The Daily Beast Podcast - I Know What Chaos Trump Is Plotting Next: Wolff

Episode Date: March 25, 2026

Get 15% off Saily data plans at https://saily.com with promo code Michael Wolff joins Joanna Coles to root inside Donald Trump’s mind in real time, as the president wrestles with the Iran war, the spectre of Epstein, and the looming midterms. From bomb threats that evaporate into last-minute negotiations, to backchannel chaos no one can follow, Wolff dissects the whiplash of Trump’s decision-making and the relentless fantasy world he inhabits—where he alone knows more than generals, elections are perpetually stolen, and every problem has a Trump-branded solution. Along the way, the conversation touches on Trump’s obsession with image and the intricate theater of power he stages, showing how drama, delusion, and ambition collide in the mind of a man still convinced only he can save America. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What is to his advantage is just the narrative that the election system in the United States is broken. And chaos is to his advantage. I mean, things are terrible for him at this point. There's another reason he's pushing this along. This is another kind of distraction. So it is going to be not that I lost because of the war, because of the economy, because of Minneapolis. Because of the Epstein files. It's I lost because the American electoral system is.

is corrupt. Michael. Joanna. I have no idea what's going on. And then it turns out neither does anybody else. Least of all. At least of all where we're going today. I mean, truly, he's stuck in a situation that he can't get out of.

What does he do? What does he do? He doesn't know. doesn't have an idea. And also there was an amazing bit that I felt we hadn't quite focused on enough when he obviously went through the weekend telling people he was going to bomb Iran, now he's not going to bomb Iran, now they're in negotiations. The Iranians come out and say, no, we're not in negotiations.

And then he says, oh, we're going to be in negotiations this week. And someone says to him, well, how is that going to be? And he goes, well, I don't know. I mean, I guess we're going to talk them on the phone because they can't get out. Well, if we were in negotiations, he would know how we were talking to them. There's a piece in the journal this morning saying no one knows. All the Arab states are getting together, as they always do in a war. You know, people do in a war.

Everybody's back channeling, but no one knows who to negotiate with in Iran. Who is the person? And then in the middle of this, you have back again, our favorites. Oh, yes. Whitkoff and Kushner, who are really in, this all comes down to Whitkoff in Kushner. We're in this war, no doubt, because of Whitkoff and Kushner, we're going to get out of this war, if we're ever going to get out of this, because Wittner, Whitkoff and Kushner are going to. I like the idea of Wittner, it's like a band.

They put their names together. Yes. Or Cushkoff. Cushkoff would be better than Wittner. Jesus. It's a problem. But I tell you what's not. problem. I loved. And we'll come back to this, obviously, because we've got a lot to discuss.

We're going to be talking Trump, Iran, Trump elections, and incredibly Trump and Elvis. It's insanity. Is there an off ramp? Is there an on ramp? Are we on the on ramp? Nobody knows anything. But what I did love this week, and I want to give it a shout out, is your substack, which is the beginning of your series on your relationship with Jeffrey Epstein. And there was a fantastic bit about how you meet him first because you're given a lift on his plane to a TED conference in Vancouver. And there's just a... Monterey. Oh, Monterey.

Okay, it used to be in Vancouver, didn't it? No, it was always in Monterey. Seriously? I thought the TED conference was in Vancouver. No, always. Okay, well, I've never been so. The original TED conference, you know, the TED conference is really broken into two. There was the original conference, and then it was sold, and then it became a kind of a,

you know, whatever, an event for outsiders rather than an event for insiders, which it was before. And that was always in Monterey once a year. Okay, well, for people who haven't signed up for Sabstack, this definitely is worth signing up for, because you're going to tell the story of your relationship with Jeffrey Epstein. You begin by the fact that you meet him because you're given a ride on his plane by someone organizing a group of New Yorkers going to the TED conference. And on the plane are various other players. And then what I loved is the description of the plane because it's a jet. It's not a regular, it's not just your regular Gulf Stream.

It's a proper jet. And you say, it's a 757. So it's a huge plane. It's a big plane. Yeah, it's a proper plane. No, and we come out because we're kind of let out. And there's all the corporate jets over there. And that's what we had.

And then we're redirected to this plane, which is on top of everything else, black. Right. So it's a black plane. A big black plane. And everybody's sitting there. And I have almost been in situations like this. They're not quite to that extent because I've usually known whose plane it was. But that thing of like, what are we all doing here?

Whose plane is it? And then you have always made the point that part of Jeffrey's success was having this incredible plane that people loved and he would give people rides. And that was the bait to get people into his world. But everybody's sitting on the plane saying, whose plane is this? And then Geraldine Laban, who at the time is the head of oxygen, the oxygen network. I don't know if anybody remembers that now, but it was a women's network, wasn't it? Yeah, I can't remember if she had already taken her.

But she was famous for Nickelodeon. Oh, okay, Nickelodeon. She created the great children's programming empire. Well, she's on the plane, and she turns to you at one point during the journey. and says this appears to be the embodiment of... She goes, I think this is the closest I've ever come to pure evil. Well, how crazy that she sort of understood it. Maybe she felt the vibes.

She did? I mean, all you felt there was the vibes. Okay, but that's a bit that I want to read because what you capture so well is that moment. So when was this? 25 years ago? Yeah. 25 years ago.

So it was the beginning. of the tech revolution, the beginning of the internet, all that stuff. And people sense that it was in their reach to make millions of this thing. So that's also sort of hanging as a carapace of ambition above everybody. Yeah, the whole world is changing at this point. And I can't. And it's hard to, it's hard to actually summon that, that sense, that sense that everything was possible, that everyone was possible, that there were no constraints on anything.

And actually, if you were constrained, you had to kind of get rid of that and rush toward whatever this was that was happening. Right. And funnily enough, I talked to a friend in Silicon Valley over the weekend who's founded countless businesses. And I was asking him about what is the feeling about the world? war in Silicon Valley and he said, no one mentions it. Only thing people are interested in is AI, how AI is going to change everything. It's all about data centers in the sky. He was furiously

investing in data centers in the sky. But just that sense that in Silicon Valley, no one is paying attention to this war. It's all about the future. And you get the sense of that feeling, again, there is a new boundary to be broken. And just remember that when people say all about the future, effectively what that means is it's all about the money. Well, I was just going to say, right, it's all about the money. All right, so you've got a, I'm just going to read. It's a short paragraph, but I loved it. Private planes, those attended by decorators, speciality craftsmen and engineers,

with overhead bins removed, seating reconfigured into lounge areas and entertainment space, color schemes of muted pastels. And on this one, a mirrored and lacquered bedroom cabin, we all peaked in. certainly suggested excess, but this is the bit I loved. Also an experience that if you were trying to participate in the new world, you were grateful not to miss out on. And it's that understanding that you want to at least smell this and see this and be part of it. And then still, it was hard not to feel the unlikeliness and undeserved privilege of being here

and hard to summon the confidence that might seem to be required. It was just so not middle class. But there was a willing suspension of disbelief too. We were here after all. So that meant something perhaps that we should be. And that sense of the future, you want to be part of it. And this is the gateway to it. Anyway, I thought it was a fantastic column.

Oh, thanks. I appreciate that. Can we just mention the other, the fascinating comment when you, so there's a scene that. with the Google founders who comes skipping onto the plane because they're excited because they know a big plane is in their future. But then there's also another moment where you go on with Epstein. He offers you a lift because you're going somewhere else. And he says to you at one point, Today's sponsor is a travel essential.

It's called Saly and it's one of those products I wish I'd known about, frankly, years ago. Whenever I'm traveling and I arrive at my destination, the first thing I do is try and get on. online, largely to check what's going on at The Daily Beast. Panicking about Wi-Fi is not a great way to start a trip, but this is where Saly comes in. Saly is an ESIM app from the security experts behind NordVPN, and it gives you instant affordable data in over 200 destinations around the world at a fraction of what your carrier would charge you for roaming. Using it couldn't be simpler. Before your trip, download the Saly app. Choose your data plan for your destination turn on salee's e-sim as soon as you arrive you're immediately

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All the details are in the podcast episode description box. And it's just, so on this one, on the way out, there's quite a number of, there's a dozen people or so. but he's going to L.A. and I had to go to L.A. for something. So I literally hitch a ride on that, on that leg. And the only people on the plane are the three pilots. The three girls who have, and I described this, have accompanied him. And they sort of act like the airline hostesses.

It's completely unclear who they are and what they are. But they're back on the plane. and then Epstein and me. And that's the entire number of people on this 757. All right. So three pilots, three air stewardesses, who are the kind of girls dressed in black with long blow-dried hair that he has around him at all times,

and you. And then he says to you, he says we're on, and we're just getting situated. And you're kind of in this thing. What do I do here because this is? How do you comport your? yourself on this large plane that no one else is on.

Right. And also there's always a special gratitude that's involved to someone who's giving you a lift on a plane. Yeah. And he says to me, and this is language that I've never heard before, and I don't really quite know what it means. One would know what it means from this vantage point, but from that vantage point, and this is the only the second, I mean, I've flown out with this, with this guy, and this is, this is, this is, this is, this is, this is, this, is essentially part of the first meeting with this person who I don't know. And he says, the following. He says, do you want to ride back here in the petting zoo or up front with the pilots? Now, this is, I'm whipsawed by this, by this, by this, this thing. Because I don't really know what the first thing that he said, what does that actually mean? Could it mean what it might? might seem to mean, but then you're whipsawed by the other thing to ride in the cockpit

with the pilots, which is frankly something I have always dreamed of doing. I've always wondered what that must be like, what that feeling must be like. So you immediately dismiss whatever you've heard, this petting zoo. That just goes out of your head and you said, yeah, the pilots. And then, but as soon as you agree to that and then you're there, you're thinking, what was that? Did I hear that correctly? Right. And then, but it doesn't matter because you put it out of your head

because you are riding up in the cockpit, which is an experience that I've never had again and an extraordinary experience. This wraparound windows with the plane, this large plane, which seems to move so slowly in and out of the clouds and you can actually feel it's sort of the waves of this thing. I mean, I would have gladly sat in this plane for the rest of my life. I think that's as excited as I've ever seen you, the five-year-old, your inner five-year-old sitting in the cockpit with pilots of a plane.

Anyway, it's a fascinating read. I can't wait for the rest of the series. And it just reminds you of that weird time and how people get sucked into people's orbits because they think they're important or they're going to promise. something and when you have a huge plane like that it feels like this man has a validation already no and it's very hard from from what we know now and the the narrative as it exists it's very hard to for anyone to understand where Jeffrey Epstein came from how you wouldn't immediately recognize him as as a completely bad guy what and and so to go back to the beginning of this story and then trace it through, I think my hope is the context

of the story will make sense instead of from this point looking at it backwards now. Everybody says this doesn't make any sense at all. Right. But in fact, on the plane, you were beginning a relationship with a man that turns out to be, as you have said to me, the most diabolical man of the 20, what century are we in? 21st century. Anyway, it's a fascinating read. And are we at war?

Are we not at war? I think you mentioned whipsaw, but there's such whiplash about what's going on. You know, I look out of the window, it's a beautiful day, the grape hyacinths are growing on my deck, the weekend was fabulous, and then you're like, but are we at war? Is this the beginning of something that could really spiral out of control with someone at the center of it who no one has any idea what he's going to say next including him no my my 10 year old that dinner last night could this turn into a world war i said no it couldn't well you have to say that to a 10 year old right um yeah i'm i'm i'm actually not sure that it that it could because i mean

it's this peculiar situation of i mean no one is going to come to the defense to the Iranian defense. At the same time, and we have complete military supremacy over Iran, but at the same time, they seem to be in the catbird seat. They appear to hold all of the leverage. How did Donald Trump get himself into this situation? Well, that's a rhetorical question. Right.

Well, and I want to know what you're hearing from people that I know you've been speaking to, but also just that the derision he holds for other presidents for not having done this. And his comment, well, you know, one of the presidents, he told me that he wished he'd done this. Of course, they all come out and say, no, we didn't. And this fantasy land that he seems to live in is quite incredible. I mean, it's a fantasy. You think that this, yes, this is, that this is a fantasy. But the weird thing about this fantasy is the fantasy seems to change minute by minute.

So it's not as if, you know, I mean, George Bush and the Iraq War, that was a fantasy. But it was a coherent fantasy. I mean, it all went cropper, of course, but they were there. They had outlined this. They were just wrong in all of their assumptions. So, but Trump doesn't even seem to have any assumptions. And they could change, I'm sure they will change today. Where are we at this morning?

This morning we're at he's going to negotiate, except he doesn't know who he's going to negotiate with, nor does he nor does he know what he's going. to negotiate. What does he want? What would we take? What would they give? None of this is clear. I know.

I mean, except that. They have a stranglehold on the Strait of Hormuz, which could have been anticipated. We have Marines steaming their way there, maybe to hold the Iranians off. The Iranians are threatening to poll the neighbors again. We don't know what they're, we don't know how.

to break this strangle hold. Right. And incredibly, the Iranians appear to be, although we don't know if this is true because we don't know who's actually saying it on behalf of the Iranians, that they now want compensation, which is such a Donald Trump move, right? Remember when he was hustling the DOJ for quarter of a billion dollars for the hassle that he'd gone through during his period out of power at Mar-a-Lago? It was like, you guys owe me $230 million.

A number he clearly picked out of his, well, wherever he'd picked it out of, his note. perhaps, but the Iranians seem to be giving it back to him. It's very likely that the result of this is that the Iranians will make money and will benefit from this. And will Jared and Steve make money from it? Jared and Steve, I think that we can always, the fundamental, the bottom line is that Whitkoff and Kushner always make money. Trump went to Graceland.

The obvious comparison is Trump and Elvis. Well, I think we have a clip of him. So I knew Frank Sinatra. I knew most of them. Unfortunately, I never met Elvis. And that would be one I would have liked a lot. But I do like his music, I will say. So thank you for inviting me.

I appreciate it. I mean, first thing, I have never put those two together, which is my fault. Because they really do belong. together. They really do have a, have a, have a, have a, they share a look. They do share a look. I mean, Donald Trump would look good in there as Elvis. I'm quite surprised he hasn't dressed up as Elvis for one of his Mar-a-Lago parties, which he still goes to at the weekends, despite the fact we're at war. So this weekend, he was at a Ritzie Republican fundraiser at Mar-a-Lago. But there's another interesting thing there that,

that this also signals, which I hadn't thought of, is that he is not part of that Elvis moment, that Elvis cultural moment. I mean, he is, I mean, what did, he immediately went to Frank? Right. I mean, you know, because he's much more of a rap pack kind of guy. and the Elvis thing actually at that I can the Elvis thing was was kind of cratering as he was so by the mid-60s Elvis was sort of out of it to say the least sadly and and so he probably has never had any interest in Elvis and he doesn't play Elvis on the plane so Elvis is not on his mix right well and he He's a YMCA guy, which is the 80s, right? He's not doing the swivel hips of Elvis. He's doing the kind of weird, that weird thing he does with his hands.

So we're inside Trump's head. A big chunk of it is obsessed by the wall. Or maybe not. That's, you know, I kind of wonder about that. Is the war really holding his attention or actually does he just want to get out of this thing? Well, and we're in week four now too, which is a long time. to hold his attention? Except the thing that has held his attention,

and it has been really the foundational point of his, kind of of his entire political career, and still holds his attention and is back to the forefront of his attention, which is elections. Right, and that they're rigged. And this seems to me, I mean, his determination to try and get the Save America Act passed, and again, he's hitching all sorts of things to it as he did with the Big Beautiful Bill, is he creates a problem that doesn't

exist. Then he seems determined to find a solution for the problem that doesn't exist, therefore creating chaos and doubt in the American election system. Therefore, also creating a narrative. So this is the drawing. This is reality television. Right. So the reality television of it all is that the, that the, that the, that the, that the, that the, that the, that the, that the, that's a electoral system doesn't work. Right. It doesn't work.

It has all kinds of holes in it. So then that, that, that, that, that, that gives room to all kinds of fraudsters, corruption. Um, and it's a threat to you the voters. And, but here is Donald Trump saying, I can. save this. Only I can save this. And it is it is the thing that if I don't win, this is why. Right. So it's also got from the beginning just as you know, even before the 2016 victory, he was on about they're going to steal it from me. Well, and the whole idea that he lost 2020 because he couldn't believe that he would lose against Joe Biden. And then he's also got this, these two

extremes that he holds in his head as well, that he is the only person that can solve this because he's the most important person and only he knows how to make these decisions and he knows more than anybody else. Something he's always saying he knows more than the generals. And then this sense of it's all rigged against me, they're all out to get me, the kind of paranoia and the grandiosity at the same time. But do you realize how complicated this is to create this entire world, to live inside of this world,

to occupy it, then to bring so many other people inside of it? I mean, he has brought, for one thing, he has brought the entire Republican Party. Now, all of these people in the Republican Party, every last one of them, 100% understand that the election, that the United States,

the election system in the United States works pretty well. They understand that. They believe that. And they also understand that 2020 was he lost the election. Nobody. There is nobody who thinks otherwise. So there is only one person. I mean, this is really kind of incredible,

one person who thinks otherwise. And does he really think that? Or does he just think? that it's a good thing for him to create this drama? No, I think that you need to actually, in order to sustain this, in order to stay in character, you have to believe it. And I have sat with the man as he has gone over these numbers.

The numbers come out, you think, oh my God. He has no idea where these numbers come from. He has no idea what he's talking about, but nevertheless he is in the way. pig heaven with these numbers. And he's just made them up? He's just made them up or he's heard them from somewhere. Somehow they have come to him in a way that he has come to believe they are legitimate and genuine. I do believe that he believes that the election, the 2020 election, was stolen from him, that he is absolutely, absolutely the rightful winner. Now, no, again, nobody else,

Nobody in his family, nobody among his advisors, nobody and nobody in the leadership of the Republican Party. Nobody in the White House. Everybody saw. I mean, I was sort of around at this period, and you would just see one after another of the people in the White House. You know, they were just, that was the gesture. I was like, don't ask me.

And then they were out of there. So what happens when the bill doesn't get passed? You know, I don't know. So the bill, from everything that we know, this bill cannot be passed. And this is the Save America Act, which is basically, I mean, it basically means that you have to show a significant threshold. of identification. Right. And I think you need proof of American citizenship. Well, that's what I'm saying. It's not just, you know, I don't even think it's just a driver's

license. Right. You know, it's passports, it's birth certificates. It's a, it's a whole threshold here, which an enormous number of people in this country can't get over. I mean, very few people actually, I mean, the numbers of people who actually, in America who actually have a passport is, you know, its own peculiar kind of scandal. Right. That is to say, very few people have a passport. Right. And lots of women change their name when they get married and then you have to find your

marriage certificate. You have to find your original birth certificate. The whole thing isn't. No, so, and it is. You're right. There is no problem here. There is nobody. Nobody is making any kind of credible accusations that, you're, you're, you're, you're

there that the American voting system is rife with, well, non-citizen, in this case, non-citizens voting. Nobody. Right, but what an interesting and cynical and frankly horrifying thing to do to try and get at the very center of democracy by saying it's rotten to its core, all sorts of illegal people vote. the results are not valid. I mean, it's hard not to think. Well, let me, there have always been rules about who can vote.

Right. And they go from the unacceptable and ridiculous at times in American history to the procedural. And the procedure here, and if you say to people, well, do you think? and that's what they do. They say that's the question, well, do you think that only American citizens should be allowed to vote? And then everybody says, oh, yeah, that's, yeah.

Because only American citizens are allowed to vote. Right. But the insinuation, obviously, is that people, all kinds of people who are not American citizens are voting. Well, and specifically the Democrats. He keeps saying the Democrats want all sorts of illegals to vote. Yes.

But any, but this is, this is, so you set that up, shouldn't, should only American citizens be allowed to vote? And then people say yes. And then they say, well, okay. Then shouldn't they have to prove that they are American citizens? And there is some vague logic to that, of course. But the other interesting thing is it's not actually clear that this will benefit the Republicans. Well, that's what I was going to come on and ask you, because the assumption is somehow that this is going to benefit the Democrats. It's going to limit the voting pool.

Right. We know that. And it might considerably limit the voting pool by 20%, possibly as much as that. But it doesn't necessarily mean that it is going to limit the Democratic voters, although the Democrats are afraid of that. And there is a certain degree of logic, you know, and I'm trying to think actually what the logic is. And I think the logic is young people, it will most stymie a set of groups. Young people, black people. Well, and also as Donald Trump, he says he loves the uneducated.

Uneducated people are less likely to have a passport. And they're probably less likely to be able to access their documents. It's a bit of a generalization. Well, it is because there's a lot. A lot of, there is more, more uneducated people or people with fewer, have had fewer years in school. Let's not call them uneducated. People who have had fewer years in school. I was using his name, his word for it, are more likely.

I love the uneducated. I love the uneducated. He said that. I'm going to make a plea that you don't do Trump imitations anymore. Okay, fair enough. I just don't want to give him the benefit of an English accent. But many of more people with fewer years of schooling are more likely to vote for Donald Trump. Okay.

So what does that mean? And I think what this means is it's just, what is to his advantage is just the narrative that the election system in the United States is broken. And chaos is to his advantage. And to create a bubble of uncertainty and controversy around that is reverts to, no matter what happens, reverts to his advantage. So if he loses the midterm, let's assume, this is not going to, let's assume, this is not going to pass. So why is he doing this? And I'm actually answering my question in real time to myself. The reason he is doing this is to set up and to continue the narrative.

When he loses the midterms, this is, this then becomes the issue. This then becomes the reason he lost the midterms and he lost the midterms and he lost the midterms illegitimately. And again, we have, we've set up the enemy here. Right. Because it doesn't make any sense. Everybody knows this is not going to pass. In order for this to pass, they would have to do away with the filibuster in the Senate, which nobody wants to do. Neither party wants to do. So, therefore, and he's basically said, don't do anything else. Don't pass any other legislation. Don't work on anything else. It must only. be this, this which is not going to come to pass. So why would he be doing this? Now, you know, you can't discount the possibility that no one has told him this can't possibly pass. But I suspect

that that must be obvious enough for even him. So therefore, why is he pushing this forward? He's pushing this forward because he has pushed this story forward from day one of his political career. That's what his essentially his politics is founded on this, on this, I was going to say belief, but, you know, it's no one else's belief. And so it's on this narrative. Let's just call it that. Okay. It's his story. It's his story.

It's his story. So if he wins, the system is perfect, and if he loses, the system is rigged. Yes, but he's not going to win. So the system is going to be rigged. Well, we don't know he's not going to ring. We don't know he's not going to. We're, we're, I thought that would be a pretty, I would say, safe speculation. Yes.

I mean, it's a terrible. I mean, things are terrible for him at this point. There's another reason he's pushing this along. You know, this is another kind of distraction. So it is going to be not that I lost because of the war, because of the economy, because of Minneapolis. Because of the Epstein files. Because of Epstein, it's I lost because the American electoral system is corrupt. And you, my voters, have been cheated. That's the cliffhanger. We'll be back on Thursday to actually talk about Donald Trump's brain.

I mean, we're inside his head the whole time, but I don't feel I ever leave his head at this point to you. I mean, that's the other thing that's so fascinating that he's got this grip on all of us. Yeah, and we're going to go. I mean,

what, I mean, we are in an era that we are ruled by a dummy. So let's let's get into that. How dumb is dumb? Well, we're going to do a proper examination of his brain, in as much as one can. But we're going to do that on Thursday.

So if you have been, thank you for watching. I'm not sure what my favourite part of this conversation was. I'm always trying to think about that as we wrap up. So much of it. But really this idea that he's creating a problem that doesn't exist to finagle the results of the election. And I do think it's much more serious than people perhaps, Well, it's fundamentally about democracy, of course. But then it's fundamentally about the way he approaches politics, the way he approaches everything, which is not just creating a problem,

a problem that doesn't exist that only he can solve, but that's part of it. But a full story structure. This is reality television in which he can create. the drama. And he is the drama. Don't forget to subscribe to The Daily Beast. We are independent media. We got some criticism for reading ads, which I thought was a little unfair because media has always survived with ads, but the Daily Beast is an independent media company. So that's why we run them. And there was one in particular about me recommending a skin product called One Skin, which I have been using. And I asked the, I asked few. to remark on whether or not my skin is looking any better because it's a controlled environment.

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