Best Wishes, Donald | The New Yorker

As someone who once devoted several months to studying Donald Trump’s career and habits, an endeavor alternately excruciating and pleasurable, I wouldn’t have predicted that I would find nothing amusing in his big-footing about and pretending that he had something worthwhile to offer our republic in its hour of great need. When, against my wishes, in the late nineties, I was cajoled into writing a Profile of Trump—the pre-“Apprentice” Trump—I focussed on two fundamental questions: What did he actually do as a businessman? And did he have an interior life?

As for the latter: one Saturday in the winter of 1997 I spent a morning and afternoon with Trump one-on-one, touring construction projects, in Manhattan (office building) and Westchester County (golf courses). He drove, and I sat in the death seat, taking notes. As we cruised up I-684, I asked Trump about his early-morning routines. What time was he awake? Five-thirty A.M. What time did he arrive at his desk in the Trump Tower? Seven or seven-thirty. How did he spend his time before leaving for the office? Reading the newspapers, etc.

“O.K.,” I said. “You’re basically alone. Your wife is still asleep”—he was then married, but not for much longer, to Marla Maples—“you’re in the bathroom shaving and you see yourself in the mirror. What are you thinking?”

From Trump, a look of incomprehension.

Me: “I mean, are you looking at yourself and thinking, ‘Wow. I’m Donald Trump?’”

Trump remained baffled.

Me: “O.K., I guess I’m asking, do you consider yourself ideal company?”

At the time, I deemed Trump’s reply unprintable. But that was then.

Trump: “You really want to know what I consider ideal company?”

Me: “Yes.”

Trump: “A total piece of ass.”

So, regarding the question of an interior life, I ended my Profile with the observation that Trump, who delineated three categories of his real estate offerings—luxury, super luxury, and super-super luxury—“had aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul.”

Trump never challenged my facts, but—surprise, surprise—he hated what I wrote and has taken opportunities across the years to verbally assault me publicly. Most memorably, in 2005 he attacked me in a wonderfully deranged letter to the Times Book Review, which I still regard as the signal accomplishment of my career. Also, framed and hanging in my bedroom is a hand-scrawled message from Trump in which he informed me, “Mark—You are a total loser—and your book (and writings) sucks! Best wishes, Donald.” (Some money exchanged hands—$37.82—as did a couple of Band-Aids, an uplifting correspondence that I described during the New Yorker Festival in 2009, a video of which is below.)

Plumbing the particulars of Trump’s business dealings turned out to be extremely labor-intensive. It was not a high point for Trump, financially, as I wrote at the time:

In fact, by 1990, he was not only at risk, he was, by any rational standard, hugely in the red. Excessively friendly bankers infected with the promiscuous optimism that made the eighties so memorable and so forgettable had financed Trump’s acquisitive impulses to the tune of three billion seven hundred and fifty million dollars. The personally guaranteed portion—almost a billion—represented the value of Trump’s good will, putative creditworthiness, and capacity for shame. A debt restructuring began in the spring of 1990 and continued for several years. In the process, six hundred or seven hundred or perhaps eight hundred million of his creditors’ dollars vaporized and drifted wherever lost money goes. In America, there is no such thing as a debtors’ prison, nor is there a tidy moral to this story.

Still, Trump deserves credit, as it were, for rescuing himself by successfully leveraging his name. As long as others were willing to put up the money, “TRUMP” kept being slapped on buildings that certain people wanted to occupy. His greatest achievement, of course, was branding himself, and his running-for-President nonsense was conceived as an extension of the brand.

During an online chat earlier this week, the question arose whether Trump’s current antics are good or bad for his business. Hendrik Hertzberg opined that “he’s willing to lose money on running for President.” I respectfully disagree about the “willing” part, though the bottom line might nevertheless turn out that way.