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Michael
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Ryan
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Michael
No judgments. But that's weird. Okay, one judgment anyway.
Ryan
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Michael
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Ryan
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Michael
Hey, Meta, tell me what kind of dessert this is. That's a stroopwafel, a Dutch waffle with spiced syrup in the middle. Is it sweet? Yes. Perfect for a snack or dessert. Mmm, delicious.
Ryan
Get answers on the go without interrupting your flow. Ray Ban Meta Iconic style meets Meta AI available at Walmart and other authorized retailers. Fox News is now streaming live on Fox 1. When news breaks, we don't just report it. We go beyond the headlines to get the full story. Get live coverage in depth, analysis and perspectives from the voices you trust all in one place. Whether you're at home or on the go. Stay connected to the stories shaping our world stream. Fox News on Fox 1 download today. This is a difficult and awkward discussion inside the Trump circle. This birthday. I know of one situation in which this was brought up. How to kind of counter program against this. Trump completely cut that off, cut this person dead. No discussion of this, no wanting to go down that that path. He now deflects to the 250th birthday of the United States. That's the birthday that counts. That's the birthday they should be thinking about. Anything not to have people thinking about his 80th birthday.
Michael
Michael Joanna so this is a special birthday issue of Donald Trump.
Ryan
Not our birthday.
Michael
No, not our birthday though it is our 125th episode. We started less than a year ago tracking Donald Trump and his presidency and we thought it would be a good thing to do on the eve of his 80th birthday as the President enters his ninth day decade to reflect on how we got from there to here. And in honor of his birthday, I am wearing a T shirt with gold on it. I just would like to point that out since the Oval Office is now smothered in gold and there are gold statues in D.C. and it's not just
Ryan
how we got from there to here, but More extraordinary how, how he got from there, from an outer borough, Queens real estate developer to here, the President of the United States. Not just the most important person in the world, something that I'm not sure he was ever interested in, but the most famous person in the world, which is what he was interested in. And it may be at this point, the most famous person who ever lived.
Michael
Wow. The most famous person who ever lived, which of course is his dream. And he's recently been reflecting, and we can talk about this as we talk about his legacy. Perhaps towards the end of the podcast, you know, he's been comparing himself with Napoleon and great figures.
Ryan
Reflecting. Reflecting is an odd word to use.
Michael
All right. He hasn't been.
Ryan
Context.
Michael
Okay. Because he. He doesn't reflect.
Ryan
He may be the most famous person in the world, but he also may be the most. The least reflective person in the world.
Michael
Right. Well, he certainly thinks he's more famous than Jesus, more famous than Napoleon.
Ryan
Well, he clearly is more famous than all of those people. I mean, I genuinely believe that if you. That the measure here would be. And obviously with vastly greater communications, vastly, all of that, that does give him an advantage. But even with that advantage, he is more famous than any American president, arguably always the most famous person in the world has ever been. That is his skill, his accomplishment to get inside people's head, to be the only person, anybody, to crowd out everything and everybody else.
Michael
Right. So he's achieved his life dream. Well, where do we begin, Michael? Do we begin with him in Queens as a child? And before we begin, of course, I have to remind everybody, please press the subscription button. We're trying to get to 700,000 subscribers in the next couple of weeks, if we can do it with your help. But we're planning to cover all of it in this episode.
Ryan
I would begin in the 1980s because that is the moment that Trump is made the Trump that. That we know. And it's important to understand that this is a. That the 1980s were actually the break. The world cleaved at that point, especially in New York. The broke and bohemian city became this new city of avarice. I mean, everything was remade in the reflection of money in the 1980s. And I think we think of New York as that now, but it wasn't before of. It was a city of. Of. Of. Of crack. Of intellectuals. Well, the city of crime and crack, but it was also a city of intellectuals, of the theater, of. Of the. One of the largest industries in the. In New York was the book publisher. Most, at least one of the most influential was the book publishing industry, the magazine industry. It was, you know, to be a rich person. There were lots of. Lots of rich people, but they weren't that rich, and their status was equivocal. You had a much, probably higher status if you were a book person or an intellectual or a theater person. In New York City, money was a peripheral attainment. And then the 1980s came, Ronald Reagan, deregulation, new financial instruments, and suddenly it was the city of people making more money than one had ever imagined could be made. It was the city of all kinds of figures in the financial industry, and it became the city of figures like Donald Trump and Jeffrey Epstein. And it was. It was really a moment that recreated the culture as we know it. And Donald Trump became one of the avatars of this.
Michael
Right. And perhaps it was best reflected in popular culture by the movie Wall street, which elevated New York once more to a sort of sexy city where famously, the line greed is good came from.
Ryan
Yeah, well, I think there are a lot of things. Bonfire of the Vanity is obviously a, you know, a terrific account of that period. But again, and it was that period, this new moment, out of which the figure of Donald Trump came and the operation of it, this, that that money was available. Debt was available to anybody who kind of pretended that they were worthy of debt. I don't know how any way to put it. These are people who, in ordinary times, banks would not have supported people would not have lent money to, but they lent money to Donald Trump because he was Donald Trump, because he was this braggart, because he managed to get his picture in the newspaper constantly. He sort of commandeered Page Six, the New York Post gossip columns, where he became a regular feature. And he was able to raise money against this image, the image of Donald Trump. And he came to understand this. The more famous you got, the more money you would have access to. So put his name on buildings in as big letters as possible. So he became this. I, you know, this real estate developer. But not just a real estate developer. You know, he made investments. He became a. The guy in Atlantic City who.
Michael
Who.
Ryan
A casino. A casino magnate in Atlantic City. Just. Just let me point out, the vote that I am most proud of in my life was cast when I was a. I think just. It may have been one of my first votes. When I lived in New Jersey, where I grew up and was still voting. I voted against gambling in Atlantic City. That was a failed vote, but for me, it remains a proud vote.
Michael
You're eating French fries at the beach and you want to take a quick dip in the ocean, so you put a seagull on watch. That's not security. That's catering for the seagull. There's a reason you wouldn't trust a seagull with your fries. Just like there's a reason why Morgan and Morgan is America's largest injury law firm. Morgan and Morgan has a proven track record of fighting for the people for over 35 years with over $30 billion recovered for their clients. Morgan and Morgan knows a thing or two about fighting to get you the compensation you deserve. Hiring Morgan and Morgan is like hiring an army to go into battle. They've got more than a thousand lawyers and 100 offices nationwide. If you're injured by someone else's negligence, you deserve to be paid. Not all law firms are the same. Hire the wrong one and you may be be before you even start. If you're ever injured, you should check out Morgan and Morgan. Morgan and Morgan will fight to get their clients the best results. And their fee is free unless they win. For more information, you can go to forthepeople.com Trump. Can I just point out here that so much of this, especially as regarding Donald Trump, was built on smoke and mirrors. So you refer to the fact that he was constantly in Page Six. Well, one of the reasons he was constantly in Page Six was because he himself was pretending to be his own publicist in the name of John Barron and calling the New York Post with stories about himself, which was one way to get yourself out there. But it wasn't as if other people were calling up with stories and saying, oh, Donald Trump, it's absolutely marvelous. You must write about him. He's an incredible guy. This was all self fueled from his inner engine craving attention. And I would, I would, I would
Ryan
push back on that.
Michael
Of course he would. Of course he would.
Ryan
You know, he became, you know, and I remember, you know, I mean, Rupert Murdoch and I spent, spent an amount of time talking about this, this because, because he hated Trump. I mean, he thought Trump, Trump stood for nothing. But more importantly, he thought he was a great tabloid figure, which Trump turned himself into. So Page Six became, there was a symbiotic relationship there. Page Six wanted to promote Donald Trump because he was good copy.
Michael
Right? And he was good for business. Good for business, totally.
Ryan
So being good copy was one of the things that Trump understood. But, and it, so it wasn't, you know, so I mean, the, the empire, so the Trump empire, as, as, as we know it sort of came together in the 1960s. And then would progressively come apart. But it was, you know, involved buildings in New York, involved Atlantic City. In 1985, he bought Mar A Lago, and that was one of those deals. All of this had the vague, you know, corruption was never very far from this. He also bought an airline, the New York, the shuttle between. Between Washington and New York, and Washington and New York in Boston. He bought that, and it almost immediately, by the first debt payment, went into bankruptcy. And then in, and I think this is 1987 or 88, he publishes this book, the Art of the Deal, which is the thing that really makes him suddenly a national figure, because the book goes gangbusters. And again, this is related to the 1980s. You know, this is a zeitgeist moment. The 1980s suddenly is. Everybody thinks that money is. Is easy. Everybody thinks that all you have to do to get rich is do a deal. Trump was exactly on top of that, of that, of that. That cultural moment. And he became hugely famous through this, Right?
Michael
I remember when I moved here as the bureau chief for the Guardian for the first year, all anyone would do from the news desk is call me and say, can you get an interview with Donald Trump? Can you get an interview with Donald Trump? Because he represented in the UK the epitome of the American businessman who had opinions about everything and, as you said, gave good quotes, understood what you needed to do to be at the center of a story, to be on the front page of a tabloid, to dominate the gossip column, Page Six. And it was the era of junk bonds. And everything seemed, to your point, about deregulation, everything seemed possible. And looking from the uk, where I was observing this as a journalist for the Guardian newspaper then and for the BBC, everything seemed so exciting. It all seemed bigger, the stakes were higher, and you had these flamboyant characters. And of course, no one could be more flamboyant than Donald Trump.
Ryan
And of course, the price of flamboyance was bankruptcy, which then as soon as the 1990s came. I mean, this is actually incredible because obviously the price of flamboyance is bankruptcy.
Michael
And.
Ryan
And yet the price of bankruptcy turned out not to be failure and humiliation. So. But at any rate, the 1990s come everybody. He goes into a debt crisis. His real estate is in debt, Atlantic City is in debt. He can't support Mar A Lago, so he has to turn it into a country club. The airline has to be sold, the Plaza Hotel. It's a catastrophe. But. But the interesting thing is that he recovers from this. And so you have one of those glaring examples, one of those confounding examples of the power of brand.
Michael
Well, the. The power of brand. And also using bankruptcy and the rebouncing from bankruptcy is a sign of resilience. I mean, Rupert Murdoch did it too, right? He was on the cusp of bankruptcy at one point.
Ryan
Well, yes, but Rupert Murd was on the, you know, I mean, actually went hat in hand to the. To the banks, managed to hold his empire together and then rebuild it. Trump never really did that.
Michael
No, he just moved on to next things.
Ryan
He just kind of sort of cast aside the business itself, understood the power of brand, and then from there just exploited that. There was no business after that. There was no. Effectively, there was no Trump business. There was just Trump the brand who became a licensing organization. And that was a part of this incredible denial, which obviously still goes on. Pay no attention to all of these bankrupt businesses that I represent and that I bankrupted. Pay no attention to that. I am Donald Trump. I am the author of the art of the Deal. I am Donald Trump. I am Donald Trump. Repeated and repeated, repeated endlessly. And look at all of these. And this then became part of the brand. Look at all of these models who are on my arms. And then he. And then, you know, there were these beauty pageants and all in. All of this. So somehow the piece of DNA which almost all of us have, which is our. Tells us that we have been shamed and humiliated and we must go hide in a corner and. And the best we might do in life is to do good works and. And hope that someone. Someone forgives us. Doesn't occur in Donald Trump. He just goes on. I am Donald Trump. Just remarkable. Spotify. It's Jay Shetty. Are you one of those media strategy people scrolling through spreadsheets, searching for an audience that pays twice as much attention to your ads than they do on social. Let me introduce you to fans, and they're here with me on Spotify. Trust me, I know fans. They don't skip, they stay for hours, they don't move on, they manifest. They're not a demographic group. They're fans. Spotify advertising. You're among fans.
Michael
I'm going to repeat it too. The idea that bankruptcies somehow demonstrate that he is resilient, that he keeps going. And to your point, he didn't keep going in business. He just kept going on in the business of being Donald Trump.
Ryan
And it didn't bother him that he became, well, not just a character. A character, but a caricature. You know, he was So I first, I mean, I used to see, I used to see Trump in the, in the 80s almost. It seemed like anytime you went out at night, there would be Donald Trump just kind of a shark moving through the, through the crowds, always with a couple of sort of henchmen behind him or wingmen or whatever you want to call, call them. Probably one of them was Jeffrey Epstein at the time. And you would just kind of stand back and look at this guy. And then I had never met him then. You just knew who he was. But when I was at New York magazine In the later 90s, he used to start to call me up because I was the guy writing about media. So he kind of made, made that, made that connection. And he would call me, you know, and he would call me. It was really, a lot of people would call and complain about whatever the magazine had said about them, but he would reliably call to complain when he wasn't mentioned by the magazine.
Michael
Just, just, just as a quick aside, when people call to complain about you writing about them or what you'd said about them, how did you deflect?
Ryan
Yeah, you know, I just, usually just listen and go, huh, huh. You know, thanks, I understand. You know, you just, you, you just, you actually try not to engage because they're just going to yell at you. So, and with Trump, that's the way I would do it too. First thing, you had no, there was no alternative because he didn't give you a moment to speak. It would just be Donald Trump motor mouthing at, at you. And he was never, I mean, he was, there was never, never a hostility. It was always vaguely amusing, digressive. Always. He would try to offer you stories so gossip that, that he knew you ought to be writing about so and so who's, who's, you know, who's a terrible person. And so, and then you, you could kind of dine out on. That was a, was an interesting phone call to get, but always this promotion. I mean, you begin to think of him, doesn't the guy ever sleep? Doesn't the guy ever. How could you be so shameless as to call up magazines and demand promotion, demand publicity? But that was Donald Trump very much Donald Trump. He was, Give me, give. I will do anything to, to become the center of attention, to take the stage. Now as a result of that, he became, of course, ridiculous. And you know, there was a, there was a point in the, late, in the late 90s when, you know, Peter Kaplan, who was running the New York observer at the time, you know, one of the kind of arbiters of who was up and who was down in. In the city power structure. And then Peter declared that nobody could write about Donald Trump anymore. Donald Trump was a cliche. Was a cliche of power. Forget him. And I think that actually kind of became the conventional wisdom about Donald Trump. He was a joke and he was finished. And nobody should take him seriously in any way, shape or form.
Michael
How ironic, given that Jared Kushner, his son in law, ended up buying the New York Observer.
Ryan
Yeah. Nope. Many ironies and many in, you know, the small fishbowl of New York City. This is a cross. There so many axes cross at so many points. And now the axis that crosses is, of course, the Apprentice years, which reinvents Donald Trump.
Michael
Before we get on to the Apprentice years, can we just have one moment on the art of the deal? Because the author who wrote it with him, is it Tony Schwartz?
Ryan
Tony Schwartz, an old friend of mine, we used to work together. Sure.
Michael
Right. Has. Has, you know, said that he regrets writing the book now. But I think what's fascinating about the book in as much as it's sort of America's self help of how to become a millionaire, how to become rich, from a man that's constantly teetering on the edge of bankruptcy at the time that the book is being written, is his cynicism, is Donald Trump's cynicism. What becomes clear in the publication of that book is Donald Trump's cynicism about the gullibility of Americans that they will pay him for advice.
Ryan
Totally. But this is a complicated thing because, remember, Donald Trump didn't write this book and Donald Trump didn't read this book. So.
Michael
But he did promote the book. He did promote the book and he put his name on it.
Ryan
It's a reflection of the reflection of Donald Trump. He had made himself into this character, and then Tony Schwartz could translate this character into a book written by Donald Trump that was not written by Donald Trump. So the levels, the mirrors of irreality in the entire Trump story are kind of constant. And this is. The book is a pretty good reflection of this.
Michael
But at some point, and perhaps Trump doesn't realize the irony of it, but at some point, there is the thread there that continues through his, his presidential campaign and his presidency that Americans are gullible, that they will buy anything, that when he tries to help himself in the way that he has done in this presidency, which so far seems to have netted him around $4 billion, he says, he openly says people don't care. He Said I could stand on Fifth Avenue, shoot someone. People don't care. This sense that he is such an emblem of success to people that they don't care about the chaos around it.
Ryan
Yeah, it's success, too, but it's also in the performance. The people are engaged in this story. They're kind of a lot of people on his side. He's the hero of this story. He's the guy who shouldn't have succeeded, who does succeed, and he's the guy who manages to hold our attention. Everybody else, remember, I mean, this is a kind of main, main cultural fact of our times, that you can't hold people's attention. Everybody falls by the wayside. Everybody becomes yesterday's news except only one person who doesn't.
Michael
I know. It's astonishing how I know. And just at the point where you think, oh, he's going to disappear as a fan. Failed New York businessman who once overreached, he is remade by the British producer Mark Burnett in the Apprentice years.
Ryan
Okay, before then, let's get on to that, because that's pivotal. But as a preface to this. So there's a restaurant in New York where a lot of media people and business people went for lunch for many years. They still go. It's a place called Michael's. It's on West 55th Street. And it's a place where. Where I went often.
Michael
And Michael, you had a regular table. It was table number five. Whenever I met you at Michael's, it was always the same table. It was against the wall where you were able to see the entire room and the entire room could see you and who you were eating lunch with. Cause that's the point of Michael's. There were power tables. It's like a kind of the Kremlinology of understanding Michael's. Especially on a Wednesday when people went there for lunch. It was once a weekly column, I want to say, in the observer, that they would actually track who was going there anyway. You were always there at table number five.
Ryan
So at any rate, at the table. So I was having lunch with somebody, and at the table right next to our table was Donald Trump, who was having lunch with somebody. And, you know, so only a half an arm away and because everybody knows everybody at Michael's, there was a lot of cross table talking. And at any rate, when whoever I. The person I was with and I. And we were sort of talking to Trump and who he was with. But at that point, a successful producer of reality television. Let me not say who this was, but comes up to us in speaking to both tables and says, you know, just a kind of high, you know, back slapping kind of thing. And, you know, and somebody says, you know, I mean, geez, how you doing? You just had a great success. And amazing. Everybody was always complimenting everyone about how amazing they were at Michael's. And then they would leave and say terrible things about them, of course.
Michael
But it was a bit like an office canteen for the media, I think it's fair to say. Everybody knew everybody.
Ryan
And then this producer of reality television says, pauses when somebody says, how is it going? And this isn't great what you've done? He says, this person leans forward and says, you have no idea how much pussy I'm getting. At which point Donald Trump says, how much?
Michael
So that was why you went to Michaels. That was why you went to Michaels.
Ryan
But then within a very short time, of course, Donald Trump would be approached to do this reality television show. And it's important, I think, to acknowledge that a whole list of other more successful and prominent businessmen were approached before Donald Trump, and they turned this down. Donald Trump, however, accepted this, this idea that he would, he would play the consummate businessman on this show, the Apprentice. And I guess, you know, history has changed on that, on that decision.
Michael
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Ryan
It's just important to keep in mind here that he comes to the. This television show when he's finished in New York, right? New York is his stage. New York is his town. New York is where he succeeded. New York is his life. And it rejects him kind of ignominiously. So this is the point in which he uses television to find an altogether new market for himself.
Michael
And we should also point out that at the same time as there's been a financial revolution, there's been a financial. There's been a revolution in telev with the arrival of reality television. And who is the dominant producer here? It's Mark Burnett. He's a British producer who showed up in Hollywood. He's done Survivor. He makes the Apprentice. He goes on to change the landscape of primetime television. And we exit the first episode of the Apprentice. Trump has fired someone. There's no money at stake here. What's at stake. Stake for the winner of the Apprentice is a job in the Donald Trump Organization, which, you know, of course, these people are desperate to get, and it remakes Donald Trump.
Ryan
And just to point out here that there really is no Trump Organization. I mean, the Trump Organization is essentially a little family holding company administering the licenses to. To all of these buildings which have the name Trump on, which they don't own. It's just the Trump name that has been licensed to this. And they do a little hotel management, but they. They really own Very little. And it is just a, you know, they're a small time hospitality organization, basically.
Michael
Well, New York has rejected Trump, but the rest of America falls upon him as if he is the new American Idol.
Ryan
No, and really, I mean, remember, the Apprentice becomes the number one show and for the next 14 years. I mean, it's. From a political standpoint, it's almost incomprehensible that for 14 years he's the star of a top rated reality television show in an American culture that is crazy for reality television and crazy for success.
Michael
Crazy for stories of success. The kind of Willy Loman, you know, the Hustle. The Hustle. And Donald Trump plays this helicopter flying limo passenger with all the status symbols of success.
Ryan
Well, just to point out that Willy Loman was the opposite of that.
Michael
Well, no, no, I know.
Ryan
Willie Loman was the failure.
Michael
I know. But what I'm suggesting is that there was a part of Trump, Trump that was a Willy Loman character that was frantically paddling under the surface to keep the illusion of success. And then along comes a television show which actually makes him into a success. Willy Loman never got that opportunity.
Ryan
I want to refine this of somewhat, because Willy Loman is a person who is suffering all of the time, whose failure is. He has. He has imbibed his own failures.
Michael
Yes, okay, fair enough.
Ryan
Trump is another character. He's Sammy Glick. He has no moral center, no sense of shame, no sense of failure, no even understanding of when he has failed. He just keeps going. And that's the remarkable thing about this guy. Nothing. All of the things that would have felled any other normal human being just roll off of him.
Michael
Well, and certainly would have felled any politician. Right, Any politician would have been felled by what happened to him. But he has a remarkable ability to just keep going. To keep going and to understand the
Ryan
power of attention and then to understand. I mean, actually. So one of the things that happens, and we'll get to this, is that as the show starts to fade and it takes a long time to fade, I mean, this is the Apprentice is extraordinary television.
Michael
And we should just. And again, reminding people of television at the time, it was, you know, this was before YouTube, it was before Netflix. He had 20 million viewers for the first episode. 20 million viewers. And though, as you point out, the show faded, it was over 14 seasons and it dominated the ratings, as he knew because. As he knew because he was obsessed by the ratings.
Ryan
Absolutely obsessed. Always, always knew the ratings. But so he's at this point, it's another inflection point. This is, he's going, he's looking at ignominy. What happens to television stars after their television shows get canceled? Ignominy. Your, your the worst thing.
Michael
Ignominy or ignominy. I've never heard it pronounced as ignominy. Is that the American pronunciation?
Ryan
Well, it's, it's the New Jersey pronunciation.
Michael
I've never heard it said like that, but I like it.
Ryan
And, but at any rate, and it's true for all people who get pushed out, off of television, you know, their lives have been so accustomed to being in the, in the public mind, when they're not in that anymore, they die, actually. I mean, their actual death might be years off, but they have, in their own sense of self, died.
Michael
Can I just remind people as well that Trump, at this point, or at least for most of the Apprentices, was incredibly highly paid, very well fluffed talent. So, you know, when you're that successful in a television show and when the television show revolves around you, which it very much did, because he understood what role he had to play on the show, you get treated incredibly well. You have all your needs met. And then there is the moment, as you say, of ignominy, where it fades and the next day you are nobody. And he must have been very afraid of that.
Ryan
Yeah. No, and also, just, also an important note. When Trump begins the Apprentice, he's pretty much broke. And it's the Apprentice that gives him an amount of financial security which he has not had up until this point. But anyway, during the Apprentice, one of the ways he promotes the Apprentice is by announcing that he's going to run for president. And this begins in, I think, 2008 in a serious fashion. And in 2008, he picks up the Obama birth certificate thing. He becomes the premier birther. But he's using this not so much out of an interest in politics, but in order to promote the Apprentice. So, but then we get to 2014 when the apprentice really starts to look like it's in, you know, that it is within a short period of time going to go the way of all television. And then he starts up again in order to, again to promote the Apprentice, to say he's going to run for president and somehow against the specter of the Apprentice getting canceled, and somehow in his own mind, in understanding that running for president is the great promotional opportunity for anyone. I mean, the ultimate promotional opportunity that becomes a reality. I am going to run for president. And it starts in 2014. And then in 2015, he actually announces
Michael
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Ryan
Wayfair.
Michael
Every style, every home. And he comes down the gold escalator at Trump Tower with Melania in a way that he has done in the show. The gold escalator in the show is very much a visual tool that they use.
Ryan
This is the moment. He is doing this and he's doing this with an understanding that this is all about promoting the Trump brand. He never once thinks he is going to become the president of the United States. This is a, you know, it's just what he has always done. How do you, what is the next step in promoting the name Donald Trump?
Michael
Well, and we should remind people that the Republican Party also thought he was a joke and also thought he was doing this to promote his brand. Didn't take him seriously. This was still the party of Jeff Flake, of Mitt Romney, of, you know,
Ryan
moderate Republicans, of Jeb Bush, who was the leader in the, going into 2016. I mean, the, the 2014, 2015 frontrunner
Michael
was Jeb Bush, low energy Jeb, who was quickly dispatched by Donald Trump. And of course, on the fringes was the Tea Party that had really come up and been, you know, given more oxygen by the choice of Sarah Palin as John McCain's vice president. So you were aware that there was this sort of right wing of the party that was coming from, it was coming from sort of rural areas, but it was still very much on the margins.
Ryan
Yes. And there was still the reasonable assumption that Sarah Palin was a death knell of that. I mean, she was so she basically brought down John McCain or, you know, certainly did nothing to help the campaign. And she stood as that figure. Okay. This is all that. This represents the weakness of the right wing in America.
Michael
Right.
Ryan
So, and in fact, so Trump comes along and there is a moment and it's, you know, I think the most telling, the telling moment and the historical hinge probably is the first, the first Republican debate in 2015, the summer of 2015, in which you have, I can't like 12 Republicans on the stage and these debates, the first debate very early in the season, television debate, you know, usually get an audience of, you know, at best, a couple of million people. Donald Trump's. This debate feature with Donald Trump in it draws an audience of 25 million people. I mean, it's unheard of in politics. I mean, and it should have been. It should have been the moment in which people said, okay, there is something. I mean, something has happened here. Now, of course, this was read as just, donald Trump is an entertaining figure. Donald Trump is just a ridiculous figure. Donald Trump is a novelty. And that's what this is all about. And it may well have been. That's what this is all about. But that turned out also to be a politically. A politically powerful message, a politically powerful Persona.
Michael
Well, and we should remind people that one of the things that people like about Donald Trump is he doesn't behave as a politician. And the moment we understood that was that very first debate when he came up with nicknames for people, when he didn't seem to care. When clearly when you watch it now or you watch clips of it now, and it's interesting to go back and see, he's like, I mean, the attention all goes to him, and everybody else standing around him just shrinks in his presence.
Ryan
No, there's a moment in that debate when there's just the pro forma question that's always asked, blah, blah, blah, you want to shoot yourself. They say, will you support whoever is the nominee of your party? And everybody goes, oh, yeah, down the, down the road.
Michael
Of course they do.
Ryan
Yeah. And then they get to Donald Trump and he pauses and he says, I don't know. No, I mean, and it's suddenly like, yes, my God, here is a person who is somehow distinguished from all of these other clowns.
Michael
Right, right. Okay.
Ryan
So moving on, there's another. I mean, to me, this is another point, another tell everything point. In the spring of 2016, I do my first interview with Donald Trump in his political career phase.
Michael
And I remember you calling me and saying, you're never gonna guess what I'm about to do. You were in Hollywood, you were off to see him in his house, and you were just, you were also laughing about it, but also understanding that this was a moment and that, you know, this could be pretty interesting.
Ryan
You know, I thought he was a great character. And also, you know, I have always. I always, you know, certain was liked him, was amused by him. I had certainly no animosity toward, toward, Toward Donald Trump. And you could sit around with him and he would say these things that nobody else would say and what's not to like? And you know, a ridiculous figure, but not a hostile figure. So anyway, we sat around in his house in Beverly Hills, and who even knew he had a house in Beverly Hills filled with all this kind of cast off hotel furniture? And I was there, sitting in his living room with Jared Kushner was there. And we're just talking. Eventually I get to the question, which is again, a pro forma question of all politicians, and I said, okay, tell me, why do you want to be president? And all politicians flub this question or hesitate or go, you know, go. Kind of a cottonmouth.
Michael
Well, Ted Kennedy perhaps being the most famous example.
Ryan
Yeah. And nobody, I mean, you know, the real reason they want to be president is because of their own, you know, to satisfy their own egos, really.
Michael
Anyway, vanity, human risks.
Ryan
Anyway, Trump does, he doesn't falter at all on the answer this. I asked the question, why do you want to be the president? And he says, quote, to be the most famous man in the world. So it is very clear to him, there's no pretense otherwise, this is it.
Michael
And then, and also the irony of you, he's sitting there in his mansion in Beverly Hills, in Hollywood, in the land of the imagineers. And one of the things that he says in the Apprentice, where he's always giving out his sort of lessons, lessons, his homilies to these, you know, kids who are hoping to make it big, is he's. His whole thing is think big. You always have to think bigger. Just keep thinking bigger.
Ryan
And then having said that, having provided that answer, then at that moment he snaps his fingers and says, jared, how famous am I? And Jared says, very famous, sir.
Michael
That is a great scene for the movie. In fact, I think there's only been one, one movie, which was the movie called the Apprentice, which was about Trump's apprenticeship to Roy Cohn, one of his mentors. And that was dogged with legal issues. I mean, incredibly.
Ryan
Yeah, no. And they found it hard to get a distribution distributor. Distribution, yeah. No, so.
Michael
And did Jared say it with a sense of irony at that point? I know he was going to go on and be his campaign manager, but no, zero irony.
Ryan
No. He said it as. He said it as a son. And I have sons in law. And, you know, sons in laws kind of move around in a very tactical way.
Michael
Cannot imagine your son in laws. I mean, poor, poor son in laws.
Ryan
They're very nice. I mean, believe me, I am lucky to have the sons in law I have, but I am a father in law. They are the sons in law. And Jared is in that role very tactically and tactfully moving around his father in law and responding to him in a strategic, always, I think in a highly strategic way. And so this was yes. To say there was only one answer to say yes, you are very, very famous.
Michael
And of course, the beginning of your book Fire and Fury starts with Trump incredulous that he has won. He's taking a call from Rupert Murdoch, Melania is crying because she didn't want him to win. And then the rest is an almost unimaginable history.
Ryan
I mean, it's incredible to realize and I think people find it difficult to realize, if not impossible at this point that there was no, there was no hope, no possibility in the Trump mind that he was going to become the president of the United States. And he would tell people that he won any he was winning, it didn't matter the outcome of this. He was won. He comes out of this having gained an enormous amount. His he is significantly closer to his goal of becoming the most famous man in the world. Actually. He may have reached this goal through the campaign, but within the campaign itself, no sense that this was ever going to work. In fact, frankly, no sense that it should work. And then remember, along the way, there's the grab them by the pussy in which the Republican Party, the Republican National Committee comes and says, we need you, you really have to withdraw here. You know, and this is, this is really just a month before the election itself. So there is no sense, no hope, no possibility that this is going to happen. And then of course, it happens.
Michael
Well, we spend three episodes a week to delving into what's going on and the whole presidency of it all. But given that this is his birthday weekend, he's going into his ninth decade, he will be the oldest president by the end of his presidency. What do you think he what's inside his head at this point as he celebrates America's 250th anniversary? And do you think he thinks about legacy?
Ryan
Well, I think there's a couple of things. I mean, I know that there has been this is a difficult and awkward discussion inside the Trump circle, this birthday. And it has been, I know of one situation in which this was brought up, how to kind of counter program against this and also against the background of Biden and how that affected his age and the perception of his age and the fact that they failed to successfully program against that affected his presidency. So what should they do? And isn't this worthy of a substantial discussion? Well, Trump completely cut that off, cut this person Dead. No discussion of this, no wanting to go down that path. And in fact, he now deflects to the 250th birthday of the United States. That's the birthday that counts. That's the birthday they should be thinking about. Anything not to have people thinking about his 80th birthday.
Michael
Does he know that people worry about his health, that they worry about his cognitive health, that they worry about his physical health, his cankles, the bruising on his hands, the fact he falls asleep in Cabinet meetings and other meetings? He appears to be able to fall.
Ryan
Fake news. Fake news. It's just what they're saying, what the Democrats are saying. Fake news. Look at him. Never been, never been better. Couldn't give, you know what. Then he'll, he'll recount how many speeches he's given and how few speeches Biden gave and how much he does and how often he talks to the press and how, and, and, and whatever his. He, he actually always reverts to his public, to his public life, to how much he is in public, as though that proves that he is an indomitable creature and not a weak guy who has to have a private life.
Michael
And what about the fight, the UFC fight to celebrate America's 250th anniversary? Why did he plump for that?
Ryan
Well, he's a UFC supporter and, and has always been in the ufc. Has been. And, you know, and the guy, what's his name?
Michael
Dana White.
Ryan
Dana White, you know, has been such a major Trump supporter. I mean, Trump's, I mean, part of Trump's career, which, which we, you know, of the, the many aspects that we have glossed over is his as a sportsman, promoter, and, and, you know, in a sense, it's his real life. And if you, you know, and I once had a discussion with, with him about, about what he would have been if he wasn't this, and he reverts to that, I would have been in the sports industry. I, you know, I'm a good sports promoter. I'm the best sports promoter when I do this. There's no, unlike, you know, etc. Etc.
Michael
Right. His usual hyperbole. And what do you think, what do you think the next two and a half years of his presidency will bring in as much as anyone can predict anything about the most unpredictable character on the landscape?
Ryan
Well, I've told you that it would not seem unlikely to me that the next two and a half years will bring death and his, I mean, not necessarily ours, but that could happen also. But who knows? I mean, It's Donald Trump. The next two and a half years will be about Donald Trump. That's, I think, the thing that we can safely predict. Whatever he does will be about him. Whatever he does will be about. About how he wants people to think about him. Whatever he does will be about wanting people to think about him in any way possible, as long as they are thinking about him. But then very likely he might keel over and die.
Michael
Happy birthday, Mr. President. Michael, so much fun talking to you. I love talking about those days in the 80s because when I was in the UK, it was really New York suddenly became this thing that everybody in London became obsessed by. People in finance were obsessed by it. People in book publishing, in media. It just felt like this incredibly exciting, vibrant, big place. And here we are.
Ryan
Yeah, big place. Money. It was just money. Just people were infected by money. Everybody infected by this, by this new disease.
Michael
So we'll be back with a regular episode of Inside Trump's Head, God willing, on Tuesday. Michael, do you want to thank our team?
Ryan
You mean God willing because you think Trump might die or we might die, who knows?
Michael
I'm just. I never want to. I never want to take anything for granted.
Ryan
Well, let me thank our team who really, and I can almost get sentimental about this because they do carry us through this. We have no idea what we're doing.
Michael
125 episodes in, we still don't really know what we're doing except we just are clamoring around Inside Trump's Head.
Ryan
So Ryan, Heather, Rachel, Neil and John, thank you so much.
Michael
So the good news is we have so many bebeast tier members now, there are too many names to read out. And we really appreciate your support. I sold my car in Carvana last night. Well, that's cool. No, you don't understand. It went perfectly. Real offer down to the penny. They're picking it up tomorrow. Nothing went wrong. So what's the problem?
Ryan
That is the problem. Nothing in my life goes to smoothly.
Michael
I'm waiting for the catch. Maybe there's no catch. That's exactly what a catch would want me to think. Wow. You need to relax. I need a knock on wood. Do we have wood? Is this table wood? I think it's laminate. Okay, yeah, that's good.
Ryan
That's close enough.
Michael
Car selling without a catch. Sell your car today on Carvana. Pick up fees may apply.
Ryan
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Michael
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Podcast Summary: Inside Trump’s Head – "I Know Why Trump Is Dreading His 80th Birthday"
Hosts: Michael Wolff & Joanna Coles (The Daily Beast)
Episode Date: June 14, 2026
On the eve of Donald Trump’s 80th birthday—and the podcast’s 125th episode—definitive Trump biographer Michael Wolff and journalist Joanna Coles take a deep dive into the psyche, history, and legacy of the man who has arguably shaped the 21st century more than any other. Framed as a candid reflection on Trump’s journey from brash New York developer to the “most famous man in the world,” the episode illuminates why Trump is so sensitive about turning 80 and how his pursuit of fame has always overshadowed concerns about age, legacy, or even his own health.
“He may be the most famous person in the world, but he also may be the most... the least reflective person in the world.”
— Michael Wolff (00:04:07)
“I am Donald Trump. Repeated and repeated, repeated endlessly.”
— Ryan (00:16:37)
“The more famous you got, the more money you would have access to.”
— Ryan (00:07:55)
“You have no idea how much pussy I’m getting.” / “How much?”
— Unnamed producer & Trump at Michael’s restaurant (00:29:00)
“To be the most famous man in the world.”
— Donald Trump, answering Wolff’s question on why he wants to be president (00:48:34)
“Very famous, sir.”
— Jared Kushner, snapped to by Trump, in response to “Jared, how famous am I?” (00:49:22)
“Whatever he does will be about Donald Trump. That’s, I think, the thing that we can safely predict.”
— Ryan (01:57:09)
“But then very likely he might keel over and die.”
— Ryan (01:57:09)
This episode is a candid, sometimes wryly funny, and sharply observed look at the forces that have shaped Donald Trump—and how, on the cusp of 80, those same forces are shaping his refusal to bow to age or contemplate legacy, his enduring focus remaining firmly on being the center of the world’s attention.