When someone earns a presidential nomination, their biographies are immediately splayed out on the media's metal examining tables and dissected. Every detail of their private lives, every inhalation, is a revelation: Mitt Romney gave people forced haircuts, Barack Obama was once an obnoxious stoner, Hillary Clinton spent years as a teenaged Barry Goldwater supporter. Donald Trump, though, as in all things, is different.
For three decades, Trump has been part of the New York tabloid ecosystem, to such an extent that him being allegedly good at sex was a front-page Post story. Not that his entire life has been documented—it's somehow disturbing to think about a baby Donald Trump, for instance—but from the 80s on his every move, from real estate deals to bankruptcies to feuds to marriages to divorces, has been recorded by a gaggle of reporters and photographers entranced by Trump's hair and the ever-moving, ever-quotable mouth beneath it.
Back then, of course, Trump was a relatively inconsequential figure. A rich guy, sure, a rich guy who made a big deal out of being rich in a kind of you-see-this-watch sort of way, but who was ultimately just a salesman selling himself. The stakes were pretty low—he'd close the deal or he wouldn't, his casinos would change hands or not, but either way, who cared?
One of the best pieces of writing about Trump from that pre-campaign, pre-birther era comes from New Yorker writer Mark Singer. His 1997 profile of the real estate developer is a classic of the genre, and memorably described Trump as leading "an existence unmolested by the rumbling of a soul." Later, when the profile was collected in a book of Singer's work, Trump denounced the writer in a letter to the New York Times Book Review, a piece of publicity that boosted the book's sales. In gratitude, Singer sent Trump a thank-you letter and a check for $37.82, and Trump replied with a missive that called Singer a "TOTAL LOSER"—but the self-proclaimed billionaire also cashed the check.
That story, along with the original profile and Singer's observations about the campaign, is packaged in a slim book out this month called Trump and Me. In a field crowded with volumes about the GOP nominee, it's a worthy attempt at getting past Trump's impenetrable hair and inside his head. I called up Singer to ask him what it was like to have Trump lie to his face, and whether or not he thinks the Donald is actually happy.
VICE: What were your initial impressions of Donald Trump when you met him in 1996?
Mark Singer: After I first met him face-to-face, I came back to the office and said, "Wow, this guy is a performance artist. This is a persona I have to deal with, not a regular-type person with whom there is the usual give and take between a writer and a subject." There was an artifice that was present throughout that was obvious to me from the get-go. This is a person who really choses to be a persona rather than to live the sort of unmediated life you and I might prefer.
He never dropped that persona of all the hours you've spent with him?
Trump's never not in character. He's got a problem now because that persona that he has been cultivating is obviously not useful to him if he wants to win the election. (This presupposes that he actually does want to win the election.)
Is that persona you saw basically the same one everyone sees on TV now?
This is a different manifestation of the same person. The main thing that Trump did that surprised me, between 1997 and now, was birtherism. I couldn't see how that served his interest, even if you assume that there's no such thing as bad publicity. I just couldn't get over that he was engaged in this.
I didn't know that Trump was a racist. I'm not an idiot, but I didn't really see it before 2011 [when he accused Barack Obama of faking his birth certificate]—and then it was obvious to me that it is indeed part of what motivates him. I assume that there had to be some other motive and to this day I can't tell you what it is, other than some function of this person's incredible insecurity.
Trump said a lot of stuff to you while you were reporting the profile that wasn't true. What was it like having him say that stuff to your face?
I didn't mind it. There was not much at stake and my feeling as a reporter is, I love nothing more than being underestimated by a person I'm dealing with. If Trump viewed me with contempt, if I was a nullity, a non-entity, that was all fine with me. It makes my job easier, frankly, if he sees me as this kind of harmless, hapless, schmuck. He wasn't lying to me in a special and particular way. He was just being himself. There were little lies.
It was like this scene I described in the book: he goes up and he shows me his apartment, and I get out of the elevator and he said, "I normally don't show this to people." [The apartment had been featured in magazine spreads.] This was evidence of someone who is a compulsive liar—I quoted [former deputy mayor] Alair Townsend in that piece, saying she wouldn't believe Donald Trump if his tongue were notarized. It was very obvious to me that this was a person who had a very casual relationship with the truth.
Do you still think that he basically has no internal life?
You tell me. How could a person who talks about himself, is as obviously self-involved as he is... To be that self-involved, it just obviates that he's sort of self-reflective. Self-aware examination that's what I mean by an "interior life," where you actually get honest with yourself about what it is you're actually doing in the world. Where you have existential thoughts predicated on how other people respond to you. Most of us, if we recognize unpleasant things about ourselves, we might be in denial about it, but we at least engage in the activity sometimes.
I wrote that line about him, "the existence unmolested by the rumblings of his soul," before I read this biography that just came out last year by Michael D'Antonio, the Newsday reporter, called Never Enough. I quoted in the book the line where Trump says, "I don't engage in self-analysis, because I might not like what I see." That's the closest I've come to any evidence of self-awareness on Trump's part.
The media has been criticized for giving too much attention to Trump, especially during the Republican primary, and not properly and aggressively covering him. Do you think he played the media?
They played themselves, too. There's no question that his persona was entertaining, whether you're watching MSNBC or FOX, whether you think you're rubbernecking at a roadside accident or he's actually getting you excited because he's saying things you want to hear. I feel guilty using the word entertaining , but I think that's probably a reasonable adjective. I didn't have anything to say about all this last year. I was just watching it. I didn't want to write anything about it. I didn't want to join the chorus. I didn't want to add to the attention. That was my feeling for the first several months. Then I realized this guy's not going away.
I kept waiting for people to do the reporting. I mean, Trump University had been out there for a long time. There was so much else that you could do to expose the fact that this guy is not who he claims to be, even remotely. He doesn't have $10 billion. Nobody knows exactly what he has, but it's a fraction of that. So why was the press not on that story? That was a huge failure. I don't want to make that blanket statement because there were people that were doing it: Politifact, the Washington Post, the New York Times was starting to do it. But there was still a lot of time during which Donald Trump was treated as credible when he didn't deserve to be. I'm not saying the press is to blame for Trump, I think Trump is to blame for Trump, but there certainly was a vacuum.
The one qualifier is, the people who really support Donald Trump, they don't care what the press publishes. But that group isn't big enough to win an election. There's a group in the middle who needed to be exposed to the facts about this guy and it took a long time for that to happen.
OK, last question: Do you think Donald Trump is happy? Do you think he's a happy person?
That's a really good question. [long pause] The reason that's a hard question to answer is you want to know whether there's a real person who is Donald Trump, as opposed to Donald Trump this persona. The real person we can ascribe all kinds of human emotions to. But the public Donald Trump "persona" [pause] doesn't function according to any conventional norms of human behavior. It's like watching an actor who's playing a role in a movie or a play and asking asking if the character is happy or if the actor himself is happy. They're two very different things. So I'd say the answer is unknowable.
But I'm operating on the assumption that there's no such thing as an emotionally naked Donald Trump. The Donald Trump who's very thin-skinned, when the persona has been eroded or somehow removed—what's exposed is this insecure creature. Now that's a real person, that insecure person. But the thing that makes it confusing is that the disconnect between the bluster, the bravado, the bombast, and this insecure, thin-skinned, hyper-reactive child—that's where the disconnect is most apparent.
This interview has been edited and condensed for clarity.
Trump and Me is out on July 5 from Penguin Random House.
Follow Harry Cheadle on Twitter.