Bulwark Takes - Karoline Leavitt Is Getting Out. George Conway Thinks He Knows Why

Episode Date: August 29, 2026

Karoline Leavitt is leaving the White House and George Conway has a few thoughts about her tenure as Donald Trump’s press secretary. Andrew Egger and George give their takes on Leavitt’s talent for lying, deflecting, insulting reporters, and never losing her cool, even when defending the indefensible. They also look at the potential candidates to replace her, including CNN’s Scott Jennings, and ask whether he has what it takes to become Trump’s next professional gaslighter. Watch as George makes the case as to why replacing Leavitt may be harder than it looks.Get your tickets for The Bulwark's Good Fight Tour this October, coming to Charlotte, Columbia, and Atlanta. (https://www.thebulwark.com/events)

Hey, everybody. Welcome to Bullwork Takes. I am Andrew Eger, joined by the inimitable George Conway. George, I don't think we've ever done a bulwark video together. No, we have not. It might seem. But we've got a good one today because it's Carolyn Levitt's last day as White House press secretary was yesterday. It's the end of an era at the White House. She's heading off to spend more time with her family is what she is telling us. And also may be one of the rats fleeing the sinking ship. That's a little bit more speculative slash opinion on our part. But we figured we would do a bit of a wrap up here, look back at some of the highlights, some of the highlights, some of the laughs, some of the tears.

Exactly, exactly. So, George, before we get going on this, any leading thoughts on, on, you know, Carolyn and what she's been up to, what she's up to next? She's a very, very accomplished liar. Really good at it. I mean, not, I don't like to say that people are good liars, but she has an ability to just say things regardless of their truth without batting an eyelash and then repeating them even when challenged. And that is the absolute prerequisite for a spokesperson for Donald John Trump.

Yeah, yeah. I'm right there with you, by the way. I feel like I have this extraordinary amount of weird, like, professional respect for her as a political actor, not as a person, really, because there's a certain amount of, you have to leave a lot of, you know, your soul on the, on the cutting room floor in order to turn yourself into this useful. You have to not have one, actually, I think. If you actually had one, it would show every so often. You would look uncomfortable. So, and I think you wouldn't be able to do the job. So I think whatever soul extraction has occurred in her life, it occurred well before this year and last year. get right into it. Actually, I should say one more thing. Before we get started with that,

let me just say to everybody out there, go ahead and like the video, go ahead and subscribe to the channel. That kind of stuff helps us out way more than you can know. We're all just sort of slaves to the algorithm around here, and the algorithm loves us so much more when you subscribe, gets us on other people's screens, helps us to get the work out there. Enough of that. George, let's play Carolyn. I think it's insulting that you're trying to test my knowledge of economics and the decisions that this president has made. I'm now regret giving a question to the Associated Press. Arguably no one in the media

who loves manufacturing and pushing hoaxes more than Jeffrey Goldberg. So it is substantiated, not just by that video and the physical evidence that everybody saw on display in the Oval Office, but also by another outlet in this room, the Associated Press. So you should take it up with them if you believe the claim is unsubstantiated. And that's a ridiculous line of questioning. So if there were peaceful protests on Saturday for the military, parade, President Trump would allow that.

Of course the president supports peaceful protests. What a stupid question. How did the White House decide that it is appropriate for Jared Kushner to be working on matters that involved Qatar, the UAE, Saudi Arabia? Three countries that combined have given him more than $2.5 billion for his investment firm. I think it's, frankly, despicable that you're trying to suggest that it's inappropriate. This administration has done more with respect to transparency. Let me just pause this for one minute. We've seen all the techniques in just this, I don't know how many minutes that was, probably 45 seconds worth of clips, but we've seen all of the techniques.

One is just a flat out lie, right? I mean, there was a discussion in there where she's saying that there's evidence of white, I mean, the context is stripped from this clip, but she was claiming that there was evidence that they were basically a genocide in South Africa because there were a bunch of crosses in a picture. And she just, you know, she just continues the lie. She was challenged by a reporter. She just continues the lie. The other is to be to change the subject. I'm insulted that you're challenging my view on economics, which was in response, I think, to a question from a reporter, we said, listen, I've paid tariffs. Tariffs are paid by the importers, not by China or the exporters.

And she, you know, she can't answer that question. So she says, I'm insulted that you are. challenging my knowledge of economics. And then, you know, the undercurrent there is that you're being something of a misogynist because I'm this young woman and you're some grumpy old guy. And then, you know, there's deflection. There's insulting the reporters, talking over them, being completely unresponsive. And there's always flat out line. And that's, that's, you repeat and rinse. And her ability to do that is, Really, I mean, it is unmatched. We haven't seen anybody quite do that as well as others, but I don't think that's a good trait.

That's not saying, I mean, who would you, what job would you give her in the private sector? Who needs this type of person? You think she could be a corporate PR flack? Because no one's going to believe her. No one's going to believe her. This is the one job you could really get away with doing that because you're working for one guy. And your audience ultimately are people who, you know, hate the press and don't hate the truth and are watching Fox News to for their own, to validate their views that they don't ever want to see challenged. And by shutting down the press and by repeating lies, she serves that function. And she also serves that function for Trump because Trump is, I mean, the truth of the matter is Trump was always a pathological liar. He lies instrumentally to convince people of things that benefit him. But now he's delusional.

He's psychotic. He lives in his own world, which is why the, you know, I've talked about this, I think, last week. Why, you know, the Natalie Harp thing bears such significance, which is because he helps create and seal that fantasy world that he lives in where he can, you know, where he can take over the show. straight of Hormuz, even though we don't actually have control over, where we have won a war, where mission accomplished, like the meaning he said yesterday, and where he can rename lakes at will,

and all of these things. And that's what she, that's, you know, she performs that function for him. And no one else in the world, it's hard to see anyone else in the world who really needs that service. It's the combination for me, just just watching her throughout her tenure. The thing that always was so striking to me was the combination of flexibility. You know, Donald Trump is never, that's the thing about him. He'll lie all the time, but his lies won't even stay straight, right? He'll be lying one way, one day. He will turn on a dime and swing the lies in a different direction. She was always able to stick right with him. And also just the complete imperviousness, right? There was never really like crack in the armor. She never was able

to get knocked off of her game, never really able to get ruffled or flustered, or if she was kind of backed into a corner like you were just saying there, a very seamless quick pivot to, I can't believe that you would go there. You're really insulting me personally right now. Real party foul, we're going to move on with this. And again, never really betraying any sense of like instability or unbalanced. If you remember like back in Trump's first term, a lot of his press people did struggle with this sort of thing. I mean, they would get flustered. They would get sort of personally angry. because, you know, it was plain that they were kind of having to work overtime in their head and in their soul to sort of like bring themselves even into alignment with these various ridiculous things that the president was asking them to say. It never really felt like a struggle for Carol and Lovett.

And that was, that made her very politically useful to the president. Just one other moment I'll pick out from that montage was I believe it was leading up to the president's military parade last year, that that birthday parade that he threw for himself. when he had said something in the Oval Office, like, if any protesters come out, they will be met with really heavy force. They'll be met with heavy force. And Carolyn Leavitt was asked about that. And that was when she said, of course, the president supports peaceful protest. What a stupid question.

And moved on. I mean, like, that's just such a little crystal vignette of the way that she did this job for so long. We should keep going with this clip. When it comes to Jeffrey Epstein, then any administration ever, nobody in recent years has faced more bullets and more violence than president. President Trump. This political violence stems from a systemic demonization of him and his supporters by commentators, yes, by elected members of the Democrat Party and even some in the media. Oh, there you go. We could have just gotten to the end, it turns out. We cut in too soon.

Play the victim. Again, we saw play the victim and then we saw, you know, transparency. Well, yeah, he was forced. He was forced to disclose all the Epstein. I mean, it's just so completely ridiculous. I mean, there was another one, I think, I remember where she said that the Epstein scandal was a hoax. And some reporter asked, well, what's a hoax about this? We see the documents. He goes, I'm not saying the documents are. I'm saying the whole narrative is a hoax. And, you know, she just completely just goes, steers off in another direction when.

The hoax is the idea that Democrats care about crime is another thing. Yeah, yes, yes, yes, yes, yes. Total, totally, you end up, you start arguing over here about topic A, and she just goes off into, you know, hyperspace and lands in some other universe. And, you know, in order to go back, you have to say, no, no, you didn't answer my question. And she is, you are just absolutely, I should not have asked you a question. Yeah, next. You have control of the mic, you control the situation.

I have to say, and I'm going to call Sarah afterwards. You deserve combat pay for sitting in that room from time to do. time as you do. I don't know how, I mean, I would lose my mind sitting in there. And I just wonder, do reporters really think, I know you're supposed to be asking the questions, but do reporters really think those sessions are useful for anything? Because I've never thought they were useful for anything, particularly in, in the Trump administrations, because they're not, they're not actually good faith forums in which to receive and exchange information. I think, well, two things.

First of all, if you think I should deserve hazard pay for sitting in there, you should see the way I actually am in there when I go, which is barely ever in a seat at all, but sort of like squashed in the aisle, you know, cheek by chisel. Yeah, in the side. Yeah, right. I saw that. I see you in the side.

Yeah, yeah, yeah. But no, it's a really good question. I mean, I think that for the most part, the utility of the briefing room is to be able to have a human person up there that you can have this sort of back-and-forth interaction with, where you can kick the tires on the administration's claims and you can kind of try to catch them out in the weak points of the argument and the parts that they would like to gloss over or that they would just as soon have people not pay attention to. And again, that's what she was so good at, is just not ever showing a weak spot that could be exploited by any of these questions.

The weak spot is the sort of the old Washington definition of a gaffe, which is what if she accidentally came out there and told the truth someday? And that just isn't, you know, And as long as you have a spokesperson who's not willing to do that, I'm not sure that kicking the tires is a useful function other than to just sort of stub your toe. And I think of it as in a historical context, I was reading the final days, which is the Woodward and Bernstein book about the last few weeks of the Watergate scandal. And there was a lot in there. One of the big sources in that book was John Ziegler, and there was a lot in there about the press office and about the, you know, and Nixon had a really, was big, big on public relations,

his one of his senior aides, H.R. Holliman was an advertising agency executive. You know, those people were actually were mad by the time that Nixon resigned, the people in the press office, except for Ziegler, who was just sad and disappointed, that they were lied to by the president and that they were sent out to repeat lies. And ultimately, lies that were uncovered, lies about, you know, whether, why Nixon had sent the CIA to tell the FBI to shut down the Watergate investigation and when Nixon knew about the cover up. Ultimately, lies are what killed him.

And the big difference between then and now is the willingness of people, people to, you know, for political reasons, to accept and repeat and to tolerate lies. I mean, the Republicans in the House and the Senate weren't willing to tolerate lies past a certain point. They were willing to tolerate spin, but it became apparent that the president was lying his ass off. They left him in droves. And then the people in the White House were mad because they were lied to. They actually, because they looked up to the president, they expected that, how, higher, they expected higher, a better level of behavior from the president, the highest office in the land.

That's all gone. That is absolutely all gone. And nobody bats an eyelash when they just spout out demonstrable lies. And that's the big difference in, you know, that's why we can have a Caroline Levin. That's why the best person for the job now is Scott Jennings, who is a practical. I don't think you. I don't know that he'll be his, I don't know. It'll be interesting. I hope he gets the job for him. Let's talk about this in just one second, the question of who it might be next. The one last thing I would say about Carolyn again on her way out the door, you know, end of an era, like I've been saying, to your, to your point here, people said early on, people kind of scratched their heads. They were like, Trump has picked the youngest press secretary in history for this job. That, you know, obviously she has not been around Washington nearly as long as most people who would be this role. Is she going to have command of this stuff? Is this going to be a mistake?

I think for exactly the reasons you're talking about, it ended up being a useful pick because this was a person who had spent her entire life in the sort of post-truth-Truth-Trump era, where what it meant to be a Republican was to make certain moral and intellectual accommodations for this guy who is pathologically unable to tell truth from lies, who's pathologically just narrative-driven

in everything that he says. And to her, that's just she didn't have to, It's one of those you merely adopted the darker was born in it. It's all she's ever known. Yeah. Yeah. That is a really good point, Andrew. That is a really good point.

You know, for those of us who lived in the era where actually truth mattered, not, you know, not as much as sometimes you'd want, but at some point, you just, people would just stop listening to you and they'd hold you in disgust and contempt if you lied to them too often and you'd feel guilty about that. And it was shame. You know, she, absolutely. I mean, you know, let's see. Let's see, Donald Trump went down the escalators in 2015, 11 years ago, and so she was 16. This is all she's ever known. You're absolutely right. That is a really, really good point.

Younger is better than that. And that's a very good point. And it's a very sad point for our society. Yeah, and for what's coming next. But so speaking of what's coming next, let's now turn, you were just mentioning there has been a lot of reporting. A lot of names have been thrown around, some more preposterous than others. One name that does seem like it has been getting a lot of real attention, both in terms of speculation, but also people in the actual decision-making areas talking about him, is Scott Jennings, you know, longtime political operative, CNN commentator. One of the sort of leading commentary voices, I guess, of the MAGA right today, you'd say, can you just kind of talk a little bit about what he would or wouldn't bring to the table?

I mean, I've seen some people throw cold water on the idea that he would get picked, ironically, perhaps, because he's too close to Mitch McConnell for Donald Trump's taste, which would be a pretty fun reason for him not to get it, nothing about his actual, you know, vices or behavior or anything like that. But just talk us through the possible future of Scott Jennings, White House Press Secretary. Well, I think he'd be, in some ways, perfect for the job. He's not of that same generation as Caroline. I mean, he's a bit older, so he knows, he lives.

in an era where people actually told the truth from time to time. And I think that may be why part of the, that's part of the reason why some people in MAGA don't like him. I mean, he actually condemned the violence on January 6th and was critical of President Trump for stirring that up. And that's, that's unforgivable to some people. And that's, that's part of the reason why he's being opposed. On the other hand, he is a practice. He will just gaslight you to death. Okay. He has, he has signed, glommed right on to the Caroline Levitt School of just, you know, you lie, you change, you deflect, you engage in what aboutism and make false equivalences, and you insult, and then you always go back to lie.

And he, that's what he does. I mean, I, it's just what has always amazed me is that CNN has paid him for so long to lie to its viewers. I actually said that once during the 2024, in 2024, I said that one morning on Casey Hunt's show. I have to say, I mean, look, I mean, you know, Scott's lying, and that's the problem with the Republican Party. It is continually addicted to lies. Wait a minute. What am I, what am I lying about? You're lying. You're lying, Scott. You're lying about the law. You're lying about what the jury was charged to find. They don't have to find it on the law. crime. They had to find the intent to cover up an underlying crime. I don't think there's enough

of that on, you know, when these people are gaslighting us. We need to start saying that this is a lie. That's a lie. And I know reporters are too polite in the, in the briefing room to do that, but it really would, you know, it's a fact. So I, but to go back to Scott Jennings, yeah, he meets the criteria of being a shameless liar. I mean, he just says things. He will say things that are just absolutely untrue. I think where he might not be as effective as Caroline Levitt is, I think there's a gender issue here. You can't play the victim of, you know, pretend like, oh, you're being misogynistic because you're picking on poor old, poor old 27-year-old blonde me. And there was one clip I was looking at, this morning where Caroline Levitt was being asked whether Stephen Miller would apologize to the family

of Alex Prattie. On Stephen Miller's comments, will Stephen Miller be apologizing to the family of Alex Pritty for calling him, quote, an assassin who tried to murder federal agents despite the fact that, as you say, this is still under investigation? Look, again, this incident remains under investigation, and nobody here at the White House, including the President of the United States, wants to see Americans hurt or killed and losing their lives in American streets.

And we mourn for the parents as a mother myself. Of course, I cannot imagine the loss of life, especially losing one's child. And that same empathy from the president goes for the parents of angel families, parents of victims of illegal alien crime across our country as well. And that's exactly why the president continues to be

wholeheartedly committed to deporting the worst of the worst criminals from our country. But she actually did a good job of the empathic for, you know, the fake empathic. I mean, to say that Donald Trump has empathy for anything, anyone or anything is gaslighting of the highest order. But she did, you know, her being a young woman who gave her an advantage there being able to pull that off. So she has an advantage, I think, over, over, Scott Jennings in that regard, but Jennings is a great gaslighter, and he'd be perfect for the job. And I think CNN would be better off if he got went to his real job, which is the real job that he's suited for, which is the lie on behalf of a liar. Yeah, yeah.

I actually, I do think that Levitt had, and probably still has, one advantage over Jennings that is even beyond just what you've laid out. That's just the age and gender thing. I mean, obviously she has used that to great effect. But I also think that her ability to stay unperturbed and unflappable is not something that Jennings is nearly as good at doing. I mean, I'm sure you've seen a billion times like I have that clip where who was he was talking to? Adam Mochler, somebody, some Gen Z Democrat on Abby Phillips show where he just like completely loses his composure and is swearing at this like 25-year-old kid who is going after his position on the Iran War. I was only a few years old while you were in the administration defending prior endless wars. Now, this war is failing.

Eight weeks is endless to you? Okay, you said it was going to be four to six weeks. Wait a minute. I debated you on TV four to six weeks ago and you said we were weeks away from it. Now you're making condescending remarks because you can't defend the fact that this war is not going your way. Wait, one more time. Not going. We name one political concession.

Honestly, I'm not going to have this guy's name on my face. Everybody hang tight. Honestly. That is the sort of thing that Carolyn Leavitt has. has like never done. Right. You can't lose your temper, but you're going to engage in fake indignance. Yeah, yeah.

And that's, she has done the indignation thing. She's done that. I can't believe you'd say that. I'm really, I'm really insulted that you would say that. But even that has always been controlled from her. She's never kind of like lost her cool up there. I mean,

I think that that might be a thing that, that, you know, it would be easier to knock Scott Jennings into that sort of classic Sean Spicer type crash out at the, at the White House podium than it has ever been for, for, Carolyn Leavitt, which would be not to the president's benefit. I think it would be a real detriment on the job.

Which is interesting because it would be more like the president's responses to things. I mean, you know, Trump does get angry. And I'd love to see Stephen Chung up there. That would be great. That would be just, that would be highly entertaining. He would be, you would just, you know, call people fuckface and whatever. He would just, that would be interesting. He's amazing.

One long, one long career long crash out. against the media, yes. Any other names we should be paying attention to here? You know, I really don't know. I mean, it's going to be hard to replace her. I mean, everyone, everyone, I mean, we saw, as you mentioned in the first term, there were different people who had their different strengths. I mean, there was Sarah Huckabee, Sanders, who, she's not all that bright. And she was, she could get flustered. And she did have, there were inklings of conscience there, are we so often? which is, I think, why she got flustered. Then you had Stephanie Grisham, who was actually a good person deep down,

and she was smarted up never to stand up there because she, I think she knew she wasn't capable of lying to that extent. I don't know. Who else? Who else do we? I can never remember how you pronounce. Kaylee Mackin. Oh, Kaylee McKeeney. She was the closest, I think, one. She was the, she may have been the model for this one. for proto caroline yeah yeah the proto carolm but i don't know who else who else is he's gonna it's gonna be hard and it's going to be a a baptism of fire for whoever it is because nobody nobody nope there's nobody else out there um who has been doing this to the extent that she i mean she did she she did most of the briefings right she really there wasn't really a second there wasn't really a number two who would

fill in every so often jd jd bans would show up everyone's in a blue moon and do the breathing Well, vice presidents have nothing else to do. George, if you were called on, would you serve? Trump or generally as a press secretary? I just meant, yeah, if you got the phone call tomorrow. But I guess, yeah, generally, it's an interesting question, too. I would say, you know, I'd say like, you know, that's an interesting. I really would like to see more of the Epstein files.

I don't think that goal. I don't think that'd last more than like five minutes. Yeah, I don't know. I have to say, I mean, one of the things, one of the reasons why I wouldn't wish that job on anybody, right? Because it's not, it's not a win-win situation. And it's unless you are willing to actually absolutely sell your soul, absolutely, and if you're, unless you're absolutely capable of remorseless, conscienceless lying and deflection, you know, you will fail at that job as far as Trump is concerned. And I gather he's not a pleasant person to work for these days. I mean, I've seen some reporting in the last few days about how he's

just screaming at everyone as a reality crushes his delusions around him. And so I don't, I wouldn't wish that job on anybody, unless Scott Jennings, I would absolutely wish the job on him. Yeah, well, we should all be so lucky as to move into the Scott Jennings led future. All right, I think we can leave it there. Thank you, George, for coming on to talk about the tenure of Carolyn Levitt, 2025 to 2026. Thanks for your service, Carolyn. You were actually pretty good at this job, as we have discussed, and we hope the president will be worse off for no longer having you.

Thanks to everybody out there for watching and for subscribing to the feed, and we will see you all next time.