The FRONTLINE Interview: Tony Schwartz

September 27, 2016
by Jason M. Breslow Digital Editor

For 18 months in the mid-1980s, Tony Schwartz was at Donald Trump’s side, shadowing and interviewing the New York businessman for Trump’s best-selling memoir, The Art of the Deal. Schwartz co-wrote the book with Trump, earning a $250,000 advance for the project and half of the book’s millions in royalties. He says that at the time, his job was “to create the most appealing portrait I could of this man I had been paid to write a book on behalf of.” But today, Schwartz is an outspoken critic of Trump, and says he regrets the role that The Art of the Deal played in catapulting Trump to new levels of fame.

In the below interview, Schwartz speaks at length about his relationship with Trump during research for the book, and why based on that experience, he has become a critic of Trump. After this interview was conducted, The New York Times reported that Schwartz offered to help Hillary Clinton in preparing for the 2016 presidential debates.

This is the transcript of a conversation held with FRONTLINE’s Jim Gilmore on July 12, 2016. It has been edited for clarity and length.

Talk a little bit about his claims about writing the book and how important writing the book, even when he announces for the presidency, that The Art of the Deal is such an important document that he’s written.

I was a little surprised when Trump announced his candidacy in Trump Tower, and within several sentences he said, “We need a president who wrote The Art of the Deal.” And I thought, well, I wrote The Art of the Deal; I’m not sure I actually would make a good president. And then I thought, wow, that’s predictable for Trump. He actually probably has gotten to the point where he thinks he did write it.

What do you mean, he didn’t write it? What was his participation?

I wrote The Art of the Deal, and Donald Trump read it, so far as I know in a couple of hours based on the number of marks he made on the manuscript.

When was the first time you met Donald Trump, and give us your first impressions.

The great irony of the fact that I ended up writing The Art of the Deal is that the very first article I wrote about Donald Trump was an extremely critical article on the cover of New York magazine called “A Different Kind of Donald Trump Story,” about his attempt to evict rent-control tenants from a building he owned in order to turn it into a luxury condominium. He hired a very well-known “relocation” company to find a variety of ways to make life unpleasant for tenants. And the funny thing about it is — not so funny — that he bungled the whole thing, and those tenants were able to keep him from evicting them for many, many years. They had him tied up in knots in courts and were able to hold on to these apartments for an incredibly long time. I wrote that story, and the cover of that issue was an illustration of Trump looking like a thug, kind of sweating and greasy and pretty unappealing.

He loved it. He absolutely loved the cover, so much so that he put it up on his wall almost immediately, and I became his best friend — or he treated me as if I was his best friend in the sense that he liked the piece so much that he wrote me a lovely letter about how great it was and everybody was talking about it.

You have to understand that this is 1986, and he’s not that well known yet, and the idea of being on a magazine cover was relatively new to him. So, as someone who really believed that all publicity is good publicity, this was a great piece of publicity.

Even lousy publicity?

Yeah. I mean, extremely critical of him and of what he did. And yet, from his perspective, built his name.

Tell me about the meeting where you walk in and he’s talking about the book.

… Some months after I wrote the New York magazine article, I went back to Trump to do the Playboy interview, a long interview. I started to ask him a series of questions, and he seemed not willing to give me answers to most of them. At some point 15 minutes in, I said, “You know, if you don’t answer these questions, there’s no interview.” And he said: “Yeah, but I don’t really want to. I just signed a deal to write a book.” And I said, “What’s the book?” And he said, “Well, I guess my autobiography.” And I said, “Well, you’re 38 years old. You don’t have an autobiography yet.” And he said, “Yeah, I know, but they paid me a lot of money, and I’m going to do it.”

And I said, “If I were you, I’d write a book called The Art of the Deal, because I think people believe you know something about deals.”

And his response?

His response was: “Great idea. You want to write it?”

Tell us a little bit about the process of writing the book, your first interviews and how that goes and what you do next.

Well, I think Trump probably thought you snap your finger and there’s a book, so I think he was a little surprised to discover that it was actually going to take a lot of time, and he wasn’t happy about it. I think one of the central under-recognized facts about Trump is how severely limited his attention span is. It’s really, really hard for Trump to focus on much of anything for a sustained period of time, with the exception of talking about himself.

So you were doing these interviews, and what would happen?

The very first interview I did with him, I got about 20 minutes into the interview, and he said, “How long is this going to go on?” I almost wasn’t sure what he meant. I said: “Well, there’s a lot of questions to answer. We’ve got to fill 300 pages, so we’ve got a long way to go.” And what happened was he just got increasingly irritated and impatient, and his way of responding to my questions was in very, very brief, you know, three-, four-, five-word sentences. It was a bit of a war from the start to try to extract real information from him.

Even for a book that’s partly autobiographical, he doesn’t want to think about the past?

You know, Trump said to me over and over again, “I’m just not interested in the past; I’m interested in the present.” From a Buddhist perspective, that would be pretty attractive. … The reason I think he didn’t want to talk about the past is that he’s almost like a sieve or a black hole, and the need for constant reassurance and evidence that he matters, that he’s great, that he’s successful, that he’s handsome, that he’s all of these things, represents a kind of unquenchable thirst. So most of his time is spent trying to fill himself back up, because it’s leaking all the time.

So where does that come from?

… [his father] was a tough, hard driving guy who had very, very little emotional intelligence, to use today’s terms. He was a tough, hard driving guy who didn’t traffic in emotions except perhaps anger.

And did he respect that? What did he get from that?

Well, he had this older brother who ended up becoming an alcoholic, dying at a young age, and I think another significant factor in Trump’s development was, “I’m not going to be him.” And I think he saw his brother as being intimidated by his father. So he set himself out to be the very opposite of that with his father and with everybody else that he dealt with for the rest of his life.

There’s this thing about winners and losers. Where does this come from, what is it? There’s only winners, there’s only losers, there’s no gray.

… I do think it’s a reflection of the fact that the way the game got played in his household was if you did not win, you lost. And losing was you got crushed. Losing was you didn’t matter. Losing was you were nothing. Losing was you’re his older brother, Fred, and you become an alcoholic and die young. So the frame was pretty stark.

… What was he saying?

I think Trump was in rebellion from a very early age. The character that he became was set almost in concrete. And his self image, his self definition, was built around the idea that he was one tough son of a bitch. And that meant in classrooms, that meant with teachers, that meant with his father. And I think he takes great pride, since his perspective has never really changed, in having won at that game. And in many, many ways, he has won at that game. He earned a ton of money, he married a lot of beautiful women, he bought a lot of spectacular homes and material objects.

He is sort of the embodiment of a certain kind of the American dream.

You found that the interviews were difficult. You ended up on the telephone in the end. Explain how involved you were for how long, because it defines how much you know about how this guy operates.

At a certain point, I realized that it was fruitless to try to interview Trump. In fact, when it really hit home for me [was] a weekend that I was spending with him at Mar-a-Lago. I went up to my room there, and I called my agent, and I said: “I can’t do this book. He just won’t cooperate.” And she said: “Well, write it down. Send me a letter, and we’ll deal with it when you get home, because, you know, I don’t want you to be the person who caused this to fall apart.”

On my flight home, I realized I had a kind of small epiphany, which was, hey, he talks on the phone all day long. That’s what he does, and he’s talking about his deals. Maybe if I just sit on an extension phone listening to his conversations, I can extract enough of what actually happened to write those deals in his voice and then fill in the details that he doesn’t provide from the people he’s on the phone with later. And I presented that option to him, and he said: “Great. Sounds wonderful. I don’t have to do any more interviews.”

For I would say close to a year, I spent hundreds and hundreds of hours sitting in a chair eight feet away from his desk holding a phone and listening to what he was saying to almost anyone. In fact, I can’t remember a time when he said, “Hey, Tony, I really don’t want you to hear this call.” I had a belief that if he could have had an audience of a million for those calls, it would have been all the better.

What did you learn from that?

Well, I learned what moved him and what motivated him. What he liked was attention. What he liked was action. He liked to be on the phone with people he thought mattered, but not for very long. At any given moment during a call, if another call came in, his two assistants were instructed to walk in with a yellow Post-it Note that said the name of the person on the other line, at which point almost invariably Trump would say, “Hey, gotta go. You’re the greatest,” and hang up the phone, pick up the next extension. It was one call after another, and I did reflect that in the first chapter, in which I pulled together some of the best of that and turned it into a week in his life.

As you were doing your research, you were finding that he had a different point of view about the stuff that was being agreed to or that was being said than the persons on the other side of the phone.

Well, what I found as I took notes on what was going back and forth in these calls … is that when I went to talk with other players in the deal, it would often turn out that they had a very different story to tell about what actually happened in that deal.

There was a, you could call it very gently and gentlemanly a difference of opinion, but in those places where I went and looked, it was usually the case that the person other than Trump was telling me the more accurate story. In Trump’s version of the story, he was the hero, and it was always a larger-than-life story.

And the view from the other people would be what?

Well, the view from other people would be so-and-so had a big role to play in that deal and maybe bigger than Trump, or what he told you happened there actually didn’t quite happen that way. I don’t know what you want to do with this, but here’s what actually happened. People would tell me a variety of ways in which the story actually was not quite so wonderful as Trump had made it about himself.

“… Within several sentences he said, ‘We need a president who wrote The Art of the Deal.’ And I thought, well, I wrote The Art of the Deal; I’m not sure I actually would make a good president.”

There’s an amazing paragraph in the book where he talks about “truthful hyperbole,” as he defines it. Explain what you wrote, what it means, and how he viewed the fact that it was going to be in the book when he first read it.

After five or 10 or 15 of these conversations with different people who he was doing business with, where I realized, hey, I’m not getting the truthful story in many cases, I was troubled. It bothered me. And it was quite clear when I would go back to him that he was not interested in debating it and that his version was his version. So I had to figure out a way to tell these stories without knowingly violating what I knew to be true. I could have done that because it was his book, and I was just the ghostwriter. But I didn’t want to do that, and yet it was important that I tell some of these stories.

So I came up with the phrase “truthful hyperbole,” and of course it’s a ridiculous term, because there is no such thing as truthful hyperbole, but it’s kind of a winning phrase. It really does capture a way in which he sees the world. The truth doesn’t mean much to Donald Trump.

Why is that important to understand?

… At the time I was writing The Art of the Deal, the story I told myself was this is a book by a modestly well-known real estate developer, inconsequential. What’s the big deal? So if he lies, who really cares? Today he’s running for president for the United States, the most important leadership role in the world. I don’t believe he has a different relationship to the truth than he had then, which is a very thin one.

So why does it matter?

Why does it matter whether the president of the United States tells the truth? (Laughs.) Yeah, I mean, you didn’t mean it this way, but it’s a good question. In a civilized society, we operate on an assumption that what another person is saying to us is factual. If we lose that connection, we’re in chaos. And I fully believe that Trump would pay as little attention to the truth as president as I observed he did 30 years ago when he was making deals to buy up property.

Immediately afterward, you were reading the reviews, realizing you had created this character that people now believe was the truth. That’s a pretty fascinating position to be in.

It never occurred to me during the time I was writing this that my job was anything other than to create the most appealing portrait I could of this man I had been paid to write a book on behalf of. So I was surprised — I would go so far as to say I was stunned — when Christopher Lehmann-Haupt wrote the first big review of the book in The New York Times, and it was an absolute rave. I had never thought that good reviews were one part of the likely equation for this book. I always thought it was a book that could sell well, and that’s why I had taken it on. I don’t say that with any great pride, but that is why I took it on.

This was mystifying at first to me. In a sense, I realized that I created something different than the person I had encountered when I began to read the reviews.

And the effect of this book being so successful is what? I mean, the fact is, this is early on in his career. Hitting at that moment, what did it do, and [what was] Donald’s attitude toward it all?

… I am imagining without knowing for sure that for Trump, the success of the book was a little like, … “Oh, really? I actually am going to be as big and famous as I always wished I could be.” I think there was a little bit of awe, not that he would have showed it much, but I think there was a little bit of awe and utter and complete delight in the success of the book.

And what was his reaction?

I would talk to Trump in the months after the book probably three times a day. He would call, and it was always about a letter he’d gotten or a next piece of the deal itself, selling it to another country, to be published in another country. I was the source of news about sales, so he always wanted to know how many copies and where are they selling and how is it doing compared to other books and the same kinds of things, the same kind of comparisons that he makes today.

He was avidly interested in every aspect of its success. Very often, he would actually come down from his office in Trump Tower and set up kind of shop on the ground floor, signing books for people who came into Trump Tower, sometimes hundreds of them, and the lines would go out the door and selling. I don’t think it was a big percentage of the overall sales, but I think he loved connecting the book with a sale.

Because this book did what for his career at that point?

At the time, the main thought I had about the success was that he recognized he could translate it into building his brand and translate it in a big way, not just in New York, not even just nationally — internationally, because the book exploded all over the world. I think he at the time was primarily thinking about how this was going to make his business bigger than ever. Favorite phrase of Trump’s: bigger than ever.

I remember that in the months after the book, I talked to him very frequently, and then it started to trail off, and I might talk to him in the year after, the second year after, once every three months or six months. Invariably I would call and be put through very quickly, and Trump would come on ebullient and say: “Can you believe it, Tony? Can you believe it? Bigger than ever. Can you believe it?” It was so predictable that I would tell friends about it. I’d say, “I’m going to call Trump right now, and here’s what he’s going to say.” And sure enough, he would do it.

What did you start the book with, and why is it essential to understand?

… I started the book in his voice. I mean, the whole book is in his voice saying, “I don’t do it for the money; I do it to do it.” The whole notion was to create a picture that didn’t feel so greedy and avaricious as it might otherwise. It was to turn it into an art form. It was called The Art of the Deal as opposed to Grimy Commerce. What’s so amusing about it, as I look back is, of course he did it for the money. He did it primarily for the money. So that was nonsense. And, you know, I have him say something like, “Deals are my poetry.”

Well, “poetry” is not a word in Donald Trump’s vocabulary, and I don’t think he spent a lot of time reading Wordsworth in the deep of night. In fact, I don’t think he’s read a book of any kind other than his own in his adult life. So I wanted to make him more appealing than he would have been if he was simply a rich guy making more and more money.

And you succeeded.

And I succeeded, judging by both the reviews and by the number of copies that were sold. But I’ve been grappling with that success and its shadow for many, many years.


I made a decision at the age of 35 to write that book partly as a lark and partly, or even more so, because it was a way of earning a bunch of money, and potentially a big bunch of money, quickly. I told myself a lot of stories to rationalize that, and it certainly never occurred to me that Trump would become president or even think of being president.

But as he began to be more of a public figure, I felt responsible in some way for having helped to create the opportunity for him to go out there and have an impact. As we got to the point where he actually decided he was going to run for president, not just say he was going to run for president, now it’s almost like I created a monster. It’s ridiculously arrogant to say I created him; I get that. But I contributed to his creation, and in that respect I feel guilty, and I feel responsible to do my best to set the record straight before he ends up running a country that he’s not remotely prepared to do in a reasonable way.

You saw him day in and day out. You saw him with his family. You saw him in many different situations. One thing you’ve said is that emotional-wise, he lacked emotions. Even anger was used as a tool in a lot of ways. Describe that part of him and why it’s important to understand [that] about him.

I don’t think Donald Trump has an inner life. I don’t think there’s something different going on inside him than you see going on outside him. It’s not just that he’s not introspective; there’s nothing in there to introspect about. Again, for me to label him is unreasonable, but he certainly strikes me as someone without much of a soul or a conscience or emotional range that you would associate with most human beings.

What fulfilled him?

You know, I think every human being’s core need is to feel a sense of value. Trump is no different. … I honestly believe that his deepest hunger was for– has always been for attention and he had exhausted the ways in which to get attention. He’d gone so far beyond what most human beings can even imagine that he was at the end of that road still hungry and that’s the primary reason he ran for president. He wanted the attention of the nation. He wanted the attention of the world. And he’s gotten it.

Was there any light moment, time where you sit down and have a heart-to-heart where he’s asking you about your life or anything like that?

He would almost never ask me anything about myself. I think he got a kick out of the idea that he believed he was kind of turning me into a businessman. It was my job in doing this book to be as comfortable a presence in his life as possible. I don’t think he had a clue who I was, and if he had, he would have gotten way far away from me because I saw the world so profoundly differently than he did.

Trump almost never asked me anything. He did know my name, and my wife typically would answer the phone, or at least most of the time answer the phone when he called in the evening. When I was talking to her about it recently, she said to me, “You know, he never knew my name.” That’s probably 100 or 200 exchanges without having known her name. That’s Donald.

Because you were useful to him.

That’s in some way the simplest way of describing the way Trump operates. He is interested in you for as long as you are someone who can be useful to him. That’s what he means by a friend. “You’re the greatest.” “You’re the greatest” means you’re serving my desire at this particular moment. If you go the other way, you will either become some version of what he’s called hundreds of people over the last several months, or his sworn enemy, or both. His notion of how life works is people do what I want them to do, and I get stuff done. And if they don’t do what I want them to do, I want nothing to do with them.

“In Trump’s version of the story, he was the hero, and it was always a larger-than-life story.”

I’m just going to go through some of the history that’s in the book that you write about, and tell me what you can tell me. Any stories that you have of him with the father or anything that helps define that relationship?

… By 1986, his father was a much older man and probably had some form of dementia, I imagine, and so he was certainly no longer the powerful figure he had probably been when Donald was young. But my feeling about his attitude toward his father was actually that he was contemptuous, that this guy worked in the outer boroughs; his office was in Avenue Z. He had no class; he had no presence. He wasn’t a star. He was like a — certainly he would have respected the fact that he made a lot of money, but I think he thought, my life is about being something other than what my father was.

Did he say anything about his father, positive or negative?

No. You know … I could almost sense that he would steer clear of saying anything that he thought wouldn’t come off well. Now, he had an unusual sense of what coming off well meant, but by his standard, saying something negative about a member of his family was part of what he wouldn’t do, no matter what he actually felt.

The relationship with the mother: What did you see? What did you learn?

I didn’t see much, and I didn’t sense that he spent almost any time with his parents by that point in his life. I think he was dismissive of his mother, as I think even potentially his father was. But I think he was dismissive of his mother. She wasn’t important. He so clearly valued men more than women. He was so much more comfortable with men than with women. Women were, you know, sex objects pretty much. If you could find a woman who was good at a job, fine, have her do that job; he was willing to do that. But his life, really, his focus around and what the people he would contend with were men.

Though he hires people like Barbara Res and a smart woman like [Louise] Sunshine and such that seemed to surround him, was there also an attitude that they were less competition for him?

I think the reason that Trump hired women in some fairly high roles is that he was the most practical of human beings. “I want to get what I want to get. If this person seems like they’re going to be better doing it, I’ll hire that person, even if she’s a woman.” Now, it is notable that I never saw a person of any color other than white at the Trump organization and would be very surprised if there are many today, even though it’s probably a much bigger company. I did not see that same sense of “If that’s the best person I’ll hire them” extend to black people or Hispanic people or any other.

The whole story of him as a kid and his father sending him away to military school — was he a problem kid? What was going on that you found out about?

Trump himself painted this story of his early years as being like just the toughest kid in class, the toughest kid on the block. Now, the block was Jamaica Estates, and emphasis on the word “Estates.” He was not actually from a real tough neighborhood. But I think it meant a great deal to him from early on to be seen as the tough guy and to challenge people and to be kind of untamable. At a certain point, I think his father decided, “We’ve got to get this kid under control,” and off he went to military school.

I will say that if you’re just talking the ability to survive, clearly Trump was able to thrive in that environment. He was able to use some blend of his sort of street smarts and his self-confidence or his arrogance to kind of run the show. …

All right. So he comes to New York in ’71. He takes over the business of his dad basically at that point, but he moves to Manhattan. Why?

… From the very first time I met Trump, I thought of Saturday Night Fever and [John] Travolta, that he was the kid who grew up as an outsider to where the real action was, and he was acutely aware of it. He always had his eye on what he thought was a glamorous, Hollywood-ish life, and that was the life of Manhattan. He wanted to cross that bridge and make it in the world that he thought making it mattered in.

So he starts living the life. He goes to the clubs. Le Club is one of the places he hung out. He meets Roy Cohn there. The importance of it? What was he doing at that point, and then the importance of Roy Cohn and what becomes that relationship. Why so important?

You know, he’s a kid [who] wants to figure out how to make deals, to figure out how to establish a presence for himself in Manhattan. He’s right to believe that that’s not easy to do.

But he finds a way?

So he makes a connection with Roy Cohn. Well, Roy Cohn is one of the most connected people around … and will do anything to get what it is he wants or his client wants. I want that guy on my side.

He also learns from him?

Let’s say there’s no question that he comes to understand the world of zoning and politics and deals made on the down-low that Cohn was so good at helping to make happen.

The first case that he’s involved in is the FHA [Federal Housing Administration] race case in 1973 that Roy fights for him. Do you want to tell us anything about that? You talked about it in the book a little bit.

The government brought a discrimination suit against Trump and his father for keeping blacks out of the buildings that the Trump family owned. …

Roy Cohn takes that case on. They drag it on for years.

Exactly. … This is a classic example of where Trump begins to demonstrate something he talks about all the time today, which is he’s a counter-puncher. Somebody comes after him and says that he’s done something nefarious and horrible, and he just goes back at them with all guns blazing — you know, boom, boom, boom! — and admits nothing. Never admit anything; never say you made a mistake. Just keep coming. And if you lose, declare victory. And that’s exactly what happened there. He lost as clearly as you can lose, but he loudly proclaimed his victory.

Did he learn that from Roy Cohn, or was that just something that was a philosophy that he also agreed with? Is he learning at the knees of the master, or has he found a partner in crime?

I think there’s no question that during this period where he was spending time with Roy Cohn and getting educated about a lot of stuff, this was a match made in heaven. …

Talk a little bit about the early days of how he finally gets into the business in Manhattan.

It’s kind of the perfect situation where, you know, it’s easy in some sense to be an entrepreneur if you have somebody behind you with deep pockets. He did do some things that were pretty swaggering and pretty risky, and he did get pretty far out on a ledge in terms of risk. But he also knew that he had a father back home who was capable of bankrolling all of this. So it wasn’t like there was no safety net. If this failed, he was going to go back to Brooklyn. That was the worst thing that was going to happen.

He sure didn’t want that to happen, and I do think he was very, very clever and crafty and unburdened by conscience. Pushing any ethical line so long as it was not explicitly illegal was very comfortable for him. And he understood how to play people; he understood how to flatter people. I think the whole story of the Commodore Hotel being turned into the Grand Hyatt was in part a function of how well he played people, how well he did the deals.

He used the political connections?

He had a lot of things going for him, you know. He had enough money. He had political connections that had come through his father and that Roy Cohn also could provide. He had the ingredients in a depressed era, one of the most depressed eras that New York had been through in decades. And it was the perfect time for him to take advantage of a down market.

But the bottom line on this is the Grand Hyatt became a huge success that leads to what? What does it do for his connections with the administration? What does it do with his connections with the banks? What does it do with his ability to create what will become his masterpiece, which is the Trump Tower?

It’s quite clear that in addition to the fact that he made a very, very successful deal, one that’s successful to this day in the Grand Hyatt, that he’s also in a position of building his credibility and building his knowledge base and building his group of contacts and his understanding of how to wheel and deal in a complicated environment.

By the time he’s ready to go after the land on 57th Street that becomes Trump Tower, he has a lot more marbles in his jar that he can use to shoot.

And the importance of the Trump Tower project to him?

Yeah. I mean, look, 57th Street and Fifth Avenue — before there is a Trump Tower, has Bonwit Teller over here. It has Tiffany’s over here. It’s on Fifth Avenue. It’s at a critical part of Manhattan. He’s a guy from the outer boroughs looking at what’s the prize. If I’m going to win the biggest prize, what is it? I don’t think it’s so surprising that he would say it’s that location. Location, location, location. I mean, that’s been a belief for hundreds of years.

I think what made Trump different was much the same as it was when he went after the Hyatt deal, is he’s a young kid, and he’s willing to shoot for the moon and not to take no for an answer. I think his confidence and call it what you will, real or not, his ability to project confidence was a huge factor in his being able to do deals that real estate people of much greater experience not only didn’t do, but probably didn’t even imagine trying to do.

“… As he began to be more of a public figure, I felt responsible in some way for having helped to create the opportunity for him to go out there and have an impact. As we got to the point where he actually decided he was going to run for president, not just say he was going to run for president, now it’s almost like I created a monster.”

The Bonwit Teller reliefs that are destroyed causes huge bad PR for him. Tell me a little bit about the story about the reliefs and how he viewed that whole controversy that blows up.

Trump, as he’s building Trump Tower, ends up destroying these bas-reliefs that are in front of Bonwit Teller. In his mind, it’s like they’re junk, and I’m building my building, and what’s the big deal? Then there is this incredible outcry. He’s much younger than he is today, and he has to back-pedal somewhat. In the book I very much encouraged him to be humble and to acknowledge that maybe that wasn’t the greatest idea. And it’s one of the few times in the book, and I think one of the few times that I know of in his life, where he’s been willing to say, “I was wrong,” or at least come close to saying that.

I think it’s pretty typical of him. Art is not something that interests him. Sculpture is not something he knew about. Building the building on time and under budget or on budget, that’s what he knows, and that’s what he was focused on.

And the lesson he learns about controversy is what?

The clear lesson that Trump took away from all of this was the worst publicity in the world can end up being good publicity, meaning yeah, people said terrible things about me, but they sure know who I am. And a month later, or three months later, they don’t remember what it was they didn’t like about you; they just remember they know your name.

… Through luck, timing, location, public relations, design, the Trump Tower takes on this mystical aura. Describe that. By the time it’s built, after all that they went through to make it happen and everything else, why does it become this thing in his head, but also in the city’s head? What does it become?

Well, you know, one of the things he does is he gets Ada Louise Huxtable, who’s sort of the dean of architecture critics, to say some really positive things about the design. It is a very unusual design in the sense that there’s so much gold and there’s so much marble and it’s another Hollywood version of, or a Las Vegas version, of what good taste is. It’s like it’s the brassiest, the boldest, the most visible, is the best.

That’s what Donald Trump is?

Yeah. I mean, Donald Trump wants maximum attention, and you walk into that giant atrium in Trump Tower, and it’s hard not to pay attention.

We take a turn here to the bad days. Let’s talk about the banks first. He’s at the point now, after Trump Tower, where the banks are coming to him —

No question.

— and giving him money. What is his reputation at that point? What is his star factor? How are banks viewing him?

Once Trump Tower was up, there’s no question that Donald Trump had access to money far beyond his father’s; that any bank is looking for a good risk that they can lend money. There’s always the instinct to, particularly as times started to turn and the real estate market got better, there’s always the hunger of these banks to find people to give their money to, and Donald Trump became one of those people.

How would they treat him?

Oh, there’s no question that the bankers who did business with him treated him with respect, and they understood instinctively what his need was, which was to be seen as the smartest and the greatest and the coolest. And those who got to do business with him got good at doing what he wanted them to do.

And his reaction to the fact that these guys were all at his beck and call?

Well, of course he loved having these bankers available. He was in a period of really feeling he was kind of running the show in a big-time way and that anybody was going to be responsive to his commands and his desires.

And that leads to purchases like the [New Jersey] Generals, the Plaza, the yacht, the shuttle, and then the casinos, the Taj eventually. Just explain those heady days. If there’s piles of money to be had, well, let’s play?

Yeah. I mean, these are heady times, and Trump was interested in the most high-profile kinds of deals, acquisitions, and in spreading his wings. So airlines, cool. Goes after the shuttle, about as high-profile as you can get. Unfortunately at that time, a horrible business, and the thing tanks, and he has to get rid of it. The USFL is tough men, like he wants to go up against the NFL. … In other words, he wanted to get in on the cheap and win, and he got crushed. Yet it was so high-profile that we had to write a chapter about it, and that was one of the tougher chapters to make into a positive story, but a positive story is, I think, what it ended up being, like all the rest of the stories in The Art of the Deal.

And the yacht and the casinos. Did he ever talk about the debt that he was accruing?

No, I don’t think Donald Trump spent one minute worrying about debt. I’m not even sure that I think Donald worried after [his company] was in bankruptcy and the banks had actually fundamentally taken over his life and put him on an allowance — albeit a big allowance, but on an allowance. I don’t think he really believed that it was over for him for one minute.

I know the Taj and everything else opens after the book, but it was all sort of in the works.

It was in construction.

What was the Taj to him?

Well, I think the Taj was the Taj, meaning it was the biggest of all the casinos. It was the biggest, the best, the brightest. In his mind, bigger is always better. … If I own more, then I’m more likely to be successful, or I’m more likely to have it be profitable, so that’s the next conquest I’m after.

You write about the scale, the glamour and the cash flow as Donald’s — the way Donald looked at it. Explain.

…Yeah, it’s pretty obvious when it comes to the scale, the glamour and the cash flow that the scale was far and away the biggest of the casinos. The glamour was partly it is so big and you call it the Taj Mahal, you’re making a very particular statement. The cash flow was at that point not what it was actually doing and whether it was profitable, but the amount of money that Trump imagined it bringing in. He loved — I mean, this is a guy who I think if he could have had a room full of money, he would have visited it frequently and thrown it up in the air and played with it. I mean, he loved money.

Cash flow was very, very appealing, and it wasn’t for a period of time after that, after the book, that it became clear that the cash flow in was dwarfed by the cash flow out. Cash flow by itself is no big winning game.

Politics. Around this time, he’s about to really get involved. It takes place right after the book comes out, but tell me what you know. In ’87 he starts speaking out.

Yeah, right after the book was published, he went up to New Hampshire and did a kind of trip to test the waters for a run for president. Not for a moment did I think it was in any way serious. I thought it was another great promotional piece for the book. It was, for sure, in his mind another way to build his brand, to get his name out there at another level. This wasn’t politics in my mind. This was promotion; this was marketing.

But he has his political backers and he’s got his political advisers telling him this is good stuff to do. In fact, he’s putting out these full-page ads talking about foreign policy. Does he talk about any of this with you?

Well, no. By this point, the book is just about to come out. It’s not going to be part of the book. No, I think he had one or two advisers, most notably Roger Stone, who’s … whispering in his ear. And when you whisper, “You could do it; you could do it,” to Donald Trump, you’re going to get a receptive audience. I don’t believe that Trump himself felt that he was running for president, but in his grandiosity, he felt like, “I’m an important guy, and when I have something to say and I can say it — I can spend $40,000, $50,000 dollars and put a full-page ad in The New York Times, by golly, I’m going to say it.”

That’s all later. But he also comes back when the Reform Party comes to him in 2000?

Well, I think once the notion got stirred up in him, it never went away. I mean, it’s been around for 16 years now, and it has risen and fallen in intensity, in seriousness.

June 16, 2015, he’s in this magnificent Trump cathedral, otherwise known as Trump Tower, and he’s up at the top of the elevator, and you watch it, I assume, on television like the rest of us.

I watched it on my laptop at the end of the day.

What do you see in what he does on that day? The baiting, the Mexican stuff. But also define what you see in that day and also explain what you recognize, what you don’t recognize, in the man that you sat in the office of for a year listening to day in and day out in endless number of telephone conversations.

As I watched Trump make that announcement after coming down the escalator with his beautiful third wife, surrounded by his kids, I thought to myself, this candidacy is going to last about a week, I’m sorry to say. Of course many people made that same misjudgment. Throughout his life, I have to say this is a man who has been underestimated. That to me is, as I sit here several months before the election, what I find most terrifying, is that the same way that I laughed and cringed at what he was saying in that announcement and said to myself, “Well, if he had a chance in the remotest way, he just stepped all over it,” I was wrong.

At this moment in time, Hillary seems to be leading by 4 or 5 percent, but also overwhelmingly from an electoral perspective. … Given how long I’ve known Trump, I have the fear, and I will tell you it is a fear — it’s close to a terror, and it’s somewhat of an obsession for me to watch — that he could, once again, completely surprise and astonish people and become president. …

“… This is a guy who I think if he could have had a room full of money, he would have visited it frequently and thrown it up in the air and played with it. I mean, he loved money.”

His use of the media, shown certainly in the campaign, certainly by the attention that is given him, the amount of time that is given him, why is that important, and where did that come from? And did you see that in him in the man that you worked with?

Yes. If there’s any aspect of Donald Trump that I would say has genius, it’s in his ability to manipulate and own the media. It’s in his ability to attract attention to what it is he wants to get done. He recognized that — what I think he has recognized always, and especially in this campaign, is that the way he shows up in the world, people can’t resist paying attention to and watching. It’s like a car accident, and you can’t turn your eyes away, and that that would serve him well.

You know, I think he’s gotten, in some sense, the luck of a period in history — and maybe he even deserves some kind of perverse credit for having recognized that this is something he could exploit for his own ends, and exploit it he has.

The Apprentice and the 340 million viewers, his peak of fame and also a launching pad. What do you think that did for his career, for his ego?

I don’t know how many years The Apprentice was on, but I never watched it, not a single time. I didn’t avoid watching it out of some kind of protest. I just wasn’t interested. …

… All right. Well, just talk about the selling of the name then.

I think it was post the publication and success of The Art of the Deal that it really dawned on Trump that he could make a huge business empire out of putting his name everywhere, “God, I don’t have to kill myself trying to buy up land and deal with zoning boards and go crazy, and half the time it doesn’t work anyway. Why don’t I just sell my name?” And he’s still selling it.

Puts it on buildings he doesn’t own, puts it on water he doesn’t make, puts it on universities that he has really very little to do with?

Right. Yeah, his idea has always been, how do I earn the maximum amount of money doing what I do? What’s actually underneath that? Not so important.

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