Pivot - On with Kara Swisher: Maggie Haberman Makes Sense of Donald Trump

Episode Date: October 10, 2022

Hey Pivot listeners! The Pivot team is off for the Monday holiday, so instead of your regularly-scheduled episode, you're getting an exciting surprise: an episode of our sister podcast, On with Kara Swisher! You're welcome, and we'll be back on Friday with more Pivot! Donald Trump has said journalist Maggie Haberman is like his “psychiatrist” — a remark she dismisses as a meaningless and failed attempt at flattery. Yet Haberman does have a deep understanding of what makes the former president tick, cultivated through years of covering City Hall in New York City and then Donald J. Trump for The New York Times. Her recent book, “Confidence Man: The Making of Donald Trump and the Breaking of America,” tells Trump’s origin story and chronicles his unexpected takeover of the Republican party and his consolidation of power in Washington. “He’s not a political genius,” Haberman tells Kara, “he is a genius about human emotions and a certain darkness in what animates people.” So will Trump run again in 2024? Haberman says that “he’s backed himself into a corner where he has to,” but she’s not sure whether she'll be covering him. Before the interview, Kara and Nayeema talk about the newsmakers: Elon Musk’s about-face on the Twitter deal and Peter Thiel’s financing foray into key Senate races and ... a conservative dating app. Don't forget to follow and subscribe to On with Kara Swisher here! You can find Kara and Nayeema on Twitter @karaswisher and @nayeema. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Just go to Indeed.com slash podcast right now and say you heard about Indeed on this podcast. Indeed.com slash podcast. Terms and conditions apply. Need to hire? You need Indeed. Hi, everyone. It's Kara Swisher. Pivot is off today for the holiday, but instead you've got an episode of my other podcast on with Kara Swisher.

I have a new podcast. If you haven't subscribed yet, what are you waiting for you? I'm not going to say idiot, but you should be listening to it. Go to a podcast app, which you're presumably on right now. Search for on with Kara Swisher and hit follow. Get on it, people. If you need a taste today, I'm going to play you my interview with Maggie Haberman on her coverage of Donald Trump. Enjoy.

From New York Magazine and the Vox Media Podcast Network, this is the Don Lemon Show with just a little less ranting. Just kidding. This is On with Kara Swisher, and I'm Kara Swisher. And I'm Naima Raza. How are you today, Kara? Good. Really good. Really good. Yeah? How was Raza. How are you today, Kara? Good. Really good. Really good.

Yeah? How was the Golden Child's birthday, by the way? Fantastic. We had a lot of celebrations at an anniversary with my wife and our second wedding anniversary, and then we had the Golden Child party. It goes on and on and on. All you do is celebrate yourself. Yeah, right.

You're offsprung. Now all I do is clean dishes is all I do. It's an excellent use of your time, because that's when you do your best thinking. That's true. So today we have an interview with Maggie Haberman, the New York Times journalist whose coverage of Donald Trump since 2015 has been, I'm going to say, unparalleled, in my opinion.

She's just released a new book called Confidence Man, The Making of Donald Trump and the Breaking of America. And before we get there, let's chat about some other big personalities. Our newsmakers, obviously, this week is Elon Musk. I know Shocker and Peter Thiel as a sidelight, who was also close to Elon. Obviously, he's sucked up all the oxygen in the room

by his recent actions. You've been talking about Elon now nonstop for how long? Oh, forever. Since I met him many, when he was at x.com, when he was a payments company that merged with PayPal. So for the last almost six months since April, we've been captivated by this kind of dizzying will-he-won't-he of Elon wanting to buy Twitter and then wanting to pull out of Twitter. He had agreed to buy the platform for $44 billion back in spring, which was $54.20 a share.

He then tried to pull out of that deal, which would have landed him in Delaware court the week after next. This week, through a regulatory filing that was made public, we learned that Elon is actually good to go for $54.20 a share. So now the deal is back on. It wasn't ever not on. Let's just be clear. He had to buy it. You can't just decide to be in or out of a deal that you signed a legal contract on. But he was trying to wiggle out of it. He was trying to renegotiate. He was trying to, but... So is the deal definitely on? Could it still go wrong? Yeah, sure. I mean, the financing could fall apart.

I think that's probably the most, the thing that could happen. Twitter might not agree. It has said it's going to accept the offer as long as the court, the Delaware court, and so forth, that's a smart move by Twitter because you just, they just don't trust him. They don't trust him.

And so I think he could own this company by the weekend. And I think he just realized he was going to have to pay something for nothing or pay a lot more for owning it. And he decided to own it. And the think he just realized he was going to have to pay something for nothing or pay a lot more for owning it. And he decided to own it. And the thing he had to pay that what he would have had to pay was significant, too. And he would have been sued, the whole thing. And depositions on this tech release of all these texts was mildly embarrassing. I think he was, if he was going to be deposed, it would have been worse. I think there's probably things he doesn't

want to talk about. One of the kind of more smoking guns in the text was on April 9th, so weeks before the merger agreement, Elon had traded with Brett Taylor, a Twitter board member and chair of the board, I believe, saying that purging fake users will make the numbers look terrible. So restructuring should be done as a private company, obviously revealing that he knew about the bots or he knew that at least. That's correct. Of course he did. Yeah. And the Delaware Chancery Court did not seem to like him. She did not seem to have much patience for Elon. She wasn't interested in delaying, et cetera. No. And there's pressure to make the deal work. I mean, he's got $12 billion of leverage, $12.5 billion of leverage. So there's real pressure. And this business has never worked.

Twitter has been fundamentally unable to grow in the way that many platforms have. So he has a vision, it seems. He tweeted that buying Twitter is an accelerant to creating X, the everything app. So talk about X. It's an idea of a super app. It's not a new, fresh idea. It's an idea that China, they have, they're all super apps. You use one app for everything, whether it's communications or payment or commerce or entertainment. You're talking about WeChat. Yeah, there's several there. And so I think that there's never been one in the US. You're talking about WeChat. Yeah, there's several there. And so I think that there's never been one in the US. You go to Snapchat for some things, Twitter for

some things, Facebook for some things, text for some things, Signal if you have another need. And so this is an idea of a super app. Yeah. The model he has for this is WeChat in China, it seems like, 10 cents WeChat. So you can actually use the app to book your cars, to make dinner reservations, to pay people. It's everything. It's real hard. It's not easy. There's a reason why Facebook hasn't done it. There's a reason why it's very hard and very expensive, and he's spending a lot of money here. So I think it's a good idea. But the question is, will people feel this way about Twitter at this point?

Do you think he's going to deliver on this free speech promise that we've seen kind of roving through these texts? Yes, yes. He's going to let Trump back on. That's really pretty much the only part. How quickly? Right away. He's going to do that before or after he lets the current CEO go because Parag Agarwal and him don't seem to go on. He's leaving. It doesn't really matter. He's gone. They don't get along. Yeah. Who do you think he'll put in? No idea, but he's got to get a good one. It's one thing I've been talking to him a little bit. I was like, who's the CEO? It's got to be a good one.

Yeah. It's got to be a good one. It looks like he's looking for an engineer, it seems. Maybe, but you need a creative. You need a creative, too. A visionary. Maybe he should run it himself. No, he's got other things to do, including settling peace in the Ukraine, apparently.

Okay, our second newsmaker this week, speaking of someone with outsized influence, is Peter Thiel, the PayPal billionaire who had been pouring money, or who has been pouring money behind conservative candidates and causes. He backed Ohio Senate candidate J.D. Vance. He's now pushing money into Arizona Senate candidate Blake Bastors. Oh, he has been. He has been, yeah. Blake worked for him. Yeah, and he's known J.D. for a long time, too. There's connections here. So you've known Thiel for a long time too his connections here so you've known teal for a long time you did that kind of camera with him what more than a decade ago more than a decade 15 years ago yeah that's the last time he spent a lot of time with me i mean i've run into him over the years but no i i i know i've been to his house maybe one or two times but uh you know he's avoided me very intelligently He's smart enough to stay away from me, I guess.

Lately, though, he's been in the news for a much smaller investment. He put $1.5 million into a dating app, which is called The Right Stuff. It's being billed as the Peter Thiel app, even though like the brains behind the operation, if I can say brains behind the operation, are people like John McEntee, who's Trump's body man.

So kind of like the Gary to his beep. Oh, yeah, that guy. The HBO reference. Yeah, that guy. But The Right Stuff is, so kind of like the Gary to his beep. Oh, yeah, that guy. The HBO reference. Yeah, that guy. But the right stuff is aimed at conservative singles who are ready to mingle. Oh, dear. And then they can get married, have a whole group of liberal children. That's exactly what's going to happen to them.

Well, the app rolled out this week as a 2.1 rating in the App Store on iPhone. I think it's only available on iPhone right now. But they posted a video on Twitter of conservative women talking about what they were looking for in a relationship. So let's play a clip. Why do you want to date a conservative? For me, at least I know that we're going to start off with some shared values. Well, the conservative men I've dated at least know how to treat me like a woman. In my personal experience, conservative guys have better manners.

I like that they understand their role in the relationship as a man. I just prefer my men to be masculine. For an app that brands itself for not wanting to be woke, they have a black woman, an Asian woman, a white woman. And they have this diversity of races showing up. And it's very funny. It's like they have to build a business. They have to appeal to the masses, you know? Oh, my God.

Like, whatever. You know, look, fine. There's apps, dating apps for Jewish people. There's dating apps for farmers. There's dating apps for older people. I don't care if they all want to meet each other. Like, honestly, like, whatever. It seemed kind of ridiculous.

I like a man who's a man. Like, it's kind of sad tropes about men and women. But if that's the world they want to live in, they can cosplay in that world just fine by me. I lived a lot of my adult life in San Francisco. And if you want to marry a goat, you can marry a goat. I don't really care. Literally a goat, like the greatest of all time or like a baba goat? No, no, like a baba goat. Either one. I don't care. I agree with you, by the way. As someone who has spent time on dating apps in the past, I don't think that this is as much of a mountain as people want to make it out to be. There are apps of every kind.

There's one called Field, which is for polyamorous, extremely liberal. How do you know about all these things? I've never been on a dating app. Kara, I've reported and written about dating at the time. So that's why I know about these things also. Yeah. Do you like them? Do you like, I've never used one. I never had the proclivity. Do I like dating apps? I think so much of life, especially post-pandemic, is virtual, and I'm into real life. And I think live your own life. Everything is a dating app. People can slide into your DMs on Instagram. You don't really need to go to a venue for dating because that's

created a world in which all the other venues aren't kind of dating appropriate anymore. Yeah, I would agree. I have to say when I talk to my son about them, it seems to, he seems to not, make him feel bad, you know what I mean? Or anybody, a lot of times people feel bad on them. And it's weird, sort of sure.

I get that lots of people, I know a lot of people who met on them, but I find real life IRL is probably better and probably more healthy in a lot of ways. But are you going to go on this app, the right stuff? Why don't you do that? I don't think they want me on this app. Why don't they send you in? Let's send you in there and let's see what you get. I have asked to join just to do some research, but no. Oh, you need to. Get in there. It's like getting on Trump social. Oh, and then you're going to fall in love with some like Trumper and then-

Well, here's the thing. I actually think, so everyone should be able to date whoever they want to date, wherever they want to date. And if this is helping people, I think finding love is a hard thing. Yes. But I actually believe in dating people who disagree with you. And I actually don't like that dating apps even let you filter for political. You know, I've got it. I learned so much. I like dating.

I like going on a date. And I like learning someone else's opinion. Good for you. But I, good for you. So that is, I mean, I'm. Sounds like you have the right stuff. Oh, there you go. Okay.

Sounds like you do. I want you to be on this app and I want you to bring home a big old Trumpy man for me to meet. Make sure he's manly. Make sure he's not like femmy. Like I like a man. That's the only part that's offensive, but whatever. Actually, that's not the only part. The one thing, so dating apps have prompts, right? Like,

Hinge, for example, has a prompt like, I know you don't. They're like, a habit I can't break is, and you can like insert, you know, biting my nails or dating multiple people on this app or whatever is your habit. So you fill in the blank. And this one has a prompt saying, January 6th was dot, dot, dot. And that I think, yeah, January 6th was dot, dot, dot. And that, I think, yeah, January 6th was dot, dot, dot. And people can fill in the blank. A tourist visit. I don't know what people will fill into that. I haven't seen it.

But I do think that tells you a little bit about the orientation. I'm going to go on there now. And they're not having the gays on there, right? Well, that is like, Peter Thiel is gay. Are they letting gays on here? Not right now, which doesn't seem like, at least they haven't from the start. So what is that? Does that change your opinion?

I don't care. I don't care. I hope Peter Thiel, I think he's married, gets all the love he needs. And I hope he makes money at this because it's about love. And everybody loves love. That's all I have to say. Okay. When we are back, we're going to be back with Maggie Haberman.

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So Cara, our guest today is Maggie Haberman, the Pulitzer Prize-winning journalist from the New York Times who's been covering Trump. And she was at New York Post, Politico, et cetera, before that. You and Maggie have known each other a long time. A long time. Very, very long. Yeah. We're friends. We're very good friends.

Why are you excited to talk to her about her book? Well, I think everyone's interested in the journalism part of it. How do you do a beat of someone everybody either hates or adores, right? Now, listen, there's a lot of people who hate him and lots and lots and really hate him. And I think the difficulty of covering Trump is that I think even speaking to him is offensive to most people. And in fact, I remember someone was like, how dare you, you know, platform this guy? I'm like, he's the president of the United States. And so how do you deal with that? Yeah, of course.

But there are big questions is how do you cover, how do you cover someone who is this, not just controversial, it's done some really dicey stuff. But I think she's in an almost impossible situation because the right and the left both think she's awful, which means she's probably doing a good job. But there are issues around journalism. What do you let people do?

How do you source these things? When people who have no rules are in charge, how do you deal with that as a journalist? Because you're operating in an old system where there was a lot of sort of wink, wink, nudge, nudging. This group is a very different thing. And so the difficulty of navigating that, I think, is a really interesting question for Maggie. Well, I actually rarely am enthused about book interviews because generally when people do book interviews, it's like a tour and I feel I've heard them everywhere, but I'm still excited about this one

because you and Maggie have such a special relationship that I think you will- I'm still gonna be tough on her. You'll be tough on her. You have to ask her the questions because she's getting a lot of heat on Twitter about what she kept on the book and what she didn't, and generally, but I think it'll be a great conversation. All right, thanks. You have to ask her the questions because she's getting a lot of heat on Twitter about what she kept on the book and what she didn't. And generally.

But I think it'll be a great conversation. All right. Thanks. Welcome, Maggie Haberman. Cara, thanks for having me. So I just want to say, you and I are friends. And we've known each other a long time. And we've also talked about the book quite a bit.

So over the last year, we've talked about the struggle to do the book and also the pressure. Because, one, there's so many other books for one. And that said, in my opinion, yours is the one people have been waiting for, because you have been the best known Trump chronicler over the time. Can you talk about why you timed it this way you waited and walk us through the strategy of doing this if you had a strategy at all? Sure. So first of all, thank you for having me. Yes, we are friends. I appreciate you saying that at the outset. I think as with Donald Trump, people are attributing a strategy to me that wasn't quite there on the book. I think this was just the timeframe that worked out for a variety of reasons. I, you know, had been part of a book project that didn't happen during the presidency, and then decided that I didn't want to do one during the presidency, because it was going to be

too distracting, basically, I wanted to focus on my day job. And then when I did do a book, I wanted to do something different. Because to your point, there are there are a lot of Trump books, I think they have all made a contribution to our understanding of his presidency. But because I come from New York, which is the world he comes from, and because I think that understanding the nature of the world he comes from and how that shaped him and how much of that he exported to Washington is vital, and I think wasn't always clear to people, I decided to make that my focus. One of the things you've worked very closely with him over the years. Has that made you like him more or less? I could apply the same thing to me and Elon Musk, for example.

I haven't worked closely with him. He's a subject who I have covered in the same way that I covered Hillary Clinton or I covered Mike Bloomberg or I covered Rudy Giuliani. I think there is a different level of fascination with Trump, and I think that's different. He has certainly granted me interviews. I have seen the various versions of Donald Trump. And I think that's different. And he has certainly granted me interviews. I have seen the various versions of Donald Trump, I have seen the one who's in salesman mode and being charming, I have seen the one who is trying to be menacing and intimidating presence, I have had the one,

you know, yelling at me about coverage, I have seen all of these versions of him, you know, and I write about this, that, you know, the people who ended up feeling loyal to him over time would often point to being taken in by the more charming version of him. They would, to a person, acknowledge what I describe as the bad Trump showing up every single time. A lot of people do assume you talk to Trump a lot, a lot more than you actually do. That's right. They just assume you have some sort of red phone into him or something like that. That perception has led the left to attack you. Why have you not talked

about that more? Why not correct it? Because two reasons. Number one, you know, there is a certain amount of how stories come together and what we do on process that we don't talk about, you know, the same reason that the journalists don't discuss sourcing, for instance. But number two, what I have discovered, Cara, is that when I say what actually happens, it doesn't actually seem to correct what people have decided is true anyway. So at a certain point, you know, I'm just going to do my job. And I hope people will see the reporting. Are there any benefits from being perceived as close? I mean, I myself, people think I'm very close to the tech people. And in fact, they're not my friends. They're not anything close to it. At the same time, I suspect I've benefited professionally because they think I have some particular closeness to them.

There were times in the White House when people would assume that Trump was a source on something when Trump was not without getting into specifics. And I suspect there was some benefit to that. But in general, no. I mean, I, you know, I think that people, people make assertions. And, you know, at this point, it's cacophonous, but that's all it is. All right, we're gonna get into that a little more later, because I think there's a lot of reasons around that. But you have in this book, I think the main theory of this book, if I'm getting it right, is a theory I have when I'm writing about tech companies, how you can't escape their DNA, their original DNA, and the origin story explains it all. Talk about that, because that's your theory throughout the book.

As you just articulated, you have to know where he came from. Can you talk a little bit in specifics about that? in the 1960s, 70s, 80s, that was, you know, corruption touched on various aspects of life, the construction industry, particularly the concrete industry, which was pretty mobbed up. It touched on aspects of the political system. New York City was a huge machine politics town and boss politics town. And Trump really learned his understanding of what politics is from that. And then it's his own family dynamic. And there was enormous racial strife. As much as New York City is seen as this avatar of progressivism, there are actually pockets of real racism that exists throughout. There's a huge us

versus them mentality that was block by block. And all of that factors into how Trump views the world and processes the world. And his views have, and I've talked about this for years, have been kind of preserved in amber in like 1980s New York. His cultural touchstones are preserved in amber. He's constantly talking about how many times he was on the cover of Time magazine. You know, national news magazines have not had their heyday recently, but that's still what he points to. And he is a man of relatively few moves that he just uses over and over again in different contexts, but he so disorients people that they just assume there is some grand strategy at play. What he is, and I also talked about this too, the flip side is he's not strategic, but he is more calculating than people realize moment to moment. Yes. And so and, and that

I think is important to bear in mind. And so I try to show the through lines and contextualize the world he came from, from when he was younger, through the presidency, and how much it meant the presidency was foretold. One of the things that's important here is the influence of his father had on him versus his mother. That seems clear that he's has was not hugged enough, as I like to always say. Was this Donald Trump baked in from anged enough, as I like to always say. Was this Donald Trump baked in from an early age, do you think? Or was he this way by nature, almost sociopathic personality in a way? I think with every, you know, a leader, when you look back at them biographically, there's always some combination of what they were born with versus what they were made with. And, you know, I certainly think that he has

personal behavioral qualities that he probably entered the world that way. And, you know, I certainly think that he has personal behavioral qualities that he probably entered the world that way. I was asked recently, what was his rosebud moment? And I said, Fred Trump. And that was, it's not one moment. It's a series of moments over time. Fred Trump is somebody who he admired and resented and feared all in one. But Fred Trump was known within the family as a very undermining father.

Ivana Trump, in her biography, described him as a quote, unquote, brutal father. And, you know, I think what that meant looked differently at different times, but he fostered competition among his sons. And that became the way that Donald Trump himself, it isn't just about parenting, it's frankly how Donald Trump ran everything in his life. You know, he fostered competition. So imprinted on his father versus his mother. Well, his mother was less of a less of a presence. You know, he would often say that he picked up a sense of glamour from his mother that, you know, she was infatuated with the royal family. But that household, according to all descriptions, was dominated by Fred Trump. So you also write about Trump, It seemed as though there were both times

a psychological thriller score and a sitcom laugh track playing behind him at the same time. It's really interesting. So was that what allows him to take off? And how do you reconcile the funny and buffoonish aspects of personality? For anyone who's watched his TV shows, you see that.

And the clearly violent authoritarian tendencies. I write about that, that, you know, the crystallizing moment for me was the one, and that what I write about that, that, you know, the crystallizing moment for me was the one, and that what I write that sentence about was when he was reading Lindsey Graham's cell phone number from a piece of paper at a rally in South Carolina in this dominance play. And I felt queasy watching this because it was, it's really invasive and potentially dangerous for Graham. And I talked to somebody else in the news business who I'm close with, and the person said, you know, it was so funny. And that was not how I

experienced it. This was how clearly how other people did experience it. You hit on something that I think is key with Trump, which is how much violence informs his idea of strength. And that idea of strength then informs what he thinks makes a good boss. And I think that that is something that a lot of his supporters admire, and then in turn find funny. So that is how you have that duality. But it's the same behavior, and it's people just choosing to see it through different prisms. Why violence? Where does the violence come from? see it through different prisms. Why violence? Where does the violence come from? I think that for whatever reason, over a very long period of time, the idea of violence has informed Donald Trump's idea of what makes you dominant, you know, whether it comes from military,

the military academy, where he was sent as a young teenager, what was widely seen as some kind of a discipline measure, you know, where his the instructors were known to be very physically aggressive with the students, whether it came specifically from his household. I'm not sure that that answer is ever going to be known at this point. But it has informed what he thinks about strength for a very long time. He speaks very admiringly and glorifyingly of violence and has forever. And one other thing I would say, Kara, too, is Donald Trump is context-free in some weird way. He speaks the same way about, you know, Mides Pesito, the former Brooklyn Democratic Party machine boss who was very corrupt. He said this to me in one of our interviews, ruling his fiefdom with a quote-unquote iron fist. It's the same language that he uses about Xi Jinping, praisingly.

And so, you know, the idea of strength is the same in every setting. So one of the things that's interesting with projecting this image of a straight, tough guy masculinity, the two formative influences of political life are Roy Cohn, who was closeted, and Roger Stone, who has described himself

as a trisexual. Really interesting people to imprint on next after his father. Well, I think that it's in both of those cases, I think these are people who number one, Roy Cohn, he had a Trump had a line about Cohn, where he described him as he brutalized for you. He said this, I believe to Tim O'Brien, who wrote a terrific book about Trump in the aughts. Trump decided very early on that he wanted a protector and defender. And he got that in Cohn. In Stone,

Stone became something of a guide for him in terms of politics. And, you know, Stone tended to the dream of a Donald Trump presidency more than almost anyone and longer than almost anyone. And so these two, what was most important was the strength part, not anything else. Strength and something about intelligence, about politics in Stone's case. I mean, Stone is a deeply controversial figure, widely condemned in our politics. Stone also actually understands politics more than a lot of the people who practice it today, who are engaging in trolling for the sake of trolling. But Stone believes in smoke and mirrors and menacing and intimidation, and that all appeals to Trump too. Speaking of intelligence, you also read about how much the president didn't get it

for a long time. For example, four years into office, he failed to grasp the basics of Senate voting counting. Is he just incapable of focusing enough to learn about topics that don't interest him? Or is he a little dumb or just doesn't care? I would describe him, generally speaking, as proudly and curious, whether there is a deeper reason behind that. You know, I think his teachers could probably speak to, but at the end of the day, he generally gets by by bluffing and cajoling and faking his way through certain situations. And when he became president, he didn't really see a need to change that, you know, and the things he got most interested in, other than sort of his pet issues, were construction projects. It was, you know, the wall, the new Air Force One, the wall, the new FBI headquarters. You know, he doesn't really

like learning what he doesn't know. I mean, the fake it till you make it is a scary way to be president, actually. And yet he took it pretty far. Took it pretty far. Well, all the way, I would say. Trump biographer Michael D'Antonio said Trump has ADD. Do you agree? I mean, I'm not a doctor, so I'm really reluctant to diagnose with actual precision here, but he certainly has attention issues that have been very widely observed. So when you interview him, he looks away? When you interview him, he jumps around topics. He actually is more engaged in interviews than he is in, say, you know, a meeting. I write about the fact that during some of these intelligence briefings, he would be like signing things for people while he was getting briefed. Now, it's possible other presidents have done that too, but it would often mean that he would go off on a tangent and talk about something else,

and the briefers would have to figure out ways to keep him focused. But, you know, the book is an examination of this personality and character traits. You're not a doctor, but what do you think the three most distinctive features are of his personality, the three most salient character traits? Well, look, we addressed one of them, which is the admiration for violence as strength and admiration of it and refusal to condemn it. There is a tremendous need to be liked. And that obviously butts against the bullying aspects of his personality. But there is a people pleasing side to him. And then the other side, and I talk about this a bit

in the book is there is a, this has been widely observed by people around him, including in the White House, there is a real loneliness to him. And I don't know how much that animates other aspects of neediness or wanting to sell people or wanting to be around people. But that was very clear to a number of his aides, particularly on things like these long flights back from foreign trips where he would call one aide up to the cabin after another just to have someone to talk to. From what you saw and heard, was that sad or depression? Because that's a character trait, depression and sadness. It's hard for me to get that far below the surface on something like that, but certainly it was prevalent and pervasive. Someone said he treated you like his psychiatrist. Did you ever feel like that? No, he said that I'm like his psychiatrist. It's a meaningless line

that was intended to flatter in our last interview. He treats all of us like we're his psychiatrists. He, you know, he would describe interviews with other people or in other settings as, you know, it's like therapy. He treats everyone as if they are there for him to work it out in real time. Also, it's a narcissist interviews a real narcissist stream, right? Because you can talk about them, you're talking about them and asking about them. He has a need for attention that outweighs any political figure I have ever seen. And we've covered some political figures who really liked attention. Bill Clinton really liked detention. Yeah. But it's just nothing like this. So you both, you and as I noted, are both native New Yorkers, and you also followed well-known,

but I would say difficult father figures into their profession. Do you relate to Trump in any way on this or not? No, my father is not Fred Trump. No, I know that. I'm aware. I'm aware. Just making clear for those listening. Clyde is not Fred Trump. No, Clyde is not Fred Trump. No, I know that. I'm aware. I'm aware. Just making clear for those listening. Clyde is not Fred Trump. No, Clyde is not Fred Trump. You've said everyone around him is a character in his movie many times. What character are you? And I'd love to know the toll that it's taken on you professionally and maybe personally. Journalist working for the New York Times is my role. I mean, really, he's fixated on the newspaper. I know that people are very focused on the me piece of it, but it really is about

the newspaper. And I'm just the person who covered him more often. And I'm from New York and I worked at tabloid. So that may be part of it. I mean, look, professionally, I was covering a president like that's actually a very important job that I was very lucky to do. And this was true for all of us in the press corps. It just never stops. It's, you know, there was one colleague who

got an Apple Watch so that he could get Trump's tweets or something all day long. There is no end to the news cycle with Donald Trump. It is one news cycle rolling frictionless into the next. And so there's just a weariness for everybody in the press corps, but that's a different issue. I think part of it is you knew him since 2010. He's comfortable with you when he first started considering the run. You're described as Trump's favorite reporter. I don't know if that's the case. Do you think that's the case? I don't. I think that people say it because they're making assumptions that we discussed earlier in this interview, but I don't think that's true at all. And I think one only needs to look at his truth social feed to know that.

Yes, I'm just going to mention that. He recently called you a liar and a creep. And yet he gave you three interviews for the book. And he's clearly interested in you over the years. There's a clear interest in you in particular. Maybe you don't think that. I don't. I really don't.

I think it's about the Times. Why is that? Because I think it's about the New York Times. I think that the New York Times represents for him the avatar of elites who didn't take him seriously. I think that that is what the Times is. Yeah. And his goal is to try to convince you or what? Yes. It's all about selling. I mean, you know, people used to say to me, and this wasn't about me, this is just about the press in general. He wants to see if he can get a good story, you know, and he really speaks in those terms. I think he once complained to Hannity that I don't write, quote, unquote, good.

He doesn't mean that in terms of the quality of prose. He means that about how he sees himself reflected in coverage. Do you think the name calling then is all part of the game? Or do you think he actually dislikes you? I mean, or is it just? I think it depends on the moment. I think sometimes he's engaging in World Wrestling Federation type attacks. Meaning fake.

Yeah, meaning amped up. And then other times I think he's very angry. And I think it's hard to know sometimes. So you wrote that, quote, Trump drove days of news based solely on his reaction to people reacting to him. And this was a perfect encapsulation of Trump's candidacy. Talk about that cycle and where it is right now because it continues. to see. Talk about that cycle and where it is right now, because it continues. It continues, but I would make the argument, Cara, that it continues right now about, say,

him taking classified documents to Mar-a-Lago, which I think is a really legitimate story. Whereas I think some of what was feeding on itself was, you know, we write a news story, he seizes on a piece of it that he doesn't like, and then he does something new, and then we cover the something new. I think it took us a while to figure out that not every Trump statement or reaction was requiring full attention. So why do you think the media didn't do a better job of resisting that provocation? It's sort of like Lucy and the football. Why was it hard to step back and explain his larger strategy to readers and viewers? I don't know how much of it is a strategy. I think it's just a behavior, number one. But number two, I think that the media sees its job as, you know, when politicians say things that are not true, or when politicians say things that are, you know, condemning of a wide group of people, I think the media sees its job as reporting that. I think that the media had never encountered somebody who used both positive and negative attention, I'm using those words in quotes, to their advantage the way that Trump does. It's just fundamentally different.

The Times recently released some audio from your interviews with Trump. I want to play a clip where you ask him about how January 6th unfolded. But what were you doing when, how did you find out that there were people storming the Capitol? How did you find out that there were people storming the Capitol? I had heard that afterwards. And actually, on the late side, I was having meetings. I was also with Mark Meadows and others. I was not watching television.

I didn't have the television on. I didn't usually have the television on. I'd have it on. It was really interesting, the reaction of people to it, because I understood what you were doing. But when he lied to you about the TV being off on January 6th, and he had no idea it was happening, I want to explain to readers why you did not say something. How did you not scream? I have been in that situation. I let them talk. But talk about that, because a lot of people are like, why didn't she stop him? Why didn't she tell him he was a liar? Because I'm much more interested in hearing what he has to say than hearing my own voice.

And at the end of the day, what Donald Trump has to say about what he was doing that day, knowing that it's probably not true, is still, to my mind, more important to get on tape than hearing myself say, but sir, that's not true. Because what I think people are hoping is going to happen in that moment is that he's going to say, oh, you're right. And that's not what he's going to do. You want to give himself enough rope to hang himself, presumably. I, the idea is, is his words, not mine. So when you're doing that, people do misperceive that, that you're in agreement. People don't understand that this is not a television interview. This is an interview to get his words. And so I think there is, unfortunately, a misunderstanding of how journalists do their job at this point.

and calculating it. This is the first time that I know of that somebody has gotten him talking about what he was doing that day. And what he said was, you know, we know from the House Select Committee has documented not true. You know, I knew from my reporting at the time that I was being told it wasn't true, but the House Select Committee had people under oath. That's a very different scenario. I think there is value in his words, because we know from the House Committee that that's not true. So the public service is getting him on the record, even if he's lying. Correct. The same as him, you know, telling me that he didn't take any documents of great urgency, which we know is we also now know is not true. I agree with you. I often say nothing when I want to say, are you fucking kidding me? Well, we're not the story.

And so I understand that that's very frustrating to people because they're at home and they want to yell. But that's not the rule. I think they want you to take them down in a lot of ways. So when you were on a book leave writing Confidence Man, you would share newsworthy information with your New York Times editors. Some of it would get published. Talk about the principles that guided your editors. And you wrote a lot about it in the beginning of the book and how you decided what to hold

because the New York Times decided which stuff they were going to. There are things that the anecdotes that fit for a book that don't necessarily make a whole news story. And the Times editors make decisions on what they think fits the New York Times report. And I'm not going to talk extensively about that, but I'm not a New York Times editor. But I was in frequent and I would actually say constant, touch with my editors throughout the process of this book. The Times is very supportive of me doing this book. They've been supportive of other people doing these books. Books are part of journalism, and they take time. They're just a different form of journalism.

So, but you're still getting a lot of heat for this. New Yorker writer Adam Davidson, who you quote twice in the book, actually wrote, why is it good for a reporter to write articles they know contain falsehoods or lack of crucial content because they're going to sell a book and want to maintain a source? I'd love your response to this because I think- I'm not going to respond to that. He can say whatever he wants. All right. Can you respond to the idea of people thinking this of reporters, not just you, but John

Bolton and everybody else, that why not do it in critical, crucial real time? Well, number one, John Bolton is a former administration official. I'm not a former administration official. I'm a journalist. So those are two different things. And I think that's important. But that is important, Cara, because people think this is all the same, that everything is all flat and the same.

And it's not, number one. Number two, I don't really understand the statement that we're writing things that we know are false. I don't write things that I know are false in the paper. Our goal is to get the best attainable version of the truth. And we do that at all times. And we're not perfect. We make mistakes. There are some stories I would go back and do again. But sometimes we learn more. And you know, the process of a book is going back and revisiting sources and revisiting anecdotes and talking to people. And we get more information that way. One story I'll tell you, I asked somebody I know had participated with a lot of books throughout the presidency.

And I asked this person, why do people take part in these books? Because I was very frustrated that there was something that I wasn't told for a news report, but I was reading it in a book. And the person said, there's no immediacy to it. They're not coming out tomorrow. So I think that it's important for people to understand what guides those who talk to us and how we get our information from them. What do you think you got wrong? I think I reflect on that a lot when I cover stuff, like what did I get wrong? I even take suggestions from Twitter and feedback. I'm like, oh, you know, you're right about that. What do you think you got wrong? And then the second part of that is, why do you get

most of the heat? I'm always fascinated by that. I mean, I can't answer why that question. That's for other people. In terms of what I got wrong, you know, I think in general, I think my coverage, I think the Times coverage, I think Washington Post coverage, I think our coverage was all really pretty rigorous in 2016. There's one area that I wish we had all spent more time on, which was his business conflicts. And I try talking about his businesses in the book. I also go back, and this isn't really getting it wrong, but it's not understanding how it was being perceived. You know, I talked before about how the media's role, we see our role as fact checking politicians or about, you know, noting when things aren't true. When he was spreading

the birther lie in 2011, I think we all covered what he was saying too much, because even though we were fact checking it, it was just spreading it further. And I think that was problematic. Yeah, I would agree. I think one of his secret weapons is giving people too much content daily that there's not enough. It's one of the, that is a strategy. I mean, that is very intentional on his part. What about the right? They seem to be angry at you also, which is funny.

The left is very angry at you, I know that. I'd love you just to talk about this being a beat. You're balancing access with coverage, covering someone widely hated and widely beloved. Is there any good way to do this? I guess I would just reject a little bit the way you just phrased that, that I'm balancing access with coverage. I call it beat reporting, let me just say.

I think the word access is a bad word. It is a bad word because it doesn't mean what people think it means. It is people assume that there's some kind of a transaction going on and that there's some kind of an agreement not to pursue certain things. In terms of the right look, I think that, you know, one of the qualities that Trump has exported to the rest of the country is fighting with the press as aggressively as he has. And I think that the Republican Party has been heading in that direction before Trump rose on the scene. But I think he has fueled it and

exacerbated it. And I think that there's a whole swath of Republicans who, you know, are very happy to take up his term fake news. I mean, it's interesting, because it might not be access, but sourcing is based on relationships. It is, it is, but it presumes that if you don't have those sources, you're not going to cover something. I'm going to cover this no matter what. And people will either talk to me or they won't talk to me, but he's a public figure, and we're going to cover it. And they certainly make hay out of, I'm not talking to you. He did that. Trump did that a number of times with you.

And one time, he said he wasn't talking to you. And I believe I was with you when he called you right then, saying he wasn't in a restaurant. I think that's true, actually. Yes. Let's get back to the book and Trump. Trump advisors got him out of testifying in the Mueller investigation because they thought he might perjure himself, speaking of someone's not able to tell the truth. And in August, he pleaded the fifth more than 400 times in an investigation by

New York Attorney General Letitia James. Where does this go from here based on the book that you've written? He has been investigated more than almost anyone else who I can think of, frankly. almost anyone else who I can think of, frankly. In some cases, it's because there are overreaches on certain investigations. In some cases, it's because statute of limitations wear out. In some cases, it's because, at least it appears, he has established relationships and he treats everything as if it's a situation to be solved. And I think that that happens over and over and over again with him. In terms of Tish James, I just want to make the point it's a civil suit. And I think the way that he tends to look at problems is, am I having a problem with a criminal investigation? Now, he ended up being fine personally in the investigation by the Manhattan

District Attorney who replaced Bob Morgenthau, whom he considered a friend, I would note. He was fine in that investigation. Tish James found a couple of new pieces of information. But if you look at that civil suit, it's a compilation of a lot of things that have been in the public domain before, and she is putting it together as an incident of fraud. I don't think he wants to deal with this. I think he certainly doesn't like that his children are named in that suit. But I think that people who think this is going to be what takes him out, I think the investigations that he has to worry about are the two DOJ investigations, January 6th related, and

really more importantly, the documents investigation, because that's a very clear story. And part of what will be at issue there is whether he took things that are truly a national security risk. And then the other is the Georgia investigation, which is a state investigation. But those are the ones. The Tish James investigation got a lot of attention. And he certainly, it was a day he had avoided for, tried to avoid for a very long time or dreaded for a very long time. But the one that's more serious is the Mar-a-Lago classified documents. By a wide mile, yeah. Is he afraid? Should he be afraid? I think the proof that he

is anxious, Cara, is that he paid $3 million for an attorney on a retainer. I was told by people who worked for him decades ago, that's the biggest retainer they've ever heard of him paying, agreeing to upfront with a lawyer. So he's certainly concerned. So Trump's lawyer, Alex Cannon, reportedly refused to comply with Trump's request to say that all the documents have been returned in February. Is it common people saying no to him over the history that you've noticed? Who can push back and isn't? It depends. I mean, you know, I write in the book how people came to learn that he always required at least one sycophant, and that he can only be told no in certain doses. But I think, you know, a lot of people put a lot of work into trying to push back on him, both at his company over time, and in the White House, but he just grinds people down,

and he demands such fealty that people move on. He famously said he could shoot someone on Fifth Avenue and get away with it. But according to you, quote, he had a perpetual fear of losing his base. What drives that fear? Wanting to be liked. It's a big group of people who like him and who are buying, quote unquote, Trump. And so I think it's as simple as that. I think he's not a political genius. I mean, what he is, is he is a genius about human emotions and a certain darkness in what animates people. But there's just basics of politics that he doesn't get, such as, you can't say politics is a game of addition and therefore the people I'm going to appeal to are QAnon, which is sort of how he approaches it. You know, he really likes people who like him. Is there anything that you think he could do to get them to leave him? Some of them did.

But I mean, there's a solid 30, 35% of the party. I mean, I'm guessing where the number is right now. But there has been this solid percentage of the Republican Party that will not leave him for anything. What you have seen in the last year and a half is aspects of his base have gotten tired of certain things. So I have some reporting in the book that he has privately said to people that he can't get credit for the vaccines because the

quote unquote radical right objects to it. He's very proud of the vaccine development, even though obviously his government didn't develop it, but they did. They did contribute to the timeline or support it. You know, the debate over vaccines and the split over vaccines has cost him some support, you know, but that said, if he's the nominee, most of these people will be back. Mitch McConnell is kind of weakly foisting himself against Trump. And Trump has responded with pretty violent rhetoric going on true social, saying he quit making a racial remark about his wife, he has a death wish. What is going on there? Trump really hates McConnell. McConnell really does not like

Donald Trump. Yeah, you did depict that. Yeah, I mean, it's really not, it's not complicated. McConnell is aggravated by Trump's presence and also won't engage with him the way Trump prefers, which is, I call you a nasty name and you respond, and then we fight. And McConnell just wants to give him no attention. But Trump is absolutely amping up his rhetoric. You know, wants to give him no attention. But Trump is absolutely amping up his rhetoric. You know, the death wish line was dangerous. And anybody who after January 6th says, oh, this stuff isn't a problem is wrong. Right. When you talk about January 6th, how difficult is he going to be to overcome that in a national election?

I don't know. It's a really good question. I have not had a sense that it's animating a ton of voters, honestly. Kara, I think that voters for the midterms who don't like Trump are much more animated by the Dobbs decision on doing Roe v. Wade. I think that we are very focused on January 6th. I think the House Select Committee is very focused on January 6th. I don't have a sense that the public is captivated the way that elected officials who are engaging in this inquest are hoping. Meaning that he's going to ride over that. Yeah, I think it will be another in a, it will be in the same way that all of our politics have become kind of flattened. It will be yet another thing that he rides past. Rides past.

So will he run in 2024? It doesn't mean a win. It just means that I don't think that will be a deciding factor. So will he run in 2024? It doesn't mean a win. It just means that I don't think that will be a deciding factor. So will he run in 2024? I think he's backed himself into a corner where he has to. I could see a world where he gets in and doesn't stay in. I could see a world where he does stay in. His heart doesn't seem to be in this the way it once did. Why so? A, I think he's older. B, I think that when you have been a president before, I think that, you know, having to go out and sell yourself this way is not necessarily fun the way it once was. I think that he misses the power of the office. He misses the power of the

office, but he likes not being accountable, presumably. Well, he's never wanted to be accountable. I mean, this is one of the issues with him. he doesn't want responsibility, he wants credit. And those are not the same thing. So, you know, his entire life has been about finding ways to avoid blame, but getting credit is very important. Who do you think the figures that will define that campaign will be? Bannon, Stone? I think neither. I think he will talk to Bannon a lot. I mean, at the moment, I think that Susie Wiles, who's a longtime Florida operative, is still essentially his chief strategist. You know, he is being advised by Tony Fabrizio. Chris LaCivita, who's another veteran Republican strategist, is supposed to be working on what I think is a campaign and waiting at the super PAC

that he's forming. But Trump always has some team of Olympic alternates waiting in the wings to work with him. So I don't know what those look like. Olympic alternates. Yeah, it's a very different Olympics, I guess. What about you? Do you want to cover this again if he runs again? Ask me again in a few months. Do you think the book will affect your ability to cover him moving forward? I mean, this is a piece of journalism. And I really tried to, you know, just present the facts. And I think I can still do that going forward. But you won't answer if you're going to keep covering him?

I, that depends on a lot of things. I don't know. All right. So, but anyone who reads this book, I have to say, will come away thinking he's shallow, racist, bullying, narcissist, con man. That's unfit for the presidency and maybe a little dumb. That's what I came away with. I appreciate your reading. What was your take? What did you come away with? This is a book that is not about takes so much as it is about context and about

describing a portrait. Describing a portrait. All right. The very last question, we asked for advice for people. Do you have any advice for Donald Trump? No, I do not. You do not. And you never give him advice. No Sean Hannity, you. No, I have no advice for Donald Trump.

All right. What advice do you have for journalists having to cover the new politics then? That their problems are not your problems and just keep doing your job, whoever they are. Excellent. Nice, Maggie Haberman. Thank you so much. Thanks, Kara. That was a great conversation with Maggie. Yeah, that was really good. It was very substantive. I really liked that she didn't take your bait on Adam Davidson. She's like, I'm not going to respond to that, Kara. He can say whatever he wants. It was interesting when you were relating to her kind of coverage on Trump and how to

navigate that relationship. You use the analogy of yourself and Elon, like Elon being to you as Trump is to Maggie. So talk a little bit about that. Well, Elon or someone like him. There's been a lot of tech figures, you know, that Steve Jobs is another one, Bill Gates during the time. I mean, I've been close to them, but they're not my friend, right? I know them after covering them. And I think the difficulty is being accused of access journal, that you trade something. And I think she's right. I think that's what's misunderstood.

She gets a lot of crap for it, more than anyone I've ever seen. It's really quite astonishing. And there's all, she didn't say it. I think there's sexism involved. I think there's a lot of stuff involved. But I think one of the things that's important to understand is no matter what she writes about him, if she slaps him around, which she does often, you know, when she does very devastating stories. She does. Or she's, or it looks like it's a little bit of like beet sweeteners, they're used to be

called. Because she's speaking to him, people who hate him transfer the hate onto her and people who love him hate her. So she doesn't win no matter what. And that's what's interesting. There is no winning because you're covering the most controversial person in American political history. You certainly are. And for the non-journalists here, access journalism is a real insult. But access is obviously important for doing journalism, but calling someone an access journalist is a real dig. And she's not that. It's a very difficult threat to do because you don't want to become their creature.

And a lot of reporters do. That is 100% true. And so that's a hard part. I thought that conflation of herself in the New York Times was interesting. She sees it as one and the same. I mean, you and I have both been at the Times. It does create, it rises you to another level. I think it doesn't matter all the Times. It does create, it rises you to another level. I think it doesn't matter all the time, but with Trump it does. Trump is obsessed with The New York Times, and so that's why it matters here. You can do a lot of great journalism anywhere, but in this case, Trump is fixated on The New York Times, and Maggie Haberman is The New York Times to him. And she had good advice, not for Donald Trump, but for journalists.

Our last segment today, before we round up this episode, is a little advice segment. Our advice lines have been ringing, the 1-888-KARA-PLZ line. No voicemail from Donald Trump yet. We're waiting for him to ask you for some. What about whatever? Yeah, Steve Bannon used his one phone call for you, Kara, don't worry. But we do have a listener question from Jake. So let's play a clip of that. Hi, Kara. My name is Jake, and I recently turned 40. And I have a gig that I really like and a field that I really enjoy. I went to film school, and for the last decade plus, I've been actually able to use my degree and be a video producer.

However, because I'm 40 and I have a few kids, I am wondering about what the next step is in my career. There's no shortage of work with video. However, I don't know if at some point I should strike out on my own, do a production company and offer my services. I don't know if I should go from company to company. So any advice that you have for somebody trying to figure out the next phase of their career, I would greatly appreciate it. And it might even help me fall asleep better at night. Thank you. Love the show. Appreciate all that you do. Take care. Thank you, Jake. That's a lot of questions for me and a lot of pressure. I think, you know, it depends on your risk, a couple of things, your risk tolerance in terms of, you know, you can always get a job and staying at one place

makes a lot of people comforted. It never has comforted me. I think you're in a profession where there's lots of need for your services. So you could afford to be a little more risky and start your own thing. It just depends if you have something to say. And that's the issue. Don't just do it just to do it. Also, you have to figure out how you like to work. I don't like to work for big companies. And I always end up leaving them no matter what. I always think it's not going to happen, but it does. And so you have to really know yourself a lot better. And then lastly, I always think of something that Steve Jobs talked about when he gave a speech at Stanford. He had just been very sick.

He had sort of two illnesses and the first one he recovered from. And he said, if you spend more than a few days hating what you do every time you wake up, you need to stop doing it. Many, many people across the globe do not have choices. You need to change. You need to change something. And so I always think, why not? You have only one life to live.

And as I always say to my kids when they're figuring out what to do, they're younger and I'm like, in a hundred years, you're gonna be dead. So maybe think about that. And so I always think about whenever I make decisions. All right, listeners, if you are in a pickle or if you want some advice,

if you like Jake or having some trouble sleeping at night and who isn't, then you can call 1-888-KARA-PLZ. Me. I'm not having trouble sleeping at night. Today's show was produced by Naeem Araza, Blakeney Schick, Christian Castro-Rossell, and Raffaella Seward. Rick Kwan engineered this episode. Our theme music is by Trackademics. If you're already following the show, you rock. If not, what are you waiting for? For goodness sake, go wherever you get your podcasts.

Look for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday for more. That was On with Kara Swisher. You can find it wherever fine podcasts are played. Pivot is back on Friday.