The Bulwark Podcast - Maggie Haberman: Trump Is Damaged and He Causes Damage to Others

Episode Date: December 29, 2022

Donald Trump is the product of an exacting and brutal father who undermined him in private, and his damaged childhood has impacted him ever since. In this encore episode from October, Maggie Haberman, author of "Confidence Man," told Charlie Sykes that Trump doesn't really trust anyone — and that the era of distrust we live in now is one of his biggest legacies.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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off your first month. That's betterhelp.com. Landlord telling you to just put on another sweater when your apartment is below 21 degrees? Are they suggesting you can just put a bucket under a leak in your ceiling? That's not good enough. Your Toronto apartment should be safe and well-maintained. If it isn't, and your landlord isn't responding to maintenance requests, RentSafeTO can help. Learn more at toronto.ca slash RentSafeTO. Welcome to the Bulwark Podcast. I'm Charlie Sykes. If you listened to yesterday's episode with Jennifer Senior, you probably already guessed that today's show features Maggie Haberman, who has had a singular education in New York corruption because of her years covering City Hall there.

Her portrait of Trump in her book Confidence Man emphasizes his ascent in the New York City of the 70s and 80s. The dynamics that defined New York City in the 1980s stayed with Trump for decades, Haberman writes. He often seemed frozen in time there. I also asked Maggie about the critics who accuse her of access journalism. Here's my interview with Maggie Haberman. basically lonely man whose own views and attitudes are amorphous and situational rather than strategic. He can be charming and cruel, generous and selfish, tolerant and viciously closed-minded. He has no strategy, no method of leadership. He does what works at any given moment. He has few personal ties outside his family, children he constantly tests and occasionally torments, and few real friends. Chaos and uncertainty dominate. Misery is a common emotion

among those in his orbit. To this day, close associates privately root for his death to free themselves from their bondage to him. Joining me on the podcast is the author of this blockbuster new bestselling book, Maggie Haberman from the New York Times. Good morning, Maggie. Good morning. Thanks for having me. So Axios describes this as the book that Trump fears most. He doesn't read books. Why would he fear a book? Well, you know, I can't speak for why Axios says something, but although I very much appreciated their interest in it, I think that the issue with Trump in terms

of how people portray him over a number of books, and he's one of the most written about people on the planet, is, you know, the portraits tend to exist as either, you know, and these are the ones that he can tolerate, as either slavish devotion from people on the right. You know, there's been a series of books written like that. Or coherent and cohesive authoritarian. And this is neither of those. This focuses on his character, and he doesn't like people talking about his character. Okay, so I want to talk about your place in Donald Trump's head. You've been living there rent-free for years now.

And Trump said that you are like his psychiatrist. Tell me about that, because clearly he has an obsession with Maggie Haberman. There's something about you and your reporting that he fixates on. What is that about? I think that he's fixated on the paper. I think he's fixated on the New York Times and has been for a very, very, very long time. You know, it represented the elites whose approval he felt he should be getting and wasn't getting when he was a young man trying to, you know, make his way out of Queens and become a, frankly, a celebrity as much as anything else in New York. And, you know, his line about, you know, she's like my psychiatrist, he said during our final interview last year. And as I write, it was a meaningless line that was, you know, intended to flatter. And it's the kind of thing that he has said about his Twitter feed or other

interviews that he's given with people. And the reality is he treats everybody like they're his psychiatrist. You know, he's working everything out in front of everyone all the time. I've heard you say this before, but it does seem to me that he thinks of you differently than other reporters, including other reporters at The New York Times, because you are a New York person. You grew up with him. You know where he came from. And it does seem that, yes, he cares about what's in the New York Times, but does he see you as a fellow New Yorker who kind of gets him in a way? I'm not trying to flat out. I'm trying to get to what's going on here, because this book is, I think, different than all the other books, because we're not going to focus on the newsy aspects. This is a character study. And you look at his character and where he came from, what the New York milieu was like, what his childhood was like. He seems like someone who desperately wants the approval of certain people, including you.

I still, Charlie, think it relates to the times. I'm just the person who covers him the most. You know, he's a very provincial person. And does he tend to be partial to people who are from New York? And I, you know, I worked at the New York Post for a long time, which at least used to be his favorite paper. Maybe that's a part of it. You know, I think he tends to gravitate more toward the familiar, but I really do think it's about the New York Times. Okay, so let's talk about this. You make the case to fully reckon with Donald Trump, his presidency, and where we're possibly going. You need to know where he comes from, this New York world, the world of New York real estate

and celebrity. You also need to know where he comes from in terms of what feels like a very damaged childhood. He comes off in your book as somebody who is, yes, arrogant and capricious, but also very, very needy. So is he damaged in some fundamental way? I mean, what is the key that we need to understand about this man's mind and his character? He is damaged, and he causes damage to others and has, you know, I mean, I think that's, it doesn't mean that there aren't people who feel like they benefited from him. And

it doesn't mean there aren't people who don't feel that way about him, but, you know, there's no question that his impact on the political landscape, you know, has in some areas and aspects of American life caused damage, but he is damaged. You know, he is the product of an exacting and, you know, in Ivana Trump's words, brutal father who was, you know, constantly praising him in public, but undermined him in private all the time and fostered a really toxic competition between Trump and his older brother, Freddie. Freddie was an alcoholic who was, you know, not able to navigate the family business the way that Donald Trump wanted him to, was not really interested in it, became an airline pilot, and died young,

you know, from conditions related to alcoholism or believed to be. And Trump in private conversations with people over the years has drawn a direct line between his brother's death and his father's treatment of him. And his mother was sort of a not hugely significant presence in the household. You know, it was really run by his father. And Trump respected and admired and feared and resented his father, not to do too much putting on the couch with him, which I really do try to avoid. But when you grow up that way, you look for someone to defend you. And I think it's not a coincidence that his other big mentor was Roy Cohn, and that he sought that model of being defended basically for the rest of his life. I want to come back to Roy Cohn in a minute. You

know, you describe his New York background. I mean, New York was a place with, you know, tribal racial politics and, you know, the world of a New York background. I mean, New York was a place with, you know, tribal racial politics. And, you know, the world of a New York developer, you know, involved backbiting, financial knife fighting, filled with shady figures, including having to do business with the mob. So before we get to Roy Cohn and other things, what was Donald Trump's relationship with the mob? He seems to have a fascination with a certain kind of, shall we say, swagger. Did he do business with the mob. He seems to have a fascination with a certain kind of, shall we say, swagger. Did he do business with the mob? Well, look, the mob was connected to key aspects of the construction industry, you know, certainly the concrete industry, which is the material that Trump chose to build Trump

Tower with. There were mob-linked figures with whom he did business in New Jersey when he was building casinos, you know, at minimum. And then there was a John Gotti associate who was a high roller at one of his casinos and who traveled with Trump and who Trump, you know, according to a former executive, wanted to give a pretty wide berth to. And then when the man came into troubles of his own, Trump claimed, you know, decades later, hardly know the guy, as we've heard Trump do with almost everyone who became a problem for him. At minimum, Trump, you know, saw the mob as sort of the price of doing business in various quarters where he was engaged. But to your point, there is a sort of a stylistic approach that I would say that he admires. So let's go back to Roy Cohn, because there's an interesting historic through line. Roy Cohn was sort of the darkest Bengali to Joe McCarthy in the early 1950s. And, you know, even after McCarthy's, you know, disgrace and censure in the United States Senate, Roy Cohn went on to a successful career and obviously became one of the mentors,

rocky relationship with Donald Trump. So did Donald Trump learn the sort of knife fighting, never apologize, always stay on the attack mode from Roy Cohn? What was Roy Cohn's influence on Donald Trump before Trump cut him off when he got AIDS? Roy Cohn first defended Trump when Trump and his father and their company were being sued by the Justice Department for racially discriminatory housing practices. And, you know, Trump was enthralled, you know, with this lawyer who, whose attitude was tell them to go to hell, and we're going to fight it in court. And Roy Cohn taught him not just, you know, don't back down, except, of course, you know, when you do, and then when you do, just pretend that you didn't back down. But Roy Cohn also taught him about using

the courts as a PR vehicle, which we've seen Trump do over and over and over again, over the decades. And everything with Roy Cohn was, you know, the government is using Gestapo tactics, and you can hear Roger Stone say similar things to another Raycon acolyte in some of his public pronouncements. So he just learned a certain type of behavior and it stayed with him forever. So you describe in great detail that the signature moves of Donald Trump that we've become somewhat familiar with, but I think probably should be on a laminated card somewhere, you know, the counterattack, the quick lie, the shift of blame, the distraction or misdirection, the outbursts of rage, performative anger,

the design just for headlines, action or claim, all of that. You also describe how this is a guy who spent decades surviving one professional near-death experience after another. So kind of fast-forwarding, how do you think that he's processing, to the extent that we can understand how his mind works at all, this current moment he's in where he's facing all of these multiple investigations, the threats of

indictment? Is there part of him that revels in this? Is he in a defensive crouch? How does Donald Trump, you know, regard the fact that he might be facing a federal grand jury indictment, that he might be facing local state indictments, that he is facing some pretty significant private litigation? For a while, he was telling people, and this is prior to the documents investigation really heating up, that, you know, that he didn't believe the DOJ would ever do anything to him. I think he's over that, after the FBI search of Mar-a-Lago. He is concerned about the Justice Department investigation, and the proof of that is that he spent $3 million on a retainer for an attorney, which is the most money that I've ever heard of him spending up front. He is aware that he is

facing significant legal exposure. I think the degree to which he lets that, you know, into his consciousness depends on the day. So given his history and his background, it was predictable that he would refuse to acknowledge that he had been defeated because Donald Trump can never lose. He can only be betrayed. He can only be cheated, right? But to what extent were you surprised by what he did in the wake of the 2020 election and the persistence of support for his big lie? I'm not surprised by the persistence in people accepting the things he is saying about the 2020 election as true, because it has become clear for a while that he has a unique hold on

his political base and that his political base will never blame him for anything and has adopted his posture that he is being wrong somehow by some hidden hand. So that wasn't a surprise. Some of the actions that he took after the election in 2020 were surprising, except I think that the behaviors around January 6th were something of a failure of imagination by officials. And what I mean by that is official Washington was expecting that he was going to try to use the military in an actual coup, right, to stay in office in a traditional coup. And it was always much likelier that he was going to send a mob up to Capitol Hill. Now, of course, his folks would

argue he didn't do that, I should note, but that, you know, he said peacefully in his speech before they all went up to march on the Capitol during the certification of the recent election. But, you know, it had become clear that, A, you know, he was able to move a fair number of people with his language and B, you know, he doesn't like to have to take direct responsibility for things. And ordering the military would have been just that. So as you describe, he's not a strategic thinker. He's not a deep thinker. There's not the core values, but he does have this certain lizard like instinct, reptilian instinct for what people want, coming up with slogans and brands. And I know you've thought a lot about this, the nature of his appeal. Clearly, he is not one of the great political minds of our time. And yet, he has this ability to know what the base wants and where it's going. And he's able to laser in on that. Give me your sense of that rather effective instinct that he has. I think that he is very,

very shrewd about the darkness of human behavior and human emotions. I think he tends to believe that everything is corrupt and therefore he can predict what people are going to do and not do. You know, I think that he reads the crowd, right? I mean, we've seen him do this with his rally crowds over and over and over again. He tries something out, he tests it to see what'll work. You know, there's been a lot of that. Yeah, like build the wall. Exactly. You described the, you know, the 2016 campaign that Trump had actually planned to drop out in

2016 after his polling numbers dropped, and then he would blame Republicans for their opposition to gay marriage as his rationale, which is bizarre now. Occasionally, there are little flares where Trump seems to admit that even he is somewhat surprised by his success and his support. I mean, the famous overanalyzed comment about that he could shoot somebody in Fifth Avenue and not lose any support. He seemed actually surprised by that. Do you think that part of him is surprised that he gets away with all this shit? I don't know about surprised or delighted or, you know, gleeful. Wayne Barrett, who was Trump's first chronicler, quoted on background in his book, which really was the progenitor for us all. A Trump friend saying that Trump doesn't

really like doing anything unless there's a little quote unquote moral larceny. And I think that I thought that was a pretty adept and astute description. I mean, you know, I think that he likes seeing what he can get away with. Now, I think that there are times where he wished he wasn't doing very well in 2016, because it's not clear to me that he actually wanted to be president, you know, as opposed to just winning. But, yeah, it's just seeing how far he can take something always. So does he want to be president again or does he just want vindication and revenge? I think that he wants both. I think he wants the power.

I think he wants the office. I think he wants the title. And I think he wants payback. So you describe him as being extremely suggestible, you know, that somebody, you know, whispers in his ear, tells him something, hands him something, and he will run with it, which of course, comes back to the key question then, well, who is he listening to? Who is he close to? And you point out that outside of his family, he's not close to anyone. So who does he listen to other than the voices in his own head? What he does is he solicits inputs from almost everyone. And I try to show that in the book. So,

you know, he doesn't have to be close to somebody to listen to somebody. In fact, he tends to listen to the people he's not close to. He doesn't really trust anybody. You know, I would argue that one of his biggest legacies is this era of mistrust that we live in now. But he looks around to see, again, it's part of his constant poll testing. And sometimes he's just soliciting opinions to find the person who agrees with his pre-existing view. So that's how you get Sidney Powell and Rudy Giuliani

sitting in the Oval Office after the election. Correct, correct. You describe a rather fraught relationship with Jared and Ivanka. A lot of back and forth about all of that. And obviously there are various camps and there's been lots of leaking back and forth. So what is the story with Trump and Jared Ivanka? I mean, obviously it's in their interest to say, you know, we were really not part of that.

We were distanced from all of this. So what's the truth here? Well, that isn't true. It is true that Jared Kushner was not around in the final few weeks in any meaningful way. He was tending to his own interests, policy and otherwise in the Mideast. And that was his big thing. But Jared was in these meetings for the first two weeks, including with Rudy Giuliani, you know, who he didn't like, but it wasn't keeping him from, you know, attending these things. Jared Kushner and Ivanka Trump were often criticized

for trying to have it always. And not unlike Trump himself, they wanted to be seen as protesting something that might play poorly. But if it started to go well, you know, they would stick around. And you know, I think do I think Ivanka Trump was really troubled by her father's behavior on January 6? Yes, I do. But do I think that she did a ton to try to influence that in the lead up to that? No, I have no reason to believe that based on any of my reporting. So based on your reporting, though, there are all these contradictions in Trump's character that are sometimes hard to follow. I mean, obviously, he's an expert at finding people's weaknesses and exerting pressure on those weak points. I think we've seen that over and over again. But he's also kind of a lonely guy who is a people pleaser. And then you also describe him

as somebody who has both the thickest skin and the thinnest skin of any public figure you've ever covered. Talk to me about that, that he's got a thick skin, but he's deeply sensitive. And I guess this comes back to why you are living rent-free in his head. Look, he is able to slough off news coverage that would flatten almost anyone else. And frankly, sometimes he rebels in it. You know, the prurient really appeals to him. He loves other people's secrets. He loves, you know, guarding his own secrets. But he tends to zero in on coverage that he thinks is insulting his intelligence or his virility or his appearance of strength or his wealth. That tends to be a huge focus of his. And also then just generally,

I've noticed over time that he tends to zero in and obsess on some tiny thing during times of great anxiety. So I would give you as an example, one of the big questions of his first day in office, which is why is he picking this fight over his crowd size? And I don't think that it was, you know, so that he could set the terms of engagement, although I think that was probably a byproduct. I think it was just that, you know, the enormity of the job was making him anxious. And that was how he dealt with it. During COVID, you described that he was much closer to death from COVID than was publicly known. Yes. And yet that didn't seem to have any effect on his approach to dealing with the pandemic. No, in fact, I write that,

you know, there was some discussion about having him do an ad related to COVID, his own experience, and he just wouldn't do it. He wouldn't hear about it. Because that would portray him as being weak or vulnerable? Correct, and relate to sickness, and he just doesn't do it. He wouldn't hear about it. Because that would portray him as being weak or vulnerable? Correct, and relate to sickness, and he just doesn't want to deal with it. And also for people who think of him as being this top-down leader, you also write that he was afraid of his own supporters, who he actually blamed his base for keeping him from getting credit for the vaccines, and he called them fucking crazy. Well, he didn't call them that over the vaccines. He's just called them that over his fervor in general. He has complained

to people that he can't get credit for the vaccines because of the quote-unquote radical right. Those are his words. He has a strange relationship with his base of supporters. There's no question about it. So look, I can't do justice to the book. I mean, it's almost 600 pages long. I mean, there are so many stories, but I'm really struck by, you know, all of sense now that he has to surround himself with a different group of people than those who were his enablers in the first term. So where would he draw the personnel for a second term, do you think, based on his past practice of running businesses and et cetera? I think it would be some of the people who we saw in the last administration. I think that he would want Rick Grinnell. I think he would want Robert O'Brien. I think that he would want

Kash Patel. I mean, I, you know, I think, I think there are a lot of people who he would like to have back. Now, it's not everybody, but there are people who he believes were with him and would do what he wanted. An old friend of his once said to me that Trump likes lawyers who will do anything. And I think that that's what he is looking for in terms of the personnel piece, which as you observe, is the thing that he really focuses on. He's not focused on, you know, policy or the way certain departments run. That's what he wants. He wants personnel. Now, going back to, and I know this is, you know, grossly simplistic, the various daddy issues and, you know, his admiration for strong manly men. To what do you attribute his fascination with people like Vladimir Putin, his soft spot for autocratic leaders around the world? Because this was also, you know, one of the one of the kinks of of the presidency that he couldn't stand people like Angela Merkel or

Justin Trudeau, but he was writing love letters to Kim in North Korea. What is that in him, that he is fascinated and has this affection for the Viktor Orbans, the Putins, the Zs of the world? Look, I think it's, and I try to describe some of this in the book, he is obsessed with violence as an animating force of strength. And strength in turn forms what he thinks makes a good boss and a strong leader. And so I really do think it is as simple as that. Well, talk to me about that, that fascination with violence. He's fascinated with violence as a sign of strength. And there were a number of times when he sort of flexed in that direction, but didn't really follow through. But what is the fascination with violence?

Well, I don't think it's more complicated than what you see. I think that he thinks that violence is a useful tool. He thinks that violence is a way to quash threats and to quash dissent. Would he have liked to have seen troops shooting protesters in the summer of 2020? Would he have liked to have seen that? I mean, he asked for that. There's a mystery. Mark Esper, in his own book, writes about this, that, you know, Trump talked about, can't you shoot them in the leg, about the protesters. You know, he would talk about, you know, shooting migrants. He would talk about wanting to create some kind of a moat around the border wall, you know, with, with crocodiles or whatever it was. I'm getting some of the details wrong, but he wanted the border wall painted black so it would burn people's hands. I mean, there is a constant

animating theme of him wanting to use violence as a tool and liking violence and admiring violence and being thrilled by violence. And cruelty. Well, so I have a slightly different view of that. You know, there's no question that, you know, I think that the Adam Serwer phrase is that the cruelty is the point. And it's a brilliant construction. And sometimes it is. Sometimes the cruelty is the point when he's trying to appeal to a certain group of people by being cruel to a different group.

But sometimes the nihilism is the point. And the cruelty is then the byproduct of that. I mean, the one word that people who work with him used over and over to describe him to me is nihilist. And that was at all stages of his life, where really just nothing means anything. And I think these things go hand in hand. So how much does he reflect the pre-existing political culture, and how much of it has he affected? Because that whole sort of political nihilism seems to be contagious, spreading out into the culture. So chicken and egg, how much of it is just Donald Trump reflecting what he

figured out was still there, shrewdly, instinctively saw. And how much has he actually changed, or in the title of your book, The Making of Donald Trump and the Breaking of America, how much has he actually broken America? So I don't think that he created the partisanship that, you know, cleaved the country. And he clearly didn't. I mean, this goes back decades and intensified in the 1990s with Bill Clinton and Newt Gingrich, got worse over a series of national traumas. You know, by the time we get to the Tea Party, Tea Party is born of a huge distrust of institutions that I remember Ron Fournier, then of the AP, was the first person to really capture what was happening in 2010. And I think that the headline of that story was in nothing we trust. That was the, he was capturing an arc. So I think Trump capitalized on that and seized on it and fueled it and then benefited from that accelerant that he threw on it. And as you say, it has grown exponentially. So the title of your book is Confidence Man. Talk to me about that, because basically you're saying this is a con man.

And again, the through line from Trump University to all of these other scams is, how did you come up with that title? I'm always interested in how writers decide what they're going to call their book. So Confidence Man is pretty edgy. It's funny that you mentioned damage because I had actually been thinking about that as a title at one point for the reasons we discussed. Confidence man can be read two ways, you know, and, and I think, and I think is, and one is that he is indeed somebody who exudes confidence. There's no question about that, you know, and that's what he tries to affix to everything he does. But, you know, the textbook definition of a confidence man, if you, you know, ye olde internet, is somebody who uses their persuasive nature and abilities to take things from other people. And I think Donald Trump has a very long history of doing that.

And yet the Donald Trump that you portray is not necessarily a confident man. Sometimes he is and sometimes he isn't. I think the confidence that he portrays is sometimes real and I think sometimes it is an artifice. So what would the title have been if he'd gone with damaged? It would have been damaged. Just a damaged Donald Trump and how he has damaged America, something like that? I wouldn't have done a subtitle like that. I think you picked up on a through line that I think is real throughout the book, which is that he had a damaging childhood.

I think it has impacted how he's behaved ever since. You know how I feel about this. But I wanted to ask you about Maggie Haberman and her critics. I personally, and I think I've communicated this to you, I think that you were the premier, the best, most professional reporter who covered Donald Trump. And yet there is this weird obsession. I find it to be a weird obsession on social media that somehow you practiced access journalism or you weren't hard on him enough. So, I mean, how do you think about that? I mean, what's your reaction? You're a New Yorker, you have thick skin, but still, what the hell? What do you think? I think people are allowed to engage with my work however they want. And, you know, some things get said that are

probably thoughtful critiques and some less. And I have to just do my job. Okay. You gave me a generic answer. That's the kind of answer that you as a reporter would never let a politician get away with. Well, it's a good thing I'm not a politician, Charlie. Are you frustrated by the fact that many people, I think, just don't understand how journalism works? They just fundamentally don't understand what a reporter does. I think that news literacy is a big problem in the country in general. And I think that one of the problems with Twitter, and I've said this before, is I think I might have said it to you, is that a lot of people are not just getting their news from Twitter,

but they're also getting their information and understanding of how journalism works from Twitter. And there's a lot of things that get said on Twitter about how journalism works that are just wrong, and sometimes said by former journalists, which is surprising. That I do find frustrating, but you know, that's a long, a long tail problem. So you have written the definitive account so far of the character of Donald Trump, but it's also, it feels like an indictment of the character of America that we elected him president and may elect him again president. That here is this man who is not really mysterious. It's not a secret who Donald Trump is. And yet tens of millions of Americans say, yeah, that's our guy. That's what we want. So this is about the

character of Donald Trump, but your book is also fundamentally about the character of us. I did try writing about, and I appreciate that you got that nuance. I did try making clear that sort of the arc of history of how he got here, the arc of what the country was interested, the fact that the country is just celebrity obsessed. And without that, Trump does not rise the way he does. The fact that entertainment and news are often blurred on television, at least in terms of how viewers are appreciating it. You know, I think that there needs to be some realization that what the news media has seen as disqualifying over time isn't always going to be seen that way with voters. That was not, you know, meant to be a condemnation just as an observation, you know, but I do think that part of why Trump was able to build this artifice around himself in the 70s, 80s and 90s, as the myth making as this massive tycoon and titan of industry York City government to try to approve a project that Trump's earliest in Manhattan observes to him, you're a very shallow person. And Trump says something like, that's my strength. I never pretend to be anything else.

And so, here we are. Here we are. And the book is Confidence Man, The Making of Donald Trump and the Breaking of America by Maggie Haberman. Well worth your time. Maggie, thank you so much for your time this morning. Thanks so much, Charlie. Thank you for listening to the Bulwark podcast. Coming up, we'll have another take on Trump and the live action threat he continues to pose. So we'll be back tomorrow and we'll do this all over again.