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A
Hey, everyone, it's me, Sam Stein. I'm here with Will Salatin, and we are going to be talking about the White House correspondence makeup dinner that happened last night. We're recording on Saturday morning. Dinner happened last night at the Waldorf Astoria. And I'll just cut right to the chase. Trump bombed, like, really badly. Really badly. Though I'm not going to say it was a complete disaster, because there are a few jokes that I thought were pretty funny, but he bombed, like, legitimately. It was uncomfortable, and the panway shots all told the story. But, Will, what happened?
B
Oh, Sam, we can. We can have a debate because your position is he didn't completely bomb, and my position is he completely bombed, but
A
I gave him credit for one or two jokes.
B
You're a generous guy. So that's. That's. You could you. You can play. So there's an expression in comedy world. He died on stage, and that is what happened to Donald Trump. So it was like. The jokes were bad. The jokes, by the way, the main point, and we can go into this, the jokes were mostly racist, sexist, homophobic, Islamophobia. It was. It was terrible. It was your old racist uncle kind of thing. So it was really. That. It was terrible. But also. But also the laughter stopped because even the MAGA people in the audience recognized that it was bombing. And so Trump recognized. He saw that it was painful to him.
A
Yeah. You knew it was going bad, and you knew Trump knew it was going bad because on several occasions, he was just going on. He was doing meta analysis. Who wrote this shit?
C
He was.
B
He was like, you know, that's how you know you're dying when you're explaining the joke. Except a professional comedian knows not to explain the joke because it just makes it worse. It was super painful. Several times there was this joke he
A
told about seniors and senators walking upstairs. Did you see that one?
C
Yeah.
B
Yeah, absolutely.
A
Let's play it.
C
I do think we need term limits in Congress. I think term limits are very important because I see what's happening. I see what's happening. The other day, a senator I knew got a text, a great guy from his wife, and she said, when you get home, I want to have you immediately come up the stairs and make love to me. And he said, I can't do both. You know what? You know, in other words, can't go up the stairs and make love. Does anybody get that? I thought that was actually pretty good. That was actually the only thing I thought was good in this whole fricking stupid speech that they wrote that was the only good one. And that went down with not exactly great laughter, I think, you know, in other words, you can't go up the stairs and make love too, you know, so we're looking for term limits. Does anybody understand this now?
A
Yeah. When you have to explain in that type of granular detail what you meant, it's both, you know, it just painful. He must have been. Well, I don't think he was dying inside because I don't think he has the capacity for that type of shame, but I would have been dying inside.
B
Yeah. So, so he blames, you heard him, he, so he blames the writers. And, and to be fair to Trump, I, So we, we should be fair. Right. The thing I'll be fair is the writers were bad. They wrote some really bad jokes. But, but also there were several points in this speech where you could tell he was reading the joke and the joke was not great, but he made it so much worse by then ad libbing something mean on top of it. So, so don't blame the writers entirely, Donald. You made it that much worse every time.
A
His delivery was really bad. He's, he can be funny when he's just riffing and being like, you know, Archie Bunkerish, but like, when he's reading jokes, they don't always land. Can I play you the one joke that I thought was funny?
B
Yeah. Let's hear it.
C
Everyone finally got to enjoy their entire very delicious beef tenderloins. Very special beef. And I want you all to know that Bobby Kennedy is right here. Personally ran over the cow. And he cut it up and he brought it here for you to eat tonight. So it's very fresh. And Bobby also suggested an appetizer featuring his favorite cut of male raccoon roadkill. But we drew the line at that, Cheryl. We said, no, we're not going to do that.
A
Okay, Come on. Yeah, you're laughing.
B
I'll give you that one, Sam. That actually, that was the highlight of the show and that was pretty early on that he did the Kennedy joke. It was, yeah, that was, that was the best joke he gave. But Sam, it's kind of interesting because to me, that joke is the closest thing to a traditional correspondence dinner joke. Right. It's self deprecating. It's about somebody in my administration and like, it's, it's, it wasn't mean, you know, it was like one of his guys, but about something that he, that Kennedy himself has joked about. So that, that was the problem is that the rest of the speech just wasn't like that.
A
Yeah. The problem was his speech was basically a Trump speech. Right. Like, it just didn't make. Let's put the. Like, he took shots at everybody. Gavin Newsom, Jimmy Fallon, Stephen Colbert, like, joked about having a third term, which you call the fourth term, because he really won, you know, blah, blah, blah, blah, blah. And then there's just, like, random asides like, let's play the Nicki Minaj one, which was just. It just felt unnatural coming from Trump's mouth.
C
Hearing the gunshots, many people yelled, get down. Get down. Which caused Nicki Minaj to start twerking. Do you believe get down. She's the only one that really understood what that meant. Quite an evening.
A
It's quite an evening. And that was like, fine. But it just. The delivery's so bad.
B
He screwed it up. Like, Sam, can you imagine if Obama. If Obama were delivering that joke? It would have been funny. He would have, like, got the timing right. And Trump. Trump just, like, killed it with the. So even. Even the best jokes he had or the least bad jokes, he screwed up with the delivery.
A
Yeah, just one on the delivery front. Doing a lot of clips for this, but. So there was a good Barry Weiss joke that could have been made really funny. And he just butchered it. And I'll. Let's play this, because this is like, there was a funny setup here. And he just kind of. To your point, he's just reading the prompter. If it felt like he didn't even rehearse this thing prior to delivering the speech. Let's read the Berry. Let's do the Barry Weiss clip.
C
I have to say that we're having an amazing. He really is reading accomplishments that the media never talks about. For example, under my administration, a once feared and powerful regime that relentlessly attacked America has finally been toppled. Their former leaders have been removed, and they're now being run by a gay dictator facing internal divisions. But I, for one, wish Bari Weiss all the best at CBS News. She a wonderful woman.
A
Oh.
B
So I couldn't laugh at some of these because by the time he got to this joke, he was. He had, like, done so many slurs. Ethnic slurs, homophobic slurs. He. He went. He went at Anderson Cooper before that and said something about. Anderson Cooper is a. What? Different. Different persuasion from me. Like, he was. He was doing some gay stuff. So the. The Weiss joke would have been funny if people understood Donald Trump to be a friend of gay people. But instead, like, with all the transgender stuff, it just comes across as mean.
A
Yeah. And I. And that was the problem for a lot of this. And this is where we turn to a more serious tone. He was just a jerk. And he said things on the stage that, you know, maybe you can be sort of slap stick about it, and maybe you can be like, you know, what's the comic dog insult? The triumph, the insult? Yeah, maybe. Yeah, you can do that. But, like, he didn't do that. He was just an. And he said things that were deeply uncomfortable at times. Never more so for me. I. I remember the Anderson Cooper one actually did stand out to me. But I thought the. The comment about Caitlin Collins, who he clearly, like, has a thing with. Like, he. She just. I. I know she got presented an award. And yeah, he talked about her in ways that I thought were so misogynistic and nasty were in the room. I would have been incredibly uncomfortable. I guess it's worth playing so that people know what we're talking about.
C
Want to personally congratulate CNN's Caitlyn Collins on receiving her award was all about me. It's a fake. She shouldn't get the award. It was a fake, but I didn't mind. I said, caitlin, congratulations. But it was fake. There's no question about it. But she's a young, attractive woman. She never smiles. I said, caitlin, do you ever smile? Smile. You have a nice position. You're at CNN fake news. You should be a happy person. So smile, Caitlin. Just smile. But we attack. And I thought Caitlin had really made it big with a major new sponsorship. But then I informed her that it wasn't her on the Bud Light can. It was Dylan Mulvaney. And Dylan Mulvaney cost Bud Light $35 billion.
B
Yeah, the shot. Shot at Caitlin, shot at Mulvaney. He took a shot at everybody. The. The sexism. Honestly, Sam, that sexist dig at Kaitlan Collins was the. The least of some of the stuff he did. There was anti. There was anti Muslim stuff. There was anti black stuff. There was, I mean, every disgusting thing you could. Sam, you know, I was trying to think of a comparison of an insult comic or a comic who died on stage doing this kind of thing. And the closest thing I could think of. You and I are old enough to remember this, but a lot of young people wouldn't. I think it's 20 years ago. Michael Richards, the guy who played Kramer, remember this? He did a comedy club, and he just. He gets upset in the middle, and he just launches into this racist tirade. And at first, people think he's just trying to be funny, and then they Realize, no, no, no. This guy's really angry and bitter and mean, and that's. That's what Trump was last night. I mean, the. The venom just came out.
A
Yeah. And what's. What's disturbing is that so many people in. In the MAGA sphere are, like, right on. Stick it to him. This is great. He's going into the lion's den, and he's just, you know, mocking them and. And launching bombs on them and all. And, like, they. They kind of eat it up. Right? They. They find the insult, they find the misogyny, they find the anti LGBT stuff great. And I look at it, and it makes my skin crawl. I. I know that there's other things you pointed out, but to, like, take a moment of professional triumph for Kaitlan Collins and to try to reduce her into a pretty little girl who doesn't smile enough, and maybe I'll compare to a transgender influencer, like, that's about as low as it gets to me, like, that. That you have to be a really small human being to do that in that moment, and that's what really stood out.
B
Yeah. And a lot of these are lines that, as you said, he uses them in his rallies and what he's done just to have some perspective on this whole thing. Donald Trump has created a world where he has rallies, where he's brought some of the worst people in our country together who share his low sense of humor, and they laugh. And so he's used to the laughter. And part of what happened last night is he had a room that was mostly people who are not like that, and they were. You know, they had a normal ethical sense, and they weren't laughing. And, you know, he didn't get the feedback he's used to. And even the people who supported him realized that he wasn't getting. So it was almost like we had a. For. For just a flat, a fleeting moment. We had a normal, healthy culture, people who. Who didn't laugh at these disgusting jokes, and it was painful to him and painful to his supporters.
A
It's such a good point. When's the last time he's ever been in a setting where the audience isn't filled with sycophants? Seriously, I can't. I mean, he went to Joe's Crab Shack or whatever once, and he got yelled at, but, like, that's literally. He's either at his club, where people literally pay to be near him, or he's at the White House, where it's just filled with staffers, or he's at rallies, which are his supporters. It's incredibly rare for this man to be confronted with people who aren't, well, you know, just absolutely slurping it up. Which brings us to the question of whether he should have been there in the first place. How do you come down on that one?
B
I look the way the last one ended. I mean, if you have political violence, I am for everybody standing together against the political violence. So.
A
Well, should he have been invited to the first one?
B
That is a tougher question. He made it. He played it up as though he decided to show up.
A
You know, there is a routine that the White House Correspondents association does invite the sitting president to these dinners, not as an. Not to honor the president, but because he's central to their coverage. And this is a celebration of the First Amendment. And in theory, the president should celebrate this kind of bedrock constitutional right. In theory. But obviously in this case, that's not really what's happening.
B
Yeah. You know, Sam, it's a really tough question because this is one of a number of things that in a normal presidency, as you just said, we do. We do this. This is the thing you do, except that we've elected this guy who is so, so different from any other president and just he's mentally unwell. I mean, if anybody who, anybody who has the guts to sit through an hour of this, which is how long this speech was, you can see the unwellness come out. And so probably if you abstract from the fact that he's president, you would never put this, you would never at your wedding, have your, you know, somebody's racist grandfather stand up and speak for an hour. But that's, that's what happened here. And the unfortunate part is that we elected him, Americans elected him, and therefore the Correspondence association and other people feel obliged to put him on, on stages where he did, where he does these rants.
A
I mean, I guess they don't have to invite him, right? They don't have to. But I don't know. I'm not going to pretend like I, you know, I know a lot of people have very strong opinions about this, and, and I can, I can see the argument from both sides. I suppose it's just really hard for me to get my head around this administration, like literally subpoenaing the records of New York Times reporters and their relatives. I mean, they withdrew it only because the judge was going to slap him down like that happening. And then, you know, three days later, you're. You see him on the dais and, and, you know, you're kind of Partying with the guy. I suppose there were not many. I don't know. You saw more of this, I suppose, but you know, they didn't, they didn't. There weren't many confrontational speeches or moments where like award recipients or speakers got up and said, you know, shame on me for the subpoenas or you need to like really respect the First Amendment. I mean, there were moments here and there, but it didn't feel like there was much by the way of protest.
B
No. You know, and Sam, that was one of the few serious moments of the speech. So everybody knows from previous correspondence dinners if you've seen them, the President does a bunch of shtick and then he says something serious about the press. And so Trump tried to do that. Clearly the writers wrote something for him and it was, you know, all kidding aside, basically no one believes in the free press more than me. While as you point out, like no other president has done this. These, these subpoenas to the reporters going to their, I mean, so he's. Even the part that is, that would be normal for another president to deliver is even when Trump is trying to say something that one would agree with about freedom of the press, it's just falsified by his own record because he's obviously doesn't believe in that.
A
Yeah, I want to play to get a sense of how weird the dynamics were around this component. I want to play the part where the Wall Street Journal is given an award about five or six reporters for the Journal given an award for their reporting on the relationship between Trump and Jeffrey Epstein, including this piece they wrote about the, the birthday card that Trump sent to Epstein that was a drawing of a naked woman and Trump signatures on it. And, and Trump freaked out about it and he filed a lawsuit against the Journal over the White House Correspondent association awarded the Journal a prize for that story. And Trump is sitting there on the dais as they talk about it. And you'll see I focus on Trump during this whole thing because I think there's a lot of interesting tells in how he reacts. Let's play the full clip, which is like over a minute and like 45 seconds. So it's pretty long. The Journal's courageous reporting on President Trump's past relationship with financier Jeffrey Epstein triggered the release of the so called Epstein Files, thousands of documents that might otherwise have remained hidden in from the public. And despite the President's threat of a lawsuit, the Journal published a story about a provocative letter to Epstein bearing President Trump's signature. Trump quickly filed a $20 billion lawsuit against the Journal revealing reporter Khadija Safdar's home address. Her family had to be relocated. The Journal was kicked off of Air Force One. But the reporters continue to file revelatory stories. Please welcome the winners of the Kathryn Graham Award from the Wall Street Journal. Khadija Safdar, Sadie German, Annie Linsky, Josh Dawsey again, Alex Leary, Rebecca Ballhaus and Ryan Barber. Their colleague, Joe Calazzolo could not attend tonight.
C
It's,
A
I, I don't know why that kind of bothered me so much, honestly, but I guess it's Trump sort of in on the joke. Of course I'm going to file a 20 billion dollar lawsuit. And I really felt for the reporter who obviously their personal information was exposed, their family had to move, and she's got to shake this guy's hand. And, you know, I think obviously you do what you gotta do. I'm not, I don't think she should have like, you know, given him the finger or anything like that. But, like, he's there and he's just sort of like, yeah, you know, of course this is what happens. And it's like, no, you don't have to. That's not what happens. That's abhorrent behavior. But they're all kind of mucking it up, you know.
B
Yeah. I mean, on the one hand, Sam, look, I'm glad, given Trump's propensities, that he's not throwing these guys in jail because, you know, God knows. But so it's good that we still have a culture where, where the President shakes the hands of the people he's attacking. But, yeah, he's like, hey, what am I gonna do? He's just sort of shrugging it off. And he later took another shot at Josh Dozy. He called him unhirable in the speech. Like, the guy just shook your hand and you're like taking another shot at him, just completely gratuitously. So there's this pretense of we all get along, but then it's so hard to figure out. There are people who think that Trump doesn't mean it when he says stuff like that, but it just keeps happening over and over again. And I felt like in the speech you could see the real Trump and the real Trump is the one who hates who, like, gratuitously. Someone wrote a joke for him about Adam Schiff and he read the joke and then he just launched into a tirade about how much he hates Schiff. And to me, that's the real Trump, the one who Hates and the one who takes shots at people.
A
Well, someone. I mean, the simplest. I forget who put this in these simple terms, but the best way to understand Trump is if he believes you like him, he'll like you. And he knows that reporters jobs require them not to like him unless you're at some sort of sycophantic outlet. And so he's not going to like you. And just for him to sit there and kind of shrug at the 20 billion dollar lawsuit and leaking of the personal information and all, like the reputational harm and personal harm he's caused these people, as if it's just part of a game that sat a little bit odd on me. And then so too did the kind of chuckles when the $20 billion lawsuit was mentioned by Wolf Blitzer, where. And I don't know who chuckled and who laughed. Maybe it was, you know, non reporters in the room. But, like, that's serious stuff. You know, he tried to bankrupt the Journal for the piece that is by all measures accurate. By all measures. And he really did personal harm, professional harm to a couple of these reporters. And to sit there and be like, that's an outrageous lawsuit. Of course, that's h. Like, you know, it just felt like it was a little bit too cozy.
B
Yeah. You know, and that's the thing that happens in comedy, though. The comedian will start it with, we'll do some jokes, and maybe they're like bad jokes. They're uncomfortable. The audience will try to go with him. They'll try to laugh along. Especially you've got some, you know, administration people, administration adjacent people in the crowd, and they're trying to, like, laugh along and encourage him and express sympathy. And what happened over the course of his speech was even that laughter stopped because it was just so painful, even to those people. So there was a little bit of a sense of decorum that began to creep back in. And it started with people just not giving him any of the feedback that he was getting right there.
A
All right, well, I feel like we've done justice to this truly bad speech that I'll just say he did speak for an hour, too. Like, that's just too long.
B
You have perspective on this, right? I can't. I was trying to remember the longest one before. I mean, Joe Biden did one that was like 10 minutes or something. I think, you know, they were half,
A
you know, they're like 20. I can't tell you off the top of my head. But, like, I remember the Obama ones, even the Biden ones, like, they were, you know, 20 to 30 minutes. They usually start, like, with a. There's a couple jokes at their own expense. Like, Obama famously did the one with the Lion King video where he's making fun of people anointing him as the chosen one. And then you make fun of the outlets in the room. I was at HuffPost during a couple of those where they. There was always a HuffPost joke about how we're stealing everyone's content, not paying them, you know, and then, like. But then it ends with, you know, we joke, but we're all here because of a shared principle and the love of free. And you hold me to account. And I know I bristle, but it's important. That's usually how it goes. But this one was an hour of just nasty diatribes. It's, like, totally Trumpian. But, yeah, that's that. All right, buddy. Thank you for doing this. Really appreciate it.
B
Thanks, man.
A
Everyone who depended on Will Salton and me to sit through that so that we could bring you this in exchange, please subscribe to our YouTube feed. Thank you. All right, take care.
Date: July 25, 2026
Hosts: Sam Stein & Will Salatin
This episode delivers a sharp, thorough post-mortem of Donald Trump's speech at the White House Correspondents' Dinner (WHCD) held at the Waldorf Astoria. Sam Stein and Will Salatin dissect the performance, highlighting its awkward delivery, mean-spirited content, and the unique challenge of a president performing for an audience of journalists rather than supporters. The episode is rich in critique, humor, and cultural context, painting a vivid picture of an event both uncomfortable and notable in the ongoing culture war surrounding the Trump era.
Verdict on the Speech:
Types of Jokes:
Meta-Meltdown:
Senator’s Term Limits Joke:
Bobby Kennedy "Roadkill" Joke:
Nicki Minaj "Get Down" Joke:
Bari Weiss "Gay Dictator" Joke:
Attack on Kaitlan Collins:
Normalization of Hate:
Audience Reaction:
Ethical and Procedural Dilemma:
Lack of Protest:
Journalists Awarded for Epstein Reporting:
Trump's Dismissive Attitude:
Ethics vs. Entertainment:
Running Time:
Contrast with Tradition:
The episode is caustic, full of insider references, and unwilling to excuse the ugliness of the event. The hosts indict both Trump's bitter, mean humor and the complicity of a political-media culture that enables him. They emphasize the abnormality of the event not just for its lack of humor, but for its ethical and democratic significance.