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Hey guys, it's Andrew Egger. Welcome to the Bulwark. Donald Trump's got some ideas for different things his troops might be wanting to do as they get to Chicago today. We are in this moment right now, National Guard troops heading up from Texas yesterday, getting ready to deploy, massing on the outskirts of Chicago. And we have this very interesting sort of backseat driving from President Trump. Here's what he posted on Truth Social this morning. Now, I guess if you wanted to, you could just look at that as color commentary. You could say, you know, this is just a thing the President wants to see happen. It doesn't really have anything to do with his, his, you know, star spangled Donald Trump brand National Guardsmen heading into Chicago today. That is one argument you could make. I am here with, with jvl, the boss man himself, to talk about perhaps some, some alternate hypotheses for, for what's going on here. Uh, jbl, how you doing this morning?
B
I mean, not great.
A
Yeah.
B
So you, it's all super not great.
A
You were on the train heading to D.C. for our live event to were reading about all this. You wrote an emergency triad that went out last night. I encourage everybody to go read it, if you haven't already. But basically just sort of taking stock of this moment. What do you see going on in Chicago this week? Where are we at?
B
Yeah. So this is, this is what worries me is what our former colleague Amanda Carpenter is now. Protect democracy. She wrote yesterday. This is a breakdown of federalism. Right. And so you have a conflict between the federal government and a state government, which is what Trump has created by demanding that J.B. pritzker activate the Illinois National Guard, even though Pritzker says it's not warranted, the Illinois Adjutant General says it's not warranted, and the mayor of Chicago says it's not either warranted or, or desired. Right. So you have the President jumping in over top of the local leaders and saying, you have to do this and if you don't, I'm going to do it for you, which is what he's done. That's one level of crisis. The second level of crisis is the governor of Texas then volunteering his state's National Guard to be deployed in Illinois by President Trump as well, and Trump eagerly taking him up on that. And now what you have is a state on state conflict where one state is volunteering to send armed soldiers to impose the will of the President of the United States on the citizens of another state. And that's different. Right? I mean, that is like I don't want to. I don't want to say the C word here because that's whatever. But. But this is, this is how big conflagrations start. And turning this into a state on state conflict as opposed to a. What could have been confined to just a legal conflict between the federal government and the state of Illinois is unbelievably dangerous. Yeah.
A
Yeah. And it's particularly remarkable that this is coming. You know, first of all, this is a thing that they have been examining, kicking the tires on the legality of for a number of months. We know that from. From reporting they've been looking into the possibility of doing this. But the precipitating event for this sort of interstate lines National Guard deployment was, was the temporary restraining order they were hit with in Portland, Oregon over the weekend. Right. Where. Where a judge temporarily told them there are no conditions on the ground to activate the Oregon National Guard here, so you can't do that. And basically, as a. Essentially just like a fuck you to that order, they then immediately tried to call up the California National Guard into Portland. And then that got the ball rolling for all of this. It's just remarkable that all of this stuff, that the fact that they're playing with fire in this really insane way is all sort of like part of this oblique, just sort of bank shot, we're mad at the courts sort of thing, but also, you know, in a more direct way, just, just the next. The next turn of the screw in this growing authoritarian moment.
B
Well, and it's desired. And this, I mean, I. It is really important for people to understand that this is not a blunder that is happening by accident. The President of the United States is attempting to foment a crisis. And it began by sending in federal agents to the city of Chicago. And either these federal agents are completely rogue or they're doing what the executive branch wants them to do. And what they're doing is behaving in a fairly lawless manner. And, you know, we have now a number of incidents which have been documented in which you have these masked federal agents assaulting citizens of Chicago, assaulting civilians, shooting pepper spray at sort of, you know, the media, who are just sort of literally in one case driving by of a CBS reporter who is in her truck driving past a nice facility, and they just decided to like, tag her with some pepper spray. There's video out today of them hitting a sort of a Presbyterian minister standing outside an ICE detention facility, just, you know, arms open, praying, and a bunch of ICE guys on the roof just decided to, like, you know, hit him in the head with a pepper ball. This stuff is real. And if you look at Pritzker's. Pritzker's long, I think it's like 80 pages, 69 pages. His lawsuit asking the court to prevent the Trump administration from doing this. He goes down, even as sworn testimony from the local chief of police in the town where the ICE detention facility facility is. And this guy's a career cop, is just like. I mean, you got to see his testimony. He's like, I've never seen anything like this. This is. This is absolutely outrageous behavior from federal law enforcement. And so to the extent that there is a crisis, Trump is attempting to precipitate it. And he is then using the. As far as we can tell, overwhelmingly peaceful demonstrations and protests against it as excuses to deploy more force. And again, I just. You can either believe that what Trump is doing is purely by accident or that he is doing this on purpose. And if. If you believe he's doing it on purpose, then you have to think to yourself, to what ends? What's the end game here? And I don't think there's a version of this story that has a nice answer.
A
Yeah, yeah. I mean, the thing that I have found so just appalling and striking. I mean, if you just think about any other time in sort of modern American history when there have been these sorts of open clashes between law enforcement and protesters or what have you, there's always this overwhelming sense that, man, something's gone wrong, something's broken down, and we need to figure out how to get past this moment and back into some semblance of normalcy, of order. And, like, different people have disagreed about the correct sort of policy levers to pull to get there, but that has always sort of been, like. It's been obvious that, like, that moment of crisis is not what anybody wants. But when you. When you hear guys like Donald Trump talk about, you know, what he wants to see as sort of, like, the baseline level of functioning law enforcement in this country, he is. He is naked about it. It's plain as day. He sees, like, an absence of cops out there in the street roughing up the bad guys. You know, an absence of they spit, we hit happening as, like, evidence that. That, you know, the. The radical left and the. The antifa and the insurgents are just getting away with it all. They're running amok. They're everywhere, and they're running amok. And if. If your feed, if your, you know, Instagram reels aren't Full of footage of cops, you know, and. And protesters, you know, just tussling in the streets all the time and tear gas flying and people getting hit with pepper balls and all this stuff. If you. If you aren't actively seeing that, then the bad guys are winning. It's this complete inversion. And like you say, it's. It's all in service of. Of getting people to this permission structure where. Where what matters is not that everybody follows the law, people in the streets and police alike, but that in this sort of street warfare that's happening everywhere, the good guys are winning. And that he wants you to see the good guys as his. His masked, military, militarized police, and in some cases, just the actual military.
B
Yeah, I mean, I. I think what he wants to do is he wants to break the public's will to protest, and he. He wants to break the public's willingness to stand up and come out with. With their phones and record things and say, this is wrong. Right. He wants everybody shut up inside their houses, meekly doing whatever he wants. That's why the no Kings protest that's coming up in a couple weeks is so important. Can I just read something to you that's. It's fascinating to me. So we are used to law enforcement behaving in very careful ways and, and not always properly. Right. I mean, you know, police going and saying bad things or, you know, or police going and giving false reports is a thing which has happened forever. But at least they. They acted as though they were professionals. I want to read you a press release from October 6th from the Department of Homeland Security. Here's the headline. Despite multiple vehicle attacks by domestic terrorists, DHS law enforcement arrests the worst of worst, including a TDA gang member, drug traffickers, child abusers, and other violent thugs in Chicago. Vehicle attacks by domestic terrorists. So again, this is domestic terrorist is a word which is being used a lot by the administration right now. And Stephen Miller has called the entire domestic. The entire Democratic Party a domestic terrorist organization. Like, I don't know. These words do have meanings. There are laws which. Which deal with terrorist organizations. And either you believe that they're just doing this for the lulls, or you believe that they're doing it because they're trying to establish a predicate to. To ratchet things up even more. And again, we're only 10 months into this. We're only 10 months into this, Andrew.
A
Yeah. Yeah. And I feel like we need to put, like, a fine point that this is not.
B
We're not.
A
We're barely even speculating. Here. I mean, we're, we're just talking about stuff that's happening on the ground. We're talking about the President's own actions. Again, you know, this morning he's just spitballing, you know, man, I really think that Brandon Johnson and J.B. pritzker ought to be in jail. Now that, that is a little bit just, just, you know, him putting on his pundit hat. But he's the one who's sending these troops into these cities. And if you want an even more sort of like direct example of this sort of thing, the other day he, he sent out a different tweet or a different truth social post where he basically said, you know, to whom it may concern, to all ICE agents and DHS agents and National Guardsmen and local law enforcement and stuff. If you burn the American flag, we're going to arrest you and put you in prison for a year. You know, so just like, just like, be advised if you are law enforcement that if you see somebody burning an American flag, which is constitutionally protected First Amendment speech, as long as you own the flag in question, that guy's a criminal. You ought to proceed with that person according to the way that I've told you to proceed with criminals, which is state violence administered on the spot. Right. And I mean, again, this is just the President's own words to the President's own troops. As the President orders these troops into these blue cities. There's no, there's no leaps of logic, there's no jumps. That's just what's happening right now.
B
Yeah, I mean, I mean, the, the law. And this is very clear. If, if person A brings a American flag, they own out into a public space and burns it and person B goes and attempts to stop them or something. Person B is the one who's committing misdemeanor assaul. And Trump is just saying, I don't care what the written law is. You, my armed agents of the state, are to do this thing instead. And unstated is, don't worry, I have the power of the pardon, which, by the way, I've already used on 1500 violent offenders from January 6th. It was the first, literally the first thing he did. Right. I, I just, I don't want to sound like my hair's on fire, but like, again, I said this before. How do we think this story ends?
A
Yeah, I mean, let me ask you about that. I mean, what's. Maybe not, maybe not. How does it end? But what seems like the next thing here, I mean, like pritzker and these guys are lodging their disapproval. There are lawsuits ongoing. There's supposed to be a hearing. What day of the week even is it? I guess tomorrow. Tomorrow there is a, there's a hearing of a, of a judicial, of a. Specifically for this, this Illinois, you know, flare up. They, there was the other district judge who already sort of temporarily slapped this stuff down in Oregon, and I guess we're going to get some of that tomorrow. What do we know about that?
B
So we're going to get a hearing on the Illinois case. And Trump said earlier this week that if the court rules against him, he's just going to invoke the Insurrection Act. And by invoking the Insurrection act, that would give him legal cover to override the court's current order. Now, I mean, a, let's pause for a minute and note that the guy, the only person in the last 150 years to attempt a violent insurrection, is going to be the one who goes and invokes the Insurrection act for a fantasy insurrection. That's amazing. But what we need to understand here is that of course, if there was an ongoing insurrection, he would have simply declared and used the Insurrection act from the start. Right. And so it is prima facie, it's not being done in good faith. Right. That will trigger another cascade of, of legal action which will wind up at the Supreme Court. And, you know, we'll see what happens. One of the things we've learned with Trump's stuff is that he has found that he can do things. And even if the Supreme Court eventually rules against him, it doesn't really matter, because by the time they get around to that, he's established facts on the ground. We saw this with the firing of federal workers. Right. Supreme Court eventually said, no, you can't do that, but it turns out they did that. They fired all those people and those people are all gone. So who knows, right? It depends on whether or not their temporary restraining order is preventing the imposition of the Insurrection Act. We are going to have a huge legal fight about this stuff. And if Trump doesn't lose decisively, then it's going to happen again and again, and it is going to happen at polling places in the 2026 election. And that, I mean, that's what this is really all about. And so it is. The legal fight itself is supremely important. What happened? Can you force Trump to back down? Right. If he loses badly enough in the courts, is this the case where he decides he's going to try to defy the courts or not? Or does he back down? We've, we've seen him back down after losing before.
A
Right.
B
The extraditions to El Salvador is, is the, the prime case of this. It is desperately important that he be defeated in court and that the courts rule with alacrity and vigor on this. I think they will, or I think they should. I would say that with everything up to the Supreme Court, which is what we just don't know. The Supreme Court is a black box at this point. And it's, again, there are two ways of looking at this. Either what he's doing is legal or it's illegal. If it's legal, then why won't this be standard ante for American politics for forever going forward? Why wouldn't we just assume that this is how the world works from here on out? And if it's illegal, then there have to be consequences. And that means Trump losing. And it means that at some point people responsible for this have to go to jail. And like, those are the only two options for the country. Unless you want this to be how it is for forever out into the horizon. Like, we are now basically a police state where state militaries can be deployed against the civilians of other states.
A
I'm just sitting around waiting for if we survive this moment, we survived the 2016 moment, we survived the January six moment. It would have been kind of nice if Congress had gotten busy in the interregnum doing something to rein in some of these presidential emergency powers. Maybe we will have learned our lesson. You know, hopefully we live through this one. Hopefully we will actually get some more laws on the books, you know, closing some of these massive loopholes that the President likes to drive his tanks through and into the streets of American cities.
B
Yeah. Let me, let me say something here, though, Andrew, and this I have. So I think the Biden administration did not do enough. Like Trump proofing of the federal government, they focused on trying to improve the lives of average Americans with kitchen table issues, and specifically of rural red state Americans with, like, spending on projects to help them. That worked out great. But I don't think ultimately you can totally authoritarian proof a system. And this gets like one of the things the founders said, right? The founders talked about how virtue in the people is required because you can't legislate morality, you can't legislate everything. Right. You can't go through, I mean, at some point the federal system has to assume that the people don't want to elect authoritarians because you cannot go through every single place and, and make a law Preventing the person who's president from acting like an authoritarian. Right. I mean, this is, you do need to have some room for emergency situations. You need to have it. And even if the Biden administration had, had really decided to try to trump proof the government, like, I don't know, do we think that they would have thought, well, we got to make sure that he can't send National Guardsmen from red states into blue states to subjugate the civilians in cities? Like, I don't know that that would have cropped up on things, you know, they would have been thinking about like, well, we got to mandate tax document disclosures for presidential candidates. Right. And I just, it's, at the end of the day, this is a people problem again. He's, he's sitting at like 42, 44 approval. And that is enough. Right.
A
It's not great.
B
He's still minus net 11, you know, upside down. But if people look at this and 42 or 44% of the country looks at Texas National Guardsmen being sent into Illinois and says, yeah, that's cool. I like that doesn't matter. It doesn't matter because that means that some critical mass of the country, not a majority, not a majority, but a critical mass of it is okay and wants this. And you can't trump proof that if 44% of the country wants authoritarianism, eventually that's what they're going to get. Yeah.
A
All I'm saying is I hope someday we get to try. You know, maybe there's no silver bullet, but, you know, maybe there, maybe there are a few, a few copper bullets we can string together and, and jerry rig some sort of, some sort of small defenses again, if we get through, if we get through what we're, what we're in right now. So we're going to keep watching it. We can probably leave it there for more great vibes and happy times like this. If you happen to be in the D.C. area, come to our live show tonight. You know, we're at the Lincoln Theater. It's going to be, it's going to be, I feel like this is, is this about the, about the speed or. We're going to try to put a happy face on and do some fun stuff as well, I gather. But there will probably be a little bit of this, a little bit of this mixed in there too. If you're not in the D.C. area or if you are, we hope you will subscribe to the feed. Thanks for watching. Head over to the Bulwark. Com, read our stuff. Read JVL's triad. Read the Morning Shots newsletter. I write with Bill Crystal. Read all the good stuff. Thanks for watching, and we'll see you all next time.
Host: Andrew Egger with guest JVL (Jonathan V. Last)
Date: October 8, 2025
In this urgent episode, Bulwark’s Andrew Egger and JVL dive into the crisis unfolding as President Trump deploys National Guard units from Texas into Chicago, overriding the local and state authorities who oppose federal intervention. The conversation examines the dangers of escalating federal-state conflict, the intentional stoking of crisis by Trump, the broader trend toward authoritarianism, and implications for American democracy and federalism.
Background: Trump has demanded Illinois’ governor, J.B. Pritzker, activate the state National Guard in Chicago. When refused by state and city officials, Trump has facilitated Texas sending its National Guard instead.
JVL’s Assessment:
"This is a breakdown of federalism. [...] Now what you have is a state on state conflict where one state is volunteering to send armed soldiers to impose the will of the President of the United States on the citizens of another state." (01:17)
The precedent of one state’s troops being sent, with presidential blessing, into another state is described as perilous and unprecedented.
Legal setbacks, such as a restraining order in Portland blocking National Guard activation, have spurred the administration to push boundaries further—shifting to cross-state deployments as a provocation.
The hosts stress this is a deliberate, not accidental, escalation:
Federal agents, especially ICE, are behaving “in a fairly lawless manner”—assaulting civilians, journalists, and peaceful protesters.
Trump’s goal is framed as breaking the public's will to protest and enforcing obedience through force.
JVL reads a DHS press release headlined: “Despite multiple vehicle attacks by domestic terrorists, DHS law enforcement arrests the worst of the worst, including a TDA gang member, drug traffickers, child abusers, and other violent thugs in Chicago.” (09:09)
Notably, Stephen Miller (Trump advisor) has openly called the entire Democratic Party a “domestic terrorist organization.” (09:50)
Trump is described as instructing law enforcement to ignore constitutional freedoms, e.g., advocating year-long prison sentences for flag burning (protected speech).
Reference to pardoning ~1,500 January 6th offenders as a precedent for the disregard for the rule of law.
An impending court hearing in Illinois could decide if Trump’s actions stand; however, Trump has threatened to invoke the Insurrection Act if the courts rule against him.
The hosts highlight the danger of the courts being outmaneuvered, with “facts established on the ground” before legal decisions arrive.
The outcome may set a permanent precedent: either it is upheld and becomes the new norm, or there are lasting consequences.
There is criticism that the Biden administration did not do enough to "Trump-proof" the federal government’s emergency powers, but acknowledgment that not all risks can be legislated away.
The core issue reduces to public will: as long as a significant minority backs anti-democratic moves, the system itself cannot fully prevent authoritarian drift.
On the scale of the crisis:
On the administration’s intentionality:
On Trump’s vision of law and order:
On the logic of escalation:
On the use of rhetoric and justification:
On the potential future:
On public complicity:
The episode underscores how Trump’s recent actions—deploying out-of-state National Guard troops over state objections—represent a deliberate and dangerous erosion of federalism, legal norms, and civil liberties. Egger and JVL contend that this is not political theater but a conscious construction of crisis designed to advance an authoritarian agenda, raising urgent questions about the resilience of American institutions and the will of the public to resist. The outcome of current legal battles may set the course for the nation’s political future.