Lawfare Archive: Are the Courts Ready for a Trump Presidency?

Summary

The Lawfare Podcast – Lawfare Archive: Are the Courts Ready for a Trump Presidency?

Date: February 21, 2026
Host: Natalie Orpet
Guest: Benjamin Wittes

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Episode Overview

This episode revisits a pivotal discussion recorded on February 13, 2025, as the legal system faces unprecedented challenges in the early days of Donald Trump’s second term. The conversation, led by Lawfare Executive Editor Natalie Orpet and Editor-in-Chief Benjamin Wittes, delves into the overwhelming deluge of legal challenges prompted by a sweeping wave of controversial and aggressive executive orders. The core question: Are the courts institutionally, practically, and politically ready to serve as the primary check on presidential power when Congress appears largely absent? The episode breaks down critical issues facing the judiciary, explores the scope and limits of judicial remedies, and examines the risks of systemic breakdown in American constitutional governance.

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Key Discussion Points and Insights

1. The Context: Why the Focus on Courts?

• Trump's Second Term Executive Orders: Marked by highly controversial measures, including mandatory immigrant detention without bond and attempts to unilaterally tear down established federal agencies.
• Congressional Absence: "The branch of government you might expect to be responsive is not … in some of these areas, there has been active congressional enabling." (Benjamin Wittes, 03:50)
• Main Legal Challenge: A tidal wave of habeas corpus petitions and emergency litigation is straining the courts as they become the central arena for contesting executive power.

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2. Four Components of the Judicial Challenge

Benjamin Wittes' analysis, based on his article "Are the Courts up to the Situation?", structures the conversation around four pivotal components:

[A] The "Blitzkrieg" Component

• Volume and Complexity: An “enormous number of executive actions” triggers diverse legal challenges, many involving thorny separation of powers issues and unclear fact patterns.
• Strain on Resources: Courts face a test of capacity: "The first question ... is, do they have the capacity to handle this number of people, this number of cases in this period of time?" (Wittes, 06:49)
• Emergency Relief: The urgency is heightened by demands for TROs (Temporary Restraining Orders) and preliminary injunctions, not slow-moving damages litigation. Immediate judicial action is required due to aggressive and possibly unlawful executive moves.
• Notable Example: "Plaintiffs are showing up asking for immediate emergency relief, and they're getting it … from judges, including from Trump-appointed judges." (Wittes, 10:47)
• Appellate Pressure: A coming "second wave" of appeals, possibly reaching the Supreme Court.

[B] Remedies: Limits of Judicial Power

• Speed Differential: Courts are much slower than the presidency; remedies may come too late to prevent irreversible harm: “You can do an enormous amount of damage before a court really has the opportunity to stop you.” (Wittes, 18:53)
• Nature of Harm: Some harms—like dismantling agencies or mass firings—cannot be easily reversed or remedied monetarily.
• Institutional Damage: “The damage to the institution you can only remediate by long institutional rebuilding over long periods of time … that's an aspect that the courts are not in a position to do, because it's actually not their job.” (Wittes, 22:51)

[C] Judicial Willingness to Push Back

• Judicial Record: Mixed history; lower courts have been quick to issue injunctive relief, but the Supreme Court is less predictable.
• Judicial Philosophy and Politics: “Each court is a ‘they’, not an ‘it’... The record of the court in restraining President Trump is quite mixed.” (Wittes, 29:41)
• Ideological and Psychological Factors: Judges’ sympathy to executive power and their fear of unenforceable orders both factor into how boldly they push back.

[D] Risks of Systemic Breakdown

• Enforcement Tools: Courts have real leverage—sanctions, bar referrals, escalating fines—even if the executive resists.
• Limits with Presidential Defiance: If the president defies a direct order, meaningful enforcement may only be possible with congressional support: “If Congress is on the President’s side, on that, the president will win.” (Wittes, 47:57)
• Reliance on Institutions: The durability of the system depends on judges’ fortitude and the willingness of other officers—especially Justice Department lawyers—to comply with judicial norms.

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Notable Quotes & Memorable Moments

• On Congressional Absence:
  "In none of these areas, substantial congressional response … in some of these areas, there has been active congressional enabling."
  — Benjamin Wittes, [03:50]

• On Judicial Capacity:
  "This looks a little bit like [the January 6th prosecutions], although I think it is mostly optical. I actually think the courts are very well positioned in a structural volume sense to deal with this stuff."
  — Benjamin Wittes, [09:16]

• On Emergency Judicial Role:
  "These are situations in which the executive branch is doing really, really dramatic stuff that facially ... seems to violate laws. ... That's not a bias that I'm reflecting. That's a reflection of the number of judges who've entered temporary restraining orders..."
  — Benjamin Wittes, [10:47]

• On the Limits of Judicial Remedy:
  "...You could really imagine a situation in which Trump loses every litigation and wins the war because he's established these facts on the ground like USAID doesn't exist anymore."
  — Benjamin Wittes, [21:42]

• On the Supreme Court's Uncertainties:
  "I don't spend a lot of time anymore confidently predicting that I know where the court's limits are. ... That induces a certain humility about one's ability to predict these things."
  — Benjamin Wittes, [33:30]

• On Judiciary as the Last Line:
  "We are putting way more weight on the courts than they should have to bear in, in this basic democracy protection, separation of powers framework."
  — Benjamin Wittes, [52:34]

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Timestamps for Critical Segments

• Context & Introduction: [01:32–05:54]
• The Blitzkrieg/Volume Challenge: [06:49–13:24]
• Emergency Relief and Appellate Dynamics: [13:42–18:06]
• Limits of Remedies & Institutional Harm: [18:53–24:45]
• Judicial Willingness & Ideological Tensions: [24:45–35:54]
• Supreme Court’s Role & The Problem of Defiance: [35:54–47:55]
• Limits on Enforcement; Systemic Risks: [47:55–53:37]
• Concluding Reflections: [53:37–53:41]

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Tone and Language

The discussion is earnest, analytical, and sometimes grimly humorous. Wittes and Orpet avoid hyperbole while acknowledging the gravity of current events, their remarks grounded in legal realism and institutional skepticism. Their focus is less on partisan wins or losses than on the enduring strength (and potential fragility) of American constitutional checks and balances.

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Concluding Reflections

The courts have so far responded with surprising agility and fortitude, but they are being tested in ways they were never designed to withstand—largely because Congress is abdicating its constitutional responsibilities. Remedies are partial and slow; enforcement is uncertain, especially against a defiant president. Ultimately, the resilience of the judicial system—and perhaps of democracy itself—depends on the continued integrity and courage of individual judges, lawyers, and supporting institutions.

"How are they doing under those circumstances? Pretty well so far, to be honest. But should they be in this position? Absolutely not."
— Benjamin Wittes, [53:37]

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Useful for listeners who want a comprehensive, granular understanding of the courts’ critical new position in the Trump era and the mechanics, risks, and unresolved questions that define this unprecedented legal and constitutional moment.

Transcript

[Benjamin Wittes]

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[Natalie Orpet]

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[Benjamin Wittes]

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[Natalie Orpet]

The event is free and open to

[Benjamin Wittes]

the public in person and online.

[Natalie Orpet]

Visit lawfaremedia.org ecpaevent that's lawfairmedia.org ecpaevent for details and to register. Want to change the efficiency game? AI it automate tedious tasks to spend more time on the future Transform the everyday with Siemens if you're listening to this, you're ready Ready to join the industrial intelligence generation. A generation defined not by age, but by a shared mindset to connect teams, accelerate efficiency and drive innovation, using the power of Aviva software to reshape industries, turning real time insights into real world growth. Discover our [e-mail] join Generation I.

[Benjamin Wittes]

I'm

[Natalie Orpet]

Marissa Wong, intern at Lawfare, with an episode from the Lawfare archive for February 21, 2026. Over the past six months, the Trump administration's mandatory detention policy, which allows immigration agents to detain anyone found to be undocumented without possibility of bond, has now flooded the courts with hundreds of habeas corpus cases a day. A key issue is if the courts are equipped to handle this massive influx of habeas cases. For today's archive, I chose an episode from February 13, 2025, in which Natalie Orpet joined Benjamin Wittes to unpack the barrage of legal challenges from President Trump's first month of his second term, sparked by the wave of executive orders that push the limits on the boundaries of executive authority. Orpet and Wittes also discussed the role of the courts in responding to expansive assertions of presidential power. And if the courts are up for the job, It's the Lawfare podcast. I'm Natalie Orpet, executive editor of Lawfare, with my colleague Benjamin Whittis, editor in chief of Lawfare.

[Benjamin Wittes]

You know, if the court fears that the executive branch is not going to follow their orders, that lessens the incentive to issue an order, because it's like announcing the emperor has no clothes, and there may be a reticence about issuing an order that you believe the president is going to defy.

[Natalie Orpet]

Today we're talking about Ben's recent article in Lawfare called Are the Courts up to the Situation? Which asks how the judicial branch is faring in the face of a barrage of Trump executive orders. Okay, Ben, so let's start with something that may seem a bit obvious, but I think actually warrants articulating, which is, you know, to set the scene a little bit for why we're even talking about courts in the way that we're going to. What is going on right now that is requiring us to focus on courts so squarely?

[Benjamin Wittes]

Well, so the obvious thing is that the president has taken just an enormous number of executive actions that are legally controversial in some cases because they flatly contradict clear statutory law, in some cases because they appear to contradict clear language of the Constitution, in some cases because they're just very aggressive interpretations of the law. This has provoked an enormous number of different lawsuits covering a large range of different activities. So the question of whether the courts are up to the task becomes a sort of acute one in that context. That is particularly the case because the branch of government that you might expect to respond in the first instance to some of this stuff is Congress, which does not appear interested in responding. So, you know, there has been in none of these areas, substantial congressional response. And in some of these areas, there has been active congressional enabling. For example, the Justice Department firings and the FBI firings have taken place concurrently with moving the president's nominees to those agencies at a fairly expeditious speed. And nobody, at least not on the majority side, seems detained by the behavior of the agencies toward employees in that context. And so in the circumstances in which the branch of government you would expect to be responsive is not, the question puts a real premium on the willingness of the courts to play this role.

[Natalie Orpet]

Okay. So to that end, we recently published a piece by UN Lawfare that we had called Are the Courts up to the Situation? And of course, this is part of a column that you've been writing on a regular basis called the Situation, which I think we can fairly say is looking at these early days of the Trump administration. And what sorts of, as you say, legal controversies are arising, what sorts of issues relating to our democratic system are presenting themselves? This one, as we've talked about, is focused on the courts and the situation as you just described it. You talk through four different components that you think are at issue when considering the role of the courts right now. So I want to start by just walking through each of those. The first one I think you aptly called the blitzkrieg component. So talk to us about that one.

[Benjamin Wittes]

Right. So the first question, whenever you have a flood of litigation like this, and these are not, you know, simple cases, these are cases that are some of them beg important separation of Powers questions. Some of them have very complicated and unknown fact patterns. For example, exactly what information did Elon Musk's people get access to in the Doge acquisitions of Treasury Department data? Right. What did they have read access or read write access? Were they government employees or not? Or special government employees? Right. So the facts are sometimes quite murky. The intrusions on presidential priority is substantial, and the president's actions are dramatic. Right. And so you have a lot of these cases covering a bunch of different subjects that are quite diverse. You know, everything from can the President tear down a federal agency established by act of Congress because he feels like it to, you know, do illegal immigrants whose children are born in the United States, are those children entitled to birthright citizenship? Right. I mean, you're talking about a just massive range of activity that is suddenly in front of the courts. The first question you're going to ask if you're thinking about the judicial capacity to handle this wave is, you know, just like, do they have the. The capacity to handle this number of people, this number of cases in this period of time? And, you know, we've had questions like that arise before. The first one that I ever ran into involved asbestos litigation. And, you know, the volume of asbestos litigation, which the. I think the Supreme Court described it at one point as elephantine mass of asbestos litigation. Right. And, you know, these cases create a real pig in the python effect in the courts. Another example of this locally in Washington was the January 6th cases. You had 1500 convictions obtained. That's an enormous amount. And some of it was, you know, during the pandemic. And so you. These are big strains on judicial resources. This looks a little bit like that. Although I think it is mostly optical. I actually think the courts are very well positioned in a structural volume sense to deal with this stuff.

[Natalie Orpet]

Yeah, I mean, I think the other component of that, of the blitzkrieg, in addition to the types of diversity describe, is that the posture at which these cases present themselves right now is also by their nature requiring very, very fast turnaround because they are seeking things like preliminary injunctions or temporary restraining orders. And so that is a very big strain right away. Of course, if they do continue onto cases on the merits, that will be a different body of work, a different, as you say, as the facts develop, there is a lot more to go through. The nature of the litigation gets a lot more complicated. And in the meantime, I think we have every reason to expect that more litigation will continue to come in TBD weather will be at the same pace, but more lawsuits are rolling in every day.

[Benjamin Wittes]

Right. And your point about the emergency relief component of this is critical. These are not actions where lots of people are injured and they want damages. Right. And so you docket it on the case, and five years later, they, you figure out how much they recover. These are situations in which the executive branch is doing really, really dramatic stuff that facially, anyway, seems to violate laws. And just to be clear about that, that's not a bias that I'm reflecting. That's a reflection of the number of judges who've entered temporary restraining orders, because on their face, this stuff seem to violate laws. Now, some of them, the administration may have arguments that we haven't heard yet, or some of them, they may have constitutional arguments that they're entitled to violate these laws. But, you know, the pattern so far across this pretty diverse range of activity is that plaintiffs are showing up asking for immediate emergency relief, and they're getting it, and they're getting it from judges, including from Trump appointed judges. Right. And so I do think the, you know, the pig in the python, there are several sub pigs. Right. And the big head of the pig is this kind of emergency litigation problem. There's going to be a secondary one, which is, you know, once a bunch of these TROs, temporary restraining orders, turn into preliminary injunctions, the preliminary injunctions are appealable. And so you're going to have a wave of appellate litigation about that. I think it's going to realistically start within weeks that will, you know, you'll have preliminary injunctions that will stabilize the situation, but then you're going to have a set of litigations, some of which will go to the Supreme Court over the preliminary injunctions. And once you have that, you're going to have to go back to the district courts to, are we getting permanent injunctions here? Did the Trump administration lose these cases or are they merely losing on the way to winning? Right. And so that's going to be a much longer wave and a long tail of litigation.

[Natalie Orpet]

Right. And of course, as soon as things go up on appeal, that's where the delay really starts kicking in. So the stock status quo becomes a very difficult question as to where things actually stand and how durable it actually is while things are chugging along quite slowly in the courts.

[Benjamin Wittes]

Yes. And also there is, you know, since nobody is going to be stupid enough to file these cases in, you know, in the districts in Texas where, you know, Judge Kaczmarek got a lot of litigations during the Biden administration, this. There's another pattern here which we can expect that these cases will tend to get friendlier to the administration as they go up the appellate ladder. So a lot of these cases are going to be brought in the D.C. circuit, in the Second Circuit, some in the First Circuit, and some in the Ninth Circuit. These are all relatively liberal circuits. And you have district judges who, you know, all seem to be responding to this the same way. So that's actually an interesting counterpoint that there's no, there doesn't seem to be a lot of dispute among the district judges about how to handle this stuff. But, you know, you get up into the appellate department and there are, you get more sort of ideological conservative judges in every circuit, actually. And then you get to the Supreme Court and there's a conservative, a solid conservative majority. And so, you know, you could imagine a situation in which the Trump administration wins a bunch of stuff, as Bob Dylan says, after, you know, wins the war, after losing every battle. And I don't think that's going to happen in a bunch of these cases because I think they're, they're actually just wrong on some of them. But there are some areas, particularly the firings, where, where I do think that's a possibility and that they could just do much better at the Supreme Court than they're going to do at the district court levels.

[Natalie Orpet]

Yeah, I do want to move on to the. Your second component from your piece, but I will just say for my own two cents there, I'm a little bit less optimistic even at the district court level, because I think it is one thing to issue TROs and even preliminary injunctions right now, because the fact of the matter, as you said, is that this method of blitzkrieg, of issuing executive orders that are inherently some of the most aggressive assertions of executive power that are undoubtedly without precedent, that are at the very least, the sort of most aggressive interpretation of what the executive's authority is that is easy for, as a legal matter, to issue the type of ruling that will freeze the status quo so that everyone can brief and argue the law and figure out whether this aggressive assertion of executive power has legal legs. And I'm not convinced that once it gets to that point on the merits, that we will see the same consistency of opinions that we are seeing right now.

[Benjamin Wittes]

Oh, I don't expect we will see consistency of opinions at all, actually. I expect we will see a fair amount of diversity. I do think the striking thing is, is that as far as I can tell, the administration has not won a single point in a single court so far. And that's striking. You know, I, you know, there's, there's been a lot of talk about how they've, they had four years to refine it and this is, they've thought it through this time. Right. And they're going into court and they're, you know, getting their asses kicked over and over again in different courts around the country in front of Democratic appointed judges, in front of Republican appointed judges. Now, are they going to have a consistent record of zero wins and, you know, X losses as X gets bigger and bigger? No, but I do think it's striking that in the first three weeks of the litigations there, they really have not notched up a single win. And, you know, that that is a, you know, a testament to how aggressive their litigating positions are.

[Natalie Orpet]

Yeah, agreed. Okay, so let's turn back to your piece. The second component that you had identified is remedies. The idea that by issuing these executive orders, it is easy to move very quickly, as we've been talking about doing it with really unprecedented levels of aggression in asserting the executive authority and some of the more, I think it's fair to say, extreme interpretations of what a president is capable of doing unilaterally. And the question for courts, of course, is if a party is injured, what are you going to do about it? What's their remedy? So talk to us about how that fits into your understanding of how the courts are meeting this particular moment.

[Benjamin Wittes]

Right. So, you know, this is a tricky one because one of the reasons the courts are not the optimal venue in which to push back against this kind of onslaught that you would want some of this work being done by Congress is that they don't move at the speed of the presidency. Right. Congress, when it wants to move fast, can move really fast. Remember, the amount of time between 9, 11 and the authorization to use military force. Right. And that is a law that has governed overseas foreign terrorist, anti terrorist operations for the last 24 years. Right. And it was passed in a matter of 11 days or something. Right. So if Congress wanted to put its foot down and say, you know, absolutely not, hell no, you're not getting anybody confirmed. And by the way, no funds for the White House helicopter or for White House operations until you come to the table on this, we would see a completely different environment than we're seeing right now. The problem with judicial remedies is that they take a long time. And so right now, the only remedies that we've seen are these, these orders to stop things in place to try to preserve the status quo. But as you see with, you know, destroying a federal agency, you can do a lot of destruction of USAID before anybody has a chance to enter an order preserving the status quo. And then maybe if you don't, you know, as we've seen in this Rhode island litigation against certain spending freezes, it takes a while to turn money back on. Maybe if you're even playing, you know, sort of playing honestly, which maybe they are and maybe they're not, depending on which agencies you're talking about. And you know, you can do an enormous amount of damage before a court really has the opportunity to stop you. And the problem with that, when you do that in a normal litigation, you know, if, if you sue me for being a terrible editor in chief and being mean to you in an employment setting, the conduct has already happened, right? And so the, the traditional remedy that courts have is, is money, right? You ask for damages and there's some, there's some amount of money that's supposed to compensate you. Well, if you're talking about destruction of a federal agency, that it's not really a financial issue, right? It's a rebuilding institutional capacity. These are things that courts don't do. And so I think you could really imagine, I forget who was it who said about the, about ancient Rome, they made a desert and called it peace, right? You could really imagine a situation in which Trump loses every litigation and wins the war because he's established these facts on the ground like USAID doesn't exist anymore more. And so it doesn't matter if he loses the litigation. You can slap a sign on a building and call it usaid. But you know, who are you kidding? And I really worry about that, particularly in the firings cases. A lot of these people, you know, have been fired and they're going to go get other jobs and they're going to file litigations and some of them are going to win their litigations and they've still been fired. You know, what, are they going to drop their now high paying jobs at big law firms to go back and be assistant United States attorneys? Are they going to, you know, people, by the time they win, the damage has been done. And it's not just the damage to them. You can remediate with money, but the damage to the institution you can only remediate by institute long institutional rebuilding over long periods of time. And I worry that that is an aspect that the courts are not in a position to do because it's actually not their job. It's the job of the President to run the executive branch. And if the president really wants to destroy the executive branch or big chunks of it, the courts can slow that down. But I don't know that there really are good remedies for some of these problems. Problems, at least not institutionally.

[Natalie Orpet]

Big institutional breakdowns don't lend themselves well even to longer term judicial oversight, for example, of cases where judges rule that something was done improperly and they order the parties to issue regular reports for some determined period of time to allow the court to sort of monitor the situation and ensure compliance with its orders. I mean, how do you translate that into to you destroyed an agency and

[Benjamin Wittes]

we're going to appoint a special master to oversee usaid? Right. I, I mean, there's. This isn't something that courts were designed to do. And so I do worry that, and I say this, the district judges have done a terrific job so far of, you know, holding hearings quickly, you know, trying to get their hands around the facts and issuing orders. But at the end of the day, the executive branch always has the first mover advantage. And if you use your first mover advantage to nuke the field, you know, the second mover doesn't have a lot, you know, you don't have a lot to work with to preserve stuff.

[Natalie Orpet]

So the next component that you talk about is the really crucial question of whether the courts even are interested in playing this role of pushing back against executive actions right now. And as you've talked about, Congress is clearly not interested. That is a role that the Constitution has envisioned both Congress and the courts would play in their different capacities. What is your assessment of whether they are likely to, to the extent it's possible to guess in advance or how that would work, what it would look like and what we should hope will happen.

[Benjamin Wittes]

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[Natalie Orpet]

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[Benjamin Wittes]

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[Natalie Orpet]

You mean from the executive branch?

[Benjamin Wittes]

Yeah, I mean the extravagance of the idea that the president can simply impound funds that he doesn't want to spend. His position seems to be that he can fire anybody in the executive branch for no reason other than that he politically distrusts them. That goes against the entire history of the civil service, which is, you know, a post Civil war thing. Right. So, you know, I think there's, there's in every way that the administration could set themselves up for failure. They have set themselves up for failure. That's on the, all of that is on the one side of the coin. On the other side of the coin, you have some justices who are clearly sympathetic to some of these ideological presuppositions. And you have several others who at different times, most notably in the Trump immunity case, have been remarkably more receptive to what I consider extravagant claims. And I, I am not a presidential power minimalist by any means. I have a certain sympathy for, you know, what I used to think of as strong executive power claims they seem mild now, but. And so I don't spend a lot of time anymore confidently predicting that I know where the court's limits are. Now. I do think that the Trump administration is likely to continue to get its ass kicked in the lower courts. And I include in that lower appellate courts with an important proviso. Every lower appellate court has a mix of judges appointed by different presidents with very different predilections. And when you create three judge panels out of those mixes, you know, even courts that seem quite, you know, on the whole, quite. I don't know whether you want to call them liberal or moderate or whatever. You know, you can get some really conservative panels on those courts. Right. And so there's going to be. I think what you're likely to see is that Trump is likely to get a better and better hearing as he goes up the appellate ladder. And there is at the top of that appellate ladder, a six judge conservative majority. Now, do you have six judges for these extravagant positions on the Supreme Court? I don't think so. Am I prepared to say confidently the way I once said there are not five votes for the idea of presidential criminal immunity? I think I've said that on this podcast. Turns out I was wrong, you know, and, and like, that induces a certain humility about one's ability to predict these things. There are two issues here, and they're different. The first is our judges ideologically sympathetic. And, you know, when Clarence Thomas swears in half the Cabinet, I think you can assume he's gonna vote to support the legality of a lot of this stuff. Now, is that he's a serious mind, he's going to read the briefs and stuff. But I think you're starting with a lot of ideological sympathy. The second issue, which I think is the more important issue, is not ideological sympathy, but fear. And this relates to the fourth category, which we haven't talked about yet. But if the court fears that the executive branch is not going to follow their orders, that lessens the incentive to issue an order, because it's like announcing the emperor has no clothes. And there may be a reticence about issuing an order that you believe the President is going to defy. And I don't think that's a problem for Clarence Thomas, but I do suspect that it hangs out there in the back of the minds of Amy Coney Barrett and John Roberts. That's just a guess.

[Natalie Orpet]

Yeah. I do want to pause for a second, though, on the lower courts, because I think this speaks both to your third and your fourth point. So, you know, as we've discussed, things slow down as they go up on appeal.

[Benjamin Wittes]

Which is good.

[Natalie Orpet]

Which is, which is good. And the Supreme Court, of course, is not obligated to take every case that is petitioned for cert. You know, it would be quite notable if it declined to do so in some of these huge cases, but particularly

[Benjamin Wittes]

at the request of the Solicitor General.

[Natalie Orpet]

Right. That said, you know, if, if there is some question of whether they would be hesitant to issue a ruling that they feared the President would just disregard, you know, do you, do you forestall that also by just declining to grant cert or by slow rolling it and not doing it this term, but doing it the next term? And I'm wondering what that says, that possibility or just the mere fact of how much slower things go once they're going up on appeal, possibly being remanded, going up on appeal again, getting to the Supreme Court, what that says about the ability and possible degree of influence that lower courts can have in issuing rulings that will, for example, freeze the status quo or that will make it so that going through with the plans that are envisioned under the executive orders currently being issued just can't move forward in the way they want to, even if ultimately the administration does win. What does that say about the lower court's ability to think through whether they. Presumably there would be a diversity of this, but I guess any individual judge, any panel of judges, how they want to think about what options are available to them to be this constitutional counterbalance.

[Benjamin Wittes]

Yeah, I mean, look, I think the. Obviously, when you're a lower court and a lower appeals court and you have a preliminary injunction blocking the President from doing something that, you know, he announced on day one. Right. It's something major policy priority. And the Solicitor General goes up to the Supreme Court and says, you know, Justices, this is a matter of urgent national importance. Says the President. There's a heavy presumption that the courts are going to, you know, they don't need a conflict in the circuits in order to, to take such a case. That said, I do think some of these cases are dumb enough that you might actually resolve them at the lower court level and not have. So let's take, for example, the birthright citizenship case, everybody assumes that's going to be decided at the Supreme Court. Why, you know, you, you have a district judge that took sort of like an hour and a half to issue a preliminary injunction and said, this is laughable, and asked, you know, where were the lawyers when this executive order was written, I assume that is going to be affirmed by the Ninth Circuit. It is not obvious to me that that's a cert worthy case. And like, it is unusual to be clear for the Solicitor General to get rebuked by the Supreme Court and say, no, we're not taking case that you say is an urgent matter of fact, presidential priority. But then again, this loser general doesn't normally ask the court to review things that are that facially wrong and dumb. And so you might actually have some of this stuff get resolved at lower court levels. The other thing is that, you know, and, and this is a point that I think Ezra Klein made on his podcast with our colleague Quinta Jurassic, that this is an administration that, you know, gets bumped, spooked pretty easily. It doesn't like pushback. And so, you know, they announce these big tariffs and then Canada and Mexico go boo and they retreat and pause it for 30 days. Right.

[Natalie Orpet]

With great talking points about how it's a win, actually.

[Benjamin Wittes]

Right. Yeah, they're gonna, you know, they're gonna say those things. They get one district court TRO after another and they make noises about defying court orders, but they haven't actually defied any court orders yet. They, although they, they are having trouble complying with some. They're not announcing that they're. We're defying these court orders. In fact, the Justice Department is bending over backwards to explain that they're complicated complying. It's not clear to me that in the event of, I mean, they will surely appeal. But there are ways to appeal where you mean to win, and there are ways to appeal where you mean to lose and be able to say you did everything you could. And it's not actually clear to me how much of the objective is to win how much or how many of these cases.

[Natalie Orpet]

Okay, you said one thing that I want to pull out and then go from there. Another piece of what courts can do is issue rulings like the challenge to birthright citizenship that say things like this is blatantly unconstitutional. I'm paraphrasing here. And it is astonishing that a member of the bar can stand here in front of this court with his or her ethical duties to candor before the court and make this sort of facially unconstitutional argument, which evokes some authorities that courts actually do have within their own courtrooms in particular, to push back at some level. So talk to us about that.

[Benjamin Wittes]

Yeah, so, you know, one of the things that happened over the weekend as people started really panicking about the possibility of violating the, the administration, violating court orders, you know, and this was stoked, of course, by a series of tweets, including by JD Vance and Mike Lee and Elon Musk, you know, all suggesting that the courts couldn't legitimately get in the way of the President's, you know, inherent authority to destroy federal agencies. And, you know, I, I think I understand the degree of anxiety about this because it really is, you know, the tectonic plates, you know, moving in a, in a sudden fashion. Right. But I actually think people are understating the amount of leverage that courts have in enforcing their orders. And so let me, let me sketch out a few of those mechanisms that don't rely on the administration's, you know, agreement, and then also make a couple of distinctions between different circumstances where the courts can have more or less leverage in, in enforcing orders. So the, the first issue is that the court's authority over people who appear in their courts is pretty, pretty broad. And if you're a lawyer who, you know, misbehaves in court, you can be sanctioned personally. You can also have, you know, have a referral to your bar. And courts actually do this, you know, and there is nothing the President can do to protect you from this. This is why the one, the, the person who, who really has no capacity for Trump to help after January 6th is Rudy Giuliani. Why? Because he had civil judgments against him and he was disbarred. And President, you know, he can pardon you if you're convicted of a crime, but he can't pardon you for a civil judgment, and he cannot force your state bar. So this is something that hangs over every Justice Department lawyer who has to appear in front of one of these courts. The second thing is that not every judgment, you know, it is ultimately true that if a court orders you held in contempt, the people who are going to hold you in contempt are U.S. marshals. Right. Who are. They're literally the ones who are going to arrest you. And they work ultimately for the President. If the court finds you $10,000 a day escalating, let's make it for Elon Musk, you know, you know, $10 million a day doubling until it, you know, every day until it assumes the entire value of SpaceX. The president, actually, that's a debt, you know, that's, that's not something that the President can easily get in the way of. And then the final thing that I'll just say is, you know, before anybody defies an order, they're going to appeal an order. And so they're going to exhaust their appeals and courts will let them, by the way, go into contempt. Appeal it. Right. That's the normal way of challenging something. So something will, by the time it actually comes to enforcement, it will have been all the way up to the Supreme Court. And a majority of the Supreme Court will have said this is a lawful order. So at that point, you're, you're spitting in the face not merely of some liberal district judge who may have been appointed by Barack Obama. Right. But you're spitting in the face of John Roberts and Amy Coney Barrett, who you appointed, the latter of whom to the Supreme Court. I think that's a much more difficult political position than for the president. And so I remain, I wouldn't say confident that we are not going to have any defiance of court orders, but I would say we have a lot of road to go down before we face that question. And I have more confidence than a lot of people do in the power of the courts to effectuate their orders. I will add one thing to that, which is that there are actually two scenarios here, and they're just different. So one is that the order is an order against some collateral figure, a cabinet official, Elon Musk, some teenager who works for Elon Musk. Right. And they defy it. An order. In those situations, the courts have a lot of, a lot to work with. Right. If you're the 19 year old working for Elon Musk and the court orders you to do X and you spit in their face, you're going to lose that fight. The second situation is the much more dangerous one. It's the one where the order involves the presidency itself. So. And so orders that the money be turned back on. USAID is prepared to do it. The President orders them not to do it. Right. And that goes up to the Supreme Court. So it really is Trump himself, not some lower figure in the executive branch or some figure outside the executive branch, but it's Trump defying a court order. That's a much more acute situation.

[Natalie Orpet]

And what does the court do?

[Benjamin Wittes]

I think that is a situation where, if we ever come to it, the court is not empowered in that situation without congressional backing. And that's why the specific procedural posture. Is it seven votes, is it nine votes, is it five votes? Is it, you know, what position that puts Congress in? And if Congress is on the President's side, on that president will win.

[Natalie Orpet]

Yeah, I mean, I think that the tools that you mention that courts have to be a bit of the skunk at the garden party. The Things that you mentioned may not hang over prosecutors as much as one might want because yes, it is true that lawyers can be fined. Sure, they can appeal that. As you said, they can drag that out a number of different ways. Sure, they can be held in contempt. What if the federal marshals, who, as you say, are directed by doj, just choose not to do anything about a court's order to hold them in contempt, even to the point of putting them in jail? What if the bar associations to whom judges want to refer them are unable or unwilling to act to hold them in any sort of disciplinary posture? And even without those extreme examples. Right. You talked about Rudy Giuliani. He didn't lose his law license until many years after the conduct for which he was being disciplined and in the meantime did all sorts of other things that led to further sanctions, for example, in the defamation case of the two election workers, Ruby Freeman and Shay Moss. So the bar associations may not have as much power or just may take too long for that to be any sort of deterrent to Justice Department lawyers who one would hope are being constrained by the powers of the courts against them personally that you were describing.

[Benjamin Wittes]

So first of all, I don't generally think the problem is Justice Department lawyers. I think Justice Department lawyers are by and large going to defend their clients interests within the parameters of professional norms and responsibilities. Well, sometimes when they depart from that, the courts have authority over them. The real issue is when people, non lawyers, defy court orders. Right. So a judge in Rhode island ordered a whole lot of OMB spending that was frozen to be turned back on. Over the course of the next several days, it became clear that a bunch of it had not been turned on. He held a hearing, the Justice Department showed up, talked about how they had sought to comply, talked about the agency's compliance, and he reiterated his order. You know, I am not saying this is a perfect system. And yes, it is easy to hypothesize. What if every component of the system breaks down? What if, you know, lawyers don't care about their bars and, you know, clients don't fear U.S. marshals. And by the way, the president tells the marshals not to do anything. Yeah. If you hypothesize a total system breakdown, you get a total system breakdown. My working hypothesis is that we have a functioning court system and I want to police every component of that and make sure that it continues to function. But I don't want to assume a breakdown and then declare that we have a breakdown.

[Natalie Orpet]

I very much agree with that approach. I think that we are in a position right now, as you've described, where we are putting a whole lot on the courts to serve as this counterbalance for which it is supposed to be joined by Congress under the constitutional separation of powers. But Congress is declining to do so. And so the judicial system is going to have to live up to all of these internal controls that you describe. And at a fundamental level, we're asking an awful lot of individual judges that make up the judiciary to have the fortitude to keep the system's integrity intact.

[Benjamin Wittes]

Yes. And other officers of the system to behave in ways that facilitate that. And that includes the Justice Department lawyers who are representing the administration in this context. So look, we are putting way more weight on the courts than they should have to bear in, in this basic democracy protection, separation of powers framework. This is not the way our system was designed to work. Congress has two powers that could end this problem tomorrow. The appropriations power. It's really three the confirmation power, the appropriation power, and the impeachment power. And if you're not willing to use those, you dump the entire thing in the lap of the courts. And that's a stress our system does not imagine the courts bearing. How do are they doing under those circumstances? Pretty well so far, to be honest. But should they be in this position? Absolutely not.

[Natalie Orpet]

Well, let's hope they can bear it. Ben Whittis, thank you so much for joining us.

[Benjamin Wittes]

A pleasure as always.

[Natalie Orpet]

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[Benjamin Wittes]

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