It was not always so. In 1996, longtime New Yorker writer Mark Singer was conscripted by his editor to profile Donald Trump. At that time Trump was a mere Manhattan-centric megalomaniac, a failing casino operator mired in his second divorce and (he claimed) recovering from the bankruptcy proceedings that prompted him to inventory the contents of his Trump Tower home. Conversing with Trump in his offices, apartments, cars, and private plane, Singer found himself fascinated with this man “who had aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul.”
In Trump and Me, Singer revisits the profile and recounts how its publication lodged inside its subject’s head as an enduring irritant—and how Singer (“A TOTAL LOSER!” according to Trump) cheerfully continued to bait him. He reflects on Trump’s evolution from swaggering buffoon to potential threat to America’s standing as a rational guardian of the world order. Heedlessly combative, equally adept at spewing insults and manipulating crowds at his campaign rallies, the self-proclaimed billionaire has emerged as an unlikely tribune of populist rage. All politics is artifice, and Singer marvels at how Trump has transfixed an electorate with his ultimate feat of performance art—a mass political movement only loosely tethered to reality.
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About the Author
Read an Excerpt
For decades, the problem posed by Donald Trump to writers, whether it was a daily tabloid reporter or a more high-minded scribe for what used to be known as “the qualities,” was that he was beyond parody. A man of rampaging ego, sufficient funds, and a neediness greater than that of an infant, Trump bestrode New York City, littering the press with one fantastical quotation after another. He was the reliable La Rochefoucauld of our city. But instead of “Hypocrisy is a tribute that vice pays to virtue,” we got “I have so many fabulous friends who happen to be gay, but I am a traditionalist.”
In the pages of the satirical magazine Spy or in the New York Post, Trump was, in the ’80s and ’90s and later, a constant. He would not have wanted it any other way. He was a real-estate marketer and he sold himself wherever he could: there he was in the corner for a World Wide Wrestling match, or humiliating wannabe Trumps on The Apprentice, or demeaning half the human race on The Howard Stern Show. This was a gentleman who went on the radio to say of his former wife, “Nice tits, no brains.” His vulgarity was unstoppable and without limit. He didn’t much care if he came off as a little crude. He knew you couldn’t resist listening. “You know,” he said, “it doesn’t really matter what they write as long as you’ve got a young and beautiful piece of ass.”
Not only was Trump beyond insult or parody, he seemed a distinctly local product, like the smell of a Times Square subway platform in mid-August. In 1960, A. J. Liebling, The New Yorker’s polymathic reporter of midcentury, set out for Louisiana to write about Governor Earl Long, Huey’s more erratic brother, with a similar conviction that his subject was not for export. “Southern political personalities, like sweet corn, travel badly,” he wrote. “By the time they reach New York, they are like Golden Bantam thathas been trucked up from Texas—stale and unprofitable.” This was the problem with Trump in reverse.
I suspect that these factors were at the root of my friend and colleague Mark Singer’s initial reluctance to write about Donald Trump when, in 1996, his editor, Tina Brown, more or less commanded him to do so. I can vouch for the genuineness of Mark’s initial reluctance. I have seen him when he is captivated by a subject—a bank collapse in his home state of Oklahoma, the wonders of the magician and scholar Ricky Jay—but he took a long time to warm to this one. But I am glad he felt the lash of editorial compulsion and moved ahead, if grudgingly, because, as it turned out, he provided us with the best, most insightful, and funniest portrait of Trump. Just as Liebling managed to make an export literary product out of half-mad Earl Long, so, too, did Singer find a way to write with freshness and wit about Trump. His profile is a classic of the form.
Chapter 1 EXCERPT
ONE ON ONE
It’s the fall of 1996. I’ve been a staff writer at The New Yorker since 1974, I’ve worked for a number of editors, and at this point Tina Brown is the editor. Those proverbial tales of adversarial relationships between writers and editors?—I’ve managed to avoid all that. I like Tina. She and I have a clear working understanding. I’ve just spent four years writing a book that was supposed to have taken me a year and a half, during which I haven’t been available to write many pieces for the magazine. So our understanding is that in Tina’s office, in her desk, there is a special drawer. In that drawer is a jar. In that jar are my testicles. One morning my phone rings—Tina: “Trump! Donald Trump! I’ve just had breakfast with him at the Plaza. You’re going to write a profile of him. You’re absolutely going to love him. He’s totally full of shit, you’ll love him! I’ve told him he’ll love you. You’re doing it!”
Which indicates that I am doing it.
I get to work. This takes several months. I go places with Trump. I try to understand his ways of doing business—the nuts and bolts, the smoke and mirrors. Early on, we reach our own working understanding: I tacitly accede to his assumption that I am his tool. It’s Trump’s world. I may watch and listen and occasionally ask questions. When permitted, I am a fly on a wall. Otherwise, as far as he’s concerned, I don’t really exist. This, by the way, I regard as optimal working conditions.
Unaccustomed though I am, I have to take Donald Trump seriously. Among other tasks, I must read many books with his name and photograph on the cover, ghostwritten books ostensibly composed by Trump. The overarching theme of this oeuvre would echo several years later, greatly amplified, in The Apprentice: We both know that you’re a complete putz,but you’re at least allowed to fantasize about what my life is like.
And that is in fact what I want to do. During ourfirst encounter, in his office in Trump Tower, I grasp that, whoever or whatever I had previously imagined Trump to be, he is foremost a performance artist. Appearance is never not, at some level, artifice. My objectiveis to apprehend the person within the persona.
Many books and hundreds of articles have also been written about Trump, and I read those, too.There’s no point in asking Trump questions he’s answered in print already. Anyway, I can come up with a few new ones—say, does Donald Trump have an interior life? No one’s ever asked him that, I bet.