Susan Glasser is editor of Politico. Michael Kruse is a senior staff writer for Politico.

The personality that looms largest over the 2016 campaign did not emerge on the political scene as an unknown. In fact, Donald Trump might be one of the most deeply studied presidential candidates ever. Beginning in the early 1990s, as the real estate mogul dealt with corporate calamities, and until last year, when he descended the escalator at Trump Tower to announce his candidacy, a half-dozen serious biographies have been written about a man who has imprinted himself on American culture in towering gold letters. But those biographies—which dig into Trump’s family history, his early business successes and later financial disasters, his tabloid sex scandals and the television showmanship that saved him—had largely receded into the depths of Amazon’s bestseller list. Now those books—which have not always been to Trump’s liking; he sued one of the authors unsuccessfully for libel—have become precious source material for those eager to explain Trump’s surge toward the GOP nomination.

Want to know where Trump inherited his entrepreneurial bent? Gwenda Blair traces it to his grandfather, who ran a series of restaurants in the Klondike that featured some of the best food in town, as well as private areas where “sporting ladies” could “entertain” miners. Who was really doing the deals that made Trump famous? Wayne Barrett will tell you the only signature that really mattered on a contract belonged to Trump’s father, Fred. What broke up Trump’s first marriage? Harry Hurt III writes that Ivana “confided to female friends that Donald had difficulty achieving and maintaining an erection.” How did a man who came perilously close to personal financial ruin sell himself as a master dealmaker? By exaggerating everything, including his net worth, which Timothy O’Brien revealed was far less than advertised. And if you wonder what now drives Trump’s pursuit of the White House, Michael D’Antonio has argued it’s the same deep neediness he felt as a child and that has fueled every business deal and attention-chasing stunt since then.


In early March, Politico Magazine convened these five Trumpologists: Barrett, a longtime Village Voice reporter; Blair, a bestselling author; Pulitzer Prize-winning journalist D’Antonio; Hurt, an author and videographer; and O’Brien, a writer and editor at Bloomberg. They gathered, together for the first time, for a discussion at Trump Grill, a restaurant in the atrium of Trump Tower in Midtown Manhattan—where Trump lives and his company is based. Moderated by Politico Editor Susan Glasser and senior writer Michael Kruse and presented in edited form below, the conversation ranged from the emotional wounds that drive Trump to the roots of his demagoguery to his alleged ties to the mob. The rest of the media might still be struggling to explain Trump’s political rise, but these five writers saw his ambition—and ego—from the very early days. Here’s how Trump the candidate came to be.

***

Michael Kruse: I’d like to start talking about Donald by talking about Fred Sr. and going back to the very beginning, to Jamaica Estates [the Queens neighborhood where Donald grew up]. What do people need to know? What should we know about Donald because of his father, because of that relationship?

Harry Hurt III: I ran into Fred at Coney Island, with his secretary-mistress, one day, and he usually went to a place called Gargiulo’s down in that area. But that was closed that day, and so I was with my researcher and we tailed them over to the original Nathan’s hot dog stand. Donald was flying somewhere at the time, and we overheard Fred wipe some mustard off his lip, like this here, and he said, “I hope his plane crashes.” And I looked at my researcher, and I said, “Did you hear what I just heard?” He said, “Yes, I did.” I said, “Well, that’s my man. That’s Fred. The apple don’t fall far from the tree.”

Michael D’Antonio: Gwenda, you met with him?

Gwenda Blair: The first time I met Fred was at FAO Schwarz, when Trump was launching Trump The Game, and Donald was sitting at a table, autographing boxes of the game, which is sort of like Monopoly only with Trump all over it, and there was a line out the door, down the street. There was an elderly gent in a faded raincoat, sitting over on the side, that I knew was Fred Trump, so I went over and talked to him. This was in about the early ’90s, and he was semi-out-of-it at that time.

The other occasion I talked to him was at City Hall, during some of the hearings about what was going to be Trump City [a controversial Trump development on the Upper West Side]. He whipped out a picture of Donald in his wallet, when Donald was very young. I think he was with his dad, and maybe he was in his early 20s. And he showed me that that’s his son, as if I wouldn’t have known who his son was. Was he living in the past? I don’t know, but he was, again, humble, seeming to me that he wanted to be there, didn’t want to get out ahead of his son. And I think this was a very diminished old age, obviously, and there was something very touching about it, actually, when he was sitting there, and very much at odds with everything I had learned over the years about his dad’s MO.

Kruse: Which was what?

Blair: Be a killer.

Timothy L. O’Brien: Hard-driving.

Blair: Hard-driving, never give up, never bog down, double down, all of that stuff.

O’Brien: Fred Jr. [Donald’s brother] was scared of him.

Blair: Fred Jr. was scared to death, and I talked to kids who grew up with them, who went to school with Fred Jr. and Donald. They said the old man was like a terror.

D’Antonio: The one telling story I heard about the father was from Major Dobias at the New York Military Academy [which Donald attended], whose main assessment of Fred was that he was very German, and by that he meant really tough, really demanding and cold.

I think everybody is always wondering about what is the original wound, you know, what caused that hole that Louis C.K. talks about that Donald is trying to fill up, and part of it is shaped like a father figure. I don’t know that he even recognizes it. Does Donald use any word other than “tough” to talk about his dad? I mean, that’s the word he used with me over and over again. He was tough. He was tough. He was tough.



Excerpt:

Trump: The Deals and the Downfall, 1992 “He disliked crowd scenes and was so formal and fastidious that he washed his hands after even boardroom handshakes, drank his diet soda through a straw, wore starch and a suit to tennis matches, demoted casino executives when he found as few as four cigarette butts in an out-of-the-way stairwell, and suggested AIDS tests to applicant bed partners. … More than condos or casinos, he’d spent his life building defenses—walls to fend off the people around him. The tally for his three homes—including mansions in Palm Beach and Greenwich, Connecticut, as well as a double triplex in Trump Tower—was 250 rooms, enough to hide in forever.” Wayne Barrett, a longtime investigative reporter for the Village Voice, is also author of City for Sale: Ed Koch and the Betrayal of New York and Rudy!: An Investigative Biography of Rudolph Giuliani.

Blair: Demanding.

D’Antonio: Demanding, right, or in Harry’s book, where he talks about the father murmuring to these children, “You’re a killer. You’re a king”—you know, this is fatherly love in the Trump universe, and it seems almost disturbed to me.

Wayne Barrett: Fred was the consummate state capitalist, just like his son. Everything he did was subsidized either by the Federal Housing Administration or the state Mitchell-Lama housing program. And so political connections were all that mattered to him. I mean, that was the key to success, and Donald inherited that, and he inherited the connections for himself.

Hurt: They were Democratic, weren’t they, largely?

Barrett: Right. Out of the Madison Club in Brooklyn. I went to see Joe Sharkey, who—

Hurt: That wasn’t his real name, was it?

Barrett: Yeah. Joe Sharkey.

[Laughter.]

Barrett: He was the county leader of Brooklyn in the ’50s, and so I asked him, “When did you first see Fred at the FHA?” And he said, “I went down to Franklin D. Roosevelt’s inaugural, and after the inaugural I went over to the FHA, and Fred was already there.”

D’Antonio: Wow.

Barrett: So Fred was on top of every loose dollar or possible subsidy, and he was devouring it.

But, you know, this debate that Marco Rubio stirred, about whether or not Fred bequeathed $200 million to Donald, I think this is the whole point. I don’t believe it’s true, but I think it misses the point, and I think it’s a point that almost all of our books make, is that all of the original deals—Fred had to come in and sign the bank documents. None of them could have been done without Fred’s signature.

O’Brien: The Grand Hyatt [a New York hotel Donald Trump bought and refurbished in the 1970s] was co-signed.

Barrett: Yeah. I tell the tale about how Fred has to come to the closing in Atlantic City, and he’s against Donald going into Atlantic City. But he goes to the closing, they sit up there and sign all the documents with all the mob guys, you know, to buy all the leaseholds. And Fred and Donald leave and they go down to the limo, and somebody upstairs realizes that Fred missed one document. And they call out the window for Fred to come back, because they’re not going to do a deal with Donald.

I mean, I had his tax returns at that time. We got them—probably Tim got them—from the [New Jersey] Division of Gaming Enforcement, and Donald was worth nothing. He was worth nothing. Even the $35 million credit line that they started with for Trump Tower was signed by Fred.

O’Brien: So this whole notion that he’s said a lot—that, “Oh, I got a million dollars from my father”—that’s just pure hokum. His father’s political connections and his financial connections launched him, kept him supported. His father bought $3.5 million worth of chips at Trump Castle [the Atlantic City hotel and casino] when the bonds were coming due, to keep him afloat so he could make a bond payment. He inherited, probably conservatively, over $150 million from Fred, so that’s more than $1 million, just for the record.

***

Susan Glasser: My question is going back to the family, the narcissism. Is Donald the first and only one we’ve turned up so far?

O’Brien: I mean, they’re very shy, actually. His brother Robert and Maryanne and his other sister Elizabeth are, I think, shy people. I think Fred was troubled.

Blair: Fred was a very shy guy, yeah.

Barrett: And Mary used to collect the dimes or nickels from the washing machines in Trump’s projects. She would go around collecting them.

Barrett: Did you notice that when he won the first primary, in New Hampshire, and he stood up there in his proudest moment, and his first thanks were in this order—Mary and Fred?

O’Brien: And then he thanked his brother, Fred Jr., which, given their history together, was a really—

Barrett: Odd. Very odd.

O’Brien: They didn’t get along. Fred, the father, didn’t like Fred Jr. Fred Jr. was an alcoholic. He was very troubled. He ended up drinking himself to death. And then after Fred died, there was a whole battle in the family over Fred Sr.’s estate, and Donald, as I recall, didn’t want Fred Jr.’s children to get Fred Jr.’s share of the estate. He tried to lock his nieces and nephews out of his share of the estate.

So then at the night of the New Hampshire primary, he’s like, you know, my brother, Fred, my brother, Fred—and he didn’t treat him very well.

Barrett: He said publicly, years ago, that Fred was his example of what not to be, because Fred was too open and generous with people, and that’s how he learned to be very wary.

O’Brien: When you talk about whether he’s narcissistic or not, I remember one thing I took away when I was working on my book about him, is when he was finishing college, he wasn’t sure he wanted to go into his father’s business, and he thought he might go out to Hollywood and become a movie producer.

He loves film, and he has this very cinematic sense of himself, and I think he thinks of himself almost as like a Clint Eastwood figure. Every time, in one of those photos, where he sort of grimaces—and his wife, Melania, does it now with him—into the lens, I think he thinks of himself as an actor in his own drama, in his own western.

D’Antonio: Is that her look?

O’Brien: You know where they both kind of squint their eyes? It’s very sort of like Clint Eastwood in High Plains Drifter.

[Laughter.]

O’Brien: Every time I see that, I think: How many years has Donald been practicing that in front of a mirror?

D’Antonio: I often think of him as a producer of his own life, that he imagined this character, started creating it. So before he was rich, he had the chauffeured car. Before anyone knew who he was, he had to have an armed guard.

O’Brien: And he knew how that would play.

D’Antonio: It’s more security than I’ve seen anywhere. No businessman I’ve ever visited has a security person at the desk, a security guy. Basically those elevator operators are security guys. You go into this locked lobby of his inner office, and there’s a couple of guys who are obviously armed, sitting there reading the newspaper, eyeballing you. What’s the purpose of that, other than to intimidate you?

Hurt: It’s part of the show. I think your point is good about him being the producer of his own life, and you might notice that quite often he refers to himself in the third person.



Excerpt:

Lost Tycoon: The Many Lives of Donald J. Trump, 1993 “Donald is so embarrassed by the sorry state of his physique that he wears undershorts and a T-shirt even when he is in bed. Thanks to a diet of junk foods and an aversion to exercise, his waist, his thighs, and his buttocks have swollen as thick and spongy as giant doughnuts. And most disconcerting of all, as far as he’s concerned, he is losing the hair on the crown of his head. … ‘The worst thing a man can do is go bald,’ he has warned one of his top executives. ‘Never let yourself go bald.’” Harry Hurt III has worked for Newsweek and Texas Monthly and contributed to Sports Illustrated, Esquire and Playboy.

O’Brien: Or uses the royal “we.”

***

Kruse: Wayne, when you encountered Donald Trump way, way back, in the late ’70s—looking at him now, what are the differences and what are the similarities?

Barrett: Well, there are a lot of similarities, in terms of the way he carries himself, you know, this kind of engaging personality. The showman was already there. But he was actually a man of some skill in those days, and I think he had an attention span that he lost in between.

But in my day, I think he had a focus on detail, he was a real builder. He was at the Hyatt site every day, on the site, checking out every detail. He was a manager and a builder, inherited from his father. I mean, look at the projects he built in the early days of his life. But fundamentally, he hasn’t built anything since my book came out. I mean, he’s not really a builder anymore. He sells his name.

O’Brien: Trump Tower was really the apotheosis, or the apex of his career.

Barrett: Yeah. He really stopped being a builder.

Kruse: And Trump Tower went up in 1983.

So some of your books [Barrett’s and Hurt’s] came out in ’92 and ’93, and, to some extent, you were treating him as a man who was dead, at least as a businessman. How was he able to resurrect himself?

Barrett: Well, you know, with all this Tea Party anger that he’s appealing to now, he was the original bailout. I mean, the banks could have put him under any day. They took tremendous losses in those negotiations and deals. So they saved him. He was too big to fail.

Hurt: He was the original “too big to fail.”

Barrett: He’s the consummate example of what his voters rail against.

O’Brien: I remember Trump’s finance chief Steve Bollenbach, who worked through the debt for him, said he had this conversation one day where they were going to take the yacht. And they didn’t want to take the yacht. And the light suddenly went on in their heads: The banks actually don’t want to control all these assets. They want him to operate out of it, and they both thought, “Wow.” That was the moment when they realized they had leverage.

You know, everything he does now, he doesn’t need loans to do any of it. The golf courses are owned by the members. They pay fees that finance it. He gets a salary from NBC from The Apprentice, and he gets licensing fees for everything else. I mean, there’s some projects, like the Chicago hotel—he got bank debt for that. Deutsche Bank loaned into that one.

Barrett: But he’s gone from the 18th floor to the 18th hole.

[Laughter.]

Blair: It was branding. It was the early branding that kicked in for him. He spent the ’80s getting that brand going. So he buys the shuttle, he buys the yacht, he buys the Plaza Hotel, everything—

O’Brien: The Generals.

Blair: The New Jersey Generals, which gets him onto the sports pages, which gets him up to a national level. So the branding he had in place, so by the time the first bankruptcy comes up, the brand is the thing they don’t want to let go of. They don’t want to foreclose and not have the name, which is so counterintuitive that the mind boggles. Like, wait a minute. This guy is in corporate bankruptcy, but his name—but that’s how it was. He could get the over-the-barrel piece for the banks, and he’s been doing it ever since. It’s the over-the-barrel piece which he did with the Republican Party now. How do you get them so they can’t get rid of you, they can’t let you go? And he’s really good at that.

Barrett: Well, the thing was that the banks wouldn’t complain, either. When they cut the deal with him, if they didn’t go on to a prosecutor—I mean, all of the financials that he gave the banks were totally false.

Hurt: And they’re liable for that, for not doing their due diligence.

Barrett: Yes. They were so embarrassed that they never went to a prosecutor. Clearly, there could have been a case made.

D’Antonio: But isn’t this sort of consistent with the way the game of politics was played by his father and the politicians and the clubhouse people? It’s like, if I bring you into my web of deception, now you’re a part of it. Now, where do you go for redress? You have no options. You have to stay with me and see it through to the end, because I’ve got you as a partner. You’re now colluding with me.

***

Glasser: What are the questions that you all still have about how he made that leap from builder to his next act as promoter, marketer, whatever, and about where he’s at now as a businessman?

Hurt: He was always the promoter. The developer was the subset, not the other way around. You’ve got the tail wagging the dog here. The dog is the promoter, the guy who invented his own life, and developing was just a part of that. And all those lies. Remember when Princess Di was going to buy an apartment in the Trump Tower?

Donald gives good quotes. But check some of those quotes. An hour’s worth of quote equals about six or seven hours’ worth of fact-checking. It’s either half-truths, non-truths, lies.

D’Antonio: That’s the big challenge of interviewing Donald Trump. Do you get anything that you can rely on? How much truth is in there and how much is distortion?



Blair: Whenever I went to interview him, I always felt like a failure, because he would never say anything. It would just be blather. He would say how great he was, and then I would then get more blather. And that is how he talks on the campaign trail. People always ask me, “Is that how he really is?”

Hurt: Yeah, that’s how he really is.

O’Brien: When you hold his feet to the fire on a fact pattern, he does not handle it well. You saw this a little bit in one of the debates, when the Fox host started putting slides up on him. He melted. He actually looked like he was melting.

D’Antonio: The one time I had that happen is when I knew his Selective Service record, where he had claimed that he was excluded from Vietnam by his draft number, and it wasn’t true. So I said, “I’m sorry to have to ask you this, but we really need to work through it.” And once we started working through it, and I talked about when the draft lottery was initiated and how there was a gap, he was eligible to be drafted during that gap, he lifts up his shoes and shows me these little bumps on his tendons, and says, “Well, this is why. I have heel spurs. I couldn’t have been in the infantry.” And through all this time he’s walking how many miles of 18 holes of golf?

O’Brien: It never got in the way of his athleticism.

Barrett: He tells us that every day, what a great athlete he was. That’s part of the spiel.

D’Antonio: He says, “I love to fight all kinds of fights,” except when it’s for your country and they might be firing back—and then he can’t fight at all.



Excerpt:

The Trumps: Three Generations That Built an Empire, 2000 “At his own father’s funeral, he did not stop patting himself on the back and promoting himself. … No matter what happened, including the death of the person who meant more to him than anyone else in the world, from whom he had learned everything he needed to know, to whom he had turned when he needed counsel or comfort or bailing out, he would never relinquish being the center of attention. He would never give up, he would never let go. When he lost, he would say he won. When he won, he would say he won more, or bigger, or faster. For him the race would never, ever be over.” Gwenda Blair, author of Almost Golden: Jessica Savitch and the Selling of TV News, has written for Newsweek and Esquire and teaches at the Columbia University Graduate School of Journalism.

Glasser: Was he belligerent back when you first started interviewing him in the 1970s, or was he more willing to engage at that time?

Barrett: I met with him the first time earlier than I should have, and he was quite charming at that first meeting, and went on for several hours. It was in his apartment on Fifth Avenue, long before Trump Tower, and his first wife, Ivana, was roaming around. She took him out to an opera, made him leave and go out to an opera. But he was quite charming, because I had no tough questions yet. I was too early in the process. I wouldn’t say I had none, but as I continued to interview him, as the story got deeper and darker, then he got very belligerent, and certainly he threatened to sue me. Well, he didn’t explicitly say that. He raised some example, I’m sure totally manufactured, of some reporter he had crushed with a lawsuit. It was an object lesson for me. Then he offered me an apartment. So it was the carrot and the stick—I got both.

Hurt: He thinks there’s no cat he can’t charm out of the tree, but then when you back him in, he goes crazy. Prior to the publication of my book, he and his lawyer, Jay Goldberg, came to scream at the folks at Norton, mainly about Ivana’s divorce deposition. And they were pounding their fist. You know, they’re very tall guys. Norton’s lawyer was a 5-foot-tall lady in about her 60s. And finally Donald got so frustrated, he jumped up and he pulls a tape recorder out of his coat pocket. He said, “I’ve been recording all this,” and our little lawyer looked at him, and Goldberg just turned like this napkin, white. “You’ve been recording this and you didn’t tell us? That’s not right.” And I’m going, “Yeah.”

They walked out and I said, “He can’t sue us now. He’s not going to sue us because they just shot themselves in the foot.”

Glasser: Tim, when he actually sued you, did you feel like you knew that was going to happen?

O’Brien: No, I didn’t think it was going to happen and then it did, and, you know, he’s entitled to it. They came after us pretty hard. I had a book publisher who hired a great lawyer, and then we cleaned his clock.

Hurt: Yeah, but at what cost? Didn’t the Times [where O’Brien then worked] have to pay a lot of legal fees?

O’Brien: He sued me and the book publisher. He left the New York Times out of it, because he knew, I think, that I could get free representation with the Times. And I think he didn’t think a book publisher would back me, but they did. They hired Mary Jo White [now chair of the Securities and Exchange Commission] as my attorney. This will sound perverse, but some of it was fun, the litigation.

Barrett: Tim, did you say he had detectives on you?

Remember when Princess Di was going to buy an apartment in the Trump Tower? Donald gives good quotes. But check some of those quotes.”

O’Brien: He claimed that he did. At a book reading, after the book came out, his lawyer approached me after the reading and said, “You’re a fiction writer. You’re going to hear about this.” Marc Kasowitz [another Trump lawyer] came up to me at a book reading. And then he had people standing, like plants in the audience, at the book reading. And they would say, “You really wrote this book because you really don’t like him, right? You really just want to hurt him, right? That’s the reason you wrote the book, right?” So they did that, and they were taping and recording it, across the street, and at that point they were building a case. I didn’t know that. I said, “No, I didn’t write the book to hurt him,” which is true.

Kruse: What was fun about getting sued by Donald Trump?

O’Brien: He sued me around a claim that by offering lower estimates of his net worth I had libeled him, so he opened himself up to discovery on all of his financials. So we got his tax returns, his bank records, everything.

He didn’t want to give over his tax returns, which we’re seeing now in the election. And there’s reasons, I think, he doesn’t want to give up his tax returns. It’s because you see what his income actually is in those returns. Later in the case, he moved to settle, we stayed in there, and then it got tossed out—he lost.

Barrett: What did the tax returns show, Tim, about charitable contributions?

O’Brien: You know, I’m not allowed to speak about what I saw in the tax returns. They were sealed. His deposition was originally sealed as well. And then Mary Jo and my lawyers made the motion to dismiss. I believe what they did is they got the deposition attached as an exhibit in the motion to dismiss the case, and that made the deposition public and that’s how it came into the public record. This is when you thank lawyers and bless them. But otherwise, everything else was sealed.

***

Blair: There are two things that seem extremely pivotal to me in what’s happened. One is the The Apprentice, that 10 years of America looking at him as the boss, that that is so, now, imprinted on people’s ideas—that they can’t get around that notion that he is the boss. If you say the word “boss,” you think Trump.

And the other thing was the birther thing. That was a real pivot, from somebody who was sort of, kind of liberal in his previous toe-in-the-water presidential things. And, because he’s a shrewd guy, really looks at the market, he saw the discontent over having a black president. He could tap that. And I think that was the take-off, the accelerator. The birther thing was a huge moment that I certainly didn’t quite get. It just seemed weird.

D’Antonio: I think his hatred for Obama is sincere and visceral. I met him in 2013 for the first time, and he made a point of repeatedly talking about how much he disliked Obama, to the point where he just was irrational.

Blair: The birther thing—when did he start that?

Barrett: Well, he actually started working it in 2011, when he thought he could run for president, so the race message that we hear in so many different places now, when he launched what he thought might be his campaign, it was a clear race message that was underlying it from the beginning.

Glasser: Do you believe that that race thing goes earlier into his biography?

O’Brien: There’s no question that he’s exploited the racial issues, and I think the birther stuff was a precursor to that. And I think we could call it true, but it’s also sort of ugly sensationalism.

Kruse: Not to put too fine a point on this—is he, himself, racist?

D’Antonio: That’s the crap he wants us all to jump into, is to call him a racist, and then he can scream about how unfair we are.

I want to go back to this thing with him suing the feds, after his father’s firm was accused of bias. So he then turns around and files a defamation suit and starts talking about how this is the whole reverse discrimination thing. That’s a dog whistle. That’s him saying, “Oh, now black people are privileged.” And this is like 1974 that he’s first offering this signal.

Kruse: Talking about welfare.

D’Antonio: Right. Well, I don’t want people on welfare in our apartments. And then, you know, the next step is Ronald Reagan talking about young bucks on welfare, welfare queens. I think this is Roger Stone, Roy Cohn, Richard Nixon, Lee Atwater crap, where they know the words to say, and they know the claims to make, that make people understand. This whole idea that a lot of white people—

Barrett: Roger [a longtime Trump adviser and former Nixon aide] didn’t come along until a little bit later than that, but that was definitely Roy Cohn. Roy represented him on that case. You know, both of these guys, Roger and Donald, are effectively sons of Roy. Roy was the second most influential person in Donald’s life, and the most influential in Roger Stone’s life.

He even sounds like Roy. I had many lunches with Roy. I dealt with Roy all the time. He would sit there and say, “Wayne has written 36 pieces on me and never said a good word. You have no idea how much business you generated from that.”



Excerpt:

TrumpNation: The Art of Being the Donald, 2005 “Donald also knew that something special distinguished his union with Melania from his previous marriage to Marla Maples. Marla, he told me, bored him. ‘I was bored when she was walking down the aisle,’ Donald said of his wedding with Marla. ‘I kept thinking: What the hell am I doing here? I was so deep into my business stuff I couldn’t think of anything else.’ Donald said his nuptials with Melania were overdue. … ‘We’ve lived together for five years, I owe that to her now,’ he told me. ‘I guess we’ll know in two years if I’m divorced again.’ And was he ready to have more children? ‘Sure, when you’re rich you can have as many kids as you want. Being rich makes it easier to have kids.’” Timothy L. O’Brien, executive editor of Bloomberg View and Bloomberg Gadfly, previously worked at the New York Times, Wall Street Journal and Huffington Post.

O’Brien: And to think that Roy had a front-row seat to Joe McCarthy, and the power of sensationalism, and blind accusations and preying upon people’s political fears. And Donald is in this line from Father Coughlin to Joe McCarthy. Father Coughlin did it on radio. Joe McCarthy did it on TV. Donald now uses social media, and he plays it like a violin.

Barrett: And look what Roy tried to do in the race discrimination case. He deposed the federal prosecutor who was bringing the case, and tried to smear them.

D’Antonio: He just was awful.

So then this becomes something that Americans—again with his bring-back-the-death-penalty advertisements, and again with “I don’t think they look like real Indians…”

O’Brien: Build a wall.

D’Antonio: Build a wall.

O’Brien: All of this stuff is preying on people’s most base fears about the threat, what they feel is a threat to their well-being.

Blair: Now he’s also piling on with insisting that the country is at the brink of collapse, that the military is decimated, that we’re about to be invaded, that it’s an absolutely nightmare scenario and we need a strong leader. It’s over and over and over again, how bad we are. We’re the richest country in the world, and we have the strongest military, but you would not know that.

Glasser: Isn’t it surprising, a little bit, the negative portrait of America, given that he clearly is a kind of guy who sells optimism, generally?

O’Brien: The Apprentice audience, the people that are buying into him as a successful entrepreneur and this poster boy for wealth—it’s a certain kind of wealth that really appeals to lottery winners’ sense of what you do when you’re wealthy. You have a huge marble apartment with giant old pictures. And there are white, working-class American voters who are afraid of immigrants and deals with China, and their plight since the ’08 financial crisis has been overlooked by elite media and elite political institutions that didn’t see Trump coming. I think that’s actually the same audience that buys into the optimism of The Apprentice.

But you know what? You can’t strike it rich and make it on your own—they feel let down by America. The political institutions let them down. The economy let them down. And here’s a guy coming in, saying, “I’ve got the solutions for all of this.”

Glasser: How cynical is that? Do you think that, left to his own devices, he would have a very tastefully decorated 1960s modernism—

Blair: Everybody has said it’s just winning and losing. That’s it. That’s everything. That’s the only value system.

D’Antonio: I think that the point that Tim made, about the big score idea of getting rich in America, and The Apprentice is an example of that. I think it’s a really tragic show, because it’s presenting people who are really in need of good careers, who then stumble around like lunatics, trying to please this furious rich guy, and it’s not about actually doing hard work, learning something, acquiring a great profession or skill. It’s about the big score, and the big score in this case is Donald’s got to give it to you. And he knows people like this.

Barrett: I think his entire message can be reduced to one word: race. I think that’s his entire message. You know, he carries New Hampshire that has the lowest poverty rate in the United States, that has an unemployment rate around 3 percent.

D’Antonio: I grew up there, and I went to school with the one black kid in the state.

Barrett: Yeah. He carries every Deep South state. Does anybody remember that he’s carrying every slave-owner state? He doesn’t even do well in Oklahoma, which was not a slave-owner state. I watched Jake Tapper and Dana Bash on CNN on Super Tuesday, and all these times they kept remarking, “How unbelievable it is that a kid from Queens is carrying this Southern state after this Southern state,” but they never even speculate as to why.

Glasser: But that goes to the point about, in his personal dealings with celebrities, he seems to have not made a distinction between African-Americans and whites.

Barrett: I think Tim is completely correct about that, when he’s had very few black people in his life, really.

O’Brien: The Trump organization is lily-white.

Barrett: It could be he’s not an authentic racist—there’s almost nothing authentic about him.

Blair: The black people he’s hanging out with are celebrities. They’re winners. Oh, if you’re a winner, that’s OK, that’s all right.

D’Antonio: So do you think, to Wayne’s point, that he is authentically anything?

Blair: I think he is authentically for him.

O’Brien: And he thrives on attention. I think he’s living the dream now, in his narrow world, where every media outlet in the country is covering him. He’s tweeting, and he’s getting 4,000 retweets every time. He is the happiest he has ever been, right now.

***

Kruse: So to go back to something you said way back, there’s a hole that he’s trying to fill. What is the hole?

O’Brien: Love.

Barrett: Love.

O’Brien: Yeah, I think it’s love.

D’Antonio: Love. What’s really remarkable about Donald is I don’t know if he understands values other than winning and wealth. So you can go into a meeting with him and say, “I’m writing this book and I’m interested in it being a good study of you.” He’ll say, “Well, if you want it to be a bestseller, it’ll be very positive about me.” And my reply would be, “My first concern is not that it be a bestseller. My first concern is that it be a good book.”

O’Brien: And accurate.

D’Antonio: I think that he doesn’t understand love. So when Hillary Clinton said, “I think we need more love,” I think she recognizes this in him, too, and that’s the message that will counteract the Trump effect.

He never said he was a failure. Everybody else said, ‘This guy is going down. He’s filed for bankruptcy.’ But he didn’t say that.”

O’Brien: The other thing, too, that I think the media has to hold his feet to the fire on is he’s gotten away with this notion that he’s a superior deal-maker, and a very successful businessman. I thought about it after he went after the Iran deal. He said, “Obama negotiated this horrible deal with Iran. It’s a bad deal, and when I get to Washington, there won’t be bad deals anymore. I’m a great deal-maker.” And then the reality, the objective reality, is that he’s been a horrible deal-maker. His career is littered with bad deals. And yet, he’s essentially now a human shingle. He’s not someone who’s a particularly adept deal-maker, if you look at his whole career.

Kruse: A human shingle, because there were the bad deals that brought him down in the early to mid-’90s, right?

O’Brien: What he was left with was licensing his name. So he licenses his name on mattresses and underwear and vodka and buildings, among other products.

Kruse: He made this transition from being an actual businessman, a person who does deals, some of which were good, to a grand promoter of his own name.

O’Brien: And the reality TV version of a successful businessman.

Barrett: This is the ultimate promotion of his own name. This is the ultimate brand.

Kruse: But the fact is that there is a middle ground. There is, basically, 1990-ish to 1995 where he is a failure.

O’Brien: He’s in desperate straits. He almost had to go personally bankrupt.

Kruse: The success is that he didn’t die a business death. The success was survival.

O’Brien: And he was a survivor, to his credit. He survived.

Kruse: Why, though, wasn’t that failure?

O’Brien: Because of The Apprentice. I think singularly because of The Apprentice. But he was a joke in between 1993 and 2003.

Blair: You know that family legacy, that family culture of “never give up.” He never said he was a failure. Everybody else said, “This guy is going down. He’s filed for bankruptcy. This is terrible,” but he didn’t say that. He continued to say he was the best of the best, the biggest of the biggest, and he went on. I think that’s a huge piece of that.

Barrett: I tell the tale towards the end of the book about after the settlement with Ivana, he goes to meet with John Scanlon, who was a New York publicist of some skill, and tries to hire Ivana’s publicist to now represent him, and tells John, who is now dead, “I’m going to make a giant comeback, and I want to be on the cover of Time again, and I want you to handle it.”

So he’s already thinking that way, in that very down moment of his life, but he knew he had bilked the banks. The banks put him back up on the pedestal. They didn’t have to, but it took a while to climb up that ladder.

D’Antonio: What about the fact that Fred died and that money became available?

O’Brien: Which totally insulated him from a lot of problems, that inheritance that he got from Fred. At one point, he needed his siblings to extend him a loan. I think it was the hard reality of family money.





D’Antonio: The first thing I think that you credit him with is this creation of himself, which is very American, this idea that I’m going to imagine what I’m going to be, I’m going to tell the world that I’m it before I am it, and then the world is going to help me become it. And he did it.

O’Brien: Think about the genesis of The Apprentice. The show got launched because Mark Burnett [the producer of The Apprentice], as an immigrant to the United States, is selling blue jeans in Venice, California, barely making it. He doesn’t have any faith in himself and reads this book called The Art of the Deal, and he thinks, “Wow, this is the bible of how you make it in America.” And then whatever it is, 25, 30 years later, he does Survivor. That’s a huge hit. He becomes a force in the TV industry, and he thinks, “I’m going to go back to the godfather of my success, Donald Trump, and I’m going to create a TV show that embodies the inspiration I felt from The Art of the Deal.” And that’s how The Apprentice gets launched, because The Art of the Deal, as Wayne knows, didn’t comport with reality, and The Apprentice is just a TV version of The Art of the Deal. It’s a total distortion of reality.

Glasser: So it’s a TV show about a book about a guy who was an invented character.

O’Brien: Yes.

Glasser: That’s now led to a campaign based on the TV show based on the book.

O’Brien: About a man who’s saying he’s a politician, who could probably never really deliver on everything he’s saying.

D’Antonio: So it’s all about this autobiography, which isn’t auto, and it isn’t a biography—which is, you know, only in America.

***

Glasser: I have been dying to ask each one of you, why this subject, of all subjects?

D’Antonio: I thought that Gwenda and Tim and Harry and Wayne had done it. There didn’t seem to be, in my estimation, a need to do it. But he’s so prolific, Donald, in the creation of himself and his image, and everyone who has written about him, you can’t keep up with all of the sparks that he throws off. So I finally said, “OK, is this something worth going back to?” And they also let me bring in this whole analysis of him as a product of a media age, and our culture of narcissism, and those are sort of concepts that we’ve been sorting through, as a country or culture, only in the last decade or so.

Glasser: Gwenda, why did you write about Trump?

Blair: By the time I started doing it, he was already a national figure. He had already done the New Jersey Generals. He’d already become national. And there are a lot of people who have giant egos. He had a giant ego; a lot of people do. But how he managed to leverage his ego to make him into a success, how he made that his brand. How he made someone whose braggadocious nature, and I don’t think that we knew that word back then, if it is a word. But his use of superlatives, the glitz, the glamour, the mirrors, everything shiny, all of that.

But that became this excess and, above all, the ego. That was something that he had made work for him, instead of getting in his way, instead of being, at most, something somebody had to overcome. He made that the selling point. How did that work? That’s what I tried to begin to get a handle on.

Glasser: Tim, you came back to it after having worked with—

O’Brien: After a real apprenticeship. I certainly first got exposed to it through Wayne. So I was very fortunate, I think, just to be trained in some ways by Wayne. And then introduced to Trump in the ’80s as this emblematic figure of the first decade in which wealth became fetishized in a really intense way in the United States.

And then in the early aughts, when I came back to it, it was first as a reporter at the New York Times, because his casino companies were in desperate straits. They were about to revisit corporate bankruptcy for the third or fourth time. And right at that moment he’s sailing very high on The Apprentice, and is then, and now, arguably one of the most famous businessmen in the United States. In other words, there was this real disconnect between, I think, reality and the TV show. And all of that, for me, led on to the fact that he’s an enormously influential pop culture figure. I wanted to write a book that looked at him as this, almost like a pop culture icon in his various worlds he inhabited, whether it was casinos, politics, Manhattan real estate, reality TV, all of these various self-promotions, and to sort of unbundle that and use a book to say as much about us as it did about Donald Trump.

Barrett: It’s interesting because it was Jack Newfield, my mentor, at the Village Voice, who suggested that I take a look at Donald, in about ’78, and then the Grand Hyatt was under construction so it was his first project. But the nexus of my interest and Jack’s flowed directly from City Hall and our interest in coverage of the state, Hugh Carey, and the city, Mayor Abe Beame. It was a political story, as far as we were concerned, from the very beginning, because between the governor and the mayor, they created a tax abatement program for him. It was unparalleled in New York and very unusual, if not unparalleled, in America.

And so the politics of how that happened, I think that’s a commentary on Donald and Fred. It’s their politics that drew me to him, and in many ways, the series I wrote, ultimately, in the Voice, which led to the empaneling of a federal grand jury, but the series that I wrote was as much about Fred, in some ways, as it was about Donald, because, in some respects, the Grand Hyatt—Donald was a front for Fred. Fred had lived through so many scandals—the FHA scandals, the Mitchell-Lama scandals—and he was so close to being out of the same club, that if they had tried to do it as a Fred project, it would have blown up. It would have blown up.

So Donald was the perfect cover for that—the glamour boy. So the degree to which it drew press attention, is about this glamorous, new, young developer coming to New York to save 42nd Street. And if it was Fred that was doing it, it would have been the old hack from the Madison Club working with the hack mayor to produce a tax abatement program that was unprecedented, and declared 42nd Street to be a blighted area.

Kruse: He couldn’t have done that without his father, and his father couldn’t have done that without his son. When Fred died, do you think he was proud of Donald?



Excerpt:

Never Enough: Donald Trump and the Pursuit of Success, 2015 “Trump also understands that even while Americans may suspect the economic game is rigged to favor the rich, they still want to be rich themselves. His rise to prominence in 1978 coincided, almost exactly, with the moment when median wages stopped growing and the earnings of those in the highest ranks took off. At that same time the mass media became swollen with lifestyle and celebrity ‘news,’ a kind of pornography of wealth and fame. As the public feasted on images of excess, Trump’s face was associated with all the tantalizing pleasures that money could buy. Obscured by hype, the facts of his life didn’t matter as much as the idea of him. Anyone who tried to grasp the ‘real’ Trump was likely to fail.” Michael D’Antonio, the author of more than a dozen books, has written for the New York Times Magazine, the Los Angeles Times Magazine and the Times of London Magazine, and won a Pulitzer Prize at Newsday.

Blair: At Fred’s funeral, where all the kids speak, all the other kids say how sad they are that their dad died, and what a terrific guy he is. Donald talks only about himself.

O’Brien: That’s an emblematic moment—Fred’s funeral is an emblematic moment.

Blair: Robert, his brother, told me he was the plow horse. He said Donald’s the racer, but Fred was the plow horse.

***

Glasser: The other thing we didn’t talk as much about was the mob connection or lack thereof.

O’Brien: We’ve got the original casino regulatory interviews with Donald, in which they were asking him about his original partners in Atlantic City, when he assembled the parcel for what became his first casino, that Trump Plaza, at the foot of the Atlantic City Expressway, which was the best site you could have in Atlantic City, because you’ve got everybody driving into town.

And he assembled a real estate site with a guy named Danny Sullivan—Wayne has done a lot of reporting on it; he was essentially a labor racketeer in the construction trade—and Ken Shapiro, who was a bag man for the Scarfo crime family in Philadelphia. Atlantic City was petrified of becoming Vegas. They wanted to make sure people coming in were clean. They asked him about these relationships, and he said he thought they were good guys, he didn’t see anything untoward about any of them, and so on.

And then, when I was reporting my book, we were on his plane, somewhere over the Midwest, and we began talking about these guys, and I said, “Did you ever think that Ken Shapiro or Dan Sullivan had mob ties?” And Trump said to the effect that—and I should go to the book for the exact quote; I don’t have it with me—but he said, “Oh, sure. I was definitely worried. There were rumors that Dan Sullivan killed Jimmy Hoffa. And, uh, yeah, maybe because I was wary of these guys, that’s what saved me,” which was completely at odds with his reported testimony in the early 1980s.

And this isn’t the only incidence of him intersecting with people with complicated backgrounds as business partners. Wayne knew a lot about Roy Cohn’s relationship with the Genovese crime family.

Barrett: It wasn’t just Genovese. The heads of all five crime families, according to federal files, used to meet in Roy Cohn’s office, because they could all claim lawyer-client privilege, and the feds couldn’t eavesdrop on any of the conversations. So Roy was pivotal with all five crime families in New York. Absolutely, totally the fact that I reported in my book is that the head of the Genovese crime family at the time, Fat Tony Salerno—who only got 100 years in prison, subsequent to this; he died there—met with Donald in Roy Cohn’s offices, and Donald winds up using a concrete company that Fat Tony controlled, at Trump Plaza.

Glasser: So what you’re saying is, yes, there’s definitely—

O’Brien: There’s a lot to be explored there.

***

Glasser: One last thing I’ve got to know from everybody. Is Donald Trump going to be the president?

D’Antonio: No.

O’Brien: No.

Blair: I hope not.

Barrett: No.

D’Antonio: I believe in America.

Barrett: I don’t think the same nation that elected Barack Obama twice could possibly elect Trump. It’s the same country. I mean, I think there’s an awful lot of racism, if you can tap into it, but I don’t think the country, as a whole, is racist. So there’s a limit.

O’Brien: The other interesting thing about it, too, I think, is that he’s not going to go away even if he loses the general election. He’s now going to be with us until he’s 150.

Glasser: See, that’s a very important point. People are very focused on this particular mountain climb, right? He’s now at a whole different level of presence in our national conversation.

O’Brien: Yes, in our lives. Now he can exist forever, because Fox will give him a TV show or something, even if he loses, and he can have an enormous political impact without ever holding office.

Barrett: I don’t think he wants a TV show. You think so?

O’Brien: I think he can’t live outside the spotlight.

Glasser: Now he’s addicted to it even more than he was before.

O’Brien: It’s like a narcotic.

Kruse: It’s nothing if not serial reinvention. Something will happen next.

***

Photographs by Jesse Dittmar, taken at Alfredo 100 in New York