“Well, what was that like?” people often ask me, at a cocktail or dinner party, if it somehow comes up that I was once a ghostwriter for Donald Trump. The question puts me in a tight spot. If my first word back isn’t extravagantly negative, I fear they’ll take me for a Trumpster, turn on their heel, and leave me conversing with my canapé.
But the truth is that the year or so I spent in his pre-carroty-orange presence circa 1990, writing a sequel to The Art of the Deal, was at times a hoot and often highly educational.
What I want to tell those who might be curious about the process behind Surviving at the Top, the business memoir that I concocted out of a series of Trump’s ultimately bankruptcy-inducing acquisitions (the Plaza Hotel, the Eastern Air Lines Shuttle, etc.), is that you can’t imagine what it’s like hanging out with a complete dolt who is widely seen as a golden boy until you’ve tried it. It was subversive fun and so much else. I laughed, I cringed, I was astounded at how a human could reach adulthood knowing so little about history, geography, literature, spelling—every grammar-school subject, really, including P.E. And I even found myself—once or twice—feeling sympathy for the incipient devil.
The true challenges of dealing with Trump in those days had mostly to do with the ambiguous role a ghostwriter plays in any subject’s life, and the fact that Trump in particular was so damn socially awkward. For example, one afternoon about four months into our project, I got a call at my Upper West Side apartment from a female assistant of his who cheerily advised that her boss was inviting me to accompany him to the Yankees game that night. He would pick me up in his limousine and deliver me back home at the end of the evening. The seats, it went without saying, would be at least as good as George Steinbrenner’s.
The only problem was, I didn’t want to go. Trump and I had been getting along fine, so well in fact that I was spending a couple of hours in his inner sanctum most days, including that one. Sometimes a ghostwriter is like a doctor, dispensing wisdom and keeping things on course; other times, he’s Mike Wallace, asking the tough questions and saying, “Oh, come on” when he smells bullshit. My role with Trump, I had gathered early on, was supposed to be that of an awestruck amanuensis, who would pluck his brilliant phrases from the air and weave them into a glorious tapestry for the world to wonder at.
In reality, I was doing the heavy lifting for a piece of hackwork I am virtually certain he has never read in its entirety, and I was resigned to that situation, but all the pretending left me exhausted. My neck hurt from nodding at gratuitous lies such as “Yesterday, Charles, I saw a beautiful naked woman walking down Fifth Avenue.” That’s a real quote.
Still, it wasn’t easy to say no to him; he was paying me enough to put my three kids through college and, with that invitation to the ball game, just might have been extending the hand of personal friendship.
On paper, it sometimes occurred to me, we should have been pals. At 44 or so he was a half-dozen years older than me, but we were both bridge-and-tunnel boys who had at least initially gone to Fordham. So, yes, I was torn, but what can I tell you? Sometimes you feel like a nut, sometimes you don’t. I had no choice but to offer robust but insincere regrets and spend the evening wondering about the ramifications. It was all part of the ride.
My neck hurt from nodding at gratuitous lies.
I originally got the call to interview for the Trump job because Tony Schwartz, who’d done an all-too-masterful job as co-writer of the previous book and created a pleasingly fictional impression of a business genius, was busy. I, after cranking out an autobiography with the highly cantankerous test pilot Chuck Yeager, had a budding reputation in publishing as someone who could work with—how can I say this politely?—strong personalities.
I was supposed to be one of a half-dozen writers who would have a brief, get-to-know-you chat with him in his Trump Tower office, but after just a few minutes things got serious and we were talking numbers, as in dollars I would be paid.
Well, not exactly talking. Trump started things off by writing a six-figure amount on a slip of paper, turning the paper face down, and sliding it across his desk to me. I crossed out his number, wrote a higher one, and shoved the paper back. After four or five go-rounds he reached over and, paying the highest compliment a germophobe can give you, shook my hand. The vaunted art of the deal, it turned out, resembled something that happens 10 times a day at Bay Ridge Honda.
As auspicious as this may sound, we hit a bump right away. Thinking it might be interesting to try softening his personality a bit, I sketched out an experimental chapter in which he mused on the differences between himself and a homeless man he’d seen on the street. It was based on an obviously apocryphal story he liked to tell, but he hated it, thinking that in print it made him look insufficiently mighty. He left a dark and growly message on my home answering machine, in full bully mode, ordering me to shred what I’d submitted and go back to the Art of the Deal’s tone of self-adulation, or take a hike.
I let a day go by, then wrote him a letter saying it was his book and he could always request revisions, but if he continued to speak to me in a threatening and disrespectful manner, he could find himself another writer. Then a funny thing happened—nothing. In our future dealings I never acknowledged his phone message, and he never acknowledged my letter.
It wasn’t my charm that lubricated the relationship so much as his love of being constantly interviewed. “Charles, I’d like you to come to Brazil with me this weekend,” he announced late one Thursday. “We can work on the plane.” Trump feared traveling, feeling the further he got from Midtown Manhattan, the more numerous and nasty the germs. However, his casino executives had convinced him he needed to pay court to a São Paulo millionaire who gambled big at his Taj Mahal in Atlantic City, and he’d grudgingly agreed to a two-and-a-half-day trip.
He left a dark and growly message on my home answering machine, in full bully mode.
To his delight, he was stampeded by Brazilian media as he and his then wife, Ivana, arrived at a luncheon he was hosting for the millionaire at a shiny hotel, but when he came to the microphone to say a few words, excitement turned to befuddlement. “First, I’d like to congratulate you all on how well you speak Spanish,” Trump began. (How bizarre was it to applaud people for speaking their own language? How Trumpian was it to get the language wrong?) An aide seated beside him tugged his sleeve and whispered in his ear. “Oh, well,” Trump went on, “Portuguese—that’s just kind of a hip, swingin’ Spanish, right?”
At the luncheon I chatted up a fabulous-looking party crasher actually named Fabula and invited her to a black-tie dinner that night that the millionaire was throwing to honor Trump. When she showed up looking like Bianca Jagger, I was given major props by the half-dozen or so executives in Trump’s all-male entourage, who couldn’t stop telling me how attractive she was.
The next morning, as we waited to board our flight to Rio de Janeiro, where we would go to the racetrack to attend a race named for the high roller, the winks and backslaps continued, despite my insistence that nothing had happened. As soon as we were at a safe altitude, Trump, wearing a serious expression, asked me to step into his private quarters at the rear of his jet. Uh-oh. Was he going to bawl me out for being naughty on the road? Actually no; he wanted advice. “Charles, when you get together with a woman in a situation like this,” he said, “will you keep in touch afterwards?”
Donald was actually relatively inexperienced with women at that point (in an unsophisticated, bridge-and-tunnel-boy kind of way). The piggish, sexually abusive Trump that E. Jean Carroll would know was still in its larval stage. I couldn’t help but feel a pang of sympathy for a man who had trusted me enough to admit his naïveté.
The only other time I felt sorry for Trump was that night I turned down his invitation to the Yankees game. Back at home I decided to relax and get my mind off work by ordering takeout, opening a beer, and turning on the ball game. “Hey, look who’s here!” the announcer said, midway through the first inning. The camera panned over to none other than Donald, who, as the crowd gasped, gave a little wave and flashed his trademark tight-lipped, rheumy-eyed smile. He was sitting right behind the home-team dugout—one of his black-suited security guys on one side of him and an empty seat on the other. He’d been unable to find a friend. I had no choice but to switch to the Mets.
Charles Leerhsen is a former executive editor at Sports Illustrated and the author of several books, including Ty Cobb: A Terrible Beauty. His latest book, Down and Out in Paradise: The Life of Anthony Bourdain, was published last year by Simon & Schuster
