The Donald Trump Conversation: Politics' "Dark Heart" Is Having the Best Time Anyone's Ever Had
Illustration by: Lincoln Agnew

The Donald Trump Conversation: Politics' "Dark Heart" Is Having the Best Time Anyone's Ever Had

At home in Beverly Hills, the candidate talks Murdoch, what he's reading, how he'll redo electoral math and Ari Emanuel's offer to script his convention.

The long day is ending for Donald Trump with a pint of vanilla Haagen-Dazs ice cream. We're settling in for a late-night chat at his Beverly Hills house, a 10,400-square-foot Colonial mansion directly across from the Beverly Hills Hotel. He's here for the final presidential primary, a California coronation of sorts, after rallies in Orange County (where violence broke out and seven people were arrested). He is, as he has been for much of our conversation — and perhaps much of the last year — marveling at his own campaign. "You looked outside before, you see what's going on," he boasts about the police surrounding his house, and the Secret Service detail cramming his garage and snaking around the pool at the center of the front drive. And he's just returned from a big donor fundraiser in Brentwood for the Republican Party at the home of Tom Barrack, the investor and former Miramax co-owner. "There had to be over a thousand policeman. They had a neighborhood roped off, four or five blocks away from this beautiful house. Machine guns all over the place."

One thing to understand about Trump is that, rather unexpectedly, he's neither angry nor combative. He may be the most threatening and frightening and menacing presidential candidate in modern life, and yet, in person he's almost soothing. His extreme self-satisfaction rubs off. He's a New Yorker who actually might be more at home in California (in fact, he says he usually comes to his home here — two buildings on Rodeo Drive — only once a year). Life is sunny. Trump is an optimist — at least about himself. He's in easy and relaxed form campaigning here in these final days before the June 7 California primary, even with Hillary Clinton's biggest backers and a city that is about half Latino surrounding him.

Earlier in the day, I'd met with Trump at a taping of ABC's Jimmy Kimmel Live! at the El Capitan Theatre on Hollywood Boulevard, where he was the single guest for the evening (musicians The Weeknd and Belly canceled upon learning of his appearance). "Have you ever seen anything like this?" he asked. He meant this, the Trump phenomenon. Circumventing any chance that I might dampen the sentiment, he quickly answered his own question: "No one ever has."

His son-in-law, New York Observer owner Jared Kushner, married to his daughter Ivanka and also a real estate scion — but clearly a more modest and tempered fellow, a wisp next to his beefsteak father-in-law — offered that they may have reached 100 percent name recognition. In other words, Trump could be the most famous man in the world right now. "I may be," says Trump, almost philosophically, and referencing the many people who have told him they've never seen anything like this. "Bill O'Reilly said in his lifetime this is the greatest phenomenon he's ever seen."

That notion is what's at the center of this improbable campaign, its own brilliant success. It's its main subject — the one you can't argue with. You can argue about issues, but you can't argue with success. Hence, to Trump, you're really foolish to argue with the Trump campaign. "I've spent $50 million of my own money to go through the primaries. Other people spent $230 million and they came in last. You know what I'm saying?" And this provides him the reason to talk endlessly and repetitively about the phenomenon of the campaign. That phenomenon is, of course, Trump himself, about whom Trump spends a lot of time talking in the third person.

You can try, but it's hard to resist this admiration for himself. The certainty of it, the enthusiasm for it and the lack of not just doubt, but of any negativity. It's all upbeat and positive. The dark, scary, virulent heart of American politics is having the best time anyone has ever had.

Trump at a May 25 rally in Anaheim. Violent clashes between protesters and police followed him through California.

If onstage he calls people names, more privately he has only good, embracing things to say about almost everybody. (For most public people I know, it is the opposite.) He loves everybody. Genuinely seems to love everybody — at least everybody who's rich and successful (he doesn't really talk about anyone who isn't). Expressing love for everybody, for most of us, would clearly seem to be an act. But with Trump, it's the name-calling and bluster that might be the act.

I offer that there are quite a number of people in New York, some we know in common, who are puzzled that the generous, eager-to-be-liked and liking-everyone-in-return Donald has morphed into a snarling and reactionary public enemy, at least a liberal enemy. This, I suggest, might be a source of the continuing dialectic — or to some, wishful thinking — that he does not necessarily believe what he says.

I might detect the most mild sort of annoyance here. Trump says it's that he just never talked about his beliefs in the past — after all, he wasn't a politician. "Who thought this was going to happen?" But his larger point seems to be that such a topic — what he says — is a silly thing to focus on. The point is not about politics, or policies, but about how people, about how many people, have responded to him. It's too big to ignore the bigness. "You heard Jimmy announce tonight that I have the most votes in the history of the Republican Party," he says by way of explanation for the larger issues at hand — i.e., him.

In a way, what this evening's Kimmel show was about was treating Trump's positions as though they are, well, Trump's positions, qualitatively different than other politicians' positions. In fact, you might logically see the Kimmel show as a devastating attack on Trump's views and claims. Kimmel flat out doesn't believe him. That recording of the PR person alleged to be Trump sounding like a PR person? Trump: "It didn't sound like me." Kimmel: "No. Sounded like you." (An exchange repeated similarly several times, with no rancor from either Trump or Kimmel.) "And oh," says Kimmel, "remember when you liked Hillary?" Trump: "I just said I like her. I say I like everybody." And there was Kimmel, at every opportunity, happily mocking Trump, the overexposed media whore.

The effect is not only not damaging, it's fun-loving, comic, even joyous. Kimmel is tickled to have such a good sport to poke fun at, and Trump is tickled that Kimmel is tickled. Everybody's in on it. There are no phonies here. Or everybody here is honest about being a phony. Nobody is taking anyone very seriously — forget what might be at stake in a presidential election. If Trump is the subject of the conversation, then Trump is happy. If Kimmel has Trump as a guest, he's happy. Everybody's happy. (Trump has a staffer take a picture of another picture of Trump when he was previously on the Kimmel show that's now hanging on the studio wall.)

It is this media frisson that, with countless other professional and amateur analyzers, I'm trying to plumb. Surely a big part of the answer lies in the nature of Trump's performance, an unself-consciousness so extreme that he has passed through hurdles of humiliation that would have destroyed nearly all others to emerge as though free of a private self. Trump is only fully alive in public. But another aspect is that, differentiating himself from every other candidate, he has a long, intimate relationship with nearly every significant player in the media and, indeed, lavishes copious praise on almost all of them. He may know few people in Washington, and care about them less, but he knows his moguls and where they rank on the modern suck-up-to list.

On Murdoch: "Rupert is a tremendous guy. I think Rupert [who for several years lived in the Trump building on 59th and Park Avenue in Manhattan] is one of the people I really respect and like. And I think Rupert respects what I've done." But what about Murdoch's grumpy Trump tweets? "When I got into the world of politics, that was a different realm for me and maybe he felt differently. But I think he respects what I've done and he's a tremendous guy and I think we have a very good relationship."

On Redstone: "Sumner, well, he's had a good run. Good run. Terrible it comes to this, but a good run. He'd give me anything. Loved me."

On Leslie Moonves: "Great guy. The greatest. We're on the same page. We think alike."

These are the bulls of his real party.

The party whips, to strain this metaphor, are the news heads: Roger Ailes at Fox News, Jeff Zucker at CNN (who previously at NBC bought The Apprentice and launched Trump as a national TV star) and Andy Lack, now the head of NBC News. Despite his tweets about the "dishonest media," Trump is lavish in his praise of all of them. I ask him to rate them. "That's an unfair question," he says, making a rare grab for politesse. "I know Jeff very well. I know Roger very well. And, less well, but I think Andy has done a very good job."

Among his frequent media and now political confidants is WME co-CEO Ari Emanuel — whose brother, Rahm, the mayor of Chicago, was once Obama's chief of staff — whom Trump says has offered to take charge of the Trump celebratory convention film. Emanuel and Trump, while at seeming odds politically, might in fact be even better united in a kind of hyper salesmanship. "He's a very good friend of mine," says Trump. "He calls me a lot. I call him a lot and we talk. He's very political. Even though he's not political, he's political. He gets it. You're shocked to hear that, right? [About the movie.] But yeah, I might do something with Ari. Does he represent you?"

Sanders called a Trump win a "real danger to the entire world" on May 27.

Trump will turn 70 on June 14, but he shows no sign of fatigue even as our conversation drifts toward 11 p.m. He's been at this since either 4 a.m. or 6 a.m. (he offers different times at different moments). "Today, I'm up at six in the morning, I'm meeting some of the biggest people in the world. I then had to give a speech to a big group, then I had to give a speech at 12 to [Dole Food mogul] David Murdock, [real estate magnate] Donald Bren, tremendous guys. Then I had to drive to Anaheim and give a speech in front of thousands of people. Then I came back and did more meetings, then I did a fundraiser tonight, then I did Kimmel. And now you. You're not a two-minute interview guy."

He hands me a water bottle from the refrigerator (it only contains water and about a dozen pints of ice cream), and we walk through the dark house decorated with hotel-like furniture (a four-star rather than a five-star hotel lobby). He reclines, still in his standard boxy suit, tie slightly loosened, with his Haagen-Dazs on an overstuffed couch in the living room (he asks me not to put my water bottle on the fabric-covered ottoman).

If there's any pattern to his conversation, it's that he's vague on all subjects outside himself, his campaign and the media. Everything else is mere distraction. But I press him about Peter Thiel, the Silicon Valley billionaire who, earlier in the day, has admitted to funding the $140 million Hulk Hogan lawsuit against Gawker. Thiel also is his most prominent Silicon Valley backer and will go to the convention in July as a pledged delegate. But Trump needs reminding who he is, and then concludes he must be a friend of his son-in-law Jared. ("Wow, I love him! So he funded it for Hulk Hogan? You think Hulk Hogan would have enough money, but he probably doesn't.") Indeed, Trump doesn't appear to be interested in Silicon Valley, except to roll off his numbers on each social media platform. ("On Facebook, I have close to 8 million people. On Twitter, I have 8.5 million. On Instagram, I have over a million people. I'm inching on 20 million people. I have friends, somebody that's a great writer, where they write a book and call me up and say, 'Can you do me a favor, can you tweet it?' " "Can you," I interject, "tweet my book, please?" "I will!")

Finishing his pint, he reflects again on the remarkableness of the campaign, asking his traveling staffers, Corey Lewandowski and press secretary Hope Hicks, as well as his son-in-law, to confirm again how remarkable it is. Lewandowski recites the latest polls (as of press time, they show Trump inching to within a few percentage points of Clinton in a head-to-head matchup), and Trump, with something beyond confidence, seems to declare de facto victory.

I broach his problems with women and Hispanics and the common wisdom that he'll have to do at least as well with these groups as Mitt Romney did in 2012. The "pivot" is the word more politico pros are using to refer to his expected turn to the center. "Unless," I offer, "you think you can remake the electoral math." He says he absolutely can. So no pivot. "It'll be different math than they've ever seen." He is, he says, bigger than anything anyone has ever seen. "I have a much bigger base than Romney. Romney was a stiff!" And he'll be bigger with the people he's bigger with, but also he'll be bigger with women and Hispanics and blacks, too. He believes, no matter what positions he holds or slurs he has made, that he is irresistible.

I ask if he sees himself as having similarities with leaders of the growing anti-immigrant (some would say outright racist) European nativist movements, like Marine Le Pen in France and Matteo Salvini in Italy, whom The Wall Street Journal reported Trump had met with and endorsed in Philadelphia. ("Matteo, I wish you become the next Italian premier soon," Trump was quoted as saying.) In fact, he insists he didn't meet Salvini. "I didn't want to meet him." And, in sum, he doesn't particularly see similarities — or at least isn't interested in them — between those movements and the anti-immigrant nationalism he is promoting in this country.

"And Brexit? Your position?" I ask.

"Huh?"

"Brexit."

"Hmm."

"The Brits leaving the EU," I prompt, realizing that his lack of familiarity with one of the most pressing issues in Europe is for him no concern nor liability at all.

"Oh yeah, I think they should leave."

It is hard not to feel that Trump understands himself, and that we're all in on this kind of spectacular joke. His shamelessness is just so … shameless. So how much, I ask — quite thinking he will get the nuance here — is the Trump brand based on exaggeration? He responds, with perfect literalness, none at all. I try again. He must understand. How could he not? "You've talked about negotiation, which is about compromise and about establishing positions that you can walk back from. How much about being a successful person involves … well, bullshitting? How much of success is playing games?"

If he does understand, he's definitely not taking this bait. I try again: "How much are you a salesman?"

Salesman, in the Trump worldview, is hardly a bad word, and he is quite willing to accept it, although, curiously, he doesn't want to be thought of that way when it comes to real estate. But as a politician, he's OK as a salesman.

Trump says he's reading Edward Klein's book Unlikeable: The Problem With Hillary.

In this, he sees himself — and becomes almost eloquent in talking about himself — as a sort of performer and voter whisperer. He is, he takes obvious pride in saying, the only politician who doesn't regularly use a teleprompter. With a prompter, he says, you can't work the crowd. You can't feel it. "You got to look at them in the eye. Have you ever seen me speak in front of a large group of people? Have you ever watched?" He reflects on the lack of self-consciousness that's necessary to make spontaneous utterances before a crowd. He cites a well-known actor (whose name he asks me not to use, "I don't want to hurt anybody"), who had wanted to run for office but, without a script, was a blithering idiot. Trump was never fed lines on The Apprentice, he says. It was all him: "You have to have a natural ability."

I ask if he'll use a teleprompter for his acceptance speech at the convention and, almost sorrowfully, he says he probably will. I find myself urging him not to, precisely for the theater of it all. The spontaneity. Who would want to miss that? Let Trump be Trump.

"Very interesting. What he's saying is very interesting," he notes to Lewandowski.

He's punted on Hillary as a topic since we started our conversation, as though to talk about her was not to talk about him. If in public he needs to treat her as his cause, in private he doesn't want her taking up his time. But I sneak it back.

"Did you ever vote for Bill?" I ask, thinking that both men have as much in common as they have that separates them.

"Let's see … did I ever? Eh, I don't want to say who I voted for."

Indeed. These two '80s guys were undoubtedly once quite in sync.

The anti-Christ Trump, the Trump of bizarre, outre, impractical and reactionary policies that most reasonable people yet believe will lead to an astounding defeat in November, is really hard to summon from Trump in person. He deflects that person, or, even, dissembles about what that person might have said (as much, he dissembles for conservatives about what the more liberal Trump might have said), and is impatient that anyone might want to focus on that version of Trump. It does then feel that the policies, such as they are, and the slurs, are not him. They are just a means to the end — to the phenomenon. To the center of attention. The biggest thing that has ever happened in politics. In America. The biggest thing is the theme. It's what he always wants to come back to. Bigness is unavoidable and inevitable. Bigness always wins.

Before Trump trundles off to bed — actually, before that, never too tired, he plans to watch himself on Kimmel — I ask that de rigeur presidential question, which does not seem yet to have been asked of him. "What books are you reading?"

He knows he's caught (it's a question that all politicians are prepped on, but who among his not-bookish coterie would have prepped him even with the standard GOP politician answer: the Bible?). But he goes for it.

"I'm reading the Ed Klein book on Hillary Clinton" — a particular hatchet job, which at the very least has certainly been digested for him. "And I'm reading the book on Richard Nixon that was, well, I'll get you the exact information on it. I'm reading a book that I've read before, it's one of my favorite books, All Quiet on the Western Front, which is one of the greatest books of all time." And one I suspect he's suddenly remembering from high school. But what the hell.

Donald Trump simply believes he is a unique individual, one whose singular conviction that he is special makes him appealing. And pay no attention to everything else.

A version of this story first appeared in the June 10 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

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