The Daily Beast Podcast - 'Weird' Stephen Miller Is Trump's Biggest Suck-Up

Episode Date: October 26, 2025

Stephen Miller is the ultimate suck-up, a master of shameless flattery whose influence keeps him at the center of Trump’s orbit. Michael Wolff joins Joanna Coles to unpack how Miller’s relentless devotion to Trump reflects the chaos and destruction in the East Wing. The two also touch on how Wolff’s countersuit against Melania has spurred a bizarre AI-generated TMZ story that falsely claimed he was writing a tell-all about the first lady. They preview their first live ‘Inside Trump’s Head’ event at the Museum of the City of New York, where Wolff promises more revelations about Trump, Epstein, and the ecosystem that enables them. Hosted on Acast. See acast.com/privacy for more information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I've gone around to several White House people, and I said, explain Stephen Miller to me. Because he's, you know, I mean, as we talked the other day, he's a weirdo. Even Trump acknowledges that he's a weirdo. So I said, explain this to me, explain this rise. How does he keep rising? And across the board, there's one explanation, and everybody rushes to it. They say he's the most incredible suckup. You have never seen this.

I mean, the flattery, the ooze, you know, when he is in the room with the president, with Trump, it just can't stop. And it's one of the few things, and as I say, several people are reporting this to me. It's one of the few things that makes Trump shut up. He just likes to listen. this whole effort to remake the color of America is really comes down to Stephen Miller's ability to flatter the president. Even more than Hegseth, he sucks up. Stephen Miller is the winner of the suck-up contest.

Michael. Oh, my God, Joanna. Oh, my God, Michael. We are going so deep inside Trump's head. but I'm worried that it's just a kind of, I think it might just be a lot of electrical fuses. I love our design here of inside Trump, so you can't see it. I love our, where can you see it? There we go. I love our design of inside Trump's head.

That's literally what it feels like it must be going on right there. What are we going to find? I can't even explain the succession of things that have happened virtually in the last day or slightly, longer. I mean, it is from the, from breaking up the, blowing up the relationship with Canada over a fit of peak, over some ad on television, to pardoning this crypto billionaire kingpin. Does he think no one will notice his own family is in the crypto business? To demanding, this is, this is like extraordinary, this 200. $30 million that the government, the government that he runs, should pay him over perceived injustices. Well, his own justice department, right? To, of course, bulldozing the White House.

Did you leave out blowing up rando boats in what started as the Caribbean, has now spread to the Pacific? It's actually even broader than that. It's like a new kind of a policy. The military can kill anyone on my orders. And then there's some statement, I mean, an extraordinary, my God, we are going to kill anybody who brings drugs into our country. We're going to kill them. They will be like dead. Now, what explains that except that the person, this person, must be head-bangingly off his rocker? Well, and he's surrounded by people that are, not having any sense of restraint around him. Pete Heggseth. Well, hold on. We haven't even mentioned the Pete Hegsef telling members of the military they're not allowed to talk to Congress

in case they inadvertently give something away. But that is, I mean, it's not to forgive these people, but it certainly can be explained. They cannot do that. They cannot. They do not have any portfolio to criticize him to certainly not to criticize him and certainly not even to advise him on a better path. It just you're out if you're going to do that. Well, and also what he's also created is this sort of constant presence in the public with his endless press conferences. I mean, it's so fascinating. The juxtaposition against Biden, who I think did six press conferences in his last year. Now, obviously, we know why. But Trump all the

time. I mean, you keep making the point that he doesn't. just talks all the time, all the time. Yeah, no, that's, I mean, he talks in private. If you're with him, it's a monologue and in public. And they're not different, by the way. I mean, he says, oh, I mean, the man is remarkably consistent. He says the same thing to everyone. I mean, it's actually, it's actually why it's relatively easy to write about him.

Because you can, you can sort of, you can track what, what he's saying from, from person, to person to person to person. So when you're talking to people in the White House, which I know you do all the time, what are they saying about this particular moment? You know, to them, it's not particularly exceptional. This is what he does. This is, you know, he goes deeper into being Donald Trump, which is the threat and which is the danger.

Now, you know, there's, I mean, I've had some conversations about, about, with them about what's, you know, the motivation here of pushing forward in ways that are, you know, can very easily backfire. I mean, very easily. I mean, $230 million, pardoning this crypto guy, bulldozing the White House. Why would you do this on any logical, from the view of any political logic, this can be and likely is going to be very damaging to you. So why would you do that? And, you know, pressing people, it's, I mean, first thing, it's Trump. I mean, that's always the explanation.

It's Trump. Don't try to question it because there's no reason. There's no, it's not going to get you any place to question it. And, you know, and it's Trump. He does these things. And yet he survives and flourish. So don't question it. But the other aspect is is people do feel he's in a rush. Now is the moment. And the moment could reverse almost at any time. I mean, if in the midterms the Democrats were to win Congress, well, that would be a serious impediment. Or at the end of these four years, he probably will be, despite Steve Bannon in his third term. despite my late at night fears, the logic is that he would still be out of office.

And he's doing this. This is it. This is the man in the moment. Well, it does almost feel like he's been told he's got a terminal disease and so he's being as disruptive as he possibly can be. I mean, the idea that we are on day, I think, we're recording this on a Friday morning. I think we're on day 24 of the government shut down. We have hundreds of thousands of government employees who are not being paid. We have TSA workers who I call. Let me finish. I have a point here that we have hundreds of decent TSA people who are turning up to make sure that regular Americans get their flights to go off and do their sales calls and go on family trips.

And he has his hand in the government till. for a quarter of a billion dollars is appalling. It's appalling. May I? You may? You may. I think it's an interesting moment because only now, at this, like today or yesterday, are checks failing to arrive for government employees.

So the squeeze is now on people, and this is literally hundreds of thousands. of people are going to start to feel this. So what's the effect of that going to be? I mean, there's going to be pressure on both the Democrats and the Republicans, but it's a new phase of pressure and a new phase of the shutdown. All right. I want to come back to some of these points, but I also wanted to say how struck I have been on your behalf for the outpouring of support with your decision to sue Melania Trump. And I will say, I've known you for 25 years, we've joked about the ups and downs in our relationships. We've had feuds. We've had a couple of

years where we didn't speak. That was largely ever one of us canceling too many lunches. But I think I've... Not me. I was not the one canceling relationships. I think this is the nearest I've ever seen to seeing you being moved. Is that fair? I mean, I've seen you through some major emotional moments in your life, and I have seen you moved by the support that people have had for you, the offering of financial support. I mean, I think it's, I think it's totally incredible. And I think it, you know, while I'm grateful for the support for me individually, I think it's also a sign that everybody is looking for something to do here. How do you push back? How do you stop this?

I mean, this is up till now and continuing now, unstoppable. Something has to be done. I mean, you know, I mean, people pour into the streets when there's an opportunity, when almost at any opportunity. I mean, but there are few. I mean, no kings twice a year or whatever, whatever that's, that schedule is. People want to be able to stand up. So, yes, so I am, but I am, I am certainly personally, personally grateful, stunned, relieved, too.

Yeah, relieved, I think. All right. So we were talking in our last episode about Stephen Miller, lots of very enthusiastic comments trying to get at who is this man that's been so responsible for the policy against immigrants. And these awful ice raids on people with masked men, jumping out and wrestling people and zip tying them. I mean, it's quite shocking. I still don't think I understand where his so-called philosophy, if one can even call it that, comes from in terms of hating people that very clearly work at the top of the American food chain in tech

in California and also literally till the fields and pick the plants and pick the vegetables and fruits that that keep Americans fed? You know, I mean, I think, I think explaining the roots of racism, which this fundamentally is, and the roots of this kind of resentment against a whole, a whole class of people is, I mean, the immigration issue is a complicated one. immigration and the Democrats have failed on this issue. And I think we can acknowledge that. I think the Democrats would acknowledge that. When you don't pay attention to immigration, when there isn't some logic to it, when you close your eyes to it and suddenly, suddenly it becomes an unstoppable force, is destabilizes governments. It's throughout Europe. That's the effect. And here it's the effect.

But this is, that's ultimately a structural question. How do you manage this, this process, this inevitable process? People want to come to this, to this country. That's a, that's a sign of health rather than the, than the opposite. But how, so how do you manage that? Then you take so, but that has to be, has to be juxtaposed to this other thing, which Stephen Miller represents, which is a kind of pure hatred, revulsion, enmity, for him to take this in that personal, in such a clearly personal way.

And, you know, I mean, I think it's, I think it's glare, I mean, the interesting thing is it's so glaringly obvious. There's no, there's no, even pretense to make this something else, to find a, to find a reasonable rationalization for this. So, you know, I mean, it becomes, and, and, and, you know, I think, I think at this, at this point, at this point, you know, you know, why one hesitates to go there for a lot of reasons. You know, this is a roundup of the Jews, but they're not Jews, they're brown immigrants. And let's have a word from our sponsors. And we're back talking about what else,

but Donald Trump's, not only America, but Donald Trump's world. And can you remind people again? Because I was struck that I didn't fully realize this. Why is it specifically Mexicans and South Americans that Stephen Miller seems to be going after.

I don't think that that's true. I think it's anybody who's brown, Indians are in this. It's just clearly not people who are white. And this goes to something that is at the heart of Maga, I think it's at the heart

of a whole of a, of a Trump thing, that this idea that we are losing, that, that within, you know, we're in the process of, of, of white Americans becoming a minority to brown Americans. And so there's the effort to exclude the people who Stephen Miller believes are not Americans, brown, brown people. So this is, you know, a fundamental to this, to this, to the Trump administration, is this rollback? How do we make America look like it looked in 1965? And that's a rollback of, of, and we've discussed this before, and I think these are the pillars of what, of the, of the, of the mega vision to roll back civil rights, to roll back, roll back, um, the, um, the, um, the progress of equity for women and for to change the, to roll back what has happened with a fairly

large amount of immigration, massive immigration over the last generation, brown immigration. So how does this work when Stephen Miller is in the room with J.D. Vance. And of course, J.D. Vance is married to a woman whose parents came from India, who's very clearly brown. How do they even begin a conversation? I've gone around to several White House people and I said, explain Stephen Miller to me. Because he's, you know, I mean, as we talked the other day, he's a weirdo. Even Trump acknowledges that he's a weirdo. So I said, explain this to me, explain this rise. how does he keep rising? And across the board, there's one explanation.

And everybody rushes to it. They say, he's the most incredible suckup. You have never seen this. I mean, the flattery, the ooze, you know, when he is in the room with the president, with Trump, it just can't stop. And it's one of the few things, and as I say, several people are reporting this to me. It's one of the few things that makes Trump shut up.

He just likes to listen. How does his career continue to flourish when everybody knows he's a weirdo? Even Trump acknowledges he's a weirdo. He's not really somebody anybody is comfortable with who you really want to be around and who you might trust on any matter because he's so weird looking at you with those with those weird eyes. But anyway, everybody responds the same way. And they rush to say it.

He survives and thrives because he's such an amazing suckup. Of course he likes to listen to this. So this is what all of this, this, you know, ice picking up people, masks, sweeping people off the street, this whole effort to remake the color of America. is really comes down to Stephen Miller's ability to flatter the president. But Michael, we are in a cabinet of suckups. Nobody sucks up as well as Pete Hegseth is always sucking up. Marco Rubio's sucking up.

No, no. Well, that's what I'm saying. Even more than Hegseth, he sucks up. So he is the winner. Stephen Miller is the winner of the suck up contest. Even more than the Labor Secretary who said, Mr. President, we have hung a huge, you know, great tapestry of your face on the side of the Labor Department, even more than that person. Yes, even more. I mean, and everybody has to do this. This is the price. These are the table stakes. How much you can, you can be absolutely prostrate in your flattery of the president. Those are the table stakes. And then you can, you can be absolutely prostrate in your flattery of the president. Those are the table stakes. And then you. you have to raise them? Who can do it even more? And that apparently is Stephen Miller.

So can you give us any elements of Miller suck-upperi? I mean, how does he go above Pete Heggzeth or the Labor Secretary? What are the words? Is it something in the tone of his voice? Does he bring him gifts? What is the... It is just these kinds of these kinds of statements. I mean, you have to, I mean, the essence of flattery is, and flattery to a degree beyond logic is shamelessness. How shamelessness are you? Your ability to say this shit that nobody else was nobody in their right mind, nobody who has a degree of objectivity or integrity or all of all of the attributes. that make for some level of skepticism and independence.

So putting all that aside, and if you can put all that aside, and it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, a thing that you, you would not, no one, no one, anyone else outside of this would, who, who, who, who might listen to it would understand that you're a, that you're just, you've, you've given up yourself, you've given up, you have no, no inner self anymore. And it's all directed to this goal of what you want, which then comes through the, this one man who needs to be, needs, needs to be flattered, not just flattered, but more than the last person who flound. He needs to be massaged and it's anyway, let's also talk about Stephen Miller's domestic life because several people have said, oh, wait a minute, didn't Stephen Miller's wife go off to work for Elon Musk?

And this was around the same time that Elon Musk appeared to the right of the president, as the president sat swinging his legs from behind the resolute desk, Elon Musk had a black eye. What can you tell us about Mrs. Miller, who I don't think lasted very long working for Elon Musk? And she was apparently devoted to him until not. So what is Mrs. Miller doing now? I think she has a podcast. Well, that's a safe, safe bet. Doesn't everybody? Yes.

Perhaps we should invite her as a guest on our podcast to explain. Okay, let's do it. Should we do that? Yeah. I'm not sure if there's a crossover in audience, but Mrs. Miller, If you're listening, we would love to invite you on our podcast. Who knows? I think they're an interesting, I mean, they're a power couple.

What does that mean to be a power couple? You know, they are two people who met each other in Washington with, you know, I mean, clearly enormously, both of them enormously ambitious. And I think both of them with a clarity about what that, what realizing that, ambition would involve in the Trump years. And the other aspect of this is to realize, and I think a lot of people around Trump have realized this, that they would not have the opportunity with anyone else. They're in, and most of the people in in the administration, from Hakeseth to Kennedy to

Bondi are not people who would have would have had success in any kind of more traditional administration and traditional evaluation of experience and accomplishment and skills. So that that

creates this that creates this really interesting kind of pressure. I mean, this is your opportunity. You're not going to have an opportunity like this again. I mean, I think Trump himself feels that, but people around Trump feel that too. That now is the time in their lives and in history. which they might uniquely prosper.

So they better do everything possible to take advantage of that right now. And I'm sure that this has felt the way in other authoritarian and despotic regimes, which are all in their, in a sense, in a sense, flukes. They're a product of a moment's circumstance. I mean, in often a terrible moment. circumstance. But kind of everyone in that situation then realizes that in a normal world, they would be excluded from a normal world. So therefore, they find themselves doubling down on their own abnormality. Well, and also what's curious is that, as you say, Donald Trump

gives them an opportunity they wouldn't have in a normal or a more normal era. And so not only does he enable them, but they enable him with their extremes. So as you say, Donald Trump isn't even that particularly invested in what Stephen Miller is doing, but Stephen Miller turns out to be useful for Donald Trump. Yeah, no, definitely. And there is this idea in other more normal, let's continue to use that word. In other more normal circumstances, the premium is on being normal. And actually, you kind of,

you kind of, you thrive on being the person who is the most normal, the most regular, the most showing up on time, the most doing it, the most conservative way. The people who, people who create the least amount of

of friction, all of those kinds of things. I mean, you've seen it many time in many offices. But this goes the other way, the people who, the people who thrive are the people who are more extreme, who are more disruptive, who are more, who more lend themselves to the Trump ethos of we've got to break something every day. All right. So there's one final point I wanted to talk to you about, and that is the sending in or the not sending in, which was the latest update on sending in troops to San Francisco.

So this was something that Trump has been threatening. Mark Beniof, the CEO and founder of Salesforce, had pleaded for Trump to do, had said, yes, please send him. troops, you know, and his hypocrisy was pointed out by Ron Conway, the VC investor who resigned from the board of Salesforce and pointed out that Mark Benioff, in fact, lives and votes in Hawaii. But in fact, apparently Mark Zuckerberg had reached out and said to Donald Trump, please don't send in troops to San Francisco.

It's not going to be helpful. Donald Trump had spoken to Daniel Lurie, the new mayor of San Francisco, who appears to be introducing all sorts of schemes which are improving, certainly the center of San Francisco. Last time I was there, it was notably improved. And people who live and work in the city are saying it's so much better than it was. And so Donald Trump said, okay, I'm not going to send in troops. What are your thoughts on that? Well, I think it's, you know, like in so much around Donald Trump, it's obvious. You know, the billionaires called him up. And he likes billionaires. He even,

listens to billionaires and likes to please billionaires. So, I mean, we're just, we're just in this, you know, in a world. And so much in the, in the Trump administration has been oriented to pleasing billionaires, especially tech billionaires who flatter him. And that and, and this was a moment in which they, you know, they, they, they called in, They monetized their flattery, I guess you might say. They monetized their flattery. And Justice Stephen Miller prostrates himself before Trump.

So Trump prostrates himself before the tech billionaires. There you go. Once again, our sponsors, who we are indebted to. And we're back, Michael and I inside Trump's head. Michael, we'll be back on Tuesday with more inside Trump's head. Wait a minute. So, you know, this suit against Melania Trump has generated a lot of press. And but one of the things and one of the first pieces of press that it generated actually came from from the entertainment site TMZ.

And it was, I would say, not only, not only. not only off, but staggeringly off. It kind of had invented a whole narrative about me that I didn't recognize, including a book that I was in the middle of writing and the title for this book. I mean, it was a book that I was writing, writing a book about Melania, which I have no interest in doing, had never occurred to me to do and would never do. but complete complete with a title and a subtitle. And then this this went out.

It was, you know, propagated throughout the, I mean, this, the internet. So anyway, we called TMZ on it, and this turns out to be an entirely AI written story, which TMC immediately apologized for and corrected and all that. But then having gone out, and now that's, story has been picked up by actual human reporters who have just cribbed from that phony story. So in this, this is just my first glaring encounter with, with, and personal encounter with AI news. This must go on then, I'm assuming all of the time, just a pure invention. Now, this is not, this is not bias or it's not, it's not anything else.

That we've said is a problem with news. It's not fake news as in a bias. It's just literally fake news, it's just which no one is responsible for. Well, and what was also strange about the story, which I read and I was like, what, Michael's been writing a book about Milano and he didn't tell me. People in my family said, how come we don't know that you were writing this book? I was like, but it also took the title of a book, The Art of Her Deal, which is a book that already exists about Melania by the author Nina Burley. So it was a sort of weird mishmash of, yes, they understood you were an author. Yes, they understood you were suing Melania. Yes, they understood there was a book about Melania. Nothing to do with you.

But they sort of put the two together and it created this third monster-like story. Totally. So it's just that, you know, and no one is at fault here. No one is trying to, you know, get me. Nobody is trying to whatever. it's just AI in the invention of reality. It's AI and the invention of reality. Well, also, I thought you were going to go somewhere else, which is you've launched a substack.

Yes, I have launched a substack. Don't you want to tell people about it? Oh, thank you, Joanna. Well, it's a, it is more Trump and more Epstein, Epstein. Epstein. And in, in longer versions, more daily versions. And yes, I'd love to have everybody, everybody come over, everybody, everybody join me. It's another chapter.

I also think that might be the first time we've got through an entire episode of Inside Trump's Head without mentioning Jeffrey Epstein. But we are going to be mentioning him when we get together for our first live event at the Museum of the City of New York. So it's MCNY.org, you can buy tickets and come with questions. It will be the day after the New York mayoral election, but we'll be talking about Donald Trump, we'll be talking about Stephen Miller, we'll be talking about all of it. But come with questions, come with your friends, come for a group outing, plan a dinner afterwards. We're kicking off at 630. We'll be through by eight, by which point you will definitely need a cocktail. And there are plenty of bars around

the museum of the city of New York. Yeah. And anything you want to know about about that I can answer about Jeffrey Epstein. There, I'm delighted to answer. And Melania, just ask. Just ask. So don't forget, November the 5th, the date for your diaries, if you're in the tri-state area, or if you feel like flying in to support us for our first actual physical manifestation of inside Trump's head. Thank you for joining us if you have been. Don't forget to subscribe to the Daily Beast. subscribe to Michael's substack, which is called Howl, based on the Alan Ginsberg poem, I'm assuming. And my last name. Oh, Wolves Howl. I never even thought of that. Howling at the moon, Michael. Howling at the moon.

There is the Alan Ginsberg poem because Alan Ginsberg is from Patterson, New Jersey. Where I am from? Of course he is. What happened in Patterson, New Jersey? It produced you. It produced Alan Ginsberg. it produced, William Carlos Williams. Dr. Williams, yes, of course. Alexander Hamilton. Hurricane Carter. Hurricane Carter.

I don't even know who Hurricane Carter is. He sounds like a rapper. Was he a boxer? He was a boxer, famous Bob Dylan's song. Okay. All right. Well, that one passed me by, but don't forget to subscribe. Leave us a comment and share the podcast with your friends.

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