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Michael Wolff
Did I talk too much? Can I just let it go? I wish I would stop. Thank you so much.
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Michael Wolff
The MAGA position is release all the information about Jeffrey Epstein. The Trump position is do not talk of Jeffrey Epstein. See? And put his fingers in his ears. Come cover his eyes. No Jeffrey Epstein.
Podcast Host (Joanna or Co-host)
So we are back. We're recording this on Thursday morning. Michael, have you recovered from your 200ft projection of your face on Windsor Castle?
Michael Wolff
You know, I think I'm gonna live with it for the rest of my life.
Podcast Host (Joanna or Co-host)
Okay, so yesterday when we were talking, you said that you thought Trump was winning the war with the media and I slightly push back and I thought you were being hyperbolic. Literally two hours later, it was announced. ABC announced that Jimmy Kimmel's show, for those of you who don't know Jimmy Kimmel, for those of you listening in the UK or in Australia, where We hear from. And also Canada, where we hear from people all the time. Jimmy Kimmel is a late night.
Michael Wolff
The entire English speaking world is at our feet. Yes.
Podcast Host (Joanna or Co-host)
Okay, thank you. The entire English speaking world. I don't know if they're at our feet, but they're definitely sending us comments on YouTube. And please keep them coming because they mean a lot. Jimmy Kimmel, a late night comedian on abc. His show was being suspended indefinitely. And literally within, I would say, five minutes of that news going out, it felt as if a chill had rippled across the entire of the United States.
Michael Wolff
Okay. And he was specifically. What do we call an indefinite. He was specifically indefinitely suspended because of comments he made about Charlie Kirk.
Podcast Host (Joanna or Co-host)
Right.
Michael Wolff
And that has suddenly. Charlie Kirk has suddenly become the third rail of American political discourse.
Podcast Host (Joanna or Co-host)
This does seem like a moment of censorship. Is it? Or is it simply a trade deal? Let's.
Michael Wolff
It is. But even before. Absolutely censorship. Fear, Rank fear. Everybody running in the opposite direction of controversy, running in the opposite direction of Donald Trump's wrath and ire. But I just want to tell a sentimental story about Jimmy Kimmel and Donald Trump, because that's where my Trump journey began. In the spring of 2016, that I first interviewed Donald Trump in his political life, in Jimmy Kimmel's green room. Trump was out in LA doing the Kimmel show. And I was invited to watch him do the Kimmel show and then to talk to him in the green room. And so an interesting point that is now, you know, coming on 10 years ago, at that point, Kimmel and Trump were completely jocular with each other. I mean, the whole mood was, you're a star, I'm a star, we're both stars together, and we're both kind of enjoying this odd moment of thinking that Donald Trump might be president. Although at the same time, we understand that that is still the most unlikely, the unlikeliest of Outco. But very much. They very much got along. When I saw Trump afterward, he was delighted with Kimmel. Delighted with his performance, of course, on Kimmel. And then actually we spoke long into the night. We repaired to his house in Beverly Hills and spent hours and hours each eating a tub of Haagen Dazs ice cream.
Podcast Host (Joanna or Co-host)
But, okay, that's such a strange visual. And of course, there is a Zelig like story of you in Jimmy Kimmel's green room with Donald Trump.
Michael Wolff
Totally. I mean, and then in the house. So he has this house in Beverly Hills, smack in the middle of Beverly Hills, across the street from the Beverly Hills Hotel, filled with kind of cast off hotel furniture and a refrigerator. When you open the door, it was just pint of Haagen Dazs. Haagen Dazs. After pint of Haagen Dazs. Can I ask what flavor that was? Vanilla.
Podcast Host (Joanna or Co-host)
Vanilla.
Michael Wolff
Although he has switched over the course of the past 10 years, he now likes strawberry vanilla.
Podcast Host (Joanna or Co-host)
But we digress from major media censorship.
Michael Wolff
At any rate. I follow this because, because the people around him are always reporting on his, on, on his ice cream preferences. But he said, you know, open the door, you know, and said, you know, took out a pint and he said, asked me, do you want one? I said no, I didn't. But he threw one at me anyway. So there we were then sitting on the couch eating our, our ice cream as we spok to the night. And what I the point I want to make, other than this sentimental one of that's where my journey began, is that there is a difference that over this time he has gone from a figure kind of, you know, I think enjoying the whole idea of his notoriety, of, of his rise, unexpected rise in politics, not taking it that seriously. And clearly over this time that has fundamentally transitioned into incredible defensiveness and incredible anger, an incredible sense of him against everybody else and in this case, obviously him against his old compatriot, show business compatriot, Jimmy Kimmel.
Podcast Host (Joanna or Co-host)
And is he also against the people that work with him? Does that animus extend TO People like J.D. vance and Pete Hegseth?
Michael Wolff
Well, it ultimately extends to everyone without question. I mean, no one gets out of Donald Trump world alive. I think that's a reasonable given. But I also think this in terms of, you know, we are at this moment, Charlie Kirk is, is killed and immediately thereafter, this becomes the, the rationale, the stated rationale for the Trump administration to crack down on the media and on free speech or as he says, leftist speech. This is not, there's, there is nothing, nothing. There is no pretense here. They have made this announcement. J.D. vance has, is, is out there, out there shilling for this. But Trump too has made it clear we are going to go after the, after the leftist media, leftist speech. So, and I don't, you know, and they, the way they went after Kimmel in this instance is that theis that the FCC chair started to make, started to object to this and that spread to affiliates. Affiliates are the television stations that carry the, the, the Kimmel show, one of the big affiliates is in the middle of a merger which they will need approval from. That's next from the Trump administration So therefore they immediately came out and said, yes, we're not going to carry the Kimmel show. And then Disney, who owns abc, the network that Kimmel is on, then they immediately announce this indefinite suspension. And that would have come from the top, from the CEO, Bob Iger. You have to step back and say, here is Bob Iger, the billionaire CEO of the most powerful entertainment company in the world, immediately, with hardly a second thought, cowering before the desires of the Trump administration.
Podcast Host (Joanna or Co-host)
Or is this a CEO making a very practical decision that his stock has underperformed the S and P. He can't afford to lose nexstar as an affiliate or indeed Sinclair, which is another affiliate. Both nexstar and Sinclair are conservatively led. And he's making a pragmatic business decision.
Michael Wolff
Well, I think it's the same thing, six to one half dozen of the other. I mean, he realizes that the ire of Donald Trump will be bad for business. And so therefore we submit to that now. I mean, it used to be not that long ago that media companies, because they are media companies, because they have to maintain a. No matter their shareholders interests, there is their audience interest, there are many other stakeholders in a media company and they have to maintain credibility. If you, if you lose that, then you lose the store, would have been the old rationale on this in this instance. Now, if you lose Donald Trump, you lose the store.
Podcast Host (Joanna or Co-host)
I would be fascinated to be a fly inside Bob Iger's inbox this morning. Also a man in his 70s, also a man who gave up power and gave up being CEO and then came back after a famous battle with the guy he put in to replace him, Bob Chapek. One of the reasons he gave for.
Michael Wolff
Kim, not a name that many people remember at this point, but very good.
Podcast Host (Joanna or Co-host)
Well, but one of the reasons and one of the rationale for Bob Iger coming back was that Disney was beginning to lose the creative community. The creative community for the most part, loved Jimmy Kimmel. Jimmy Kimmel is a rare late night television politician who actually lives in la. He makes pizza at home with Bob Iger. They are personal friends.
Michael Wolff
Also, let me point out that he's one of the few late night comedians who has been able to maintain the comic edge about Donald Trump. Other late night comedians have veered off into outrage and Kimmel has managed to maintain his focus on the absurdity.
Podcast Host (Joanna or Co-host)
Well, there's also John Stewart and John Oliver. Right.
Michael Wolff
And I think they're, and I think they're in outrage territory. Not, not, not that I would necessarily fault them. I Mean, that's where we're all going to end up. But the ability to maintain that focus on absurdity is, is a comic touch, which I think Kimmel deserves an enormous amount of credit for.
Podcast Host (Joanna or Co-host)
Well, what's also interesting is that Kimmel is very much thought Disney or ABC as a team player. I mean, this is the guy that hosts the Oscars when nobody else will. I've been to the upfront, the big ad festival where the TV companies turn up and sell their future shows, and he's been a host of that and funny and taken, you know, poked at advertisers and made the whole thing a show in a way that a lot of other networks can't do. So for them to sacrifice a team player like this also seems significant. But then Disney may go on to lose the creative community over this. I mean, I understand that they don't want to lose the Trump and they want FCC approval for whatever M and A they may have in their future. But this does feel like a moment.
Michael Wolff
I do. And on a. If we put ouri mean, I begani have spent most of my career as writing about the media and if I put that at least prior to writing about Donald Trump and if I put that hat on, I would say that this is probably a deep, deeply, an unforced error that will cost Bob Iger, likely. Let me go on a limb here. Cost him his job.
Podcast Host (Joanna or Co-host)
So interesting because the person within Disney who is thought likely to take over from him is Dana Walden, probably the most powerful female executive in Hollywood, very much admired. And of course, the complexity here is that she is well known to be Kamala Harris's best friend.
Michael Wolff
Grim. That's a, that's a, that's a grim corporate bit of politics. But I think unless someone breaks from this, I think they'll both go down. This, this is a, this is, you know, there's a lot of things in the reaction to Trump, the reflexive reaction, the knee jerk reaction, that's just serious, unthought out, knuckleheaded stuff. And I think that's a reflection of how afraid people are of Donald Trump.
Podcast Host (Joanna or Co-host)
Well, let's then just examine the dinner last night, the famous white tie dinner, which looked spectacular, I will say, watching it online and on television. Stunning flowers, everybody dressed to the nines. One was very cognizant of Prince Charles's lapel full of medals. And Donald Trump having no medals. I'm sure he's going to come back and say, I want a jacket like that with some medals on it. But Also around the table were some of America's most senior executives. You had Tim Cook from Apple, Satya Nadella from Microsoft, Sam Altman from OpenAI.
Michael Wolff
What are they thinking? What are they thinking? I mean, you know, in my, I can only interpret this. I mean, first thing, Tim Cook shows up at all, all of these, these things, the, you know, again, the billionaire CEO of arguably the most important company in the world.
Podcast Host (Joanna or Co-host)
And also sitting next to Tiffany Trump. I was like, what are they talking about?
Michael Wolff
Why is he doing this? It's, I don't. So I can only assume that they get all to get together and say, my God, this guy Trump is easy to play and all it requires is us to do some ritual bows and say some baloney and then we get what we want. And isn't it a great day for business? That's the only thing that I can assume it is, cannot possibly be that they think Donald Trump is anything other than clown, a fool, a charlatan. I mean, I know that's what they, what they, they think that is what literally what everyone who comes in contact with Donald Trump thinks, even his supporters. So again, that's, that's, that's it. But, and then the Brits on, on their part, you know, who are desperate for a trade deal. So everybody got together and decided, okay, you know, we're going to, we're going to treat Donald Trump as the real king.
Podcast Host (Joanna or Co-host)
Michael, hold on one second. We're just going to take some messages.
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Podcast Host (Joanna or Co-host)
And we're back with Michael Wolff talking about Donald Trump. One of the things that people always say about an encroaching autocracy and they always talk about Putin like this is that when Putin first took over, the thing that got canceled first was a puppet show, a comedic puppet show on Russian television. And you, you talked a couple of weeks ago on the podcast about this being frightening moment. And this could actually be what autocracy looks like, that it's not people with jackboots marching down the street. It is Jimmy Kimmel being canceled. Jimmy Kimmel, of all people, you know, in third place as a late night comedian on abc.
Michael Wolff
I mean, and it would be wrong to start there to Mark this at the beginning. It has begun long before this or it began, almost began before he actually came into office for his second term. And that was forcing ABC into a settlement that was $15 million that went into Trump's pocket. It was one of those things that certainly had they gone to a trial, ABC would have won actually they would never even have gotten to it trial. But abc, again, abc, which is owned by Disney. So this is not, this is the Kimmel, the Kimmel, the Kimmel issue is not, is not the first issue that ABC has folded on. And they folded on the Stephanopoulos issue. And then cbs, which was in the process of a merger with David Ellison, who was the Nepo baby son of Larry Ellison, who vies with Elon Musk for the title of richest man in the world.
Podcast Host (Joanna or Co-host)
Right. The founder of Oracle and soon to be owner of TikTok.
Michael Wolff
Right. So they did in order, CBS believed that in order to facilitate that deal, they had to do, they had to, they had to settle because Trump has stood 60 minutes because he didn't like the way he thought that they had edited an interview with Kamala Harris in too favorable a way.
Podcast Host (Joanna or Co-host)
The trailer was different to what they actually put out in the interview. Right.
Michael Wolff
Yes. Again, you know, another's absolutely frivolous lawsuit that Trump would have lost. But because of this, because CBS was highly aware of the pressure he could bring that might block this merger, they settle. Now we should also add that the Ellisons father and son are now trying also to buy Warner Discovery, which would make them, you know, by far the largest media company in the world. Although having said that, I think Disney may still be larger. But Larry Ellison also, let's remember, has been a very key and ardent supporter of Donald Trump.
Podcast Host (Joanna or Co-host)
Well, I may well get the ownership of TikTok. Right. Which we're expecting to hear. Donald Trump is speaking to Xi Jinping Ping tomorrow. And in theory he's going to come away with a solve for the tick tock issue. It's going to have American ownership.
Michael Wolff
So just, yeah. So let's just, just, just imagine first thing we have, we have a media business, you know, most of the, the major news app that would include most of the major news outlets in the, in, in the country already running scared of Donald Trump. I mean, scared. I mean they are bowing down. Trump brings pressure, they fold. Now that's, now we put that together with the fact that the Ellison family, passionate supporters of Donald Trump are about to corner the media market.
Podcast Host (Joanna or Co-host)
Well. And they're about to own CBS News. Well, they do own CBS News. And if they buy Warner Brothers Discovery, they will have cnn.
Michael Wolff
There you go.
Podcast Host (Joanna or Co-host)
So two significant news channels.
Michael Wolff
Yeah. No, I mean, this is. Put up the red flag at this. This is a moment which I think we will return to.
Podcast Host (Joanna or Co-host)
So Governor Newsom, who is emerging as the loudest voice on the Democratic side, is saying, Donald Trump has got dementia. Grandpa, take your meds. His social media is cutting through to some extent. There's gerrymandering going on in Texas, in various other places. What is the sort of moment of hope here for the Democrats?
Michael Wolff
Well, it's, believe me, Joanna, it's hard to find one. Were we to dig deep and hope that there is hope, we would say that Donald Trump's numbers are soft, certainly falling. Arguably, the economy is heading into, certainly the skies are dark things. There's, I think, across the board, you can argue that the news for Donald Trump is not getting better. And let's notwe should not forget Jeffrey Epstein, or as Trump says, Epstein, Epstein, Epstein. So we could, I think it is still a very good possibility, even a likelihood that the Democrats will take the House of Representatives back during, in the midterm election. And if that happens, it's a significantly different ball game.
Podcast Host (Joanna or Co-host)
All right, we've got lots of questions and lots of comments from people that have come in. One of the observations people have is that J.D. vance and the crew around Donald Trump seem almost giddy with power. Certainly J.D. vance stood in for Charlie Kirk, hosting his podcast earlier this week, and he's been out there. I think people want to know, where is MAGA on the free speech issue? Because there's been a lot of pushback against Pam Bondi, who came out against hate speech. The First Amendment is very much a core of maga, and there's been a lot of pushback against Pam Bondi. So where is MAGA actually on this issue?
Michael Wolff
I think probably MAGA is somewhat divided on this issue. Theoretically. Charlie Kirk was a great free speech advocate. Now, in his name, the Trump administration is attacking free speech. So it would be curious to see where they come out on that. But there are otheralso other issues that are kind of roiling MAGA at this point. Obviously, Jeffrey Epstein, and that's almost binary. The MAGA position is release all the information about Jeffrey Epstein. The Trump position is do not talk of Jeffrey Epstein. See? And put his fingers in his ears. Cover his eyes. No Jeffrey Epstein. So that's a, that's going to be a difficult, a difficult issue to navigate going forward. It has been difficult. It will get more and more difficult. And then, but then there's other. The vax issue is also, is also difficult because there are many Trump supporters but traditional Republicans that are going, hey, wait a minute, we want. Vaccinations are a seminal accomplishment of the modern world. What are you doing here? Can you really subscribe to RFK Jr and a lot of traditional Republicans but Trump supporters also saying, come on, this RFK Jr. This is serious, seriously nutty stuff to let this guy run the the health establishment in the United States of America. So this is the MAGA fissures I think are likely to get bigger and bigger.
Podcast Host (Joanna or Co-host)
We're just going to take a quick break for some ads.
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Michael Wolff
So if you want to grow your.
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Podcast Host (Joanna or Co-host)
And we are back inside Trump's head with Michael Wolff. Okay, so we have a question from someone whose name rather splendidly is Toblerone ksx. I actually happen to love Toblerones. They're a little bit like eating a Rubik's cube because they've got that strange triangular shape. When you put them in your mouth, you have to sort of maneuver your tongue around it anyway, especially if you.
Michael Wolff
Have one of the giant ones.
Podcast Host (Joanna or Co-host)
Oh, those giant ones are incredible. You have to eat them in several bites. But the even the normal size is a sort of puzzle to eat it. Very Swiss, if I may say. Anyway, Toblerone KSX is saying, please address the Epstein emails that Bloomberg uncovered. Thank you.
Michael Wolff
You know, I don't know where they are from. I don't know how they got them. I would like to know if anyone has ideas, please.
Podcast Host (Joanna or Co-host)
Yeah, please let us know. And these are the Epstein emails with Epstein and Peter Mandelson. Here's his former best pal who lost his job last week as the Ambassador, British ambassador to the US over his friendship with Jeffrey Epstein.
Michael Wolff
Right. While his other former best pal is being wined and dined by King Charles.
Podcast Host (Joanna or Co-host)
Someone else asking, Daphne, Daphne Mason. Daphne Mason 7423 is asking, why hasn't the Stephen Miller been replaced like so many others? And what is the significance of Stephen Miller's wife? Is she still working for Elon Musk or has she left Elon Musk?
Michael Wolff
I think she's a podcaster now, isn't she?
Podcast Host (Joanna or Co-host)
She has a podcast and she's been going through the royal family, as it were, of the Republicans. So she did J.D. vance. She's just done Pam Bondi. I'm sure she'll do the president at some point.
Michael Wolff
But Stephen Miller is, has been and remains and continues to be ascendant in the White House. He may be the most significant policy person in the White House, which is curious because Trump has always regarded him as peculiar.
Podcast Host (Joanna or Co-host)
Peculiar?
Michael Wolff
Yeah. You know, openly referring to him as strange. Do you think he's strange? I think he's a little strange. Do you think he's strange? That would be a verbatim Trump conversation. But he has persevered. I mean, and I think his charm, so to speak, is that he is. He' syou know, he channels maga. He's a MAGA guy. And I think Trump understands that that is a weakness of his, that Trump's own inclinations probably don't align all that well with the MAGA inclinations.
Podcast Host (Joanna or Co-host)
Well, we know that he doesn't want to release the Epstein files, and we know that he does want vaccinations. We should come back and do a proper episode just on Stephen Miller. He's such an interesting character.
Michael Wolff
Also, just let me add another. The immigration issues, you know, because the immigration issues are starting to show up in the economy and the bad numbers. He's reversing himself there, which is another one of those MAGA links. Mispositions, third rail. Don't go there.
Podcast Host (Joanna or Co-host)
Well, we should come back and do a full episode on Stephen Miller. And then final question from Pheasant Films. What happens when Trump defies the two court orders that tariffs are illegal and that troops in the cities are illegal? Does it go up to the Supreme Court? Can you guys please pursue this?
Michael Wolff
Well, I think it's a question. What if he defies the Supreme Court order? And, you know, the thing with tariffs is that there are probably workarounds there. You know, the Congress will authorize the tariffs. I think that they can probably achieve that. And that's probably what they would do in terms of, of troops in the streets. Again, the problem with these, with both of these issues is that there are workarounds here and there are within the law itself. There is this idea of an emergency exception, which Trump has audaciously, notoriously taken advantage of and then sort of declared him himself the final arbiter of what's an emergency. Now, what happens if the Supreme Court says that's ridiculous, as they should say? And I don't know, but I think the greater fear is that they won't, that the Supreme Court is in their. They know what their job is, and their job is to back the president, apparently.
Podcast Host (Joanna or Co-host)
Michael, four people were arrested yesterday for the remarkable projection of the Jeffrey Epstein film, which we've already mentioned. You're in projection of you, but you and Prince Andrew and Jeffrey Epstein and Donald Trump.
Michael Wolff
Projection of me. LinkedIn forever.
Podcast Host (Joanna or Co-host)
Well, you happily not in the middle of that triumvirate, but you very much on the outside trying to analyze it for us. But the four people were arrested and charged with something called malicious communications, which our news editor pointed out sounded positively Orwellian. What are your thoughts on this?
Michael Wolff
Well, it sounds British, too.
Podcast Host (Joanna or Co-host)
It does sound British.
Michael Wolff
I mean, I've always had the Brits in. Free speech has always seemed to me a kind of squeamish relationship. And if you've ever had been involved in a libel reading in the uk, I've published many books in the UK and that means they always have to be separately vetted by a U.K. lawyer. It's.
Podcast Host (Joanna or Co-host)
Well, there's no First Amendment.
Michael Wolff
No First Amendment in the U.K. you say, @ least in the past, you have said, you said to. I have certainly said to myself, thank God for the United States of America.
Podcast Host (Joanna or Co-host)
Well, thank God for the First Amendment, which is rapidly being nibbled at the edges.
Michael Wolff
Yes, but so anyway, I always think that there's this weird, weird kind of thing in the UK that they don't really want there to be free speech.
Podcast Host (Joanna or Co-host)
But if you're going to be arrested for anything, how wonderful to be arrested for putting up that remarkable video on the wall of Windsor Castle. Not something anybody anticipated. And it's made an incredible impact and as you say, it's followed the President on his trip just as he was hoping to escape the Epstein of it all.
Michael Wolff
Epstein. Epstein. Epstein.
Podcast Host (Joanna or Co-host)
Epstein. Michael, let's get together again next Tuesday when I hope you will be back.
Michael Wolff
In the US Back in the US Back in New York, back in the inside Trump's head studio.
Podcast Host (Joanna or Co-host)
Excellent news. All right, Michael, go. Well, have fun in England. I'm just wondering if there's anything I want you to bring back for me, but I don't think there is. You can get pretty much everything on Amazon now. Jeff Bezos wasn't at the white tie dinner. I bet Lauren Sanchez was sad about that because she would have loved that. And also she would have loved picking out an outfit or having Dolce and Gabbana sew her into an outfit. We've missed something there. I wonder if they were traveling.
Michael Wolff
We missed discussing Melania's royal wardrobe.
Podcast Host (Joanna or Co-host)
Also, we did off the shoulder, a yellow off the shoulder number. I did think Princess Kate looked fantastic and regal and modern all in one. And I'm very curious what it must have been like for them hanging out with Donald Trump. And to be told by Donald Trump, you're beautiful. You're so beautiful.
Michael Wolff
And she was. Melania was wearing a kind of pinkish large belt at one point, causing my wife to jump up and say, my God, her midriff is bare.
Podcast Host (Joanna or Co-host)
I thought that, too. I bet that belt and that dress both sold out, though. I actually always think Melania looks elegant. She doesn't look like she wants to be there, but she does look elegant. All right, Michael Wolff, travel back safely. See you on Tuesday.
Michael Wolff
See you soon.
Podcast Host (Joanna or Co-host)
Well, let's hope Michael gets back safely. Thank you for joining us. If you have been don't forget to join the Daily beast community on YouTube, subscribe to the podcast wherever you get your podcasts and share the podcast with a friend. It's there's goodness knows there's enough in it to sit down and argue with family members or colleagues with whom you don't agree or with whom you do agree. To the Daily Beast community, three new members, Karen White, Heidi Riley and Connie Rutherford. Thank you for your support. We are independent media and with Michael, what we try and do is go inside Donald Trump's head to figure out what on earth he is thinking about at any one time. And who knows? It's a mystery in there, but we're seeking to unravel it and as our first lady would have us do every day, be beast. And thank you to our production team, Devon Rogerino, Anna von Erson and our editor, Jesse Millwood.
Ryan Joe
Did I put the clothes in the dryer?
Podcast Host (Joanna or Co-host)
I hope they don't think I was snack already.
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Episode: Real Reason ABC Bowed to Trump on Kimmel: Wolff
Date: September 19, 2025
Hosts: Michael Wolff (Trump biographer), Joanna Coles (Daily Beast)
This episode delves into the growing tension between Donald Trump, the media, and entertainment giants like Disney/ABC in the wake of Jimmy Kimmel’s indefinite suspension. Michael Wolff and Joanna Coles dissect what this confrontation reveals about Trump’s evolving relationship with power, censorship, and how America’s media and business elite are responding to his second term. The broader context is a media landscape increasingly cowed by political pressure—and what that portends for free speech and democracy.
Kimmel’s Indefinite Suspension
“Everybody running in the opposite direction of controversy, running in the opposite direction of Donald Trump’s wrath and ire.” (Wolff, 04:14)
The Backstory: Trump and Kimmel’s Relationship
“He was delighted with Kimmel. ...We repaired to his house in Beverly Hills and spent hours and hours each eating a tub of Haagen Dazs ice cream.” (Wolff, 05:30-06:10)
Shift in Trump’s Persona
Business vs. Free Speech
“Bob Iger... immediately, with hardly a second thought, cowering before the desires of the Trump administration.” (Wolff, 11:16)
Changing Media Priorities
The Creative Community’s Alienation
Implications for Disney Leadership
“This is probably a deep, deeply, an unforced error that will cost Bob Iger, likely...cost him his job.” (Wolff, 15:05)
A “Putin Puppet Show” Moment
“This could actually be what autocracy looks like, that it’s not people with jackboots marching...it is Jimmy Kimmel being canceled.” (Joanna Coles, 19:34)
Pattern of Media Capitulation
Potential Media Consolidation
“The Ellison family, passionate supporters of Donald Trump, are about to corner the media market.” (Wolff, 23:10)
Corporate America Bowing to Power
“I can only assume that they get together and say, my God, this guy Trump is easy to play...and then we get what we want.” (Wolff, 17:39)
MAGA’s Schisms and Free Speech Paradox
“The MAGA position is, release all the information about Jeffrey Epstein. The Trump position is, do not talk of Jeffrey Epstein. See? And put his fingers in his ears.” (Wolff, 02:03, 26:42)
(From 29:52 onwards)
“He may be the most significant policy person in the White House, which is curious because Trump has always regarded him as peculiar.” (Wolff, 31:43)
“Their job is to back the president, apparently.” (Wolff, 35:03)
“Free speech has always seemed to me a kind of squeamish relationship [in the UK]...Thank God for the United States of America.” (Wolff, 36:04)
This episode paints a sobering picture of Trump’s dominance over media and the increasing accommodation—and sometimes capitulation—of giant corporate and media interests. Wolff’s firsthand anecdotes and candid conjecture, balanced by Coles’ challenging questions, provide a unique, insider’s window into the power dynamics that now define the relationship between Trump, the press, and the business world. The contest between principle and pragmatism, and the slow erosion of free speech (both in the US and UK), echo throughout the discussion—accentuated by stories both astute and absurd, and leavened by the hosts’ dry wit.