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Don Lemon
Host, The Don Lemon Show; Political Commentator, The Don Lemon Show

LEMON DROP: Trump’s White House Loses the Plot as Midterm Messaging Unravels

📅 Oct 25, 2026 Don Lemon 29 MIN 12526 VIEWS 71 SEGMENTS · 3 SPEAKERS
Former White House Communications Director Jennifer Palmieri joins Don to examine the controversy surrounding the White House’s messaging, its handling of difficult headlines, and what happens when an administration struggles to control its own story. Watch the full conversation, and don't forget to LIKE, COMMENT and SUBSCRIBE. THANK YOU TO OUR SPONSOR: Kalshi: Trade $25, get $55 at kalshi.com/r/LEMON (promo code LEMON) 18+ only. Restrictions and eligibility requirements apply. Event contract trading involves significant risk and is not appropriate for everyone. Please carefully consider if...

What Don Lemon said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Don Lemon interviews Jennifer Palmieri, former White House communications director under Obama, about White House communications failures under Trump. Palmieri contrasts Obama's handling of protests with Trump's behavior, citing his 33% approval rating as evidence of public attention. She criticizes the lack of vetting leading to Katie Zachariah's brief tenure as press secretary (five days), emphasizing the press secretary's role as a government spokesperson. Palmieri discusses her podcast 'Long Play' focusing on Southern politics, highlighting competitive races in Florida: Angie Nixon, David Jolly, and Byron Donalds. She notes Jolly's focus on undecided Black voters, Donalds' outreach efforts like a barbershop tour, and the Florida Democratic Party's success in switching 44 local seats under Nikki Fried. She describes Donalds' controversial Jim Crow comments and his challenge to Black voters, while praising Nixon's relatable campaign style.

Key takeaways

  1. Palmieri said Trump's 33% approval rating shows people are paying attention to his norm-breaking.
  2. Katie Zachariah's five-day tenure as press secretary indicates no vetting from the White House.
  3. Florida Democrats have switched 44 local races since Nikki Fried became chair.
  4. David Jolly believes 10% of undecided Black voters will decide the Florida governor's race.
  5. Byron Donalds is courting Black voters with a barbershop tour and town halls.

Numbers and commitments

FigureWhat it refers toTypeAt
33% Trump's approval rating metric 2:23
44 local races switched by Florida Democrats metric 18:03
5 days Katie Zachariah's tenure as press secretary timeline 5:22
13 points Kamala Harris's loss in Florida in 2024 metric 15:29

Chapters

  1. 0:00White House communications dysfunction
  2. 2:23Trump's approval rating and behavior
  3. 5:22Press secretary vetting and turnover
  4. 5:48Obama-era communications process
  5. 11:54Florida governor race and prediction markets
  6. 13:39Long Play podcast focus on the South
  7. 20:13Byron Donalds and Black voter outreach
  8. 24:59David Jolly's campaign strategy
  9. 27:20Race outlook and closing remarks

Questions asked in this interview

12
  1. 0:52Are we talking about Katie Zachariah?
  2. 1:37But you know, this is like, it just, aggravations and protests come with the job when you're ruling a democracy, right?
  3. 2:02There's so much of this job that is annoying when you're president of the United States, you know?
  4. 2:23When you're at 32% approval rating, it doesn't really feel like you're getting away with all of this, right?
  5. 5:11So, was I Josh, Jay Carney and Josh Earnest's boss?
  6. 5:48They are the spokesperson for the United States government, right?
  7. 8:38What do you mean we're doing this?
  8. 11:10Um, but it is, you know, it's ducks, right?
  9. 13:39I did not expect to go to Florida because I don't, you know, first of all, you know, it's a question of like, 'Is Florida really the South?' Um, uh, right?
  10. 17:08... and she manages, which I think is important on particularly in southern states or states that are, you know, very, you know, reddish to purple, um, she does it in a way that is not off, doesn't make you feel, it's not off-putting, right?
  11. 18:03And then the other thing was that you had Angie Nixon and David Jolly, who turned out to be better candidates than people expect, step up to the plate. Like there's a vacuum, right?
  12. 20:53What would you think that would say about Florida, about the South, about America?
Don Lemon 0:00 ↗
I have someone who is, um, someone I've been wanting to talk to for a long time, um, off of the campaign trail and onto the podcast if she can get her camera to work properly. I want to bring in someone now who knows exactly how White House communications is supposed to work and what happens when they go spectacularly wrong, if something like that had happened, and that is Jennifer Palmieri, who is a former White House communications director under President Barack Obama and the host and the executive producer of Long Play. And I get to see her on the tube. I heard about your podcast. I hear it's fantastic, Jennifer. I can't wait to talk to you about it. Can we talk to some news of the day? Because you're actually covering the news of the day, which is midterms and everything. You've worked inside the White House. Could you ever imagine something like that happening under President Barack Obama? I would imagine you could, but I think he would handle it a lot differently.
Jennifer Palmieri 0:52 ↗
Yeah, which, which, which one are we talking about though here? Like this. Imagine this. Which of this are we talking about? Are we talking about Katie Zachariah? We're talking about how the Vice President just handled that.
Don Lemon 1:06 ↗
Well, we're talking about, look, that, and remember the woman last week who got beat up at a, at a Trump rally, and then he called her a man and said she was fat. And we're, we're talking about, about all of it, but this happening under Barack Obama. I remember when there were protesters at Barack Obama's rally or an event that he was at, and he turned around and said, 'No, no, no, no, no, let them stay.'
Jennifer Palmieri 1:26 ↗
Yeah, let them stay and let them, and let them, let them speak, you know, let them, let them go, and then he would say, 'Okay, you've had your say, now let me have, now let me have mine.'
Don Lemon 1:36 ↗
Yeah.
Jennifer Palmieri 1:37 ↗
Let's make this some kind of teachable moment for everyone. But you know, this is like, it just, aggravations and protests come with the job when you're ruling a democracy, right? And that's like, I think how President Obama would, would look at it. And you just, you know, uh, and it, that's, it's how this crowd deals, that's not how all of this, that's not how they look at this. They don't look at this as some, everybody has their own voice. Not everybody gets to be heard.
Don Lemon 2:02 ↗
Yeah. Well, that's...
Jennifer Palmieri 2:02 ↗
So annoying. There's so much of this job that is annoying when you're president of the United States, you know?
Don Lemon 2:07 ↗
And don't they know that though? It's, they're annoyed by reporters. They're taking, you know, journalists' credentials and locking whole news organizations out of places that they're supposed to be in. When you see this level of dysfunction, what goes through your mind, Jen?
Jennifer Palmieri 2:23 ↗
Um, that I just, I think, I think about how, um, you know, it is, I, I feel like we will survive it. So that, you know, like, that's all you, that's always the first check is like, are there people that are paying attention enough to know that this is not right and this is not normal and this is, and that this is, this is not how democracy is to operate, and are we going to be able to go, um, you know, we're not going to go back to the way things were, but are we going to, can, you know, I feel like we've been through 10 years of Trump, and then as devastating as it's been and all the norms that he has broken, there's still cohesion about, you know, this is why it's not popular. This is why he's at 33% because he's not paying attention because he's like worried about reporters and, um, and you know, turnstile press secretaries and arches and monuments to himself and not, um, and you know, picking wars that we don't need. And you know, all of this is, it is, what, what is really concerning is when you don't see these things adding up to some kind of, um, exacting some kind of price. Right? This is what my husband says all the time: 'How can he get away with all this?' I was like, I don't know. When you're at 32% approval rating, it doesn't really feel like you're getting away with all of this, right? That the people are, people are paying attention to it. So, um, I feel, you know, and then I just imagine sort of at a personal level how miserable it must be inside that building.
Don Lemon 3:41 ↗
Oh my gosh.
Jennifer Palmieri 3:42 ↗
And how, um, how I really think, you know, just like how deluded, um, um, uh, you know, how sheltered it seems like Trump is from what's actually happening in the world and how people are actually viewing things. Um, and that, you know, just like a lot of people not doing, you would say a lot of people not doing their job, right? Because part of your job, and this is why it's really not, you know, being part of the communications team is one of the tougher spots to be in in the White House. Like all these jobs are hard, but, um, because you know, you're the one that has to tell the president tough things. You're, you're the one that has to deal with stories that, you know, the president doesn't like, um, and, and, and have to tell them the truth about how things are being received by the American public, um, what the polling might be like, um, you know, what you're going to be facing in terms of questions that you don't want to answer from the press because you think they're annoying or whatever it is. Um, it's like that part of the job is not fun, and if you don't, and, and I don't think Trump has people that do that part of the job for him anymore. He's not going to tolerate this kind of, the people being around, but just like...
Don Lemon 4:54 ↗
Yeah.
Jennifer Palmieri 4:55 ↗
Um, I think it's probably pretty miserable in there.
Don Lemon 4:58 ↗
Yeah. Well, look, you're, you're a former communications director, so you know, um, you know what a tough job it is to get out there. I mean, your job is kind of to oversee everything. You weren't necessarily at the podium every day. You were, you know, could I call you the boss of the press secretary?
Jennifer Palmieri 5:11 ↗
I mean, we... So, was I Josh, Jay Carney and Josh Earnest's boss? I was in charge of the, of the whole department, but we both reported to the president. It's like how we work it out, so yeah.
Don Lemon 5:22 ↗
Well, the reason I asked you is because, I mean, I think that's a great term that you said, turnstile press secretary, because five days. I say four because we first saw her on Tuesday. Remember last week it was a holiday, right? A holiday week, Monday was a holiday. And so we first saw her on Tuesday, and by Friday she was gone. How does someone get anywhere near the White House podium, Jim, without a proper vetting, without being properly vetted? I, I, what does that tell you about the people he's surrounding himself with?
Jennifer Palmieri 5:48 ↗
Just that they're, just that they don't, you know, they don't. I mean, I, I feel like, I mean, on the one hand, this woman is, you know, 41 years old, went to, barely went to law school, went to college, had a career, you know, she is an adult and accepted these jobs under the conditions that she did. And, but then at the same time you're like, wow, they just threw her out there. And you know, what I wonder is because like in my experience, I mean, it feels like there was no vetting either. That I just don't, I, I don't expect any vetting from this White House anymore. So, you know, but normally do, I mean, when we picked new press secretaries, even when Josh Earnest became the press secretary after having been Jay Carney's deputy, you know, we did a search, we interviewed people. It was a, you know, Jay let us know a very, you know, like maybe even a year in advance that he was going to be leaving because the person who has that job is not just the president's spokesperson. They are the spokesperson for the United States government, right? That other, you know, it is not, it is not a political job. It is a, it's a, it's a, it's a government job, and it's a, it's a grave responsibility to not just be speaking for the president but speaking for the United States of America. Other countries pay attention to what that person, um, says at the podium. And so we took it really, took that process very seriously, and even as we were considering people we knew really well and knew to be, um, um, upstanding, upstanding Americans as well as, you know, as, as talented that could do the, um, and could do the job well. So you, you went through, we went through a very serious process. Um, and then, but what I can imagine, the other thing that I've learned from working in, for, with President Clinton or for President Obama, as chaotic as it may seem on the outside, it's actually worse on the inside. So, you know, yeah, always. Always, you know, because this is what I used to laugh when people would say, you know, oh, I think you all are, you know, that's, there were some kind of, that, that they did that we, you know, some, something that befell us that was not great. They're like, oh, you all did that on purpose or, you know, you, you, you, you planned out that. It's like, y'all, we, we're too busy to have conspiracies here. Like that's just not how the government works. Like we don't, we, we, we control... President of the United States has a lot of power. They have very little control. White Houses have very little control over like what happens actually in the government. And, um, but I did find that a lot of, you know, like it is, it's, it is much, it's much harder to wrangle things behind the scenes than it may appear. And so it would not surprise me to learn that Katie Zakhari had very little warning that she actually was going to go out and do this press briefing.
Don Lemon 8:29 ↗
Yeah.
Jennifer Palmieri 8:29 ↗
Right. Like the most obvious example where you're like, wow, it looks like she didn't prepare at all. That's probably because she didn't prepare at all.
Don Lemon 8:36 ↗
At all.
Jennifer Palmieri 8:38 ↗
Um, I, I want to move on and just look how nervous she looks now and uncertain about, you know, what she might say. That's the, um, and maybe that's her own fault or maybe I think more likely she was put in a situation where you, you know, there's so many times I've been sitting in my little office in the West Wing where else, and you're like, hey, we're doing this. What do you mean we're doing this? We're doing this. We're doing this. We're doing this right now, you know. And these are in more traditional, uh, uh, White Houses, but just, you know, with how quickly things move. Um, you know, and the fact that even just the fact that her team comes out so late after she starts suggests like this was not well planned or, or expected.
Don Lemon 9:15 ↗
Okay. So I want to move on to talk about your pod, but let me just ask you this, and because I think as you're watching the scene that's up now, when you saw this, Jen, what did you say? What would you have done if you were in this situation where, you know, you're on the team and this happened?
Jennifer Palmieri 9:31 ↗
Um, you know, I mean, I was, it was sort of, it was actually sort of painful to, uh, it was sort of painful to watch, but I think, you know, what you would have done is pull her back. Give, you know, take a, take a breather of a few days, even though that means there's going to be a few days of speculation of why she's not out there, and take the time to get her ready. I mean, one thing that I really learned in the Obama White House is that like it's just, it's much more important to get things right than rushed, even if it means you're, there's always going to be uncomfortable moments. Either you throw somebody out there and they're not ready, or you start answering questions when you don't know the full story yet, and it takes time to collect, you know, to understand what actually happened if there was a crisis or a controversy or something that you're dealing with. And the biggest, the biggest mistake is always to rush. And even though that means you got to wait around and people are like chirping at you online and on television. And I would have taken her out and, you know, gotten her ready to really face, and, and then put her in situations where she can ease up to the podium because that is, that is a very hard thing to do.
Don Lemon 10:45 ↗
Yeah. Okay.
Jennifer Palmieri 10:46 ↗
You've seen, I mean, you've seen what these people, how much they have to parry, how much information, how much you have coming at you from, you know, domestic political things to international crises and yeah.
Don Lemon 10:57 ↗
If you're a smart, savvy cookie, you know how to answer. I, you know, that's...
Jennifer Palmieri 11:02 ↗
But it's hard. It's not easy to, it's not, it's a lot, I would say that it is a lot harder than it looks.
Don Lemon 11:09 ↗
It looks.
Jennifer Palmieri 11:10 ↗
Even just because we're just all human and, you know, when you get, when you're, you know, being deluged with a bunch of questions on, you know, varying topics with, you know, with all that's at stake, it's, it's hard to remain... Some, some people, the best people obviously make it look easy. Jen Psaki comes to mind as somebody who made it look easy. Um, Earnest made it look easy. Jay Carney, Mike McCurry way back from the Clinton days. Um, but it is, you know, it's ducks, right?
Don Lemon 11:39 ↗
Yeah. Well, I'm just saying, maybe it, maybe I, maybe I feel it's easier because I've been in this game for a long time answering questions and asking questions. So maybe...
Jennifer Palmieri 11:47 ↗
But do you know how hard it is, Don? You're good at it because you've been doing it for decades. It's very hard.
Don Lemon 11:52 ↗
You're right on.
Jennifer Palmieri 11:53 ↗
It's very hard.
Don Lemon 11:54 ↗
So I want to talk about this. I want to stay on politics, and I said because there's another major political battle unfolding, uh, in Donald Trump's home state of Florida. New York is technically his home state, but you know, now he lives there. And then Democrats are throwing some serious money behind it, $5 million to help Jose Javier Rodriguez become Florida's next Attorney General. And here's what's interesting. Some polls show that this race is neck and neck. So we look at the polls now. Republican James Uthmeier at 43% and then Rodriguez at 42%. A more recent poll has him just two points apart at 45% and to 43%, okay? But we also now in this day and age look at the prediction markets too to see where, where things are going, and they tell a very different story. I've been looking at, for example, Kalshi. Right now, Uthmeier's at 78% while Rodriguez is at 23%, okay? Now, these aren't polling numbers. They're where the prediction markets stand right now, and those numbers can change as new information comes in. So why are some polls showing a close race while the prediction market has Rodriguez so far behind? That's what makes this really, really interesting. We're two weeks away from election day, and I'm going to be watching whether that gap starts to close, okay? So if you want to go take a look at the polls, do that. If you want to go check out Kalshi.com or the app, go do that. And you can just look at it. You don't have to trade or anything. So look, when, when, when they're consumed by all this chaos and people are, you know, preparing to vote right now in one of the most consequential midterms in, in years. Uh, and, and your documentary series called Long Play is taking us directly into those communities starting in Florida, correct?

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APA

Lemon, D. (2026, October 25). LEMON DROP: Trump’s White House Loses the Plot as Midterm Messaging Unravels [Interview transcript]. Don Lemon. CEOInterviews.AI. https://ceointerviews.ai/interview/3129062/

MLA

Don Lemon. "LEMON DROP: Trump’s White House Loses the Plot as Midterm Messaging Unravels." Don Lemon, 25 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3129062/.

BibTeX
@misc{lemon2026_3129062,
  author       = {Don Lemon},
  title        = {LEMON DROP: Trump’s White House Loses the Plot as Midterm Messaging Unravels},
  howpublished = {Interview transcript, Don Lemon. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3129062/},
  note         = {Speaker-attributed transcript with timestamps}
}