Trump’s Outrageous and Illegal “Flag Burning” Order

Summary

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Podcast Summary: Bulwark Takes – "Trump’s Outrageous and Illegal 'Flag Burning' Order"

Date: August 26, 2025
Host: Tim Miller (A), with Jonathan V. Last (C)
Episode Theme:
A sharp, humorous, and critical look at Donald Trump’s recent executive order threatening jail for flag burning. Tim Miller and Jonathan V. Last dissect the legal, cultural, and political fallout, probing the authoritarian impulses, the reactions of Trump’s supporters (notably the “manosphere” and libertarian types), and the broader implications for free speech and American civil liberties.

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Main Theme & Purpose

The episode focuses on President Trump's announcement of an executive order to jail anyone who burns the American flag for one year. The hosts break down why this matter, question the legality and logic, and examine the spectrum of reactions from Trump’s base and libertarians to ordinary Americans. It’s a discussion not just about flag burning, but about free speech, creeping authoritarianism, and the culture wars playing out in real time.

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Key Discussion Points & Insights

1. Initial Reactions to Trump’s Flag Order

• Tim Miller opens by contextualizing the issue: “Trump playing the hits from 1988. …It’s like a tangible thing that people can understand. A lot of the Trump authoritarian or illiberalism stuff…gets really sort of high minded. …This is something even the smooth brained among us can understand.” (00:20)
• Trump’s statement—“You burn a flag, you get one year in jail”—is described as an “ad lib” with no legal basis, but nonetheless amplified by his press office.
  • “[That] one year in jail thing seems to have been an ad lib. It’s not actually in the executive order. …But Trump just said it because he was talking. And so immediately the White House, like, press office rushed out, ‘Yeah, yeah, yeah, you’ll go to jail for a year if you burn a flag.’” — Jonathan V. Last (01:15)

2. Law, Precedent, and Authoritarianism

• Tim questions if “this is how lawmaking works in the country? The president just decides what the sentencing rules are for things…?” (01:39)
• JBL lampoons how everything is now driven by Trump’s whims: “Donald Trump says that Roger Clemens and Pete Rose should be in the hall of fame… And then everybody just runs around to accommodate him because we're living in an authoritarian state.” (01:58)

3. The Power and Point of Small Acts of Resistance

• Small acts of defiance, such as a veteran burning a flag outside the White House, are highlighted as meaningful symbolic gestures—even if the act itself is “silly in the grand scheme of things.”
  • “It’s important for them to stand on their own principles of a free country and be like, ‘f you. No, I’m not going to do. What are you going to do? Raid my home like John Bolton?’” — Tim Miller (02:20)

4. Flag Burning: Emotion versus Principle

• The hosts admit flag burning doesn’t animate them personally but acknowledge it’s an obvious, visceral flashpoint.
  • “Flag burning has never really animated me…watching clips…when in Iran, Iranians burning the American flag, I was not pro Iran…I looked at that and be like, ‘OK, whatever.’” — JBL (04:09)
  • Tim recalls a college concert where a flag was burned: “I was maybe a little bit embarrassed being a Republican in the room…but I was kind of just like, ‘This is annoying. I'm not here for this.’” (04:38)

5. Legal Capture & Uneven Application: Who Gets Punished?

• When the protester was detained, JBL points out it's selective enforcement:
  • “He was handed over to the Park Service and charged...with starting a fire in a public park. ...We use the rules…to prevent people from just doing unauthorized [things].” (05:51)
  • Tim: “That should be a fine, though, not handcuffing.” (06:11)
  • JBL: “Everything is who, whom, right?...That’s how America works now.” (06:36)

6. Manosphere and Libertarian Reaction

• The episode’s centerpiece is the reaction from “manosphere”/libertarian internet personalities (via a Barstool Sports segment).
  • Host Kirk and his crew are live-processed:
    • Kirk: “I'm not going to burn a flag, but like that's what America is about.” (08:58)
    • Co-host: “That's freedom of speech.” (09:01)
    • Kirk: “Maybe I will burn a flag. I'll go to jail for a year.” (09:05)
    • “I need gas cheaper and food cheaper...Is anybody doing this, by the way, really? Is there an epidemic of this going on?” (09:47)
  • Tim notes, “You can feel it in his brain. He's like, I'm a free speech guy. This is wrong.…You can see him trying to find a Trump rationalization in his head.” (11:25)

7. Where Libertarian Rhetoric Meets Trumpian Practice

• JBL raises doubts about the sincerity of libertarian “cover stories”:
  • “We’re gonna see how many of these people really believe in any of the libertarian stuff or whether…the Von Mises caucus wasn’t really about economics.” (10:32)
  • Tim quips, “I think melanin probably. I think Melanin a lot.” (11:21)

8. Security Theater and Authoritarian Logic

• JBL: “If you read the entire text of the executive order, it’s less about jingoistic patriotism and much more about security. …It’s all dressing things up…‘flag burning is a national security thing’…like with the Bolton raid, ‘making America safe.’” (13:02)
• Tim and JBL connect this “security” rationale to left-wing “words are violence” — but note that Trump’s escalation is enforced with actual violence and state power.
  • Tim: “It’s kind of like the mockable stuff on the woke left…people are, like, words are violence.” (13:53)
  • JBL: “Backstopping the left words-are-violent stuff was always just…cancellation. Backstopping this stuff is violence.” (14:14)

9. Broader Warnings about Fascism

• JBL concludes: “This is how it always is. Fascist movements are taking power.” (14:32)

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Notable Quotes & Memorable Moments

• “Trump playing the hits from 1988. ...This is something even the smooth brained among us can understand.” — Tim Miller (00:20)
• “You get one year in jail. No early exits, no nothing.” — Trump clip, recited by Tim Miller (01:03)
• “He says Cracker Barrel should go back to its old logo...Everybody just runs around to accommodate him because we're living in an authoritarian state.” — JBL (01:58)
• “It’s important for them to stand on their own principles of a free country.” — Tim Miller (02:20)
• “Everything is who, whom, right?...That’s how America works now.” — JBL (06:36)
• “That's what America is about. That's freedom of speech.” — Barstool co-host (09:01)
• “Is anyone even doing this?...Was this a problem that needed to be addressed?” — Tim Miller (09:58)
• “We’re gonna see how many of these people really believe in any of the libertarian stuff or whether the libertarian stuff was always just cover...” — JBL (10:32)
• “It’s all dressing things up...If somebody burns a flag, that's a national security thing.” — JBL (13:02)
• “Backstopping this stuff is violence.” — JBL (14:29)
• “This is how it always is. Fascist movements are taking power.” — JBL (14:56)

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Timestamps for Important Segments

• 00:00–01:11 – Opening and Trump’s “one year in jail” for flag burning order
• 01:11–02:20 – Legal reality vs. Trump’s claims, the machinery of authoritarianism
• 02:20–03:47 – Symbolic patriotic gestures and veteran’s protest outside White House
• 04:09–05:17 – Emotional and cultural reactions to flag burning
• 05:28–06:36 – Legal enforcement and selective justice
• 06:45–11:10 – Manosphere/Barstool/Libertarian live reactions and conflicted responses
• 11:10–13:53 – Discussion on libertarian principles vs. practice, the Von Mises caucus, and implications
• 13:53–14:56 – Security theater, “words as violence,” and connections to the rise of fascism

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Conclusion

This episode of Bulwark Takes serves as both analysis and satire, exposing the absurdities and dangers in Trump’s authoritarian posturing about flag burning. Miller and Last argue that the order is not just a flashback to culture wars past; it’s a tangible instance of illiberal rule, selective enforcement, and the way authoritarian claims filter down to and challenge even Trump’s “libertarian” and “manosphere” supporters. Ultimately, the show urges listeners to recognize the real stakes behind these “silly” issues, warning of a pattern in which arbitrary power and violence are backstopping supposed patriotic and security measures.

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Transcript

[A]

Hey everybody. Tim Miller from the Bulwark here with my colleague Jonathan V. Last, author of the Triad newsletter. Sign up@the bulwark.com and subscribe right here to this feed. Subscribe. We got some flag burning stuff to talk about. It's like, can I just take you behind the curtain here for a second? I have an actual curtain right here. It feels a little dumb and silly to talk about this. Like I've made a commitment to myself that I'm only going to be outraged about the things I'm outraged about. And this is like Trump playing the hits from 1988. You know, like I'm going to, I'm playing an old culture war hit from like decades ago. That said, I think it is interesting because it's like a tangible thing that people can understand. A lot of the Trump authoritarian or liberalism stuff, it gets really sort of high minded and you know, we start talking about things that regular bros don't care about. This is something that even the smooth brained among us can understand. And so as that's a little teaser about a clip that I want to play here in a minute. But before we do that, let's just really quick watch Trump talking about the EO on how you're going to go to jail if you run the flag. Now yesterday in the Oval Office, if.

[B]

You burn a flag, you get one year in jail. No early exits, no nothing. You get one year in jail.

[A]

All right, jbl, before we get to the bros reaction, what do you have any, any big picture takes on?

[C]

I mean, important to know that that one year in jail thing seems to have been an ad lib. It's not actually in the executive order. It's not legal. It's not in the, like, it's not possible. But Trump just said it because he was talking. And so immediately the White House, like press office rushed out. Yeah, yeah, yeah, yeah. You'll go to jail for a year if you burn a flag.

[A]

And like, is that how lawmaking works in the country? The president just decides what the sentencing rules are for things like if, you know, I don't know if a Democrat gets back in next time, can they just be like the sentencing for, you know, whatever burning the pride flag is two years. The sentencing for doing marijuana is now zero.

[C]

Tim, this is how everything works in America now. Donald Trump says that Roger Clemens and Pete Rose should be in the hall of fame. He says the cracker barrel should go back to its old logo. He says that the CEO of Intel, the chip manufacturer, is bad. And then Everybody just runs around to accommodate him because we're living in an authoritarian state.

[A]

This is why the sandwich man is a hero, and this is why these small tokens of resistance actually matter, because they're silly in the grand scheme of things. It would be important for Cooperstown or Cracker Barrel, whose logo is terrible and Devil Trump's right about it. But it's important for them to stand on their own principles of a free country and be like, f you. No, I'm not going to do. What are you going to do? What are you gonna do? Come after me, Raid my home like John Bolton? Anyway, come at me, bro. Come at me, bro. Come and take it. Come and take it. The reaction to this has been interesting. At the White House yesterday, one of, you know, one of our people, there's some. There's some gremlins running around behind the scenes here. You don't. You don't see them. But one of our gremlins was down outside the White House yesterday. There was a veteran who did not like this and wanted to make a statement of freedom, wanted to make a statement of principle, that we still live in a free country, and that Donald Trump cannot buy fiat, tell him what to say or do or think, and put him in jail. And so he burned the flag outside the White House. I want to watch that for a minute. Do this for every single one of you American citizens. We burn the flag in protest to that president who feels that it's his.

[B]

Right to do whatever he wants, make whatever law he wants, regardless if it's legal or illegal.

[A]

All right? So just. I just want to say I'm like, I'm not a big flag burner myself. I don't. I also don't, like, care that much. Like, I didn't watch that guy. I don't know. Did you feel any feelings watching that guy burn the flag? Were you, like, mad? Were you, like, defensive of your. Of your team, of your. Of your people at all?

[C]

Not really, but I gotta be honest, I. Flag burning has never really animated me. Like, even. Even watching clips of, like, back in the old days of the 80s, like, when in Iran, Iranians burning the American flag. I was not pro. Pro Iran or anything like that. I would just. I looked at that and be like, okay, whatever. Like, you didn't. I. People get really into flag stuff in ways that I just don't.

[A]

You're not that jingoistic. I'm a little more jingoistic than you. I think I remember when I was a freshman in college, I went to See a concert, I hate to impugn them because I've seen a lot of concerts, and I was smoking a lot of pot when I was a freshman in College. I'm like, 90% sure it was the Roots. That was the concert. And they burned the flag on stage. And I remember I was less defensive of the flag in my, like, and I was maybe a little bit embarrassed being a Republican in the room while they were burning the flag, but I was kind of just like, this is annoying. I'm not here for this. I. I understand at least that feeling of being annoyed. Sure.

[C]

I'm just saying I don't like it. You know, it's not like I get all horny for flag burning, but I'm like. In terms of, like, any other protest, I just look at them like, great, good for you. Whatever. I don't care. You know, it just doesn't do anything for me.

[A]

All right, so there's that. That guy's out there. The most notable thing I want to. We can pull up the back of the video here is we don't. We don't know if he was, like, arrested or what was happening, but he was detained. He was handcuffed. He was detained for a while there on site. And so, I don't know. I guess maybe you have to do that. A disturbance outside the White House seems.

[C]

To have been handed over to the Park Service and charged. The violation about starting a fire in a public park. So they're going to. They're gonna get him on like, oh, you can't. Can't. No grilling in public parks. We use the rules set up to prevent people from just doing unauthorized.

[A]

That should be a fine, though, not handcuffing. I mean.

[C]

I mean, what should. Anything.

[A]

If you are burning, I don't know, if you are in Meridian hill Park in D.C. and you are burning, I don't know, a flag of the New York Yankees because. Because you're upset. You had strong anti Yankee feelings. Would you get handcuffed for that? I don't think so.

[C]

I mean, everything is who, whom, right? I mean, you get handcuffed if you're one of the bad people. That's how America works now.

[A]

And this is a nice transition into the thing of. I don't want to overstate it. I don't want to say that the manosphere folks have turned on Trump permanently and, like, the scales have fallen from their eyes. But this kind of thing does hit at their lizard brain a little bit. And it's true about the masked officers. It's true about this. We have these libertarian type guys that are culturally conservative. They liked that Trump made fun of the people that annoy them to be.

[C]

Able to say the R word and the P word again. I'm only saying R word and pure because I don't want us to get demonetized on YouTube.

[A]

Okay. They wanted to say the P word again. And I was on with Carousel Wisher today and she was dropping the B word a lot and I was like, can I say that or is this like a lesbian thing where you can say it and I can't. Anyway, the, they want to be able to say all that stuff and, but so they, they at least purport to claim about. Care about free speech.

[C]

Sure.

[A]

And they don't like this, I don't know, this idea. There's just something they don't like. They're not like anti comp, but they're sort of like there's the Blue Lives Matter types. We love comps in the maga coalition. But there's also like kind of the libertarian, like I'm not, I'm not part of the Black Lives Matter protest crowd, but I don't want to come fucking with me if I'm like doing a few, doing a few bumps, you know, in my car outside the football game. You know what I mean? Whom, Who, Who. Right. Exactly. So they have a little bit of skepticism. Anyway, that's a big wind up. It's the Kirkman show on barstool and, and these guys reacted live to the news about the flag burning EO and it's, it's kind of a long clip, but if you enjoy it as much as I do, it's like a dessert. Just, just, just appreciate. Watch them kind of just traverse the internal conflicts in their brain live. You see Trump signing an executive order this morning? No.

[B]

For what? And what the penalty is going to.

[A]

Be if you burn a flag, you.

[B]

Get one year in jail. This is real. Or say I.

[A]

This is real.

[B]

How do I miss this? What? Is this real?

[A]

You haven't seen this?

[C]

No.

[B]

Had a busy day, but no, I haven't seen that.

[A]

Yes. He signed an executive order where if you burn a flag, one year in jail.

[B]

I mean, I'm not going to burn a flag, but like that's what America is about.

[A]

That's freedom of speech.

[B]

Yeah. I mean, like, I don't even understand. Maybe I will burn a flag. I'll go to jail for a year.

[A]

Yeah, you won't. Not 10 years, not one month.

[B]

I don't like odd numbers, though, I'll do two years. Is anybody like the Jerry's. The people have his back on this.

[A]

Oh, yeah. People are loving this.

[B]

Like, Jerry likes that.

[C]

No one where that happens. No one's going to actually arrest you for it. Like, it happens primarily in Democratic cities.

[B]

If that happened in D.C. now, they wouldn't arrest somebody for that.

[C]

Maybe it's a war zone now.

[B]

So I'm saying. So, like, I don't know. Well, I mean, you're, you're a, you're a military spouse. That's right. So like, if. Would your girlfriend care?

[C]

She wouldn't like it, but I think she'd say, don't. You don't need to arrest for it.

[B]

I mean, yeah, right. I don't like it. It's a dick move. But like, I don't. That is nuts to me. Unless I'm missing something.

[C]

I need gas cheaper and food cheaper.

[B]

Yeah. Is anybody doing this, by the way, really? Anyways, epidemic of this going on right.

[A]

Now, people see that, like protests and stuff all the time.

[B]

Okay. That's what this is, what makes this, this country protest.

[A]

It's a dick move. It's nuts. My favorite part is when he's like, is anyone even doing this, even? Was this a problem that needed to be addressed?

[C]

Last time we saw a flag being burnt was five minutes after the order went out. Right?

[A]

Yeah. You could just, you could just see like there is, there's something. They don't like it. Right. It's not, it is not just like, oh, I disagree with Mr. Trump on this. Mr. Trump is great. Like, it goes against their, their worldview in a way that, that I think is not nothing. It's meaningful.

[C]

Yeah. I mean, this is what we're going to find out about all libertarian. Ish. People who, who basically threw in with Trump. Not there are some honorable exceptions, but most of them threw in with Trump or at least went anti. Anti Trump in 2024. And, you know, Trump has done nothing but expand the state and amalgamate power to his person. And we're gonna see how many of these people really believe in any of the libertarian stuff or whether the libertarian stuff was always just cover for, you know, the Von Mises caucus wasn't really about economics.

[A]

Yeah. I do know the listeners who aren't familiar aren't deep in the lore, might not know, but you can Google it. I don't think the Von Mises caucus was really about economic.

[C]

What do you think it was really about? Him?

[A]

I think melanin probably.

[C]

Oh, interesting.

[A]

I think Melanin a lot. I think a significant portion of it was melanin. Maybe not all of it. The other funny little element of the clip that I liked was the main guy. Kirk is like, he's trying to rationalize it. You can feel it in his brain. He's like, I'm a free speech guy. This is wrong. We shouldn't be. The people that are doing this. You can see him trying to find a Trump rationalization in his head and he's like, but they're not really going to arrest people over this. Right? And then the other guy's like, yeah.

[C]

They just did that.

[A]

Yeah. Like D.C. is a war zone now. And he says it kind of sarcastically. It's like, that's the other thing. I like that it was why I did a video on the Shane Gillis ESPY opening monologue. I don't know if you saw that, but like he's mocking Trump on the Epstein thing and I think like moving these guys from like, oh, Trump is like, we need to mock the wokes and the people we don't like to. Now it's like, oh wait, Trump is the man now. And we kind of, kind of got to mock this. Like, this is silly. Like, are people really burning flags? Is D.C. really a war zone? Is it really true that Epstein didn't do anything? Right. Those things all add up and maybe there's something, I don't know, I feel, I just feel like that is, I think, I just say it's important because I think that those kind of hits on Trump I feel like are more likely. Maybe nothing will change people's minds, but I think it's more likely to appeal to some of the folks that went along with Trump 2024 that laughed at the they're eating their cats thing than this self righteous stuff.

[C]

Yeah. And the other thing that I think they're reacting to is that the, if you read the entire text of the executive order, it's all phrased around the Ed. It's, it's much less about jingoistic patriotism and much more about security. The, the idea is the flag burning is presented as something that is incitement and a danger to the public and it's something that like the enemies of America are doing to target. It's, it's all, it's all dressing things up and like, you know, ah, if somebody burns a flag, that's a national security thing. Which is how a of the Trump stuff has happened with the Bolton raid. Right. We're making America safe. That's why we had to raid John Bolton's house. And I think that these guys. I mean, there is like a TSA security theater to it that these guys, I think, are going to react to.

[A]

It's like, this is silly. And it's also kind of like hearing you say it. It's kind of like the mockable stuff on the woke left of, like, where people are, like, words are violence.

[C]

Right.

[A]

You know? Right. Like, it's a little sensitive. It's a little over. It's not. It's not very butch and masculine to be like, I'm. I'm deeply scared for my security because some hippie burned a fl. You know, somewhere. Like, Jane Fonda is a big threat to my security.

[C]

What's different, though? What is different is that, like, the left, words are violent stuff. Backstopping, that was always just stuff like shame and like, you know, oh, we're going to get canceled.

[A]

That's a fair point.

[C]

Backstopping this stuff is violence. Right?

[A]

Violence.

[C]

And so. And. And in that way, it looks a little less mockable because these are things that people are saying because they want an excuse to commit violence. It is. It is butch in that way. Right. It's not honest. Yeah, but it is. You know, this is. This is how these movements work. And you just look through history. This is how it always is. Fascist movements are taking power.

[A]

All right, that's Jonathan Vlas. Sign up for his [e-mail] we'll be back here soon. See y' all then. Peace.