WOW: Trump’s Stupid NYT Suit Gets a Legal SWIRLY

Summary

Bulwark Takes – Episode Summary

Episode: WOW: Trump’s Stupid NYT Suit Gets a Legal SWIRLY

Date: September 20, 2025
Hosts: Tim Miller & Sam Stein (The Bulwark)

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Overview

In this lively installment of Bulwark Takes, hosts Tim Miller and Sam Stein dive into the latest legal debacle surrounding Donald Trump: his much-hyped and swiftly-dismissed lawsuit against The New York Times. The conversation is a whip-smart blend of legal analysis, pop culture references, and concerned discussion about the broader state of media, free speech, and the chilling effects of Trump-aligned legal maneuvers. Despite the ridiculousness of the lawsuit itself, Tim and Sam highlight the real-world consequences of such actions for media organizations and free speech in America.

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Key Discussion Points & Insights

1. Trump’s NYT Lawsuit Smacked Down

• Tim Miller recaps: Trump’s lawsuit accused The New York Times of being "too mean," underplaying his fame, success, and even omitting his cameo in Home Alone 2. The judge, Stephen Merryday, was having none of it.
  • Quote: “It was 85 pages of knob slobbing. And he had other business to attend to that day.” (Tim, 03:09)
• Favorite Lines from Judge Merryday’s Dismissal:
  • The judge mocked the legal filing’s “desperate need to defame with a partisan spear” and lengthy, excessive praise for Trump.
  • Quote: “A complaint is not a megaphone for public relations or a podium for a passionate oration at a political rally or the functional equivalent of the Hyde Park speakers' corner.” (Sam reading Merryday, 03:32)

2. Jokey Legal Banter

• Both hosts riff on the judge’s colorful vocabulary and speculate about whether federal judges are now competing to pen the most dramatic bench slaps.
  • The “Hyde Park Speakers’ Corner” reference sends them down a tangent about historical free-speech venues.
  • Quote: “So you get this coming across your desk and, you know, you’re like, ‘I’m going to have a little fun with these clowns. All right? I’m going to give them a swirly.’” (Tim, 05:31)

3. The Chilling Impact of Political Lawsuits on Journalism

• Sam underscores that, while the slapdown is satisfying, these lawsuits drain resources and are genuinely troubling for media organizations—even when dismissed.
  • Quote: “The Times doesn’t want to have to deal with this, obviously. It takes attention away from their work and it takes resources away from the paper.” (Sam, 07:14)
• Broader Media Landscape: The hosts discuss a rise in “silent censorship” and describe how journalists and pundits are tiptoeing around topics for fear of online mobs or political retribution.
  • Sam references the upcoming Charlie Kirk memorial service, noting the anxiety it’s causing among media professionals.
  • Quote: “There is a silent censorship happening…everyone is going around being like, ah, you know, they don't want to tick off the administration.” (Sam, 08:34)

4. Notable Quotes and Memorable Moments

• Tim wryly notes the “vituperative swirly” administered by the judge, poking fun at the absurdity of the case and the language used in the ruling.
  • Quote: “…a vituperative swirly using…what I have at my disposal, which is a pen. You know, in a legal ruling.” (Tim, 05:31)
• Discussion of conservative voices rebuking Trump’s tactics—mention of Ted Cruz and Bill Simmons standing up for free speech, offering rare bipartisan relief.
  • Quote: “I’m pleasantly…the last 12 to 24 hours have been pleasantly surprising to see some voices speak out….People need to, like, just speak out. Like, that’s all we have.” (Sam, 08:02)

5. Trump’s Latest Free Speech Hypocrisy

• The hosts play a clip of Trump conflating negative coverage with illegality, exposing his ongoing misunderstanding of First Amendment protections.
  • Trump: “See, I think that’s really illegal personally.” (10:22)
• Sam’s commentary: Trump’s “thin skin” could warp the country’s sense of free speech.
  • Quote: “He’s going to make it totally acceptable for a huge chunk of this country to absolutely abandon any semblance of free speech principles.” (Sam, 11:56)

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Timestamps for Important Segments

| Time | Segment/Quote | |-----------|--------------------------------------------------------------------| | 01:00 | Start of main conversation—Intro to Trump NYT lawsuit | | 02:12 | Tim and Sam read and mock the judge’s decision | | 03:23 | “[A] complaint is not a megaphone for public relations…” | | 04:00 | Hyde Park Speakers’ Corner explanation and jokey tangent | | 05:31 | “I’m going to give them a swirly…”—Tim on judge’s bench slap | | 07:14 | Sam: The real impact of these lawsuits on journalism | | 08:33 | Silent censorship and the anxiety in newsrooms | | 10:26 | Trump Clip: On free speech and negative coverage | | 11:45 | Sam: Trump’s thin skin and free speech |

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Notable Quotes

• On the lawsuit’s absurdity:
  “It was 85 pages of knob slobbing. And he had other business to attend to that day.”
  — Tim Miller (03:09)

• On legal complaints as performance art:
  “A complaint is not a megaphone for public relations or a podium for a passionate oration at a political rally or the functional equivalent of the Hyde Park speakers' corner.”
  — Judge Merryday, read by Sam Stein (03:32)

• On media intimidation:
  “There is a silent censorship happening…everyone is going around being like, ah, you know, they don't want to tick off the administration.”
  — Sam Stein (08:34)

• On Trump’s misunderstanding of free speech:
  “He’s going to make it totally acceptable for a huge chunk of this country to absolutely abandon any semblance of free speech principles.”
  — Sam Stein (11:56)

• On enduring the circus:
  “And we'll continue to mock him and his little tiny fingers.”
  — Tim Miller (12:37)

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Tone & Style

• Language & banter: Spirited, sarcastic, and irreverent—punctuated by genuine concern for American democracy and journalistic norms.
• Feel: The hosts juggle the comically pathetic aspects of the Trump lawsuit with the sobering reality of media intimidation.

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Takeaway

While Trump’s New York Times lawsuit offered ample fodder for mockery—both legal and linguistic—the Bulwark hosts highlight a serious undercurrent: the growing tendency of political figures to use the courts as tools of intimidation, and the subtler, ongoing threats to free speech in American public life.

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End of Summary

Transcript

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[Tim Miller]

Tim Miller from the Bulwark here with managing editor Sam Stein. It's the end of the week. We're a little punchy and we are reading this wonderful court decision smacking down Donald Trump's ridiculous lawsuit targeting the New York Times. Me and Andrew Egger, if you missed that, we'll put a link in the notes here. We, we, we broke down just how absurd this fucking lawsuit was initially.

[Sam Stein]

Is it absurd?

[Tim Miller]

Pretty absurd even. Even though I know somebody that was maybe hoping that it was successful. But we won't talk. But the judge here, Stephen Mary Day. Shout out to Stephen Mary Day. Great name. George H.W. bush appointee.

[Sam Stein]

Our greatest HHW.

[Tim Miller]

Yeah, what did I say?

[Sam Stein]

H.W.

[Tim Miller]

Greatest president of my lifetime. So it's still, it's still, you know, just the long tail of his work is still. Work is still at play here. And Mary Day response. So just, I guess briefly for folks who messed up the the alleged shoot against the Times was that they were too mean to Trump and he was basically the short of it and that they underplayed his fame and celebrity and success in business. And so they didn't note that he.

[Sam Stein]

Was in Home Alone 2.

[Tim Miller]

They didn't note that he was in Home Alone 2. And so I'm about to read some of it unless Sam, do you have a top line take before I read? Here we go. Judge Mary Day is replying to in rejecting this motion. He is, he replies thusly, the reader must endure an allegation of, quote, endure the desperate need to defame with a partisan spear rather than Report with an authentic looking glass. And another allegation that, quote, the false narrative about the Apprentice was just the tip of the defendant's melting iceberg of falsehoods. Similarly, one of the many repetitive and often laudatory toward President Trump, but superfluous allegations. The pleader states, the Apprentice represented the cultural magnitude of President Trump's singular brilliance, which captured the zeitgeist of our time, Mr. Mary Day. Judge Mary Day did not like having to read all that. His point was like, this was not necessary. It was 85 pages of knob slobbing. And he had other business to attend to that day.

[Sam Stein]

There's other parts that are so good.

[Tim Miller]

Yeah, please. Yeah.

[Sam Stein]

As every lawyer knows.

[Tim Miller]

Oh, that was gonna be my other one. This is the best part.

[Sam Stein]

I claimed. I claimed. I claim every lawyer knows or is presumed to know. That's in parentheses. A complaint is not a public forum. I can't even pronounce this word.

[Tim Miller]

Foration.

[Sam Stein]

Effective. A complaint is not a megaphone for public relations or a podium for a p. Passionate oration at a political rally or the functional equivalent of the Hyde park speakers Corner. I had to look that one up.

[Tim Miller]

What did you find? Because I was excited to discuss that. What is the Hyde park speakers?

[Sam Stein]

Have you not looked it up? I want you to have. If you really haven't, then take a guess.

[Tim Miller]

I don't. I guess I would guess that maybe it was like, it's kind of like. So in Iowa at the fair, they have the soapbox where candidates go up there and then local Iowans yell at them. And so I'm guessing there's a version of this in Hyde park, which is in London. Is it in London? I don't know.

[Sam Stein]

Dude, you nailed it. Oh, my God. You fucking nailed it. Historic designated public speaking area in London where anyone can publicly speak or debate on any topic. Topic without prior approval. Damn, dude.

[Tim Miller]

Anyone can speak on it. I didn't know that. That's not how it works at the Iowa Soapbox.

[Sam Stein]

This is what AI Google's AI is telling me.

[Tim Miller]

Google AI has been. The AI has been spitting out some falsehoods.

[Sam Stein]

It's located in the northeast corner of Hyde park near Marble Arch tube station. I did not go check that out when I was in London over the summer. Yeah.

[Donald Trump]

Have.

[Sam Stein]

Do you feel like these judges are, like, trying to outdo one another for, like the most over the top wrist slap in response to these lawsuits? I feel like that's what's happening is that they read each other's. They read each other's decisions and, like, you know what? That wasn't shaming them enough. I need to, like, you know, throw in some crazy vocabulary.

[Tim Miller]

I think it's also possible that they are. They're dealing with a lot of boring material.

[Sam Stein]

You know, this was that. Yeah.

[Tim Miller]

Like, you're in Tampa. You're in the Tampa district of Florida. Like, imagine just the kind of Ron Desanctimonious nonsense that you got to deal with on a day.

[Sam Stein]

Weird shit going on. Yeah.

[Tim Miller]

So you get this coming across your desk and, you know, and you're like, you know what? I'm going to have a little fun with these clowns. All right? I'm going to give them a swirly. We're going to give them a vituperative swirly using our. You know what I have at my disposal, which is a pen, you know, in a legal and illegal ruling.

[Sam Stein]

So just so you know, the definition is bitter and abusive language. I didn't know that.

[Tim Miller]

You didn't. I was like, somebody. One of the old conservatives I read uses this word all the time. Must have been another George H.W. bush saying. I don't know who it is, but the word is very familiar because George will use it a lot. Somebody uses it a lot. It's a favorite word of one of the old conservative columnists that are.

[Sam Stein]

It's the type of word Edgar would use and then I would take out of his copy.

[Tim Miller]

I guess we'll just throw this out. I did another separate video on this where I gave my view, but I'll get yours in this spirit. I don't know, man. I mean, these. I don't want to get too excited because I think that I'm very. Obviously, it's very chilling what the administration is doing, and I'm particularly concerned about the local TV angle and the way that they are, you know, using local media and the TikTok angle, the way that they're, you know, so there's a lot to be concerned about. And yet in their biggest picture kind of attacks here, they keep getting rebuffed, and they're losing in courts. Even. You got Ted Cruz out there smacking down Brendan Carr, and that's. That's pretty noteworthy. Pam Bondi had to pull back from her claim that the Justice Department is going to go after hate speech. You're not feeling any sense of. Just like that. They're. They're kind of. They're not really winning this fight in the public square. In the Hyde park soapbox.

[Sam Stein]

Yeah.

[Tim Miller]

Of our Internet. Let's put.

[Sam Stein]

Okay, let's separate A couple things here. One is just the lawsuit, this specific lawsuit. So just. They're gonna have to refile it, whatever. I can't imagine this goes very far, but even, like, the idea that they. This judge had to deal with this ridiculousness, like, that's. I find that not like the world's most troubling development, but it is annoying and troubling. And, you know, the Times doesn't want to have to deal with this, obviously. And, you know, it takes attention away from their work and it takes resources away from the paper. So, yeah, I'm glad that this Mary Day gave him a real slap on the wrist and. And all that, but it's not like, particularly. I don't take joy out of that. I think the fact that they had to get to this even place sucks. And then on the kind of broader question of, like, well, aren't they getting rebuked here and there? And I will say I am. I'm pleasantly. The last 12 to 24 hours have been pleasantly surprising to see some voices speak out. Like, I woke up, I saw the Bill Simmons quote, and like, that. That made me feel good, honestly. Because, frankly, people need to, like, just speak out. Like, that's all we have. Literally, that's it. And then, you know, seeing Ted Cruz say what he said, that's great.

[Tim Miller]

Cool.

[Sam Stein]

I like it. But I keep coming back to the fact that, like, even if they bring Kimmel back on air, there is a silent censorship happening. I think Jeremy Peters was. I was on TV with Jeremy Peterson. That's the phrase he used. I'm going to adopt it. But, like, this is a silent censorship. Like, everyone is going around being like, ah, you know, they want to tick off the administration. Like, people. I've talked to people in the industry, in the industry about this upcoming Charlie Kirk memorial service on Sunday, and everyone's gonna be covering it and. And watching it. Like, people are on, like, pins and needles about, like, what. What they're gonna write and say about it and the punditry around it, because they don't want to say something that would just like, you know, have a mob go after them. So that I think that subtle coercion is really. It's troubling to have to work in that way. It's grateful for working at the bull work.

[Tim Miller]

Honestly, I. It is great for working at the Bullock. I'll say. Another silver lining is so many of you have subscribed to us. Maybe it's because you canceled your Disney plus subscription over the last two days, which we appreciate. So subscribe right here to the Bulwark. We're going to keep.

[Sam Stein]

We don't have Bluey on here.

[Tim Miller]

And Bill Simmons is Bill Simmons rant was good. It was solid. Really strong. You know, I've got the hate fire in my heart that I was feeling for him from him. Really. His statements were all really good and I was listening to it and I was listening to his picks and his guessing of the lines and I miss parent corner. But you know, you also need somebody that has hate fire in your heart. I've got breaking news for you. Unless you have one thing on Bill Simmons. I have one breaking news. I don't know. We're going to go. The president, our president is talking again. He's talking. Yeah. On tv, he's always talking. Yeah. And he's weighed in on this very topic that we're not the New York Times lawsuit in particular, but on, on the free speech topic we're discussing and I want to play it for you follow up on Charlie Kirk. There's been a lot of talk about free speech this week. Do you see a difference between cancel culture and consequence culture?

[Donald Trump]

I mean, your question's a little trick question. I'm a very strong person for free speech. At the same time, when you have networks that where I won an election, like in counties, I guess it's 2,600 to 525. That's called landslide. A landslide times two. When you have that kind of, that level of popularity or voter support as I did in the last election. And yet 97 and 94% different numbers. You see different numbers with different stats. But 97, 94, 95, 96% of the people are against me in the sense of the, the newscasts are against me. The stories are 90. They said 97% bad, so they gave me 97. They'll take a great story and they'll make it bad. See, I think that's really illegal personally.

[Tim Miller]

Okay, so there you go. He's the best free speech president ever. He also think it's, he also thinks it's illegal if a news station takes a good story and makes it bad. I don't know who's the judge of that is about whether the story went from good to bad.

[Sam Stein]

Bring a car.

[Tim Miller]

He's the judge, is the judge.

[Sam Stein]

It's, it's so I mean, I said yesterday and I'll say it again, like this man, just the thinness of the skin is unreal.

[Tim Miller]

It's like some people didn't like that. I noticed on social media.

[Sam Stein]

Well, it's because I had closed my replies, but I closed my prize because I'm getting, I'm getting physical threats on Twitter, which has become horrible. So I'll open them up again eventually. But, like, I just don't have to deal with that shit. And I thin skin, too. So, you know, but I own that. But, like, look, I just feel like this guy, you know, again, we're, we're kind of moving down a path towards, like, he's going to make it totally acceptable for a huge chunk of this country to absolutely abandon any semblance of free speech principles. And I think, you know, it's great that Ted Cruz is standing up, but, like, when you condition 40% of the country to believe that you can't criticize Donald Trump or else, that's not free speech. That's not great.

[Tim Miller]

It isn't great. It isn't great. It's markable, though. And we'll continue to mock him and his little tiny fingers. Okay, Sam Stein, that's you. Appreciate you very much, everybody. Appreciate you, man. Have a wonderful weekend. We'll be back this weekend, actually. It's not like we're going anywhere. I'm sitting here, I'm in my hole. So I'll probably be talking to you this weekend and catch you then. Subscribe to the feed. Tell your friends. Peace.

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[Kristen Bell]

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[Tim Miller]

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[Donald Trump]

Goodbye, Truckee.

[Kristen Bell]

Of course, we kept the favorite.

[Sam Stein]

Hello, other truckee.

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