As a Republican political operative during elections dating back to Richard Nixon’s presidency, Roger Stone has been among Donald Trump’s core political confidantes. In the late 1980s, Stone helped Trump test the presidential waters by organizing campaign-like events in New Hampshire. He parted ways with the Trump campaign last year, but remains close to the candidate and is an outspoken supporter. 

“I don’t think he was ever serious about running,” says Stone about Trump’s early forays into politics. Trump found motivation for the current campaign, he says, when President Barack Obama roasted him during the 2011 White House Correspondents’ Dinner. “I think that is the night that he resolves to run for president. I think he is kind of motivated by it … ‘Maybe I’ll just run. Maybe I’ll show them all,'” says Stone.

In the below interview, Stone speaks at length about Trump’s early political ambitions, his role in the birther movement and how The Apprentice helped create Trump’s presidential image before a large television audience.

Editor’s Note: In November 2019, Stone was convicted on seven counts arising from the Mueller investigation, including witness tampering and lying to investigators. He was sentenced to 40 months in prison. In July 2020, his sentence was commuted by President Trump.

This is the transcript of a conversation held with FRONTLINE’s Michael Kirk on June 7, 2016. It has been edited for clarity and length.

Take me to the first time you meet Donald Trump. What are the circumstances? Walk me through it.

I was working for Governor Ronald Reagan and was assigned New York state. This is the nomination phase in 1979, prior to the 1980 election. And of course, New York was Bush country. The Republican establishment here was either for Bush, some of the guys on Wall Street were for John Connally, but virtually no one, at least among the elites, was for Ronald Reagan. And Mike Dever, who was Reagan’s body man really, gave me a card file, like a recipe box. It had about 80 cards in it which came from Nancy Reagan, which was a list of the Reagans’ friends in New York. By and large, they were all theatrical — agents, producers and so on. Half the people on the cards were dead.

But among the cards was a card for Roy M. Cohn, attorney at law. Of course I had read about Cohn; I knew who he was. I didn’t have many assets or resources, so I made an appointment to see Cohn … and I told him that I’d like to talk to him about the Reagan campaign. He was kind of like: “Sure, kid. Come on by the office, kid.”

So I went by the office and waited for a while, got my appointment and made my case as to why Reagan could win and why I needed help. Among the requests was to form a finance committee. Roy kind of sits there and listens to my whole spiel, and he says: “What you need is Donald Trump, Donald Trump and Fred Trump. They’re perfect for this. Do you know Donald Trump?” I said, “No, I only know of him.” He says: “Well, Fred is a real Goldwater Republican, a real conservative. And Donald’s a Republican, and he’d be ideal for this. Let me set you up a meeting.”

So he set up a meeting for me at Trump Tower, and I was bowled over. Wow, this guy is larger than life. I mean, he was very direct. He was very friendly; he was very direct. He did not like Jimmy Carter. He was a registered Republican. He’d given to both sides, and he emphasized that he was a businessman, that he wasn’t that political but he wanted to help. He ended up helping in a dozen ways. We needed low-cost office space. He knew the people who owned what was then a residential building next to the 21 Club on 52nd Street, which had been converted to offices and then closed. It was run-down, but it was cheap. It was ideal. So he got us a lease.

We were having trouble with the phone company because they told us we have a three-month wait for the installation of our phones. Donald called the phone company; they came the next morning. And then lastly, I specifically recall that in New York state, the collection of petitions to get on the ballot is a particularly difficult and onerous process, and we were late. They had to be in Albany by close of business on a certain date. There was no commercial service to Albany that would get you there, so Donald lent us the plane to file our nominating petitions in Albany. We made it with 15 minutes to spare.

So he was helpful in a dozen different ways. We became very good friends. For those who say he’s not a conservative, he’s not a Republican, he was there in the Reagan revolution.

What was he like then?

He’s exactly the way he is today. I’ve really detected no change other than the fact, perhaps, he’s much richer now than he was then. But he’s very entertaining. He’s very funny. He has a great sense of humor. He’s a gentleman. He can be very charming when he wants to be. He’s not that political in the sense that I don’t think he would be doing this if he didn’t think the country was going down the drain. In other words, he’s got the greatest life in the world. He loves to play golf; he’s got a beautiful family. He’s not a cocktail circuit guy. At night, he wants to be home with the family.

I don’t think he’s been on a golf course in six months. He’s got a palatial home in Florida that he barely saw this season. He’s got the greatest apartment in the world in Manhattan, but he’s sleeping in motels. So I think he’s given up a lot. Let’s face it: If he’s elected president, Air Force One would be a step down from his current plane. You could argue that the White House, which is a relatively small facility when you really see it, is a step down from Mar-a-Lago. He’s not doing this for the prestige or to be somebody. He doesn’t have to be president to be somebody, because he already is somebody. He’s the best-known business man on the face of the planet. He’s built a monolith.

Who’s Roy Cohn? What was their relationship? How did they know each other? I know they did business together.

I think Roy was Donald’s attorney, and I think he represented Donald as he was coming into Manhattan. The world of Manhattan real estate is much more dog-eat-dog than Queens. Donald’s father was a massive success in middle-income housing in the outer boroughs, but Manhattan is the fast track. It’s a whole different thing. I think to a certain extent, Roy, who was a rough-and-tumble fixer, Democrat, power within the Democratic power structure in New York City, close friend of Mayor Abe Beame, close friend of Carmine DeSapio, the boss of the Manhattan Democratic Party, I think he was like Donald’s ambassador to the world of Manhattan.

Donald at the time is just — has just hit New York. He’s come in from Queens; he’s got his bachelor pad; he’s doing the club and the scene; he’s a celebrity, or he’s becoming a celebrity. How much of all of that was just plain fun in those days?

Well, I think he’s having the time of his life. He is a bachelor; he’s an eligible bachelor. The Hyatt Hotel deal is a massive success, even though many people are skeptical that he can pull it off. It’s the fast track. He’s in the real world, and he’s a major player. So he’s really spreading his wings when he comes to Manhattan. He tells a story that his father said don’t do it, don’t go there. You can make a fortune out here in the boroughs. But Donald wants to tackle something bigger and harder. Of course he becomes the best-known name in Manhattan real estate. … Trump has catapulted himself into a brand. Even in those days, he’s a brash New York real estate guy, but he’s beginning to cultivate a national following and a national celebrity.

Celebrity is the largest single asset that he brought to the presidential race. Trump can always get covered because he’s unscripted, because he’s uncoached and unprogrammed; you never know what he might say. The only thing predictable about Donald Trump is he’s completely unpredictable.

And the networks love it.

Well, they tune in because it’s interesting. Look, Hillary Clinton is an experienced politician. You can tell that everything she says has been poll-tested, focus-grouped, roundtabled, discussed. I mean, did they test Dangerous Donald as opposed to Duplicitous Donald? None of it is genuine. It doesn’t come across as genuine. It comes across as canned and stale. Nobody puts words in Trump’s mouth. Believe me, I’ve tried for 30 years. He’s his own man. He’ll look at your briefing material; he’ll read a pithy memo; he’ll ask tough questions. But at the end of the day, he’s the one who decides what Trump says.

When you first meet him, Roger, did you see the ingredients there with this guy for a politician that could just maybe not president, but could really run the table?

Yeah, because he has that quality of charisma that Reagan had, but Bush never had; that John Connally had, but Bush never had. It’s a size. I don’t mean a physical size, although he’s a tall, broad-shouldered guy, and he’s a great physical presence. But there’s a certain electricity, a certain celebrity status that he has where you say, “Wow, this guy’s really got it.”

Did you know how the dad did business?

Yes.

They all understood you’ve got to have a politician; you’ve got to have a couple of politicians. You’ve got to have Abe [Beame]; you’ve got to have [Hugh] Carey? You’ve got to have these guys in order to do this business, because the idea of the business is don’t put your own money in it. Put either government money in it or investors’ money in it.

Well, I think that is more true of Donald than his father. His father was most famous for walking the construction sites after close-down and collecting nails to put them back in the barrel so they could be used again. His father and Donald share the same Scottish frugality. I think Trump is eminently proud of the fact that he’s spent less than any other candidate but got more votes. I mean, he really thinks so much of the political professional class is artifice, that it’s phony — the pollsters and the media coaches and the media buyers and the focus-group guys.

He has always thought that a lot of that was unnecessary. I didn’t necessarily agree with this view when he started this particular campaign, but he’s turned out to be right. In other words, you can counteract millions of dollars of negative TV ads by going on every program possible and rebutting. I never thought you could combat paid media with free media, but he bet you could, and because he’s Trump, he could get covered. So he would do five shows a day, and it worked extraordinarily well without him having to go into his pocket.

Let’s go through his political education from the first stuff you begin to try to do with him. There’s talk of a “Let’s run against [Mario] Cuomo.” Take me to that.

Most recently?

July ’87.

I think the Republican Party in New York immediately sees the potential in Donald Trump. He’s charismatic; he’s wealthy; he’s got standing; he’s got size. And politics in New York is most cyclical. This is Rockefeller country through the late ‘70s. Republicans dominate a Democratic state. After that, you have the rise of Hugh Carey, then the rise of Andrew Cuomo — pardon me, of Mario Cuomo. People say, “Well, the Republican Party here is done; they’ll never come back,” except for then they add George Pataki for three terms.

Politics here is cyclical. The Republicans are always looking for their next big star, so Republicans implore him to run for mayor; they implore him to run for governor. But in truth, all those jobs are too small for Donald Trump. He’s only got his eye on one job. He thinks there’s only one job that’s better than the job he has now, and that’s the big job.

Even back then, even in the late ‘80s?

Even back then.

So that’s fascinating.

Yeah, because he would say things like: “I don’t think I’ll ever run for office, but if I do run, why wouldn’t I go for the top? Why would I fool around with Albany?” He wouldn’t be happy living in Albany. His interest has never been in state issues. There’s an amazing consistency. I would concede that he’s changed his views on some issues, but trade, NATO — these are issues he’s been talking about for 30 years. There’s a total consistency.

Let’s talk about the first newspaper ad, the first foreign policy newspaper ad. Where does that come from, Roger?

Comes from his gut. Based on his own reading, he has decided that NATO made sense after World War II. We were rich; everybody else was poor. They were our allies; we needed to support them. Today, we are poor, and they are rich, but we’re continuing to pay. It just defies common sense. He’s felt this way for a long time.

How did you guys decide to put that ad together, spend the money? What’s the point? I mean, I read somewhere it was $90,000 for the ad.

He decides he wants to make a point. He’s the one who says, “Look, maybe I’ll take out a full-page ad in The New York Times.” He does the first draft, and he does the final draft. There’s tinkering around the edges, but he knows what he wants to say, and he realizes that if Donald Trump buys a full-page ad in The New York Times, the press stories about the ad will actually reach more people than the ad will. He understands the news cycle.

I think one of the things he really learned from Roy was the manipulation of the celebrity press, the so-called society press, “Page Six,” The Daily News. He plays them like a piano.

How does he do that?

Because he’s always phoning in the tips. He understands that you can place stories that those kind of reporters want to know. They want to know what Gloria Estefan drank when she was at Mar-a-Lago for the party. They’re looking for celebrity gossip, and Trump is a great source. He knows a lot of rich and fancy people, so he’s got the coin of the realm.

Is it good for business?

It’s great for business, because it helps build the Trump brand. Again, he’s a Manhattan real estate developer who’s known worldwide. That’s a phenomena [sic].

Why? What does he do? What is it, Roger?

Because he’s the greatest promoter of all time. He’s a promoter. He understands public relations. He understands the media cycle. He understands giving the media a little bit because they’ll just want more. He cultivates individual reporters on a personal basis. He understands how the system works. He actually understands it better than politicians, and therefore he has generally speaking, I think, always enjoyed very good press, particularly in New York state.

We’ve now written and placed the ad about foreign policy. Then there’s a trip to New Hampshire. What’s that about?

It’s 1988. He has met both [Michael] Dukakis and Vice President George Bush. He is not particularly impressed with either one of them. He’s been a supporter of Reagan, but never particularly a supporter of Bush. I arranged for the Portsmouth, N.H., Chamber of Commerce to invite him for a luncheon speech, and a local Portsmouth city councilman named Mike Dunbar forms the first known Draft Trump for President committee, sends a press release to the Manchester Union Leader, which of course gets nice pickup, and Trump flies in in his black helicopter, and of course the helicopter gets as much coverage as the speech, because they’ve never seen a helicopter like this before.

It’s a sellout. We have 2,000 people. Vice President George Bush had addressed the same Chamber of Commerce the previous month, he had 500 people, which was the biggest crowd they’d ever had. So the Trump phenomena [sic], you can see it early. Now, in truth, I don’t think he was ever serious about running in 1988. I think he liked the publicity; he liked the notoriety. It was great media, but it wasn’t the right time in terms of his business and what he was trying to achieve. He still had mountains to climb. …

He writes another ad, the ad about the Central Park jogger case. What’s the itch he’s scratching by doing that?

Well, recognize that this is prior to the rise of [Rudolph] Giuliani. Crime in New York is an enormous problem. It’s become the crime center of the world. Therefore, I think it’s a comment on the deterioration of the quality of life and the safety of the streets in New York. It’s a precursor to the rise of Giuliani and later [Michael] Bloomberg, who bring the crime rates way down. So I think the fundamental theme is toughness on crime. Also, remember in the tabloid media, these were particularly horrific crimes, and therefore there was huge public feeling about them, anger, because this woman was so badly defiled. I think it’s a manifestation of New York at that time.

Is he testing? Is he that guy? Is he just picking up pieces, getting a sense of the zeitgeist, what works, what doesn’t work?

I don’t think he’s that Machiavellian. That would imply that there’s a plan. I’m not sure that there is a plan. Even at that point, he’s not hungering to be president of the United States. It’s an idea in the back of his mind. He loves the media speculation about it. …

OK, so you go to work for him in Atlantic City?

Well, actually, at first in 1980, Reagan is elected. In 1981, my partners, Paul Manafort, Charlie Black and I form Black, Manafort and Stone, which is a lobby firm — I’m actually hired to represent him in Washington. He has a number of small but important issues. For example, the Treasury Department is rewriting the currency transaction rules as they pertain to casinos. He has an interest there. He’s built a couple of skyscrapers that are five feet taller than the FAA-allowed limit. He needs a waiver there. He buys the Trump Princess from [Saudi businessman Adnan] Khashoggi, but it’s too big to come into the Atlantic City harbor without dredging. He needs dredging permits. Those usually take three years. We got them for him in a couple months.

He has a number of small but important federal issues. I later work on some casino issues when he and Steve Wynn go head-to-head in Atlantic City — the War at the Shore, they called it. And it’s a slugfest. The fact that they are close friends today is amazing in view of how bitter and epic this fight was. … So I work for him in Atlantic City. He’s got some other minor traffic issues. But I’m handling both state and federal issues for him on and off for 30 years.

What’s the casino business about for him? Why? What is it? Is it more than just a cash cow? Is there something else he’s doing, or just a good, viable business? What’s up with that?

Well, he’s in first, and therefore, he makes an enormous amount of money on Atlantic City. The problems with the Trump casinos are not Trump casino problems; they’re endemic to Atlantic City. It has no airport to speak of. How do you get there, by bus, by car? So you have that. Also, you have the ultimate proliferation of Indian gaming in Connecticut, in New York, and that detracts from the monopoly of Atlantic City.

Trump both knows when to get in, but he also knows when to get out. And, of course, it has glitz. The Trump Taj Mahal — and I was there for the grand opening — was the state-of-the-art casino in the United States when it was opened. He does very, very well in Atlantic City, but he also knows when the structural problems and the competition get to the point where it can no longer be profitable, it’s time to leave.

… When you’re handling a lot of the other side business for him, are you also thinking about his political future? Is part of you, Roger, thinking, hmm, I wonder where the opportunities are for this guy?

I was the one who was pushing 2000. First of all, recognize that because of Ross Perot’s two relatively strong campaigns for president, the National Reform Party is entitled to federal funds. Trump says: “Wait a minute. Let me get this straight. I get nominated, and they give me a check for $58 million?” And I say, “Yeah, that’s how it works.” So this is OPM; this is other people’s money. What a great idea. So I think he explores it. But at the end of the day, the timing’s not right. We go to California, and it’s ironic, because he wraps up the California primary to win this nomination. The crowds we got in California in 2000 were — remember, California is very celebrity-conscious. They’ve had Ronald Reagan; they’ve had George Murphy, [a dancer and actor who served in the U.S. Senate from 1965 to 1971]; they’ve had later on Arnold Schwarzenegger. Celebrity is very big. They’re kind of out ahead of the rest of the country.

Trump is very big in 2000. We have record numbers that come to our events, and we’re exploring a presidential candidacy. You can see the first seeds of Trump-mania in California in 2000. But if he were here today, he would say, “You know, you wanted me to do that more than I wanted to do it.” And that would be true.

What was his reluctance?

I think he still had business things he wanted to achieve. He was still running his company. “If I leave, who’s going to run the company?” That problem is obviously solved by his adult children today, in whom he has enormous confidence and trust.

So when he leaves the Reform Party, what’s the reason?

Well, legally, the way this works is he has been a registered Republican his entire life. In order to be eligible for the Reform Party nomination, he has to affiliate with the New York State Independence Party. So he switches his registration, and of course then we leak the fact that he has switched his registration. People see that as an indicator that he’s going to run. We get a whole good news cycle out of it. As soon as he decided not to run, he went back to the party of his parents. He re-registered as a Republican.

He stays there until the Gulf War. When Bush leads us into the Gulf War, he is so opposed to the war, he switches his registration very briefly to the Democratic Party. He stays in the Democratic Party until George W. Bush leaves the scene. Then he switches back to the Republican Party.

What’s he doing?

You know, I was unaware of that sequence until I read about it in The New York Times. I never knew he had briefly become a Democrat. It’s his personal protest against the neocon policies and the economic policy of George W. Bush. He is initially favorable to Bush and I think very disappointed between the war and the economy. He’s not a Bush fan.

Is everything from that first New Hampshire trip in ’88 to the Reform thing, when you’re doing the New Hampshire trip and the two newspaper ads, that’s The Art of the Deal coming out, right? Is everything kind of cross-feeding? Is that always on his mind? “I’m branding.” You said it before. “I’m branding, I’m running, I’m not running,” whatever it is?

I don’t think it’s that Machiavellian. I think he likes coverage, and he knows how to generate it. I think it’s very ad hoc, but it’s very successful. By the way, I think his campaign for president this year has been very ad hoc. It’s totally his gut. We didn’t know he was going to raise the wall. We didn’t know he was going to talk about crimes committed by illegal aliens and illegal immigrants and that, you know, that people had been murdered and raped and so on.

And of course, the reaction of the mainstream media is “That’s it; he’s done. You can’t raise these questions. This won’t work.” Then shortly thereafter, he criticizes John McCain. Once again, the elite media says, “McCain, he’s an icon.” … It doesn’t blow him out of the race. His poll numbers actually go up.

Let’s go to the birther thing. Where’s that coming from?

Excellent question. I assume the internet. I am not the progenitor of that, meaning I don’t first bring it. I don’t bring the phenomena to his attention … But Trump understands among Republicans there’s a very substantial majority who have questions about Obama’s origins and how he just pops up out of nowhere to become a national figure and whether he was, in fact, eligible to serve as president.

That explains in my opinion why Trump zooms to the head of the polls, leading Mitt Romney in 2011, early 2012. So I can’t answer the question on the fact that he is naturally inquisitive and he likes to read and it’s out there on the Net. It’s just not traffic in elite circles.

You think he was sitting there poking around and said, “Wow, this is important.”

Or, more precisely, somebody gave him a printout and said: “There’s this terrific article. You should read this. It’s very interesting.”

What about the racial implications of it? Does he think about stuff like that?

I don’t think he ever viewed it in those terms. Ironically, when we were doing very substantial survey research for the casinos, trying to look at our customers, our potential customers, to see what it is they liked about Trump, what they didn’t like about Trump, if you had a choice of going to a Trump casino or going to the Golden Nugget, why were you going to Trump? And what we found was it wasn’t the $12 steak dinner; it wasn’t the loose slots. It was Trump. They wanted to play in Trump’s house. It was his branding. It was viewed as a gold-chip brand.

And the most interesting thing was the groups he was most popular with were African Americans and Hispanics and middle- and lower-middle-class whites. That’s his constituency. It’s not the Ivy League-educated; it’s not the people with postgraduate degrees; it’s not the elites. It’s working people. A certain part of this appeal is aspirational. In other words, “If I were rich, that’s how I’d live.” The plane, the helicopter, the mansions, the glitz — they dig the whole Trump shtick, the whole lifestyle.

There is no question that the birther phenomena [sic] dampened some of that, but even today he’s running substantially ahead of where John McCain or Mitt Romney ran among African Americans. Now, you can say that’s not a hard standard. Really? Three percent more of the African American vote and you’d be calling him President Mitt Romney right now. So it’s large enough to be significant. Now, either he can build on that — whether he can hold that or build on that, that’s what a campaign is about.

Let’s talk a little bit now about The Apprentice, because here’s this guy; he’s already, as you say, rich already. I mean, he’s had a tough road in the late ‘80s, early ‘90s. He’s hit the wall with a lot of stuff.

But the comeback makes his legend even bigger.

This is what I want to hear from you.

The Art of the Deal is a barn burner. It’s a huge best seller. It really puts him on the map as a national figure. Then he has his financial difficulties. He emerges from them, he writes —

How does he get out of them?

Well, because it’s very clever. The man has ice water in his veins. He says to the bankers: “I’m worth more to you alive than dead, so you have two choices. You can get screwed and lose everything, or you can work with me, and we’ll work our way out of this.” It’s brilliant, and he’s fearless. I mean, the guy is completely fearless.

… You know him well enough, Roger, to know whether when he was — when the helicopter crash happened, when the Taj wasn’t making the kind of money it needed to make, when the Plaza was never going to pay out, when the Princess was an expensive bauble and he finally has to face the banks, is he the kind of guy that gets depressed, that gets down on himself?

I’ve just never known him to be depressed. I’ve never known him to be negative. I’ve never known him to be insular. He was always looking to the next mountain. He was confident. I think his self-confidence is something that people read. I think it has a lot to do with the success of his candidacy. He’s a can-do guy. He always believes that you can do that deal; you can do something better. And I think he has the same attitude coming out of the ‘90s when he’s back on top after clawing his way out of financial difficulty.

So that leads us to The Apprentice.

Which is the greatest single asset to his presidential campaign, because for 14 seasons, he is viewed by the voters, by the population, in a perfect light. Think about it. He’s perfectly made up. He’s perfectly coiffed. He’s perfectly lit. He’s in the high-back chair making tough decisions. What does he look like? He looks like a president. Now, I understand the elites say, “Oh, that’s reality TV.” Voters don’t see it that way. Television news and television entertainment, it’s all television. They’re still learning about Trump. They’re getting more comfortable [with] Trump.

The Apprentice takes him into the stratosphere in terms of his celebrity. It’s coast to coast; everybody knows who Donald Trump is. Ironically — and you never see this — the first season was the biggest; the last season, 14 seasons later, was the second biggest. And the numbers are really de minimus. It’s a couple hundred thousand less viewers. That’s a long run in television. But I think it enhances his standing. Again, it makes him larger than life.

… Romney, very happy to receive his endorsement. Why does Trump want to do that? What is that all about for Donald Trump?

I think he becomes convinced that Romney has too much of a head start and that Romney is going to win. And Donald is opposed to Obama. He wants to do whatever it takes to defeat Obama. He doesn’t think Romney is ideal, but he’s a businessman; he’s superior to Obama. … I think Trump rightly believes that Romney never utilizes him properly. He does robocalls to working-class neighborhoods in some of the middle primaries, where I think he’s beneficial. But Romney never really utilizes him. I always thought that Romney was more interested in getting Trump out of the race than he was in getting Trump’s endorsement. I really think that’s what it was about.

Let’s go back to a moment in the birthers that I forgot to ask you about. The birther thing is big. He’s flying to New Hampshire at the moment that the president is releasing —

As Trump would say, releasing something — whatever it was he released, because obviously there are Internet skeptics about whether it’s his birth certificate. But more precisely, why now? Why not when he’s running against Hillary? Why not dispose of this, get rid of the issue if it’s not an issue?

What is Trump doing going to New Hampshire?

He’s beginning to warm up to run for president. Trump is able to introduce the issue into the mainstream so much so that Obama ultimately has to deal with it, and he deals with it by releasing what he says is his birth certificate.

And does Trump feel that that is a victory?

It’s a total vindication. …

Obama, at the White House Correspondents’ Dinner, uses humor, sarcasm, whatever it is on Donald. How did Trump take it?

This is just a personal view. I think that is the night that he resolves to run for president. I think he is kind of motivated by it. … “Maybe I’ll just run. Maybe I’ll show them all.”

You mention he didn’t like Obama. I’m not talking about personally, but maybe it’s also personally. What is it about Obama that motivates him in political terms?

Well, I think he was actually optimistic. He said this: It would have been great if he succeeded. Hope and change sounds great. You know, we need it. So I don’t think he started out disliking Obama, and I don’t mean on a personal level. I think he was optimistic and hopeful. But after four years, there was no hope and change, and therefore I think he was disappointed in him more than disliking him. And he saw that Romney should have been able to beat him. …

Was the birther thing about the base, the Trump base? He knows now who they are, one of the things they’re worried about, how to reach them, how to touch them. Is that what’s going on there? You think he’s finding his base, or did he already know who it was?

I think he has an ability to put his finger on issues that motivate people. I think this is also true of immigration. He’s absolutely true. We wouldn’t have been talking about sanctuary cities; we would have had immigration reform legislation if he hadn’t elevated the issue with his announcement. He made it a potboiler issue when it was, at that time, probably a secondary issue. He has had an ability to be ahead of the trend and I think to identify, and in many ways, drag issues into the mainstream that weren’t there before.

Take me to the planning, if you can, of the announcement, the escalator, the whole thing. Take me inside that. Was this all his idea?

Yes.

Were you involved? How did it work?

Actually, I had just undergone eye surgery so I couldn’t travel, so I’m keeping tabs on what’s going on by phone. But it’s his orchestration. He’s got a great sense of theater.

What did he say he wanted to do?

First of all, he wanted a big crowd. We had a big crowd. He understood the drama of coming down the escalator. He had a prepared text; he used a small part of it, but mostly speaking from the heart. And it’s wildly successful. But the orchestration of it recognizes his showmanship. He’s a showman above all.

The Mexican stuff. Man, it blows up.

Yeah, it’s all from him. He reads about it. He’s the one who elects to raise it.

What makes him say it at that moment?

Because he’s read it in the paper and he believes people respond to it. It’s something that he personally objects to, the fact that illegals are committing crimes in this country. People would not be dead, would not be raped, would not be violated if they weren’t here to begin with. I think he’s putting his hands on something that is about to become an enormous national issue, which of course it does.

Let’s talk for a minute about the media. If he was great at the tabloids in New York in 1977, and if he was amazing around the Ivana divorce, and if he was amazing about all of it, The Art of the Deal, The Apprentice, if I was to think really hard about it, I would say that the time was just exactly right for Donald Trump to come out on the stage. And cable TV is cable TV; they’re hungry for things. There’s 24-hour —

But above all, he understands the value of ratings. They wouldn’t put him on if he wasn’t getting ratings, and he wouldn’t be getting ratings if he wasn’t interesting, and he wouldn’t be interesting if he wasn’t Donald Trump speaking from the heart. It’s like a man working without a net. You’re going to tune in to see what he’s going to say because it could be anything. It’s got a daredevil quality to it. It’s genuine; it’s real. You’re holding your breath: “What is he going to say next?”

It’s so completely different than your career politicians who are so bone-dry and so tightly scripted that they don’t want to offend anybody. They’re operating off of a speech written by some 25-year-old or sophisticated focus groups or polls. Look, this is a guy who ran for president and won the nomination without paying for a single poll — no complicated analytics, no targeting, without spending hundreds of millions of dollars on positive and negative TV ads, saturating the airwaves. It’s an entirely free-communications-based strategy. No mailing, no radio ads, it’s all him. It’s the Donald Trump show on a daily basis.

He knows that because he can get ratings, he just has to call CNN or Fox or the networks and say, “Hey, I want to be on; I want to do the Sunday show,” and they’ll book him because he’s guaranteed ratings. And when they get ratings, they can charge more for their commercials. It’s business, and he understands that.

The Reform Party run, the campaign that he runs is fascinating. He’s traveling around with Tony Robbins and with sport heroes and generals. What was the thinking about? Well, it was all free; he wasn’t paying for any of this.

No, it was actually — he actually made money on it, because he had a deal with Tony Robbins where he would give 10 speeches and Robbins would pay him $100,000 a speech. Those numbers are euphemistic, but that’s as I remember it. So we would time our campaigning or our pre-campaign, our exploratory campaigning, to coincide with the time that he was in Southern California. He visits the Holocaust Museum there; he gets a tour. We do a very highly publicized event on the rooftop of the hotel for Reform Party officials. But he goes out to Anaheim where there’s 6,000 screaming people in a stadium to do his speech for Tony Robbins. He would correctly say, “I’m the only guy who explored running for president and made money on it.” It didn’t cost us money; he made money because of the deal with Robbins. …

After Romney’s defeat, I loved it when I read six days afterward, Mr. Trump goes out and trademarks “Make America Great Again.” What was going on there?

Well, I think it reflects the fact that he regretted not running. He thinks he could have beaten Obama. I think he may be right. He was very disappointed in Romney as a candidate. The slogan “Make America Great,” of course, was Reagan’s slogan in 1980. I’m not sure that Trump recalls that, but he trademarks the phrase, which indicates to me he’s going to run again.

That’s how you knew?

Well, I was certain on New Year’s Day right after Romney lost. We had a brief chat. I called him in Mar-a-Lago to wish him happy new year, and we went immediately into a political discussion. Can Jeb Bush be beat? Can Hillary be beat? Who else is going to run? He’s already handicapping. Romney’s body isn’t even cold yet, and he’s already handicapping this election. It was clear to me then he was going to run.

What does he learn from you and Roy Cohn, or where does it come from, his philosophy on politics, his understanding of attack, attack, attack, never defend, the importance of winning the anti-elite base? Where does that knowledge come from?

… The anti-elite phenomena [sic] is something he watched Reagan exploit. He understands the politics of polarization. He’s at gut a conservative. He likes the police; he supports the police; he supports the military. It’s very “silent majority,” as he puts it. He brings that back. It’s obviously originally coined by Nixon, but he brings it back as a phrase. So I think a lot of it’s instinctual. Some of it, I think, may have been learned from Roy. But his evolution is his own. He has watched what’s going on in the political realm. At a certain point, I think he recognizes, “I could do better.”

Any question in your mind that he knew he was going to crush Ted Cruz eventually?

You know, initially I think Cruz handled him very well and cultivated him. And Trump himself has said: “Look, if you say nice things about me, I’ll say nice things about you. People who treat me well, I’ll treat them well. But when people come after me, they better know I’m going to come after them.” And he will. Trump’s philosophy is if you punch him, expect to get punched back twice as hard. It’s instinctual. …

He knows that there’s nothing appealing about Ted Cruz. He’s vaguely creepy. There is something odious about him. He’s like a snake oil salesman. He’s Elmer Gantry. There’s an untrustable quality there, and I think Trump understands he’s not very appealing. When they go to nuclear war, Trump understands how to get under his skin. Why did he raise the question of the National Enquirer running a story with a picture from the Warren Commission that certainly appears to me to be Rafael Cruz? …

It’s not that it’s a burning issue in the presidential campaign; it’s that Trump knows exactly how to get into Ted Cruz’s head. Cruz explodes that morning on TV. He melts down. He gets into a shouting match with voters. He’s yelling and fighting with a 10-year-old boy on national television. He makes an ass of himself. Trump knows the guy’s done. He got under his skin.

…What did he say in Portsmouth? What was the message?

 NATO’S ripping us off. Why are we paying for this? Why don’t the Japanese pay for themselves? Why don’t all our allies, they’re rich now, why don’t they pay for themselves. Trade, we’re getting taken to the cleaners in these trade deals. So he’s already formulating his views as early as ’88.

… When you say he’s interested in the buzz and the media and the attention, is that the end, or is that a means to sell, to expand the brand? Why the interest in the media, in the popularity?

Well, first of all, it’s good for business. It enhances his business. It just keeps making him bigger and bigger. Every time he looks at running for public office, it’s a wealth of positive coverage. I think he understands that politics is show business for ugly people. In his case, he makes the transition like Reagan. He’s a celebrity superstar in the business world, and he transforms to become a celebrity superstar in the political world. The stature gap between him and all these grubby career politicians is enormous. …

And at that time in the ‘80s, when he’s doing the ads and going to New Hampshire, does he think that he can change policy? Is he just frustrated with Washington?

I think it’s a flirtation at that point. Remember, the country isn’t in the kind of difficulties it’s in today. Our politics is somewhat more congenial; more is getting done. We’re not facing the kind of fiscal crisis or international crisis or trade crisis or immigration crisis that we have today. That’s why I say this is a classic case of the time being right for a Trump candidacy. Even three years ago, I don’t think the time was quite right. Now you have a level of dissatisfaction with the voters that we’ve never seen before, and they want somebody with the toughness and the independence. His greatest single asset is his wealth because nobody can buy him, and nobody can bully him. He’s viewed by voters as his own man who will tell it like it is, whether it’s politically correct or not.

If sometimes you don’t like what he says, the important thing is that he tells you what he really thinks, and they respect that even when they disagree with him. The independence from special interests, the fact that he’s not taking campaign contributions from lobbyists or the Koch Brothers or super PACs or billionaires, that he’s his own man, I think that’s his greatest single asset. …

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