Tim & Sam Try To Make Sense of Trump’s Bizarre Interview

Summary

Bulwark Takes: "Tim & Sam Try To Make Sense of Trump’s Bizarre Interview"

Date: September 2, 2025
Host(s): Tim Miller, Sam Stein
Main Theme:
Tim Miller and Sam Stein, two Bulwark editors, break down and react to Donald Trump’s recent interview with the Daily Caller. They analyze the eccentric and meandering style of both the interviewer and Trump, discuss the content and implications of several strange moments, and offer commentary on the increasingly self-referential right-wing media echo chamber.

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Overview

The episode centers on a thorough, often bemused postmortem of a sprawling, unconventional interview that Donald Trump gave to right-wing outlet The Daily Caller. Miller and Stein dissect the interview’s conspicuous lack of tough questions, bizarre tangents—like extensive discussions over portraits, the Rose Garden, and the “auto pen”—and Trump’s characteristic meandering narrative. Through this dissection, the podcast highlights larger trends in conservative media’s relationship to Trump, the state of right-wing journalism, and Trump’s current bearings and preoccupations.

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Key Discussion Points & Insights

1. Media Bias Irony & Interviewer Approach

• Opening Irony: The interview starts with The Daily Caller’s Reagan Reese complaining about media bias, yet proceeds to ask a series of adulating, softball questions.
  • Miller:

    “You would just think there would be some self-awareness. The woman who begins an interview upset about media bias, then proceeds to ask a series of questions…” (01:48)

• Example Questions:
  • Naming a ballroom after Trump
  • Putting Biden on a “presidential wall of fame”
  • Whether Trump wants to see Jim Comey and John Brennan “handcuffed and arrested on live TV”
  • Mount Rushmore, Nobel Peace Prize, etc.
  • Miller, listing questions:

    “Would you like the new ballroom to be named after you? ... Would you like to be on Mount Rushmore?... Is the Nobel Peace Prize that you're interested in? Those are all questions from the person who is concerned about media bias.” (02:09)

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2. Bizarre Tangents & Interview Structure

• Constant Interruptions for Tangents:
  • Frequent breaks in the transcript as Trump shows portraits, leads Reese to the Rose Garden, and discourses on unrelated matters—all accompanied by in-text clarifications (“Trump and Reese walk out… Hotel California plays…”).
    • Stein recounts the transcript’s surrealism:

      “So much of it is bracketed because they keep doing random things, like they get up from their chair to go check out portraits... There's Trump and Reese. Trump shows Reese the presidential of the Rose Garden, Trump shows Reese what the Biden auto pen portrait apparently is…” (04:06)

  • Continuous asides disrupt any normal flow, resulting in a transcript "interrupted the entire time."

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3. Long, Meandering Discussion about Portraits and the ‘Auto Pen’

• Auto Pen Portrait:
  • Trump proposes hanging a portrait of Biden’s auto pen in place of Biden’s actual portrait.
    • Miller & Stein commentary:

      Miller: “…Trump is, I guess, planning on doing a wall of all the presidents, where in place of Joe Biden, it's an auto pen…” (08:43)
      Stein: “…they're going to hang a portrait. These guys are unbelievable. I love it.” (08:56)

• Obsession with Portraiture:
  • Trump fusses over whether the auto pen portrait should be black and white or color.
  • Minor details (“Washington didn't have color photos...”) spiral into extended asides.
  • Miller highlights this theme:

    “He seems a little bit more obsessed with portraits than usual, but a lot portrait talk. Yeah.” (17:00)

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4. Questionable, Incoherent Policy Answers & Wild Claims

• Stage Nine Cancer Falsehood:
  • Trump claims Biden said he had “stage nine cancer”—an invented term.
    • Direct transcript reading:

      Miller: “Can you imagine? He says he had stage nine cancer. That was, what, two, three months ago?... Stage nine, I've never heard more than stage four. Stage four is the highest. I've never... If you're stage four, you're dead...” (06:26)

    • Stein clarifies:

      “He has a Gleason score of nine, which is a specific score for prostate cancer. Stage nine cancer. I mean, I don't know what to say about that…” (07:16)

• Transgender/Right-Wing Talking Points:
  • The interviewer pushes repeatedly on transgender issues, with Trump giving vague, occasionally contrary answers.
    • Sam notes Trump’s accidental break from right-wing narrative:

      “He, like, basically just destroys the entire emergent right wing fever dream talking point...” (11:46)

• Calls for Arrests of Political Opponents:
  • Explicit willingness to see James Comey and John Brennan “handcuffed and arrested on live TV.”
    • Dry summary:

      “Trump would not bother me at all. All right.” (13:16)

  • Miller connects this to a growing right-wing appetite for political retribution (“sleepy second Epstein…”).

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5. Awkward Moments & Light Digs

• Stamina Question:
  • Reese commends Trump’s “stamina” for a long Cabinet meeting, which produces a head-scratching answer about "good genes” and a joke about being absent from public events for five days afterward.
    • Miller:

      “How do you have the stamina? ...maybe one of the ways that he has the stamina for it is that he didn't do a public event again for like, five days following.” (03:18)

• Israel and Younger Republicans:
  • Reese raises shifting Republican support for Israel, one of the few quasi-adversarial questions. Trump acknowledges the trend but meanders off into talk about the Israel lobby and Holocaust denial.
    • Summary:

      “...he just goes on and comments of how the Israel lobby is not as influential as it once was... Also a weird aside about Holocaust deniers…” (15:01)

• AI Robots & “So Much Electric”:
  • Discussion ends with Trump meandering into AI (“We’re going to have so much electric, they’re all building.”)
    • Miller closes:

      “We are getting it. This is AI. We're letting them build it. They're going crazy... We're going to have so much electric, they're all building. That's the end of the interview. No need to clarify.” (16:25)

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Notable Quotes & Memorable Moments

• On media bias (01:48, Miller):

  “You would just think there would be some self awareness. The woman who begins an interview upset about media bias, then proceeds to ask a series of questions…”

• On Trump's “stage nine cancer” claim (06:26, Miller):

  “Can you imagine? He says he had stage nine cancer. That was, what, two, three months ago?... Stage four is the highest. I've never... If you're stage four, you're dead.”

• On the portrait obsession (08:43, Miller):

  “Are we really gonna have a portrait of an auto pen in the Rose Garden of the White House?”

• On Trump's coherence (16:36, Tim):

  “So there you go. Trump is alive. Is he sounding coherent? Not exactly.”

• On the surreal vibe of the interview (04:06, Stein):

  “So much of it is bracketed because they keep doing random things, like they get up from their chair to go check out portraits... Some of this stuff is really hilarious.”

• On right-wing craving for retribution (13:44, Miller):

  “Eventually these people are going to want somebody arrested. And so they get a chance to go interview Trump... and she's over there being like, 'Why aren't you giving me the Comey perp walk porn?'”

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Timestamps for Major Segments

• Media Bias & Softball Questions – 01:00–02:35
• Absurd Interview Structure and Tangents – 04:06–05:00
• Stage Nine Cancer & Portrait Gallery – 06:04–09:43
• Transgender Issue Exchange – 10:10–12:05
• Portrait Fixation, Oval Office & Auto Pen Details – 12:05–13:08
• Calls for Political Arrests, Israel & Youth – 13:09–15:15
• AI Robots and Closing Non-Sequiturs – 16:15–end

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Tone and Takeaways

The hosts’ tone is incredulous, dryly humorous, and briskly analytical; they alternate between exasperation at the unseriousness of the questioning, amusement at Trump’s obsessions, and concern about the direction of right-wing media and politics.

Closing Message

While the episode lampoons the surreal, self-indulgent nature of the interview, it treats the broader implications—such as rising calls for political vengeance within the right, the deepening media feedback loop, and Trump’s personal state—with a critical, but never conspiratorial, seriousness. The overwhelming impression is of circus-like performance supplanting substantive journalism, with Trump both presiding over and consumed by the spectacle.

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Summary prepared for Bulwark Takes listeners and readers seeking a comprehensive, timestamped, and quotable breakdown of the episode’s highlights.

Transcript

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[Caller]

It's been so long. How have you been? Hello. I'm doing well, Dave.

[Tim Miller]

Why? Why are you talking that way?

[Caller]

Please say one for a compliment or two for a question. Yeah, this is weird. I think I'm gonna go.

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[Tim Miller]

This is a real person. How can I help you?

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[Tim Miller]

Tim Miller from the Bulwark here with managing editor Sam Stein. The Daily Caller, a right wing news outlet, dropped an interview with Donald Trump. I do believe that irony is dead following the interview. It is a doozy. There's much to get into, much to discuss. I want to start where the interviewer, Reagan Reese starts like this, Sam. She thinks it's fitting that we start with the subject of media bias and ask Donald Trump about a New York Times article that she didn't like about how they were mad at Trump for not doing the crackdown correctly. I thought that was an interesting place to start. How about you? And if you were to sit down with the President, where would you. Do you think that first question would be about media bias?

[Sam Stein]

I would have done it a little bit differently, I think. But why is that interesting to you? It's totally expected from me.

[Tim Miller]

Well, it's interesting to me because you would just think there would be some self awareness. The woman who begins an interview upset about media bias, then proceeds to ask a series of questions. We're gonna get into some of these one at a time, but I just wanna give you some of my favorites.

[Sam Stein]

Okay.

[Tim Miller]

Would you like the new ballroom to be named after you?

[Sam Stein]

That's a good one.

[Tim Miller]

Are you gonna put President Biden on the presidential wall of fame? Do you think there will be Russiagate arrests? Would you like to see Jim Comey and John Brennan handcuffed and arrested on live tv? Would you like to be on Mount Rushmore Is the Nobel Peace Prize that you're interested in? Those are all questions from the person who is concerned about media bias.

[Sam Stein]

You didn't even get to my favorite one.

[Tim Miller]

Okay, well, I said it was just a selection.

[Sam Stein]

I just. Okay. It's the best one, though. She's going on and on about the Cabinet meeting that was like three and a half hours last week. And they're doing this exchange and Carolyn Levitt, who's sitting there. I'm just gonna read it. Levitt interjects at one point, she goes, it was actually the longest televised presidential event in history. And Reese responds, and this is. This is really the best question of the bunch. Wow. How do you have the stamina for that? I like it.

[Tim Miller]

How do you have the stamina? In fairness, we don't have a stimulus.

[Sam Stein]

Actually, I'm kind of curious. What did he say in response?

[Tim Miller]

Hold on one second.

[Sam Stein]

Look, you keep talking. I'm going to look up this one. Oh, this is it. You know how good parents. It's a parental thing. You understand that genes.

[Tim Miller]

Yeah. And then he says, maybe. Hopefully you have good genes as well. Yeah. It is interesting that then following. I mean, maybe one of the ways that he has the stamina for it is that he didn't do a public event again for like, five days following.

[Sam Stein]

Are you on this? You're on this train, huh?

[Tim Miller]

I'm sorry we have to mention it, though, because I know that viewers are interested. This interview did take place Friday, August 29th at 1:27pm and we can. You can see the picture there. There's Donald Trump. He's looking a little less orange than usual, but does look alive. He's live, sitting there with his communications director, Stephen Chung, who's in two chairs. And then we've got Levitt there next to Chung, and then Reagan, Reese, the questioner. So that's. That's the picture there. You can look at that.

[Sam Stein]

It's quite the picture. Yeah. I was just gonna say the thing that I really thought was kind of. And I don't want to jump ahead of you, but there was, like, a theme to this interview where if you read the transcript, so much of it is bracketed because they keep doing random things, like they get up from their chair to go check out portraits. Like, some of this stuff is really hilarious. There's in brackets. It's like Trump and Reese walk out of the Oval Office to the Rose Garden for several minutes while Hotel California plays on the White House speakers. There's Trump and Reese. Trump shows Reese the presidential of the Rose Garden, Trump shows Reese what the Biden auto pen portrait apparently is. Putting up a portrait of Joe Biden is just going to be the auto pen and then Egypt. But there's like seven. There's seven of these brackets. They just interrupt the interview the entire time so he could go show her portraits and artwork and the Rose Garden. It's really funny.

[Tim Miller]

And while listening to the Eagles, it's been two. Two levels.

[Sam Stein]

Listening to the Eagles, it's such a classic choice for Trump.

[Tim Miller]

Yeah. So she. And there are also lots of periods where they go off the record and they just kind of drop that in there and like, you catch up the interview amid conversation. Any anyway I want. So the first big aside. So after that media bias question, they do get into the military occupation of D.C. where the questioner is just overcome with praise. They have an aside, I guess I wouldn't call this a question. They have an aside where she starts discussing her life. Another interesting strategy if you have a lot of time with the President. She says she had been in D.C. there had been a attempted break in, so she got scared. So she moved to Virginia. In Virginia, she witnessed recently a fight between a homeless man and a pedestrian. So she had to call 91 1. And so now she's upset that she says, now I'm saying now I'm like, why did I move from Washington, D.C. to Virginia right after you cleaned it up? So that's a big part of the exchange. And then he goes in to talk about how, you know, he wants to occupy Chicago.

[Sam Stein]

And he's upset because J.B. pritzker won't call him in. And then he somehow says Pritzker is kicked out of the family business. He has so many unbelievable lies in this. My favorite one was. I mean, it's like, sad, but he. He says that Joe Biden claimed to have stage nine cancer. And then he and Steven Chung are like, never heard of stage nine? I thought it only went to stage.

[Tim Miller]

We're gonna read that transcript.

[Sam Stein]

Okay, sure.

[Tim Miller]

This is during the auto pen section. We'll get. We'll just explain the whole section. But here we go. This is a brief aside, but can you imagine? He says he had stage nine cancer. That was, what, two, three months ago? Then Reese replies, I know you were at the golf course that day. I was with you, Trump. Stage nine. I've never heard more than stage four. Stage four is the highest. I've never. If you're stage four, you're dead, Reese. How come we didn't know about it beforehand? That was suspicious. To me, Trump especially. Stage nine. Is there such a thing? Stephen Chung chimes in. Never heard of it. Carolyn Levitt chimes in, me neither. And then we are bracketed. We pause that conversation to look at the auto pen portrait. So there you go. I mean, I do think it's important just to say Joe Biden does not. They haven't heard of it because it doesn't exist.

[Sam Stein]

It doesn't exist. He has a Gleason score of nine, which is a specific score for prostate cancer. Stage nine cancer. I mean, I don't know what to say about that. Like, does Trump actually believe that he. Trump. That Biden said he had Stage nine?

[Tim Miller]

It seems like it, yeah. Or is it a bit that he just kind of forgot that it was a bit.

[Sam Stein]

It's a weird. It would be a totally weird bit to be like, Stage nine, that doesn't exist. He should be dead. Ha. No. It's befuddling.

[Tim Miller]

So they got to Biden based on, as you mentioned. Let's see. She was. She was asking about transgenderism. I want to come back to that in a second. Trump. Trump gets kind of sick of that conversation and wants to move on. Pretty f. So he moves on by. By asking her, did you realize? Or putting up beautiful mirrors and portraits in the Rose Garden. She said, no, she did not realize that. He said, we're doing what's called the Presidential Wall of Fame. And then they go out to look at it, and then the Biden conversation starts because Reese asked the question to Trump, are you going to put Biden up on the wall? Trump says, no, I'm going to. Instead of putting up a portrait of him, I'm going to put up a portrait of the auto pen. Reese is tickled by that and goes on to tell him that that's a very Trump idea. Very Trump. Very good.

[Sam Stein]

Calls it hilarious.

[Tim Miller]

Yeah, hilarious.

[Sam Stein]

I thought it was a joke at first.

[Tim Miller]

Seems like not a joke. He goes on to then show her, like, the draft photos of the auto pen that they're considering for the spot. So Trump is, I guess, planning on doing a wall of all the presidents, where in place of Joe Biden, it's an auto penny and one of those.

[Sam Stein]

Brackets, it says, Trump shows Reese what the, quote, Biden auto pen portrait will look like in the Rose Garden, they're going to hang a portrait. These guys are unbelievable. I love it.

[Tim Miller]

Yeah. He. He is also caught of the 2020 stuff. Obviously. He goes on to. To explain why the auto pen is going up. It's because he actually lost. And then that's when he gets into the stage nine cancer. So I. Is that real? Are we really gonna have a portrait of an auto pen in the Rose Garden of the White House? I mean, if you judge the bracket by the bracket, feels like taking the patrol a little too seriously, you know? But I don't know you. You've kind of come around on that on the new Rose Garden, right? You, like.

[Sam Stein]

You cannot pass that off on me. You are the one who's been praising this man since the sense of interior design.

[Tim Miller]

From day one, I said, I like the Oval Office. The oboe pan patio. I've never liked from the start. Okay.

[Sam Stein]

The Oval Office has become, like. It's, like, metastasizing. It's a stage nine gold explosion. Okay. That thing, like, maybe a few ornaments, but, like, it also is now, like, grown everywhere. It's like, yeah, it's overgrown gold.

[Tim Miller]

I want to get back to. So, again, how did we get to this? Where they were visiting the Rose Garden, listening to Hotel California, talking about how they're going to put up a portrait of the auto pen in the White House. We got there because Reese really wanted to corner Trump on transgenderism. She first asked about the transgender shooter at the Minnesota Catholic Church and asked whether Trump thinks gender ideology played a role in the shooting. Trump does the Trump thing where he's kind of like, well, it could, but you never know. And then he goes on to how it's a very sick person. And then Trump in this one is the one that is actually brings a sensible fact to the conversation where he's like, you know, generally, it's people that aren't transgender that have been doing the shootings. Right. That did not satisfy the Daily Call reporter who went back in and said, do you think transgenderism on kids is a safety threat? Trump replies, say it again. Trump doesn't understand, like, the brain broken terminology that they're using. She repeats. Trump then goes, look, I had it in the military. We had it. It was there for me, and I ended it. That's not really a coherent sentence, but I think what he's saying is transgender people were in the military, but he banned them, which is true even though he didn't. He pretended like he had bones first to not volunteer in the military. And then he goes down and he starts talking about this, and you can kind of tell she's gonna ask again. And that's where he takes a hard right turn. It's just like, have you ever seen the Rose Garden? He's like, I'm not gonna get Pinned down by this craz. Show you these portraits.

[Sam Stein]

Let me show you these portraits.

[Tim Miller]

I got.

[Sam Stein]

No, I, I missed the part where he basically said, you were right. Where he says, if you, if you look. It was a long time, but generally it's people that aren't transgender. He, like, basically just destroys the entire emergent right wing fever dream talking point about this Minneapolis shoot. I had totally missed that. Good catch, buddy.

[Tim Miller]

All right, we can move back on. And I, I feel, I feel remiss not to get to this point. The, the discussion of the portrait gallery was so long in the Rose Garden that I, I hadn't scrolled all. There's also a period of time where Trump's concerned about using a black and white portrait of the auto pen because the other pictures are in color. And then Reese points out that George Washington didn't have colored photos back then. Appropriate. And then Trump goes on to talk about for himself how he's not using the one with the smile and he wants to use the one where he is. He's grimacing. Then he goes on to do an aside about the auto pen, about your friend Ian Samsung. He discusses Ian Sams, who had worked for Biden and said that he'd only done Biden twice. And this is how deep this person is in the lore. Like, he doesn't know what's in the big beautiful bill, but he knows Ian.

[Sam Stein]

Sam's three meetings with Biden.

[Tim Miller]

He knows. He knows anything that's happening that feeds his various conspiracy theories. Okay. It does go on even longer.

[Sam Stein]

It goes on and on.

[Tim Miller]

We're gonna have to stop. It's a 54 minute interview, give or take, and it feels like at least 15 minutes was talking.

[Sam Stein]

There were two. There two somewhat newsy elements of it. I'll just gloss over them very quickly. One, Reese asks, so James Comey and John Brennan, would you be comfortable seeing them handcuffed and rested live on tv? Trump would not bother me at all. All right. Whatever she does, press him on Israel.

[Tim Miller]

And really quick, the other thing on the, on that part she's asking him about is, is Gabbard declassifying the Russiagate documents and how they've referred the case to doj.

[Sam Stein]

So she's coming around and she's coming along.

[Tim Miller]

I just mentioned this because I think that it's kind of a sleepy second Epstein that's growing for them, which is the fact that, like, eventually these people are going to want somebody arrested.

[Sam Stein]

Oh, yeah.

[Tim Miller]

Eventually these people are going to want somebody arrested. And so they get a chance to Go interview Trump. The right wing media types, they're going to have more opportunities. This is what they're pressing him on. And she's over there being like, why aren't you giving me the comey perp walk porn?

[Sam Stein]

No, she wanted it. She was like, do you think it's a possibility that. And yeah, you're probably right on that. Then finally one Shia says, do you crave the Nobel Peace Prize, Trump? No. So there you have it.

[Tim Miller]

No, but then he goes on and says, yes, I know he says no, but he's like, but yeah, but if I say that, you can't put it in. What were you saying on Israel? We lost that. Oh.

[Sam Stein]

So there was, there was, there was a little bit on Israel where she actually, this is the only time where she kind of pushes like some sort of quasi adversarial questioning where she was like, look, younger Republicans are not like into Israel. They're just not. And I think the question is, okay, there's a growing group within maga, American First Coalition Republicans, especially young Republicans, who are skeptical of our support for Israel. Are you aware of this group? Are you worried about it? And Trump says, yeah, I'm aware of it. And then he just goes on and comments of how the Israel lobby is not as influential as it once was.

[Tim Miller]

Yeah, he does. Also a weird aside about Holocaust deniers. And you know, you have people that deny it ever happened. They're deniers. You have people that deny the Holocaust ever happens. So they're going to have to get that war over with that it's hurting Israel. There's no question about it.

[Sam Stein]

Not sure how the two relate, but.

[Tim Miller]

Yeah, he's just kind of jumping all over the place. It's a weave, I guess we're calling it. So then the Mount Rushmore Noah Peace rise. Then we end with a discussion about whether he was the man of the Year or not. Time man of the Year one was upset they changed it from man of the Year to Person of the Year. He thought that was noteworthy as they've gone woke. And then he mentions the fact that he thought maybe to get around him naming him, since this obviously should be him, they might name an AI robot. And then he, then he gets off on a deep aside about AI robots. Rhys interjects, saying that if you want to be cool with Gen Zers, you'll start calling them clankers. Trump ignores that suggestion. And then he finishes the interview by saying this, we are getting it. This is AI. We're letting them build it. They're going crazy. They can't believe I gave it to them. I'm giving them the right to build. Right. We're going to have so much electric. They're all building. That's the end of the interview. We're going to have so much electric, they're all building. There's no way. No need to follow up on that. No need to clarify.

[Sam Stein]

Well, at that point, Carolyn Levitt did end the interview, according to the transcript, at 2:21pm so.

[Tim Miller]

Yeah, right. Yeah, but that's an interesting place.

[Sam Stein]

So much electric. So much electric.

[Tim Miller]

So much electric. So there you go. Trump is alive. Is he sounding coherent? Not exactly.

[Sam Stein]

We don't know it's a transcript.

[Tim Miller]

I just meant like, do the sentences have subject, verb, any worse than.

[Sam Stein]

Any worse than prior? I don't know. How do you judge that?

[Tim Miller]

That's a good point. I'm just let, I'm just, I'm just reporting. I report. You decide on what the transcript says.

[Sam Stein]

He seems a little bit more obsessed with portraits than usual, but a lot portrait talk. Yeah.

[Tim Miller]

And we'll have to keep an eye out for that, for that auto pen portrait. And I guess we can confirm that Trump was alive between 1:27pm and 2 2:21pm on Friday.

[Sam Stein]

Are you really getting, are you really getting deep into this? Is this real?

[Tim Miller]

I'm not.

[Sam Stein]

I want to know.

[Tim Miller]

I don't think that he's like dead and there's a Trump. I had multiple people come up to me.

[Sam Stein]

I had multiple people come up to me this weekend. Is he dead?

[Tim Miller]

No, he's not dead. I do think, I do think he looks peaked and I think that, I think that there was an interesting protrusion on his, on his brow today that I was taking a close look at. And I, I think that if you would have, if you would have consumed all the content that I produced for a Sam, you would know a lot of it. My theory is basically just that, like due to. Dude is whipped. He's 79, he's tired, he's been running. He's been running a big, you know, an intense.

[Sam Stein]

Just even playing that amount of golf is tiring.

[Tim Miller]

Yeah. And so, you know, and he's got the hand issue that the Queen had. You know, we're keeping our eye on it. That's all I'm saying. We're keeping our eye on it. All right. That's Sam Stein, he's the editor. He's keeping me in line, making sure I'm not out there offering any views that are not fact based. We're just keeping our eye on it. That's all I'm saying. We'll see you guys soon. It.