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A
Hey, guys. Me, Sam Steinman @ the Bulwark, back with my bud, Tim. We are here to talk about Chicago as the next battlefield, apparently for Trump's wars. He put out a bleep that was ominous to say the least. Saying what was it that he likes the smell of deportations in the morning. Is that what it was? I forget what it was.
B
It is. Yeah, it's right here. I love the smell of deportations in the morning. Chicago about to find out why it's called the Department of War. Then three helicopters and then Trump and an AI image with chi Apocalypse now with fire and stuff. I'm a little confused about. I thought that they were talking about how the city was already on fire and that law and order was going to bring peace. I'm a little confused why in this AI image, Trump is kind of overseeing a city of a reign of fire on the city of Chicago.
A
It's a really good point, Tim. You got him.
B
It just seems like there's some inconsistency in the messaging there.
A
Fair enough. All right. Actually, I want to talk about that, but I think the bigger thing to talk about is Megyn Kelly. So Megyn Kelly was doing her show and she was with Bhatia and they were talking about.
B
I don't think Bhatia has reached one word. She's not in Beyonce territory yet.
A
She is for me.
B
I was on Bill Maher with her.
A
And I really had a good time with her, so I don't want to.
B
She was on Bill Maher with Sam. She's kind of a populist. Right type. One of these. I was left and now I've gone MAGA type people.
A
Okay, well, Batya and Meghan, I go by first names only. Here they're talking and Megan drops some interesting analysis about the prospect of Trump forcing the National Guard to go into Chicago for this purposes. Let's watch Megan and then get Tim's reaction.
C
On the flip side, watching this happen with Pritzker in Illinois where Trump is saber rattling about sending troops next, saying, quote, it's going to happen. That'll be interesting. I it's going to be a legal battle because he's very limited in what he can do outside of Washington, D.C. you can't just send them into random cities in support of just fighting crime like that. You really can't do without the invitation of a governor. I'm sorry, but we can't have it. He does not have the constitutional permission to do it. And I think, and I hope I'm sorry for the People of Chicago, because I wish their governor would be better and ask for help. But I think Trump knows that. I think it was just a saber rattle. It very clearly is not constitutionally permissible. He cannot do it. I really hope he doesn't do it because I don't want a world in which I'm siding with Governor Pritzker over President Trump. But I will if he does it because he can't do it legally.
B
Megan, just calling balls and strikes. Love that from Megan. She might invite me back on the show sometime soon. And Megan have had a falling out. You know, I haven't heard from her nasty DM a couple little while ago, but it's been, that's been, that's been it. So I'm always available, Megan, if you want to chat it through. I agree with her on this, on the Chicago thing. I think it's the Megan speaking out of this leads me to believe that there are real like internal dissent and conversations about this. I don't suspect that she's just popping off about this. I suspect she's heard from people around, around Trump on this question. And I, and to me, I just, with Trump, you can, you always never really know, right. Is he just doing word diarrhea and shooting from the hip or is he saying something because, because he's not a really good poker player. He's kind of revealing where he's going to go. Like, you don't, sometimes, you can't really tell. And in this one, like earlier this week when he said, you know, we're looking into Chicago, we're looking at it very strongly. We're also looking at New Orleans. You know, we've got a great governor down there who's going to welcome us. We'll see how it's going to turn out. You know, I did a video on that. People can go watch my feelings about that. But to me, that signaled that he was considering like not, you know, do it, not challenging the courts in this way. I mean, he got rebuffed in L. A, as Megan mentioned in that video. And it's like, well, maybe the path of least resistance here, you know, if you're, or whatever metaphor you want to use, you're dipping your toe into the authoritarian waters. Maybe, maybe the first step is to not go over the blue state governor's heads, but go to blue cities and red states where you think the governor will welcome you and, you know, see how that goes. And then, you know, maybe if something happens in Chicago, there's a, there's a murder, you know there's some, you know, protest or murder or some, some reason where you can have a plausible excuse to go in based on a fake emergency. Then you go into Chicago later. To me that like with no inside info, just sort of reading the tea leaves, watching what they're talking about, I think that's where they're going with this. And on the one hand I think that it's just the most mild amount of good news and I think shows the importance and the effectiveness. The importance of the legal pushback against the regime is that like they've been brushed back a couple of times. I mean they're still doing a lot of authoritarian shit, but they've been brushed back a couple times. And if they don't go into Chicago, this will be a later. The latest example of it.
A
I got a few, I got a few things I want to push on that. One, what did Megan DM you? I'm kind of curious. Two, if you need, if you need a murder in Chicago as justification for going in, well, Chicago's got those. Don't worry, you have the justification. Three, I totally agree with the idea that they're probably ramping up a little bit here. So DC they could do because of the home rule stuff. LA was a little bit iffy. They had the riots, they use that as a fig leaf. But the riots were really confined and they got brushed back in court. I think they is your boy, Governor Landry and he calls in the Guard and they go into New Orleans or something like that where it's much more legally found. It's a solid legal foundation for that. And then they push off the Chicago stuff. That said, that said, I am sort of curious if they try to draw a distinction between ICE operations ramping up those and a anti crime operation because we've seen all these signals that they're using this base north of Chicago. They're going to get the military involved in some sort of ICE operation there. And that's got different legal ramifications than just going in with the National Guard to tamp down on crime. So that's where we're at now. The blue state governors have been pretty aggressively pushing back on this. And Westmore was talking about Illinois, Pritzker was talking about Illinois. How do you think they're dealing with it? Like, I don't really know what I would do in that situation, but it strikes me that they're hitting some right notes.
B
Yeah, I think Pritzker has been really strong and more. I'm both the threats to more were a Little less acute. But I think that Pritzker's messaging on this has been really good. And you know, again, making it clear that it's going to be a fight, you know, is an important, is an important first step here. Right? Because like, you know, Trump is in some levels like an insane honey badger that just like goes and bites anybody that he wants to. But like, but you know, there's still limits, right, to like what a man can do, what a 79 year old aging man with bruises on his hands can do. Right. So it's like, okay, maybe this is not worth the time versus the other thing. So I think it's been good that they've gotten some brush back pitches. I think that there's some more extreme ideas for the blue state governors as far as what they could do with the National Guard that is under their control that I, the JBL has pushed out and other people that I think are probably at this point not needed. But I think that they should have all options on the table. So, and I think that's my view. I think the blue state governors so far on this have acted pretty good. I mean the rubber hasn't really met the road yet now, you know, and I think that like that's the thing like in Chicago when they come up with some pretense, whatever the big balls of situation of Chicago is like the question is what do you do then? And so I don't know. I just one other thing, I want to extend my comment from earlier because your observation about ICE is really correct. And I think that like maybe they split the baby a little bit and have like a big ICE operation in the States and say that, you know, we've gone after a couple murderers in Chicago and it's a migrant crime that we're going to stop. And because it's hard to totally back down once you've done the shypocalypse now meme.
A
Yeah. And I thought that was sort of when he put it up, you know, initially I was just like, ah, this is no stupid AI generated thing that he's got going on. But a lot of people were like taken aback by it. And then I, and then I kind of hit me like he, you know, if you take the literal act, you know, literal reading of what he's saying, he's like, he's declaring war on a blue, on a city in America. I mean like, I'm not trying to like, I don't want to like seem hysterical about it, but if you just read it literally, that's what he is saying. And then I was just like, that's so.
B
And he wants the double meaning. Here's the thing. Always of like, take him seriously, not literally thing. It's like he wants both. Some of his base who wants there to be a war on Chicago to be excited about that. And then he wants the. Whatever, you know, to be able to have the other members of his coalition be able to say, oh, the liberals are so crazy at this. Oh, they're pro. Clutching their pearls. And I don't have my pearls on. But, you know, you know, it's a Sunday. It's not really pearls day. It is. It's intentional. He wants that double meaning. And. And like, it's ominous. It's not. Not ominous. Yeah.
A
I mean, that's the thing. It's like he still posted it. Like, even if he's trying to get aroused out of people. Like, it's not necessary. You don't have to do it. Sometimes you don't. Don't need to post anyways. All right, ma', am, you got to go.
B
You don't want to hear about the Megan, do you actually.
A
Oh, you're going to read it? Yeah, I kind of do.
B
Oh, no, no. I guess I pull it up. But the. I mean, it's not really that it's about what you expect. I mean, I, as a PR flack when Megan was at Fox, like, I worked with Megan a fair amount, like, booking my candidates on there. We knew each other. Okay. We had a couple of. How would I put this? Rocky. Interviews with various candidates of mine. We had to manage that together behind the scenes. So, you know, we felt like we'd been through some trials together. And I did a Tweet back in 2020 making fun of Brad Parscale. Remember when he was like the first campaign manager, second of Trump, then he was outside his house in his underwear. There's a. Bumps.
A
Were there Big issue. Yeah.
B
And I was making fun of him. And Megan thought that was insensitive and thought that I had let TDS get the better of me. And then we went on to a lengthy series of DMs back and forth where I said we should hash this out on one of our various platforms. She did not want to do that. And then. Yeah, nothing. Nothing since then, she didn't reply to my last dm. So there we go. I'm still waiting for a reply. Four and a half years ago. So. Megan, it's been 60 months anyway.
A
All right, Megan, if you're watching this, Tim's just constantly refreshing that dn.
B
Counting down the minutes.
A
All right, thanks, man. I'll talk to you later. And, guys, subscribe to the feed. You got good stuff like this. Talk to you later, too.
Podcast: Bulwark Takes
Date: September 7, 2025
Hosts: Sam Steinman (A), Tim Miller (B)
Main Theme:
This episode dives into recent comments from Donald Trump about sending troops into Chicago, analyzing the ominous social media messaging and legal boundaries, and featuring a notable moment: even conservative commentator Megyn Kelly admits Trump’s threats are illegal. Tim and Sam explore the significance of these statements and discuss the political and legal nuances, offering insight into the broader implications for U.S. democracy and law enforcement.
Megyn Kelly (clip – Legal stance):
“He does not have the constitutional permission to do it… I will if he does it [take Pritzker's side] because he can’t do it legally.” [02:53]
Tim Miller (on GOP internal dissent):
“I think this signals real internal dissent… I suspect she’s heard from people around Trump on this question.” [02:53]
Sam Steinman (on justification language):
“If you need a murder in Chicago as justification for going in, well, Chicago’s got those. Don’t worry, you have the justification.” [05:20]
(Sardonic summary of how excuses for federal intervention might be manufactured)
Tim Miller (on Trump’s approach):
“With Trump, you always never really know, right. Is he just doing word diarrhea… or is he saying something because… he’s not a really good poker player. He’s kind of revealing where he’s going to go.” [02:53]
Tim Miller (on the meaning of Trump’s meme):
“It’s intentional. He wants that double meaning. And… it’s ominous. It’s not, not ominous.” [09:02–09:40]
Summary for New Listeners:
This episode is a sharp, accessible breakdown of Trump’s latest authoritarian-leaning rhetoric about Chicago, blended with astute legal and political commentary—made especially notable since even Megyn Kelly (a frequent Trump media booster) calls out the illegality of the proposal. If you want an informed, behind-the-lines take on why these debates matter and what they might signal for 2025 politics, Bulwark Takes provides just that.