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Brian Halligan
Behind every scaled company is a founder who started with nothing but a scrappy idea and a willingness to take the leap. The podcast Long Strange Trip CEO to CEO dives into those beginnings with leaders who built their company from the ground up to unpack the early chaos, the pivotal choices and the moments that changed everything. In each episode of Long Strange Trip, Brian Halligan, co founder of HubSpot, speaks with leaders to unpack the real stories behind scaling their companies, everything from the emotional toll of leadership to the tactical decisions that shape a company's future. Learn from leaders like Vlad Tanov of Robinhood, Parker Conrad of Rippling, Sasan Gadzari of Intuit, and more. Whether you're an aspiring founder, seasoned CEO, or simply curious about the stories behind the CEOs on the long Strange Trip of building endearing legendary companies, this is a show you can't miss. Tune in to Sequoia's new show, Long Strange Trip to hear from some of the top CEOs who are defining the new CEO rulebook. Long Strange Trip is available everywhere you get your podcasts. Long listen to Long Strange Trip today.
Marissa Wong
I'm Marissa Wong, intern at Lawfare with an episode from the Lawfare archive for February 1, 2026. On January 26, Judge Katherine Menendez of the District of Minnesota held a hearing on whether to issue a temporary restraining order on behalf of the state of Minnesota and the cities of Minneapolis and St. Paul. The restraining order would pause the U.S. department of Homeland Security's Operation Metro surge. The 10th Amendment's Anti Commandeering Doctrine was a centerpiece of the state's legal argument in the hearing to put a stop to what, as Minnesota's lawyers put it, appears to be the largest federal deployment of law enforcement in U.S. history, with over 3,000 federal agents sent to the Twin Cities, a majority of which are Immigration and Customs Enforcement agents. For today's archive, I chose an episode from January 27, 2025, in which Benjamin Wittes, Scott Anderson, Anna Bauer, Quinta Jurecic, Alan Rosenstein and Amelia Wilson Discuss the first 10 executive orders signed by President Trump during his second term and some of their potential limitations, including the 10th Amendment's anti commandeering doctrine.
Benjamin Wittes
It's the Lawfare podcast. I'm Benjamin Wittes, Lawfare's editor in chief, with senior editors Scott R. Anderson, Anna Bauer, Quinta Jurecik, and Alan Rosenstein, and with Amelia Wilson, a law professor at Pace University.
Amelia Wilson
I think it's probably, again, a situation where the administration has learned that they can issue outrageous declarations like this and it will be then litigated in the courts, and they're kind of going to work it out and figure it out as they're litigating it. And again, with the Muslim ban, that worked. So why not think that it might hear?
Benjamin Wittes
In a live recording on January 23, we discussed the first batch of executive orders by President Trump in his second term, including suspending enforcement of the TikTok ban, the birthright citizenship Order, and so, so, so much more. So, Alan, you have been our TikTok guy. Let's start with the TikTok executive order. What did Mr. Trump do? And should anybody care?
Alan Rosenstein
I will admit to being very naive. I thought that when the supreme court upheld the law 9 oh, we'd have some clarity. And if anything, now I feel like I will never be able to stop thinking about TikTok, which I resent. I would just like to put that on the record. So shortly after taking office, Trump issued an executive order that did two things with respect to the law that went into effect on the 19th that prohibits app stores and cloud providers from serving TikTok unless TikTok's Chinese owner, ByteDance, divests. So the executive order does two things. One, it orders the attorney general not to enforce the law for 75 days and also not to enforce the law for any conduct that took place for the 36 hours between when the law went into effect and when the executive order was issued. And this is important because the fines at issue are quite steep. They're $5,000 per user. TikTok has 170 million users. So that is almost a trillion dollars of liability for companies like Apple or Google that previously hosted the TikTok app, and Oracle and Akamai, which provided hosting services at TikTok. It's also important to those last two entities because unlike Apple and Google, which complied with the law and are not, at least as of right now, distributing the app on the App Store, Oracle and Akamai, midway through the 19th, apparently, after being told by some individuals on Trump's transition team that he would immunize them, decided to turn the lights back on for TikTok, thereby, within probably a matter of hours, accruing potentially tens, if not hundreds of billions of liability as a bunch, as millions and millions of TikTok users flock back to their platform. So one thing the law does, as I mentioned, is it pauses the enforcement for 75 days. And it also, the second thing, this is quite unusual, it orders the attorney General to send a letter to all of these companies assuring them that providing services to TikTok would not violate the law and would not therefore create liability, even though that is an obviously false statement, given how clear the law is, that providing services to TikTok is very much not permitted and does very much create a lot of liability. So we're in a situation now where you have one set of companies, Apple and Google, which, despite the assurances of the executive order, are, I think, wisely not providing services to TikTok, and then another set of companies, Oracle and Akamai, that actually, even before the executive order and now, certainly now that the executive order has been issued, are going to continue providing services to TikTok for at least 75 days. Though presumably Trump can keep issuing more executive orders, more extensions, as he presumably tries to put together some sort of deal by which the Chinese government permits ByteDance to sell TikTok to someone in the United States.
Benjamin Wittes
You know, we have talked about this before, but I just want to get it on the record here. What is the basis, as you understand it, for Akamai and Oracle's confidence? You have a statute that says.
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Benjamin Wittes
You can't provide services to TikTok, and you have a presidential executive order that says yes, you can in pretty facial violation of that statute. What is the basis on which to assume that yes really means yes here?
Alan Rosenstein
So, as with, as with many things in the second Trump administration, I think we are rapidly exiting the realm of law and entering the realm of something else. But I'll play along. I'll do some good faith legal analysis, just because I think the best argument for companies like Oracle and Akamai is what's called the doctrine of entrapment by estoppel. So entrapment is the doctrine of criminal law that if government undercover really kind of really induces you to commit a crime, they have kind of caused you to commit the crime, and therefore they're not then allowed to punish you for that. The doctrine of entrapment by estoppel is a variant on that fact pattern. And the idea is that if a government entity tells you that you are allowed to do something and you reasonably relied on that assurance, the government entity cannot then turn around and punish you for it. So I have a classic example might be you're at a red light and a police pulls up next to you and says, I need you to get through this red light really quickly. There's an emergency and you say, okay. So you drive through the red light, you have violated the law. Right? You've driven through a red light. The police, however, cannot then punish you for driving through that red light because they, in a reasonably authoritative way that you reasonably relied on, told you to do that thing. So the idea, I guess, is that if at some point Trump changes his mind and tries to prosecute these companies for this conduct, they will be immunized because Trump told them that he could do that. And again, to play devil's advocate, you know, if it was just the non enforcement order, I think the argument would be quite weak based on how courts have tended to apply this doctrine. But the order admittedly goes beyond pure non enforcement enforcement. It purports to interpret the law. It purports to interpret the law to say that as long as you are doing this during this time period, you are not violating the law. And it's important to remember that at the end of the day, although there is a Department of justice and an Office of Legal Counsel in our constitutional system, the President is the chief law enforcement and law interpreter of the executive branch, whether or not he has a JD and so this is an official statement of the President interpreting a law. And so that probably strengthens the case. Nevertheless, despite my attempt to steel man what these companies are doing, this is almost certainly not going to work for several reasons. First, with respect to the time period between the 19th and the 20th, so between when the law went into effect and when the executive order was issued, and again, remember the way the law is structured, this is when Oracle and Akamai probably got the bulk of their liability exposure. Assuming, and I don't know, but I'm assuming that tens of millions of TikTok users suddenly flocked to the platform once it was returned to service, I don't think there's any argument because he was not the President. He was just a guy. Now he was the President Elect. But we only have one president at a time. So nothing he says is authoritative until he takes the oath of office on the 20th. So I think for that period, there's just no good argument. Then there's the problem that the statute of limitations for enforcing the civil penalties under the statute is Five years. And that of course gets you to the next administration. So if the next administration goes after these companies, I think it's gonna be very hard to say that what President Trump did binds the next administration. And then finally even as to President Trump, even though part of this executive order is purporting to interpret the law, how do I put it diplomatically? This is all so patently stupid, like these interpretations are so ridiculous based on this law, which is not a complicated law, that I think most courts would say, especially given that these companies are very sophisticated, hundreds of billion dollar companies that can hire the most exquisitely sophisticated corporate counsel, they're the most sophisticated parties imaginable, it was not reasonable for them to rely on this government assurance. So again, I think their best argument is this entrapment bias stoppable argument. But if at the end of the day someone decides to sue them, the government that is, I think they're going to, to lose. And that's why I think that ultimately we have exited the realm of law and this is just their own political considerations. Like for whatever reason, probably I would hope over the objections of Oracle's general counsel, you know, Oracle CEO, you know, Larry Ellison decided he wants to help Trump. There's some larger geopolitics at stake. He thinks Trump is going to get Congress to immunize him. I don't know what the play is here, but I think the law is pretty straightforward.
Benjamin Wittes
All right, and this is a question I'm going to ask to each and every one of you in turn in combination with Anna Bauer. Is there litigation yet over this?
Alan Rosenstein
So there is not litigation over this in part because it's not, and this is maybe also part of these companies calculation. It's not clear who can sue here. You know, when Congress passed the TikTok law, it was obvious who could sue TikTok and its users. But if the President is issuing a non enforcement order, it's not clear what, like who, who would sue over what, who would have standing. Now there might be a, I would not be surprised if there is a shareholder suit down the line because these companies will have to disclose this as a material. These are all public companies, they'll have to disclose this as a material risk. And if I were a shareholder or an enterprise and securities lawyer, I'd be extremely grumpy about this. But that would be kind of a collateral way of getting at this issue. So it really won't be, and realistically it won't probably be the case that Trump goes after these folks, but. And this is the last thing I'll say. Oracle has now put itself in its position not just to being open to this liability risk, but now having this hanging over it as kind of blackmail for the next time Trump comes to these companies for a favor. So even though there's no, like, active litigation, I'd still be very nervous if I were Oracle's lawyers.
Benjamin Wittes
All right, let's turn to Scott. Scott, there have been, unlike TikTok, there have been a raft of orders affecting the foreign policy of the United States. Tick them off. What's the president done so far that is worth noting in these areas?
Scott R. Anderson
Sure. You know, a lot of things touched on different aspects of what can be considered foreign policy. United States trade aspects, immigration aspects. I'm going to set those aside so that we can circle back and add those in if you want. But in terms of core foreign policy, traditional foreign relations actions, I think you can bundle them into kind of three categories. The first are a series of executive orders that try to implement what the administration is branding as the America first foreign policy agenda. This amounts to little more in a lot of cases, or at least in the case of the lead executive order doing this to more than an executive order directing agencies to implement the American first foreign policy agenda, which is agenda that says we put America first and American interest first. So it's not clear exactly what this means in all contexts. In at least one context, we, we have some idea, at least temporarily in context of foreign assistance. As part of this effort, the administration on day one suspended for the next 90 days all US foreign assistance, but subject to potential exceptions. We know this has already raised concerns among Ukrainians, among certain other folks who are relying on assistance in that period, that this might interfere with their assistance. We'll have to wait and see what plays out. Obviously, 90 days is a window where certain assistance partners might be able to weather others are going to face more imminent pressure. But there is a mechanism built into it to accept that there are going to be exceptions or efforts to move forward, forward before within that window. So that's kind of the one set of buckets there. Another bucket is a variety of counterterrorism related actions and including kind of narco, terrorist or action in relation to cartels. The biggest one here is an executive order that purports to direct, although it doesn't actually quite direct, the designation of cartels in Mexico and elsewhere as terrorist organizations. It actually sets up a process by which the Secretary of State and other relevant officials are supposed to recommend whether those organizations should be designated as foreign terrorist organizations or Specially Designated Global Terrorist organizations, which are two different terrorism designation regimes under U.S. law. That has a difference that matters, which I'll explain in a second. So it doesn't quite go that far to actually initiate those designations. But it starts this process where we're supposed to be a recommendation, I think in just 14 days relatively soon of action to be taken one way or the other by the Secretary of State. We just saw yesterday a follow up executive order that does a similar thing regarding on Sarala, the Houthis in Yemen, specifically starting a process to make a recommendation regarding FTO designation. They're already an sdgt, so that's not in the mix. Although it's worth noting the fact sheet, the White House really said that they will be designated as an fto, even though the executive order doesn't say that. And technically it's statutory authority that's signed to the Secretary of State, which might be why there's that kind of gap for the cartel. The this differentiation is notable because there have been a lot of calls, including during Rubio's confirmation hearing from Republican legislators saying designate the cartels and fto. Why hasn't this happened yet? Engaging activity that fits within the definition of terrorism and we should be maximizing our penalties against them. The problem with that is that FTO designations, and particularly they're linked to material support laws, unlike conventional sanctions applied through the SDGT regime, aren't subject to licenses or exceptions. So when you're applying the entities that are controlled territory or heavily involved in conventional commercial activities in territory where Americans or people with ties to America need to do business, they become a huge problem because all of a sudden all these people trying to do legitimate business like they can't because of the risk that they will end up doing business with a designated entity. We're usually used to dealing with this in places like Yemen. That's why Ansar Allah was undesignated as an FTO after by the by administration after Trump left office. Right now we're dealing with wrestling with that in Syria with hts, which is designated fto, and designating Mexican cartels, at least many of them as FTOs would bring that same problem much closer to home. So during Rubio's hearing, actually heard both Rubio and Senator Cornyn from Texas both express reservations about using FTO regimes. So I wouldn't be surprised if a number of the cartels actually don't end up getting FTO designations. They will probably get STGT designations, which themselves are a little redundant with counter narco terrorist sanctions that already apply through a separate regime. But, you know, they kind of layer it on the little belt and suspenders approach. But an interesting little bit of nuance around that there. The third bucket is a pair of treaty withdrawals that reinstate treaty withdrawals. The Trump administration pursued one from the Paris Agreement, which Trump administration withdrew from during its first time in office, and the Biden administration reentered the second for the World Health Organization. Really the World Health Organization's constitution, its foundational international agreement that the Trump administration started but was not able to complete within the one year required period. And the Biden administration then, then canceled, so it never actually went forward. Notably, both the withdrawals have problems in a way, weirdly, that they didn't have when the Trump administration started them last time, at least not to the same extent. The Paris Agreement withdrawal says that it immediately considers all obligations nullified and enters effect immediately. Paris Agreement says you can't do that. It requires a one year withdrawal period. And the Trump administration's own office legal counsel said the president's ability to exit treaties is conditioned on the terms of the treaties. They haven't gone back or at least hadn't gone back as of 2020. Back to the sense, disavowed George W. Bush administration first term theory that the president can just nullify international agreement at any point on his own authority. That's a view the Justice Department hasn't held a long time, including under Trump administration's prior view. So we're not sure what's going to happen there. The WHO withdrawal, meanwhile, which is kind of a bigger problem for them, I think, says they're not going to make any payments this year. Well, the 1948 statute, which imposes the one year withdrawal requirement and that authorized the United States to join the WHO in the first place, also says you have to meet all your fiscal obligations for the year in which you withdraw. So if you take Trump's executive order on its face, you're violating those conditions. And notably, that's a situation in particular where you could see a lot of people having standing because that money goes to WHO and then goes from WHO to lots of other partners, including American organizations that are research partners.
Benjamin Wittes
Has it generated any litigation yet?
Scott R. Anderson
Not yet. I actually haven't noticed anyone who's really seen the who, seen the problem with the who. It's something I mentioned to a few folks on social media and I may write something up on it. They faced a similar question when they tried to do this last time because they were very wishy washy as whether they're going to keep meeting their financial obligations. And I think you would probably need a little while for the harms to ripen to have a credible case for standing for a private party. But there's definitely, I think, some potential there. So depending on the Trump administration handles that, that might end up being a friction point, maybe could result in litigation. I don't know quite enough about who programming to think who the most likely actor would be there, but those are the kind of core foreign affairs functions, executive orders we've seen so far. Again, there's trade items, immigration items, other items I can talk about, domestic deployments, military stuff that I'm happy to elaborate on, but those are the foreign relations ones of a note.
Benjamin Wittes
Excellent. We will come back to the military deployment ones because first we should set up the larger immigration discussion of which those are part. Amelia, there's been a lot of talk about some of these, very little talk about some others in the immigration space. Give us an overview.
Amelia Wilson
Okay. How much time do we have? Just kidding. It has been a dizzying couple of days. I will do my best to provide everyone the broad strokes of what we've seen, both through the executive orders, which have made some pretty sensational splashes in the news, but also some of the more subtle actions the agencies have already taken to implement some of these orders. Well, we'll start with the biggest. It's called the Protecting the American People Against Invasion executive order, hot off the.
Benjamin Wittes
Press and Protecting American People Against Invasion involve, you know, a cordon of ships along the Atlantic and Pacific coast to prevent foreign armies from attacking the United States.
Amelia Wilson
Your question is really valid because what you're really getting at is sort of the heart of why even call it this. And that enables us to understand not just the scope of this executive order, but the goals and the timelines. So it is not a literal encasement of ships. That could be a way we would see it manifest. But the more immediate way that it's designed to be implemented is directly on the border and also engaging interior enforcement and infrastructure needed to accomplish what has been called during the campaign season, mass deportations. So the invasion, qualifying or characterizing immigration, even legal immigration at the border, because there is a process that is legal, that is observed by many asylum seekers. But declaring that an invasion shifts essentially or sort of strips those potential immigrants of their rights to a full and fair hearing. It also engages the military and domestic law enforcement. So if you read that order, it contains many, many parts that are really critical to understand. And if you don't mind, I'll just kind of tick through some of them. So the first is to expand what's called expedited removal. Expedited removal is a form of a kind of. It's a pipeline to quickly deport a person who previously that was construed to be under. Within a certain period of the border, if someone was encountered and they hadn't been in the United States very long, they were subject to expedited removal. But under this new executive order, expedited removal has basically been expanded to the entire interior of the United States. So what that means is if a person is encountered and they cannot prove that they have been present in the United States more than two years, they can be expeditiously deported without a court hearing and without the right to see an immigration judge. Another aspect of this order is really unlike anything we've ever seen. It's a registration process. So it would require noncitizens who are here without authorization or who are undocumented to affirmatively come forward and kind of announce themselves to an undetermined agency. So that part hasn't been spelled out, but they would need to present themselves, give their fingerprints, and essentially, yes, register. If they don't, there would be criminal liability for that failure to comply. Another aspect of this order is to which you're already probably hearing some rumblings about, in certain states that are deemed sanctuary states or localities that are sanctuary localities, is the revocation of all federal funding to states and municipalities that have sanctuary provisions in place. Another is to expand enforcement agreements between ICE officers and local sheriff's offices, police departments, and so on, to essentially deputize local, you know, law enforcement agents who are not federal to engage in or cooperate with ICE activities. The next is to cancel any sort of, like, federal contract with NGOs who are providing any version of legal assistance to non citizens. And then, of course, to order agencies to review Biden's decisions to expand or extend what is called temporary protective status. That's just one of the orders, and there's actually many more. So I want to pause and ask you, Ben, if I should keep marching through the orders or jump.
Quinta Jurecic
Right.
Amelia Wilson
For what probably a lot of people want to know about, which is the new sort of understanding of the 14th amendment, the creative reading of the 14th amendment, we'll call it.
Benjamin Wittes
Yes. So let's pause over this first order and just ask how much of this is likely to go into effect? Is there litigation to enjoin it? It's really easy to issue an executive order saying nobody has any rights, it's a little bit harder to take away people's rights in practice. So how much of this actually is likely to change anything?
Amelia Wilson
Well, we've already seen implemented today and yesterday aspects of some of these orders which I can talk about because the agencies are then directed to sort of interpret the executive orders. And they've already done so. But just to jump backwards, because you ask, you know, how likely, you know, well, we see challenges. What is the success on the merits? It's hard to predict right now. But of course, you all know that within, I guess it was the last hour, hour and a half, there was a judge who did issue a temporary restraining order of the, the new Birthright Citizenship Executive Order. And so what we do at least see in the moment are, you know, strong reactions that was, there was also a lawsuit filed by the ACLU challenging the. By the way, the order is called Protecting the Meeting and Value of American Citizenship. So we did already see, we've seen a lot of pushback. Many legal organizations are mounting responses to some of these orders and they will have strong legal standing to do so. Just to give you an example, there's an order called Guaranteeing the state's Protection Against Invasion. It's kind of like more slang term for this would be the asylum ban. The asylum ban is in conflict with the Refugee act of 1980. It is possibly in contravention of the Convention against Torture. So there's legal basis. Absolutely. To challenge any number of these, these executive orders. Some predict that, that Trump is kind of doing, pulling another Muslim ban where he's like, here, let me just throw this against the wall and see if it sticks. And I'll kind of work out the details later. And, and you know, with the Muslim ban that did actually work out for him, it worked in his favor. Maybe he's not anticipating that all of these will work. I will just as a last note, in terms of like the viability of some of the, the challenges to these orders, the revocation of any, the threat rather to revoke federal funding for states and localities that are deemed sanctuary probably runs afoul of the 10th Amendment's long standing anti commandeering doctrine. The federal government can't force states and local governments to enforce federal law. They have the right to opt out of federal laws. So we'll see how that all plays out. And I could go on and on, but even down to the work permit provision, where there's a statutory right for persons who are in some immigration proceeding to, to obtain A work permit that has now been revoked by executive orders. So to the extent that Trump can succeed in with a stroke of a pen, you know, essentially like revoking laws, I. I'm optimistic that that can't happen. But then again, I feel like we're living in a very surreal world right now, and it feels a little lawless.
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Benjamin Wittes
All right. Anna, has any of this leaving aside the the birthright citizenship order, has any of the stuff that we've just talked about yet generated litigation we should discuss?
Anna Bauer
Yeah, So I think Amelia already mentioned that there is a suit related to the expanded expedited removal that was brought by the ACLU in the District of Columbia. But one other thing I'll mention that has not resulted in litigation yet but is relevant to the immigration executive orders is this internal memo that was sent out on Tuesday by by Acting Deputy Attorney General Emil Bovey, who is a former criminal defense attorney for Trump. In that memo, it cited Trump's executive orders related to immigration enforcement. And Amelia already mentioned that there's, you know, this kind of threat around withholding funding related to sanctuary cities. But in this memo, it also directed attorneys general offices in the United States to investigate or prosecute local or state officials who are not willing to comply or assist in immigration enforcement insofar as it goes to carrying out these executive orders incited a number of statutes that could potentially be subject to violation and investigation by federal prosecutors. And I wanted to note this particularly because Amelia mentioned the anti commandeering doctrine. It certainly seems that, you know, a threat of prosecution being used to kind of compel states to enforce federal immigration policies could run afoul of the anti commandeering doctrine. And so if that is something that becomes, you know, an issue, it certainly could be subject to litigation in the future.
Benjamin Wittes
All right, so with that, let's Amelia turn to the 14th Amendment order, which, as I understand it, has been sub tro'd this afternoon. So what would it do if it were in effect and what do we know about the status of it?
Amelia Wilson
So, yes, I'll have to be really imaginative and trying to understand how this would actually be implemented. But of course, just like to lay out, you know, the sort of basic landscape of what happened in the last couple days. Although it actually, we were saying before we started that there's a contingency of very conservative legal scholars who've been building the framework for this for decades, but I'm getting ahead of myself. So essentially the Protecting the Meaning and Value of American Citizenship Executive order declares that the federal government's not going to recognize the U.S. citizenship of persons born after, I think it's February 19, 2025, on U.S. soil, aka birthright citizenship, will no longer be recognized if the child's mother is unlawfully present or has temporarily lost her status, and the, the child's father is not a US Citizen or a green card holder. So that's what it says now, how that might actually be implemented or what that might look like, it's really hard to know. I guess there's a first question, which is if states are issuing birth certificates, what happens then? Are they directed not to do that if there's a child without, I suppose, verifying the immigration status of the parents? It's not clear what this would look like for persons who are engaging in surrogacy. It doesn't explain what would happen to a person of a single parent of single parentage or, you know, being raised by, by someone who's a single parent. So there's, there's all kinds of questions here. And, and I think that if it were, I mean, it is not retroactive, it's prospective. But if, if you imagine how this would, what this would look like, it would almost instantaneously, like, invalidate the citizenship of many people in the United States and would do so even for members of the military and members of Congress and so on and so on. So it, it is, it is pretty bonkers, I'll say, from an immigration attorney's perspective. But we've been aware of this argument, this very nativist argument, for decades. I guess I hadn't imagined it would really present itself in such a manner and now is actually being reviewed as something that might be credible, but it wasn't divined several days ago. It's been in the works for a while.
Benjamin Wittes
And Anna, tell us about the litigation over this. There's been quite a bunch of suits filed on this, right?
Anna Bauer
Yeah, there's been at least six suits that have been filed over this in various federal jurisdictions. Maryland, Washington, Massachusetts, California.
Benjamin Wittes
But not Matthew Kaczmarex, Court in Texas.
Anna Bauer
No, no. Judge shopping to Texas with this particular case. Ben. So I don't think that there are any surprises, but today we had our first action, as it's been mentioned, in terms of temporary restraining order. There were some choice quotes from the judge, who is an 84 year old Reagan appointee, who heard argument on this initial question of a temporary restraining order. He said things like, where were the lawyers when this decision was being made? It boggles the mind that a member of the bar could stand there and say that this order is constitutional. Things to that effect that I think really underscore precisely the extent to which this order just flouts the Constitution and decades of Supreme Court precedent. And so the judge put a TRO on implementation of the executive order. It does take effect nationwide for 14 days. And my understanding of the order is that in any event, the order would not have taken effect for another 30 days after its issuance. But nonetheless, it certainly is an indication of what is likely to happen in these other cases. And in this case, when the judge considers the actual matter of a preliminary injunction in some of the other cases, we already have hearing dates on preliminary injunctions. I believe that it is in Maryland on February 5th and in, forgive me if I'm misremembering the state, but it might be Massachusetts on February 10th. So, so we will have a number of proceedings with respect to this order in various district courts. But it, it is clear to me at least that this is just a blatantly unconstitutional order. And I think that most district courts maybe, you know, there are some who would not enjoin the order, but I think that most district courts are going to have a pretty easy job of making a decision on this order.
Benjamin Wittes
Right. If, if the administration is going to win this one. It is going to be at the Supreme Court by having the Supreme Court reverse precedent, not by any faithful lower court following precedent to it.
Quinta Jurecic
All right, Ben, can I, can I ask a question, actually?
Anna Bauer
Of course, yeah.
Quinta Jurecic
Amelia, I'm really curious for your your thoughts on the way that the order was drafted in terms of the fact that surely the administration knew that this was going to be immediately litigated. It struck me that, you know, obviously arguing that the 14th Amendment doesn't guarantee birthright citizenship is going to be a stretch under any circumstances, but there were ways that they could have drafted the order that might have been a little bit easier to defend in court than what they actually went for. So, for example, there's a legal theory that Judge Ho and the Fifth Circuit has kind of been mentioning that undocumented immigrants specifically, that their children would not be entitled to birthright citizenship, but the order goes way beyond that and would strip birthright citizenship from anyone who doesn't have a parent who's either a green card holder or a citizen. And I honestly didn't know how to read that decision because I had been expecting sort of undoc to target specifically the children of undocumented immigrants. So I was just curious for your read on, like, is this ideological that sort of go big or go home? They really thought they could get it through the courts. They didn't care whether they could get it through the courts. Like, what is going on here to.
Amelia Wilson
Ask me to contort my brain to try to understand what they're thinking is I just, I don't know that, that I would be able to do it in good conscious. I mean, but I, I guess, I mean, I agree with you. It is curious. The language is really very curious indeed. And I've puzzled over that conjunction moment in this with the, the mother being unlawfully present. But then the father is not a US Citizen or green card holder, which kind of is the same thing. So I'm not really sure.
Anna Bauer
Right.
Quinta Jurecic
And why is it written so that the, the mother and father are in different categories?
Anna Bauer
It's bizarre, right?
Amelia Wilson
Exactly right. And so it's almost written to fail in a, and if I, I hope and I, and I do believe, like, even if I weren't invested in this conversation, I think it's, it's, it's, it's all, it's just facially specious and it's, it's probably going to fail anyway. I think it's probably, again, a situation where the administration has learned that they can issue outrageous declarations like this. And it will be then litigated in the courts. And they're kind of going to work it out and figure it out as they're litigating it. And again, with the, with the Muslim ban, that worked. So, so why not think that it might here where clearly it's going to end up in the Supreme Court. And now he's got a, a very favorable raft of judges on his side that he's personally placed in on the bench. And so maybe they're just thinking this is it, this is the moment.
Benjamin Wittes
Yeah. Just a reminder that what happened in the travel ban case was they issued the first version, it litigated fairly far, they then pull it and replace it with a second version, and then you have to litigate that all over again. And then they did it again with with yet a third version, which was the version that the Supreme Court eventually upheld. All right. I want to shift gears now, staying on the subject of immigration, but moving to the use of the military to enforce immigration law. Which brings us back to Scott R. Anderson. So, Scott, talk about the use of the military executive orders vis a vis the border, a matter about which I just want to flag for readers that there is a terrific piece on this on Lawfare by Chris Mirasola, who could not be with us today, but I do want to flag that piece for you on this subject. Scott.
Scott R. Anderson
Yeah, absolutely. A phenomenally useful piece that Chris sent us. There's a couple of executive orders where you see this question of using the military to a enforce the border or potentially even participate in deportation efforts and things like that, although that's actually like not as quite as consistent as border security throughout. What's really interesting about it is that it pairs conventional statutory arguments in various regards with broad claims of presidential constitutional authority, inherent constitutional authority. This comes to kind of two separate executive orders. One is executive order protecting states states against invasion, which should not be confused with the other executive order says protecting Americans against invasion. There's two that are protecting us against invasion, and then there's also a clarifying the military's role in protecting the territorial integrity of the United States. The latter executive order basically directs northcom, which is, you know, one of these joint commands that is responsible for activities in the Northern Hemisphere basically around the United States, and it's Canada, Mexico to reevaluate and develop plans to play a more active role in defending the role of independent the territorial integrity and particularly against invasion of the United States. Right. But it leaves open this open question saying, well, what is the legal under authority under which the President will be doing this. I think the answer for that comes in the other executive order I mentioned, which advances this very broad idea that a the President has. Has an obligation, or at least the federal government, I should say has an obligation under the guarantee clause, Article 4, Section 4 of the Constitution, to protect the states against, among other things, invasion, also protects against democracy and domestic violence were requested by state authorities. But the invasion bit is the relevant constitutional language here. And that executive order makes this argument that the President has broad authority to satisfy this obligation on behalf of of the federal government because of course, federal government involves Congress as well. And traditionally this has been, I think, understood to be a shared authority and that he basically makes a determination that that obligation is not being met, the obligation to defend against invasion and that he has a constitutional authority to ensure it's being met, even where this is implied. But I don't think it's just read too far between the lines, even where the congressional statutory authority doesn't go that far and doesn't give him what he needs to do it. He notes there are several statutes that give broad authority in areas and he leans most directly on several in the INA about deportation authority and other authorities. But he says, hey, we also are ready to use the President's inherent constitutional authority. And when you marry that argument with the other argument about setting up the military to play a much more active role in these sorts of border enforcement tasks, it really raises this possibility that we are seeing a push against the conceptual mechanisms and the conceptual statutes and other authorities that have been used to involve the military in border enforcement, other types of enforcement in the past. There are lots of statutes that allow for military participation in things like combating narcotics trafficking that have been used to deploy military forces to the border in the past. But they are traditionally understood to not be an exception to the Posse Capitatis act restriction. And so they are understood to not fully authorize the sort of law enforcement activity that involves a direct conflict between soldiers and civilians. At least that's how the executive branch has traditionally interpreted them, although they could change that. And so that's not a full answer. You have the Insurrection act, which Trump has suggested that he is going to think about doing in the next 90 days. If I recall the time period successfully to do that, though, he has to declare a proclamation and find a finding that there is either national security conditions, domestic violence, or a failure to enforce federal law. Certainly a possibility he could do that would federalize troops on the border. But that is an Exception to Posse Comitatus act limitations would allow that sort of direct conflict. But it's pretty extreme measure. It has a lot of people, a lot people nervous. We know there are strong pushback back in his prior administration against that idea from the Defense Department. Instead, when we saw him deploy troops to Washington D.C. during Black Lives Matters protest, that was under 502F, an authority where state authorities can volunteer state National Guardsmen to pursue missions under kind of federal direction. That's another avenue where president could do this. And those people, because they're not technically federalized, are not technically subject to PCA limitations either. But maybe that's not checking the box quite enough here. And this is yet another avenue by which to achieve this outcome. Notably, it's not clear where this goes exactly, because if you were to do any of this, I think you, any good government lawyer would say, well, we're going to lay out Belton suspenders. This with all these different statutory arguments first or whichever ones we can apply to this particular situation. And then the constitutional argument will be the backup argument. Right. So it's not clear that the President is going to directly rely on this constitutional argument, like at least in the first instance of most of these cases, but it's gonna be hanging over a lot of these actions and there's gonna be this question. It's insofar people, as people assert statutory limitations on the President's authority in this space, maybe he'll turn to this constitutional argument. And I suspect what we'll see is a lot of arguments from the Trump administration, from the Justice Department, kind of like we saw after 9, 11 during the George W. Bush administration, where they use broad claims of constitutional authority to leverage for constitutional avoidance in interpreting right relevant statutes. So basically pushing to say you should interpret statutes to give us maximum authority because doing otherwise risks having to face this difficult underlying constitutional questions about our inherent authority. And a few places it's worth noting, maybe hints at the idea, kind of reads like they're trying to formulate as an exclusive authority, meaning something Congress couldn't restrict. That would be a pretty extreme thing to do. It doesn't say that expressly anywhere. It always describes as an inherent authority on the part of the President, which can mean a kind of shared authority with Congress. But I think you could see a little bit of a framework there for that if push came to shove, at least as a possibility.
Benjamin Wittes
Just a quick correction matter. At the beginning of your answer to this question, you sparked a little confusion in the chat because you referred to protecting the federal Obligation to protect the states against democracy. And I, I clarified, I think in the chat that you meant there, the Republican guarantee clause, but I didn't want to speak for you. And so what is the precise requirement that the federal government guarantee the states?
Scott R. Anderson
The guarantee clause guarantees the states democratic. The federal government, the United States. So Congress and executive branch together guarantee the these individual states, democratic governments, protection from invasion. And they're upon petition by state authorities, the governor or the state legislature fund available or sorry. That the state legislature or governor fund available against domestic violence.
Benjamin Wittes
All right, that is what I just wanted to make sure that we weren't saying that the federal.
Scott R. Anderson
That was from memory. I may have fudged that slightly, but I'm like, that's 99.
Benjamin Wittes
Your summary is correct this time.
Quinta Jurecic
All right.
Benjamin Wittes
Finally, Quinta, we have an executive order against the weaponization of the federal government. This got a lot of attention Monday night when it came out. It's gotten a bit less attention since Monday night. What does it do? What does it not do, as you say?
Quinta Jurecic
I think it's probably gotten a bit less attention because it doesn't immediately do anything, really. And it's, I should say it's kind of of a pair with another executive order that's entitled Restoring Freedom of Speech and Ending Federal Censorship. So where obviously the weaponization order is about the supposed weaponization of government by the Biden administration, this is about supposed censorship. By censorship. The administration seems to be referencing content moderation on social media platforms to the extent that it was encouraged by the federal government or possibly beyond that. And what both these orders do is essentially direct the attorney general and the Director of National Intelligence in the case of the weaponization order and just the attorney General in the case of the censorship order, to take appropriate action to review the government's actions over the last four years and send the president a report with recommendations for appropriate remedial actions to be taken. And that's kind of it. So unlike specific executive orders, often there's an executive order will say, you know, this, the head of this agency is directed to look into this issue and give me back a report in, you know, 60 days or 90 days or 180 days. In this instance, it's just left totally open. This could take as long as the Justice Department and the Office of the Director of National Intelligence wants. It could take until, you know, the last day of the Trump administration. And it's also not clear what it means to take appropriate action to review these activities. It's not clear what remedial actions might be recommended, like what the range of options is. It's not clear even what the range of activities are that that are being investigated, because as I said, regarding the censorship order, it's defined really, really broadly. And then on the weaponization order, it's also just very, very unclear. The top of the order has this sort of language that I think is familiar to anyone who's followed Trump's complaints about being politically persecuted, about that this is a weaponization of prosecutorial power to upend the democratic process. That's a direct quote. What is he actually referring to? There are some specific examples. He refers to the January 6th prosecutions, for example, as an example of weaponization. He refers not by name, but to a case that is clearly that of Douglas Mackey, who was a Trump supporting sort of Twitter troll in 2020, 2016, who was prosecuted for posting information that was, the Justice Department argued, was meant to trick voters into not actually voting if they supported Hillary Clinton. So Mackey, he was convicted. His case is currently on appeal. There's other reference to investigations of parents protesting at school board meetings. So that is a reference to sort of freak out among the Republican Party about the fact that the Justice Department had sent a letter early in Biden's tenure about the fact that the Justice Department was going to be taken seriously, you know, threats against school board members, for example. So this is really an extraordinarily broad range of examples that sort of are really a grab bag of, you know, grievances that have been voiced in the sort of maga. Right. And it's not clear how far they extend. And so ultimately, basically every part of this is vague except that we know that the Attorney General and the Director of National Intelligence have been directed to conduct this review.
Benjamin Wittes
I want to turn at the end here, Anna Bauer, to any other litigation that may be have been generated by any of this or that, any you anticipate that has not yet been filed, but we expect to be coming down the pike. What do we know about other litigations that are. I mean, this is an immense amount of policy, and all of it is controversial and a lot of it generates standing for some of us or for somebody. What other suits exist and what others are you looking forward to?
Anna Bauer
Yeah, so let me mention two suits that are or two pockets or kind of groups of suits that are related to some of the executive orders. The first are, is a number of suits that have been filed related to doge, the Department of Government Efficiency that is being led by Elon Musk, the Order of Operations Here, though, Ben, is a little bit odd in that DOGE had not even been created by executive order when these suits were filed. They were all filed in the District of Columbia by various advocacy groups. But they, the three of them essentially challenged doge's compliance with transparency laws under the Federal Advisory Committee Act.
Benjamin Wittes
We call it the Faculty here.
Anna Bauer
Yeah, what was the headline that we once had FACA around and find out.
Benjamin Wittes
Yeah, it lends itself to good headlines.
Anna Bauer
It's, it's a great title for an acronym for a statute. But so essentially there's transparency rules that these types of, you know, advisory committees, these kind of task forces or bodies that are really not like within government itself, but they're advising on government operations, corporations, they have to comply with various, you know, ways of staffing it, of hiring for it, disclosing documents or communications related to it, all of these various things. So these suits were filed like basically 20 minutes after Trump was inaugurated that claimed that Doge, which had not yet officially been established as any kind of body, either governmental, quasi governmental or non governmental. The claim in these suits is basically that DOGE was not complying with faca. So then Trump creates DOGE by executive order. And I think what these suits imagined is that DOGE would stay as a type of advisory committee or quasi governmental body, but instead what Trump did was create DOGE within the office of the Executive government. And so it's a bit of an odd thing here where I think that these suits, there might have to be an amended complaint. I'm not entirely sure that there's any way that the Federal Advisory Committee act actually now applies because DOGE has been differently constituted than people imagined it would be by this executive order. There is another suit, though, that relates to DOGE that is about getting, you know, FOIA ing materials that relate DOGES communications during the presidential transition with omb. And so that might, you know, continue. But I think that in terms of some of these other suits, the plaintiffs maybe have to go back to the drawing board and do an amended complaint. And then the other thing that I will mention is that there is a another suit that is related to the schedule at reinstituting Schedule F Executive Order, and that has not yet gone forward other than just the complaint being filed.
Benjamin Wittes
Yes. And for those who are wondering, why have we not talked about any of the civil service oriented executive orders? The answer is twofold. The first part of the answer is, how much do you expect us to do in an hour? I mean, you know, we're 57 minutes done and we haven't said word one about these executive orders orders. We're going to deal with that in a different podcast. The second reason is that we have an absolutely superb article on this subject by a scholar named Nick Bednar, and we hope to sit down with him and talk through specifically all of those executive orders in its own session. So we didn't do pardons today because they're not an executive order, and we did them in a special session. We will do other executive actions. These were the ones we thought we could cram into this hour. As you see, it's a lot of territory we're covering. All of these subjects deserve a lot more time and attention than we're able to give them. Right here. There are summaries of all the relevant documents on Lawfare, and we are rolling out analysis of the documents beyond the summaries as we produce it. So keep your eye on the site. We have generated a special page that identifies all the materials as well as all the various analytic work people are doing. And that is a sort of special executive order page on the front page of Lawfare. So please check that out. Thank you to Amelia Wilson. Thank you to Anna Bauer Quinta, Jurassic Scott R. Anderson and Alan Rosenstein. It feels like years ago that I talked to Alan Rosenstein and we will be back soon. Thank you all for joining us. The Lawfare Podcast is produced in cooperation with the program Institution. You can get ad free versions of this and other Lawfare podcasts by becoming a material supporter of Lawfare using our website lawfairmedia.org support. You'll also get access to special events and other content available only to our supporters. Have you rated and reviewed the Lawfare Podcast? If. If not, please do so wherever you get your podcasts and look out for our other podcast offerings. This podcast is edited by Jen Patya. Our theme music is from Alibi Music. As always, thanks for listening.
Amelia Wilson
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Date of Discussion: January 27, 2025 (Rebroadcast February 1, 2026)
Host: Benjamin Wittes
Panelists: Scott R. Anderson, Anna Bauer, Quinta Jurecic, Alan Rosenstein, Amelia Wilson
This episode brings together Lawfare editors and contributors to analyze the first ten executive orders signed by President Trump in his second term. The panel explores the legal, constitutional, and policy implications of these orders, focusing particularly on their ambitious scope, immediate legal challenges, and notable reliance on contentious doctrines like the 10th Amendment’s anti-commandeering principle. The conversation covers executive actions on immigration, foreign policy, tech regulation (notably TikTok), the use of the military domestically, birthright citizenship, and orders addressing claims of federal government “weaponization.” Throughout, the panel highlights the practical limits of executive action, the potential for (and early occurrence of) litigation, and broader themes of institutional pushback.
Entrapment by Estoppel: Alan explains this as the best possible defense for Oracle and Akamai, who restored services to TikTok, but considers it unlikely to withstand scrutiny given the statute’s clarity.
Legal Limbo: Companies like Apple & Google are avoiding risk; Oracle & Akamai may be exposed to massive liability.
Notable Quote:
“As with many things in the second Trump administration, I think we are rapidly exiting the realm of law and entering the realm of something else...This is all so patently stupid, like these interpretations are so ridiculous...that I think most courts would say...it was not reasonable for them to rely on this government assurance.”
— Alan Rosenstein [10:03]
[12:04] Litigation Status: No active suits yet, largely due to complicated questions of standing and the political nature of non-enforcement decisions.
"The Paris Agreement withdrawal says that it immediately considers all obligations nullified and enters effect immediately... Paris Agreement says you can't do that. It requires a one year withdrawal period."
— Scott Anderson [16:00]
"Declaring [migration] an invasion...strips those potential immigrants of their rights to a full and fair hearing. It also engages the military and domestic law enforcement."
— Amelia Wilson [21:55]
[35:45] Amelia Wilson: Explains the EO’s dramatic break from the 14th Amendment and the practical chaos it could create.
"It boggles the mind that a member of the bar could stand there and say that this order is constitutional."
— (Unnamed Reagan appointee judge) [38:33]
[41:06] Panel speculation on the administration’s strategy — purposely drafting broad and likely-to-fail orders to reach the Supreme Court, banking on favorable judges.
"It’s almost written to fail... I think it's a situation where the administration has learned that they can issue outrageous declarations like this. And it will be then litigated... With the Muslim ban, that worked."
— Amelia Wilson [43:07]
"It really raises this possibility that we are seeing a push against the conceptual mechanisms and the conceptual statutes and other authorities that have been used to involve the military in border enforcement in the past."
— Scott Anderson [48:32]
“This is really an extraordinarily broad range of examples that sort of are really a grab bag of grievances that have been voiced in the sort of MAGA right. And it’s not clear how far they extend.”
— Quinta Jurecic [55:22]
On Extrapolation Beyond Law:
"We are rapidly exiting the realm of law and entering the realm of something else... It was not reasonable for [these companies] to rely on this government assurance."
— Alan Rosenstein [10:03]
On the Challenge to Birthright Citizenship:
"It boggles the mind that a member of the bar could stand there and say that this order is constitutional."
— District Judge, per Anna Bauer [38:33]
On Executive Orders as Political Gambits:
"It's almost written to fail... [The administration] learned they can issue outrageous declarations like this and it will be then litigated in the courts... With the Muslim ban, that worked."
— Amelia Wilson [43:07]
On the Broad Use of Executive Power:
"It really raises this possibility that we are seeing a push against...statutes and other authorities... used to involve the military in border enforcement."
— Scott R. Anderson [48:32]
On Orders Against “Weaponization”:
"An extraordinarily broad range of examples... a grab bag of grievances that have been voiced in the sort of MAGA right."
— Quinta Jurecic [55:22]
The conversation is marked by a serious, often incredulous tone as panelists parse both the technical legal arguments and the broader implications of Trump’s aggressive early executive actions. There’s broad skepticism about the legality and constitutional soundness of many orders, recognition that litigation is essential and inevitable, and a pointed sense that political and legal turbulence is not only anticipated but, in some cases, intentionally courted by the administration.
This episode provides a comprehensive, clear-eyed discussion of the immediate Trump executive orders, illuminating both the detailed legal mechanics and the wider stakes for U.S. governance and constitutional order.