In 25 years at Vanity Fair, I wrote probably about a quarter of a million words for the magazine’s monthly “Editor’s Letter.” Looking back, I devoted a disproportionate number of those words to Trump.
I have a long, curious history with the man, going back to the early 80s. He’s threatened to sue me a number of times, he’s tweeted the rudest things about me, and he’s begged me for favorable coverage. He’s also invited me to two of his weddings, dinner at Mar-a-Lago, and regularly (and valiantly) tried to convince me that he wasn’t “short-fingered.”
When he announced his run for the presidency, I thought the American public would see right through him. They didn’t—they saw around him. So I was seismically wrong there.
But looking back at the words I wrote about him for Vanity Fair (never mind what we did in Spy and what I’ve written for Air Mail over the past year and a half), I could see I had a hunch that his presidency would be a slipshod affair like so much of his life had been up to that point. I thought he would be venal, incompetent, petulant, vindictive, irrational, untruthful, and downright destructive. I also figured his time in office would end badly. I was overly optimistic on all counts.
Trump’s left the country and the Republican Party in the same sort of state he left his bankrupt casinos: broken and bleeding. A shambles.
I had a hunch that his presidency would be a slipshod affair like so much of his life had been up to that point.
December 2015: “With each passing month, the shelf life of Donald Trump’s erratic, if entertaining, presidential sideshow continues to befuddle the smart money in Washington … ”
“My guess is that it is only a matter of time before Trump says something that even his staunchest supporters will find unforgivable.”
February 2016: “It’s interesting that Donald Trump’s ‘Silent Majority’—the adherents to his vision of the American future—have put their shoulders behind the loudest of loudmouths in a field of loudmouths. Nothing, it seems, is beyond his disdain or ridicule … ”
“Americans who don’t buy into his act are coming to realize what New Yorkers have known all along: that Donald Trump is one of the more vainglorious and vulgar people ever to enter the public arena.”
November 2016: “Through word or action, Trump has promoted gun violence, bigotry, ignorance, intolerance, lying, and just about everything else that can be wrong with a society. And yet he marches on, playing to a constituency that just doesn’t seem to care … ”
“I don’t think he will get to the White House, but just the fact that his carny act has gotten so far along the road will leave the path with a permanent orange stain. Trump, more than even the most craven politicians or entertainers, is a bottomless reservoir of need and desire for attention … ”
“At this point, I suspect that Donald Trump is deeply regretting his rash decision to run for the presidency. It’s difficult to know if he envisioned the kind of scrutiny that seeking office would bring down upon him and his family. The thing is, megalomaniacs tend to believe that whatever they say or think is fact, regardless of how at odds those notions are with reality…. This is the point when men—and it’s largely the preserve of men—wade into swamps of trouble … ”
“Trump’s family members, exposed to myriad slights, speculations, and accusations, no doubt wish he had left it all alone. The brand, such as it ever was, is tarnished, perhaps permanently.”
“My guess is that it is only a matter of time before Trump says something that even his staunchest supporters will find unforgivable.”
February 2017: “A preening and vindictive strongman at the top, living in gilded opulence, and surrounded by generals and business cronies. Is this what a junta looks like? … Does the walk-up to a Donald J. Trump presidency seem like one long string of Onion headlines? Bit of both, actually. We’re on our way down the rabbit hole, and nothing is what it seems … ”
“In the time it takes to build a house, a nation that was forged on inclusiveness has begun to accept the most extreme forms of the unacceptable as a new normal. In word and deed, the president-elect has turned on a tap of hate—and it will be a while before we can turn it off … ”
“Trump went straight to the voting class—specifically, that great swath of Americans who feel they have been left behind in the wake of epic technology disruptions, the banking scandals of the Great Recession, and the influx of immigrants from places they have trouble finding on a map. Baby-boomers make up a sizable portion of the Trump base. They inherited a world ripe with the promises of a good life—or at least one better than their parents had. Many of them found this new, moneyed iteration of the American Dream. But the ones who didn’t—and they are the majority—feel like diners who have come late to a buffet where all the shrimp and lobster have been taken. Trump, still gnawing on his shrimp, tapped into this disaffection with great gusto … ”
“But no amount of grifter charm can conceal his alarming disregard for facts and truth…. Trump not only doesn’t know the unknowns but appears to have no interest in even knowing the knowns … ”
“As he drags family members into the administration, a certain amount of sympathy has gone out to Tiffany Trump, the president’s daughter with his second wife, Marla Maples. In the end, being the forgotten Trump may turn out to be an asset.”
“Trump went straight to the voting class—specifically, that great swath of Americans who feel they have been left behind.”
March 2017: “Even the Republicans, who have ridden this stalking horse into office, holding their noses in the hope that they can manipulate him into furthering their agenda, are now mulling their options … ”
“As it stands, the president’s wife is not turning out to be the paparazzi bait one would have expected…. She gamely showed up for the post-inauguration balls—which on television looked about as festive as a Walmart on a Sunday morning. And as for the First Couple on the dance floor, I’ve seen cozier body language in a hostage situation … ”
“Make no bones about it. The First Family are interested in one thing: furthering themselves and the so-called Trump brand … ”
“The president’s muted response to the North Korean launch could have something to do with the fact that he may understand that he has more in common with his counterpart in that country than he would care to admit. Goofy haircut? Check. Boxy frame and ill-fitting suits? Check. Erratic and unstable personality? Check. Simplistic way of looking at the world? Check. Primitive vocabulary? Check. Hates the country to the south? Check. Brooks no opposition from underlings? Check. Thin skin and a tendency to disproportionately lash out at critics? Check. Father gave him his career? Check … ”
“The description in The New York Times of a staff unable to figure out how to turn on the lights in the Cabinet Room of the White House was image enough. The paper also reported that Trump stalks the halls of the private quarters at all hours of the night in his bathrobe, firing off Twitter missives. I don’t know how that bathrobe description plants itself in your mind, but I think less Noël Coward silk and tassels and more leisure fabric with food stains, a high hemline, and karate sleeves … ”
“Republicans, who should know better, have flocked to this man for reasons of self-advancement or outright venality. My guess is that many of them will live to regret their attachment to him … ”
“If the half-dozen or so Republican senators who are not walking lockstep with the administration can corral another half-dozen of their colleagues to join them, there is still a chance for the rest of us and the world. And they will be heralded as heroes.”
April 2017: “Trump may be a joke, but the chaos and destructive forces around him are not. If he can cause this much havoc during his first few months in office, imagine what the country and the world will look like at the end of four years … ”
“That Trump’s supporters continue to line up behind him remains a mystery. For the Republican leadership—the Vichy Republicans, as they have been labeled—their collaboration will bear a stiff price down the road … ”
“If he can cause this much havoc during his first few months in office, imagine what the country and the world will look like at the end of four years.”
“When the dust settles, the real history will begin. There might be the occasional hack willing to trot out some semi-fictional hagiography on this administration. But, in the end, proper historians and serious journalists will descend in droves to mop up the lies, the half-truths, and the criminality. Trump’s legacy and that of his family could end up in tatters. The self-lauded Trump brand may well wind up as toxic as the once self-lauded brand of another New York–Palm Beach family: the Madoffs.”
June/July 2017: “A serial liar in the office or home is one thing—and stressful enough. But a serial liar in the highest office in the land is something else altogether. Couple that with an erratically fragile ego, a severely diminished mental capacity, a lacerating temper, and access to the nuclear codes, and it’s going to get a whole lot hotter in here … ”
“Trumpian! The word “trump” formerly was a verb used in polite bridge and whist circles. Trump, the man, is now up there with Hercules and Sisyphus with his own branded adjective. I’m not completely sure what it stands for. But when it finally settles into the lexicon, I’m certain that it will be a disconcerting combination of petulant, preening, ignorant, shameless, vulgar, paranoid, vainglorious, reckless, imperious, impulsive, unhinged, callous, corrosive, narcissistic, intemperate, juvenile, disloyal, venal, chaotic, squalid—what have I forgotten? Oh, yes!—and just mind-numbingly, epically incompetent … ”
“As the country emerged from the ill-fated first 100 days of the Trump presidency, the odor of permanent scandal was already palpable.”
August 2017: “When the historians finally weigh in on the Trump presidency (and it’s never too early to start), they will have a troubling question to answer. It’s not why many good Americans, angered and disgusted by the dysfunction of Washington, were misled by Trump’s mendacious rhetoric. The real question is why powerful people who … knew better—and who now know exactly what kind of man Trump is—continue to support him and make his presidency possible. These are the same men who have in the past publicly called Trump a racist, a xenophobe, a jackass, a man of sickening sexual crudeness, and unfit to serve as commander in chief. Trump in his characteristic way has called them things you wouldn’t say about your worst enemy … ”
“Perhaps one day Trump will cross some line that will sufficiently offend their corroded sense of propriety—go too far even for them. You’d have thought we had passed that point a dozen times or more already. If that point is ever reached, and one or more of them peels off and lets his conscience overpower his ambition, the nation will owe them scant thanks.”
September 2017: “But, really, don’t you wonder when the actual work gets done? When does the self-proclaimed deal-maker of deal-makers make his deals? When does the manager of the most complex organization in the world do his managing? When does the president do his actual presiding? If you do get answers to any of these questions, please share them with the rest of us. Because, to be perfectly frank, aside from storming around screaming about the unjustness of everything and trying to erase the legislative landmarks of his betters, the president doesn’t appear to be doing a whole lot. Which, based on his track record as a businessman, may be a good thing. Still, it’s hard not to get the sinking feeling that the U.S. is a big, rudderless ship heading out into open seas with a captain muttering under his breath and rolling ball bearings around in his hand.”
October 2017: “Our timing in bringing a man like Donald Trump into the White House really couldn’t be worse. The man is clearly unfit for any kind of public office, let alone the highest office in the land.... He still has the neo-Nazis and the racists, which must give him some comfort.”
Maybe next time someone—anyone—will listen …