.S. attorney's offices all over the country and the district courts. And I think what you're starting to see is that migrating its way up the chain and you know, even where the appellate courts are, you know, they're more insulated from the facts. The idea that you can't trust the record or the representations of the United States federal government to be with anywhere, you know, close to accurate. Sometimes there's a joke going, going around called the presumption of irregularity, which is, you know, right. Do. Should you now presume that when government makes a factual representation to a court, not merely not presume that it's true, but should you presume that that factual representation is the opposite of the truth? And I, and I think this is a, this is a methodological question. I mean the, the specifics of that one is a joke. But the, the general question of how do you regard a government statement in court is a matter on which there is method, ongoing methodological change in the courts.
Host of To The Contrary Podcast
Well, we could be seeing a sea change then in the legal culture because as you point out, there has been this long standing presumption of regularity, the presumption that the government is telling you the truth. And if in fact the courts decide, no, we can't rely on that anymore. I mean, that is going to be a dramatic change. Let me talk to you about something that happened in Chicago. You probably saw this again. This is from the New York Times. Sarah Ellis is in the Federal District Court for Northern District of Illinois. She had Gregory Bovino, who is the face of the ice Brute squads. She had him on the carpet, so to speak, you know, made him come into to the court and then she lectured him for more than an hour. You know, read, read Bovino restrictions that she had previously said as part of a lawsuit over tactics that agents are using and cited examples of times his agents appeared to violate those restrictions. They used tear gas in a neighborhood where children were about to march in a Halloween parade, Judge Ellis said. They failed to warn residents before tossing tear gas canisters at them, she said, noting an incident in which an agent threw a canister out, out of a car window as it drove away. So this strikes me is that these, the at least the district court judges are rapidly losing patience with them. They're becoming more aggressive in calling them in and basically saying, you know, our rulings are not suggestions for you. We are watching you. We want you to report on a daily basis to us. So that just give me your sense of the aggressiveness with which some of the courts are now looking at, you know, at what ICE is doing in places like Chicago.
Ben Wittes
Yeah, so there's two. This is a multi leveled issue. So one level is a compliance question. When a court issues a ruling about what ICE is not allowed to do in Chicago, and then, you know, what tools does it have to actually enforce compliance with its orders? There is no question that they are being much more aggressive about that and they're not assuming that their orders are being followed. But there's a different level of this, which is more than what you're seeing in Maryland in cases like Judge Sini's courtroom in Abrego Garcia, which is the government makes certain representations in order to get the court to do certain things or to allow it to do something. Those representations turn out to be, pardon me, bullshit. And how many times can you throw bullshit in the face of a federal judge before she starts treating your representations differently? And so recently there have been a set of representations that federal judges have just been like, I'm not taking that at face value. You, somebody needs to file an affidavit under oath making that factual representation. So it's not enough to have a lawyer stand up in court and say the position of the federal government is X because Y fact. Right? Instead, now if you want us to do anything, because why fact, somebody has to swear to Y. And that means if Y turns out to be wrong, turns out to be a lie, that so and so can be held in contempt for that. And so making them dot every I and cross every T in terms of the facts that they are representing to a court before, you will take those facts as, as anything. Other than somebody said something. Right. Yeah. And you're seeing that in case after case after case, in court after court after court. And that is all antecedent to what you're describing, which is now the court has issued an order. The government is not complying with the order. You know, that's a thing that makes federal judges very angry and in which they do have the ability to do things.
Host of To The Contrary Podcast
Make them angry.
Ben Wittes
Yeah. As a general matter, making federal judges angry is a bad idea, Charlie.
Host of To The Contrary Podcast
Yeah. And was generally understood in the legal profession. Okay. Let me ask you about one last case, and this is unfortunately speculative. We all saw what happened when the president woke up and was triggered by that Canadian television ad by Provincial. The provincial government of Ontario about tariffs using Ronald Reagan's own words. Okay. And he immediately shut down all the. All the negotiations with Canada, imposed a 10% snit tax on them because he was so angry about this ad. The thing I wanted to ask about, though, is that what seemed to, you know, as you look at that, and I know we don't like to spend too much time going through the actual language of the Truth Social Post, but Trump seemed to have been particularly upset at the thought that this ad was an attempt to influence the U.S. supreme Court, which is hearing a major case about the constitutionality of his tariff power, that for some reason he thought that. What? I don't know, that Brett Kavanaugh would wake up and see this ad and remember, hey, you know, Ronald Reagan was against this kind of a terrorist. Maybe I should rule a different way. But I guess the reason what I wanted to ask you about was, first of all, this is a major case. I have been assuming, because I've become deeply cynical, that the court is not going to strip Donald Trump of his tariff power. But that whole incident would certainly suggest that it's on his mind. So talk to me about that. He obviously has some anxiety about it, otherwise he wouldn't have mentioned it in this context. Correct. You agree?
Ben Wittes
I do. I also think that, you know, first of all, I'm not an expert on iipa, the relevant statute, or on tariffs. And so most of what I know about this subject is kind of through osmosis rather than through close.
Host of To The Contrary Podcast
We all survive.
Ben Wittes
Look, if you read iipa, it is written in a very broad fashion. And normally when you delegate, when Congress delegates to the President the power to do something in very broad terms, particularly in the national security space, that is interpreted to mean the president gets to do novel stuff with this. There are a few things that in this case may cut the other direction. The first is that no one had ever understood IIPA before as being about tariffs. And so there was certainly some concern at the Federal Circuit that, you know, that this is a federal emergency powers issue with respect to sanctions, with respect to. It's not a tool of economic statecraft for trade. And so if you can do anything under iipa, does that give, does that just swallow the whole tariff regime, the whole, you know, a whole bunch of other trade authorities? So that's one question. The second question is, of course, that this is a court that, as a general matter, is very suspicious of broad delegations of congressional power to, in the, particularly in the economic regulatory space, to federal agencies. Now, the President is not a federal agency, but he is, you know, if you're suspicious. And of course, this comes up as what's called the major questions doctrine, right? And, yeah, kind of rolling back the ability of the Congress to just say to the executive branch, you know, if you think X is in the public interest, do anything, you want to deal with it.
Host of To The Contrary Podcast
Right.
Ben Wittes
And that is a traditional conservative kind of bugaboo. Now, and the court in, in recent cases, in these delegation doctrine cases, has been more specific, more sort of concerned to that Congress actually have limiting principles in, in its delegations. So if you apply that logic here and then you interpret IIPA super broadly, because it's written super broadly, you get into this, well, why, maybe you should apply the major questions doctrine and say, hey, we need, we need something to limit this. Congress needs to be a little more specific. I don't think the court is likely to do that in the national security context, but it may. And then there's the final issue, which is what you might call the clown with flame flamethrower issue, which is IPA is a national security statute for situations in which there is some emergency reason to, or national security reason to do something, something. And the President's conduct here belies the idea that there is any kind of national emergency. Right. Tariffs are on, they're off. You know, they're at 120%. I'm mad at you. You've been mean to me. So I'm going to put in tariffs. There's never, only in the litigation does this get framed as a national security decision. And I think you could imagine the justices, or at least some of them saying, wait a minute, the record here is not a record of national security decision making. We, we defer to the President on national security judgments. But here the president's basically said Canada insulted him. So, you know, Here the president has, you know, basically said he wants, you know, he's, he's treating this like a, like a routine business negotiation, not and not a national security matter. And therefore, you don't get to use national security tools in that way. So I think those are three different ways. The Supreme Court could approach this with some skepticism. If you're asking me do I think this is likely to go against the President, the answer is no.
Host of To The Contrary Podcast
Yeah, that's what I would come down. And by the way, we also ought to mention that at any time Congress could step in and reassert its control over, you know, tariffs and taxes and spending. You know, this is our earlier conversation. The Constitution makes it very, very clear that this is a congressional power. Now, they may delegate it, but this is still one of their powers. And so if Mike Johnson and John Thune and on a bipartisan basis came in and said, hey, you know, why don't we be the body that determines what kind of taxes we pay? They could do that. Okay, one last question, because I'm trying to. I am. Eager minds want to know what happened at your Ukrainian lounge music event.
Ben Wittes
Yeah. So this was actually because you're a.
Host of To The Contrary Podcast
Man of many interests. Many, many.
Ben Wittes
Well, this one, many took me by surprise. So it was not, first of all, it was not my Ukrainian lounge music event. It was one that a woman named Valeria Vov, who, who is a Ukrainian singer, was giving a concert of this incredible body of, of 60s and 70s era folk inflected Ukrainian kind of lounge singing. And she was doing it with another Ukrainian singer and with a, actually Sicilian guitarist. And the. I saw some video clips of this singing and was kind of wowed by it on Instagram. And so I bought a bunch of tickets to this thing for myself and for friends. It was a fundraiser for, for a, it was a fundraiser for a group that is trying to buy equipment to evacuate vehicles to evacuate Ukrainian soldiers from the front lines when they're injured. So it's a super good cause. So I bought a bunch of tickets and then the venue canceled on Valeria, I think because they got a better offer from somebody else for that would have been worth more money for that night. And so I called a good friend who persuaded her pastor to make the Olivet Mount Olivet United Methodist Church in Arlington available for this concert. And we moved the concert from the evil venue to the social hall of this church. And then. And we ended up sort of hosting it and it was, I ended up filming it. And you can, you can see my, on my substack the video of some of this music which, you know, this is music that the Soviet Union was willing to kill to prevent from existing because it was sung in Ukrainian and it had a little bit of a nationalist edge to it. Putin is still trying to wipe it from the face of the earth. That's part of what the full scale invasion is about, is the destruction of Ukrainian culture. And so last weekend, you know, we were able to allow one concert to happen that preserves this stuff. And I have to say it's incredibly beautiful and and really, I cannot wait to listen really interesting music. We we pulled out two songs from the concert and you can find them on Dog Shirt Daily.
Host of To The Contrary Podcast
I we will link to that as well. Ben Wittes, thank you so much for all your time and your insight. Trying to make sense in a senseless era. So good to have you back on the podcast.
Ben Wittes
Great to be here.
Host of To The Contrary Podcast
And thank you all for listening to this episode of to the Contrary podcast. You know, why we do this, why we continue to do this. I don't need to remind you, do I? But yes, I think we all need to remind ourselves that we are not the crazy ones.
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Date: October 30, 2025
Host: Charlie Sykes
Guest: Ben Wittes (Editor in Chief, Lawfare)
In this engaging episode, Charlie Sykes and Ben Wittes take a tour through both the comically absurd and the gravely serious state of American governance in 2025. From internet inside jokes about the “administrator of DOGE” to deep concerns over executive overreach, the pair dissect key legal and institutional developments, wade into ethical conundrums facing the Department of Justice, and explore the erosion of Congress’s power. Wittes delivers a sharp analysis of constitutional principles, alarming administrative trends, and the changing role of the federal judiciary—all spiked with humor and a touch of personal storytelling.
Quote: “Anna did spend more time on this question than any other collection of human beings amalgamated.” — Ben Wittes [03:39]
Quote: “What were your best memories when we actually had a Congress that would show up?” — Charlie Sykes [05:01] Quote: “One thing that we’re seeing is a war on the sort of 1870s era idea ... the civil service.” — Ben Wittes [08:12]
Quote: “The executive is unitary...but the power is actually pretty limited. Congress has immense power but the power is diffused.” — Ben Wittes [10:02]
Quote: “Why is it that members of Congress of a Republican persuasion are so much less courageous than people in inflatable dinosaur costumes?” — Ben Wittes [11:16]
[14:04–23:38] Sykes asks about Trump’s self-dealing claim seeking $230 million from the federal government.
Quote: “If you’re willing to give me some money, who’s going to stop you?” — Ben Wittes [21:47]
Quote: “It seemed like it was much more likely to be some kind of troll or a disinformation operation. But ... it quickly became clear that this really was Lindsay Halligan.” — Ben Wittes [27:35]
Judicial Frustration:
A pattern emerges: lower courts issue rulings against federal overreach (e.g., restricting ICE and troop deployments), only for the executive branch to provide false information or simply disregard the orders.
Breakdown in Trust:
Wittes notes a culture shift: judges are no longer assuming government lawyers tell the truth, upending the so-called “presumption of regularity.”
Quote: “There’s a joke going around called the presumption of irregularity ... Should you now presume that when government makes a factual representation to a court ... it’s the opposite of the truth?” — Ben Wittes [39:20]
- **Case Study:**
Judge Sarah Ellis’s aggressive oversight of ICE tactics in Chicago demonstrates judges’ increasing willingness to demand accountability via daily check-ins and affidavits.
Quote: “How many times can you throw bullshit in the face of a federal judge before she starts treating your representations differently?” — Ben Wittes [41:24]
Quote: “Here the president’s basically said Canada insulted him ... There’s never, only in the litigation does this get framed as a national security decision.” — Ben Wittes [47:58] - Prediction: Wittes doubts SCOTUS will overturn the president’s tariff authority.
Quote: “This is music that the Soviet Union was willing to kill to prevent from existing because it was sung in Ukrainian and it had a little bit of a nationalist edge to it.” — Ben Wittes [53:30]
The episode moves between sardonic humor and analytical depth, lacing legal insight with incredulous laughter at the absurdities of 2025. Sykes & Wittes blend sober warnings about democracy's drift with wry detachment—encouraging listeners to pay attention, stay engaged, and hold onto hope and context in seemingly senseless times.
This episode is a must-listen for anyone trying to keep sight of constitutional principles, legal ethics, and the reality—both comic and tragic—of America’s ongoing institutional crises. Ben Wittes’s legal clarity, historical perspective, and personal anecdotes provide both a diagnosis and a tonic for listeners who, as Sykes notes, “are not the crazy ones.”