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Donald Trump’s Biggest Mistake Might Have Been Getting Elected – Vanity Fair

On May 19, 1962, at an event at Madison Square Garden celebrating John
F. Kennedy, about to turn 45, Marilyn Monroe stepped onstage to sing.
Wearing a dress that matched exactly the color of her skin, a sort of
glowing, gleaming pale, and every bit as tight—a dress, in other
words, that took off her clothes—she made “Happy Birthday” sound
like the lewdest of suggestions, an invitation to sin no mortal man
could resist. In that moment, it became clear that, even if the cake
hadn’t yet been served, our president had already let our movie star
blow out his candle. Pop culture had officially unofficially seduced
politics.

Which is why Donald J. Trump is not America’s first pop-culture
president. There was Kennedy, of course, but also Reagan, Clinton,
Obama. In fact, as far as the past 50-plus years go, Trump’s almost as
much the rule as the exception, the same ol’, same ol’, more or less.
It’s the pop culture that’s changed.

WATCH: Donald Trump Thinks Donald Trump Is the Man

When a movie version of his life story was proposed, Kennedy had one
actor in mind to play him: Cary Grant. Grant, the man-about-town of his
time and ours, the savoir fairest of them all, was the creation of
Archibald Leach, from the slums of Bristol, England. It’s never been
matched. Acknowledging the potency of the fantasy he’d conjured, his
blessing but also his curse, he said, “Even I want to be Cary Grant.”
Meaning he wasn’t. Meaning nobody could be.

Yet that’s precisely who Barack Obama is. It’s the style: an
ultra-stylish style that doesn’t involve primping or fuss. It’s the
manner, too: civilized, self-aware, masculine, though with a faint hint
of ambiguity. Critic Pauline Kael called Grant “the most publicly
seduced male the world has known.” Like Grant, Obama is a love object.
Not passive—reticent, withheld. He doesn’t chase the girl, but he gets
her all right. And he gets her by getting her to go after him. Why, we
(yes, we’re the girls in this scenario) practically threw our votes his
way.

Trump’s erotic stratagem was different but no less effective, and
embodied in his campaign slogan, “Make America Great Again.” The first
time I heard it my reaction was somewhere between hostility and
dismissal. What is this “again” shit?, I wondered. We’re great now,
the richest, freest, most powerful country on the planet. It’s just more
of his dark, divisive noise, I concluded. And it is. But it’s something
else too, as I realized during a conversation with Republican strategist
Steve Schmidt, a pro and very smart and no fan of Trump’s. He referred
to the slogan as “brilliant.” I thought about it some more, and my
thoughts about it began to change. Brilliant I won’t grant. But it does
have a low cunning that might be better than brilliant.

THE 2016 ELECTION WASN’T HILLARY VS. TRUMP. IT WAS MOVIE STAR VS.
REALITY.

Here’s what Make America Great Again is the equivalent of: a guy, a
little long in the tooth, a little broad in the beam (Trump, let’s say),
spots a sensational-looking girl, a girl who’s so far out of his league
it’s a joke (America, let’s say). Instead of complimenting her on her
loveliness, he informs her that she needs a nose job, a tit job, braces,
and to lose 10 pounds. The girl is about to tell him off, really let him
have it, except something stops her. It’s a thought, a devastating one,
that maybe he’s right, that maybe it’s everybody else who’s shining her
on and he’s actually leveling with her. And just like that, in a single
moment, she’s his. At least until she wises up, and that could take a
while.

So we’re clear, I did not vote for Trump. I regard him as a calamity and
a disgrace, the worst thing to happen to this country in my lifetime.
And yet, and yet, I respond to him. When he, a draft deferrer, venereal
disease his quote personal Vietnam unquote, said of John McCain, who had
exhibited such ferocious courage in that Hanoi prison it nearly defies
comprehension, “He’s a war hero because he was captured. I like people
who weren’t captured,” I laughed. The laugh was involuntary, just
popping out of my mouth. What it was also was shameful, appalling,
horrific. It meant that if I hadn’t entertained such a thought myself I
was capable of it. Another way of saying, I was shocked because I
wasn’t. The laugh, therefore, was not so much a signifier of amusement
as recognition.

Though also of amusement because, for someone who’s essentially
humorless, Trump is fun-nee. The sheer recklessness of the things he
says takes the breath away. How dare he? But again and again he dares.
He’ll attack, assault, degrade anyone. At his rallies there was the
sense that even he didn’t know who he was going to go after next. So,
built right in was the frisson of suspense, which is one of the reasons
they were the hottest ticket in whatever town they happened to be
playing. Translation: he turned everybody on. Hillary, by contrast, at
her rallies was calm, earnest, respectful. Translation: she bored asses
off in all directions. Every move she made felt stage-managed, canned.
Not so with Trump. He didn’t need a teleprompter or even a prepared
speech, would just saunter up to that podium and start to blow, to
shpritz, to wing it, basically, and successfully, because he understood
how to capture a crowd’s attention. Hijack it, really.

It’s a talent he’s been cultivating for years. Don’t forget, Trump’s
spent much of his career clinging to the bottom rungs of the
entertainment industry: Miss Universe pageants, WrestleMania IV, V, XX,
and 23, and, of course, The Apprentice. No prestige pictures with
blue-chip directors for him, no HBO limited series, he wasn’t knocking
them dead on Broadway or standing-room-only at Carnegie Hall. Guy’s
played one toilet after another. And in so doing he’s honed not just his
performer’s instinct—at events like WrestleMania, where he once
body-slammed Vince McMahon before shaving the W.W.E. chairman’s head,
his contact with the audience is direct, nothing between him and it,
skin on skin, bareback, baby—but his common touch, as well. (Have you
ever watched Miss Universe or WrestleMania? The Apprentice? Me neither.
A lot of people have, though, and, dollars to doughnuts, they’re the
ones walking around in those little red caps.) A related aside: the
irony that a billionaire who started out life a millionaire has become
the Working-Class Hero is forever being remarked upon by the media.
Like, how much of a nitwit is Average Joe for imagining that Trump is
his man. But it’s Average Joe who’s got it right. Trump is Average Joe
except filthy stinking rich, i.e., a winner. He’s managed to acquire
money without acquiring sophistication. He still talks like a kid from
Queens, has a taste for flashy cars and women, and lives in houses that
make one long for the understated elegance of Graceland. By the way, I
bet he watches Miss Universe, WrestleMania, and The Apprentice, and not
just because he’s keeping an eye on his investments.

And gutter showbiz has, I’d contend, shaped his worldview. As president,
he’s turned a Supreme Court nomination into a Bachelor finale, less
selected his Cabinet than cast it (“If I’m doing a movie, I’d pick you
. . . General Mattis”), and cannot shut up about ratings (he opened
the National Prayer Breakfast by remarking on the tanking popularity of
The Celebrity Apprentice, asking the room full of lawmakers and
dignitaries to “just pray for Arnold [Schwarzenegger, the new
host]”).

Before I get to what Trump is, what Trump isn’t: a businessman. Rather,
he’s a showbusinessman, part con man—how many bankruptcies has he
declared? little guys has he stiffed?—part ham actor impersonating a
businessman. Even more so he isn’t a president. The first few months of
his administration have been somewhere between Dr. Strangelove played
straight and Dr. Strangelove played camp. What he is is a reality star.
In fact, you could argue that he invented the concept. I was born in
1978, not in New York, and yet he’s been on my radar since I can
remember, his life, his loves, his scandals constantly in the tabloids,
and what are “Page Six” and the National Enquirer but the Ur-E! and
Bravo?

The 2016 election wasn’t Hillary vs. Trump. It was Movie Star
vs. Reality. Not only because Obama was Hillary’s most dynamic surrogate
but because practically every star in Hollywood—movie, though TV and
music, too—campaigned on her behalf. And yet Reality won, proof that
movies don’t hold sway over the public imagination as they once did, in
itself proof that the public wants a different type of relationship with
its stars. Stars used to be exactly that: radiant entities to be
marveled at from a distance. Thanks to social media, however, the
24-hour news cycle, distance is no longer possible. Perfectly O.K.,
since an up-close view is what we truly crave, each pore, each wrinkle,
each pimple in high definition. And who’s interested in seeing a posed
photo these days? Better the ones without makeup or undies or even
knowledge. (When a star’s lover or ex-lover sneaks an intimate shot and
then leaks it—ooo-wee, pay dirt.) And beat it with your puff pieces
already. We don’t care about Johnny Depp’s charity work. What we’re hot
to know is, did he really smack Amber around and openhanded or closed
and was he loaded at the time? We continue to be moved by beauty. We’re
also moved, though, and more powerfully, by ugliness: physical, social,
moral. Our stars are still stars, only the term now is ironic since we
don’t look up at them but down.

Trump never feigned virtue during his campaign. And that’s what made
him, for many voters, the authentic candidate. He was a brute and a son
of a bitch, except he, in the immortal words of Real Housewife Bethenny
Frankel, “owned it.” And owning it, in the reality-TV world, which,
let’s face it, is the world we are currently living in, absolves all
sins. It’s why everything that was sure to bring him down—calling
Mexican immigrants rapists, ridiculing the disabled, speculating on the
menstrual cycle of a news anchor, etc.—didn’t, if anything increased
his strength. He became a mash-up of Simon Cowell, Spencer Pratt, and
Teresa Giudice, a super-villain, as impossible to kill as he was to stop
watching.

Interesting to note: traditional stars are bowed but not broken when it
comes to Trump, indeed reality stars in general. They responded to his
inauguration party the same way Jay Z and Beyoncé responded to Kim and
Kanye’s nuptials—by staying away in droves. Well, rejecting the
pretensions of the peacocking parvenu is one of the sweetest pleasures
left to the fallen aristocrat. Also interesting: it’s Obama, the younger
man, and seemingly the more modern in every conceivable respect, who’s
the throwback.

There’s something Trump is every bit as fundamentally as a reality star,
and that’s a stand-up comic. Lenny Bruce, specifically. (Hey, if Bill
Clinton was, according to Toni Morrison, our first black president, why
can’t Trump be our first Jewish?) He’s an eighth-rate version of Bruce,
to be sure, and an unwitting one. Has none of Bruce’s hipness or
perspicacity. He does, however, have Bruce’s shamelessness, and Bruce’s
free-associative, buggy style, and he goes as far as Bruce. His mocking
of McCain was, in fact, like an updating of Bruce’s “Jackie Kennedy
Hauling Ass to Save Her Ass” routine, and equally as blasphemous.

Timing is, of course, everything. It was in the 50s that Bruce, the
lounge-lizard dark prince, started to slay at the clubs in the more
happening cities. Now these days, the present day, is the polar opposite
of that tight-assed decade—gay couples can marry! movie about queer
black youth takes big prize at Oscars! transgender woman on the cover of
this very magazine!—except think again. The 2010s, with its safe
spaces and trigger warnings, its don’t-say-thises and don’t-think-thats,
where feeling like a victim is the hot pastime and male burden is the
new male privilege, are, in certain ways, even tighter-assed, a
neo-Victorian era masquerading as the waning days of the Roman Empire.
Political correctness is just another form of fascism. (That fascism now
comes from the left doesn’t make it any less stifling.) People are
almost comically alienated from their instincts. The super-ego reigns
supreme.

TRUMP SPENT HIS CAREER CLINGING TO THE BOTTOM RUNGS OF THE ENTERTAINMENT
INDUSTRY.

Enter Trump, pure id. No cruelty-free-tofu-nibbling,
prissy-European-taste-having, sorry-excuse-for-a-man man he. Unh-uh.
He’s a big butch American hot dog. He’s not tortured by the idea of
using torture. And a nuclear-arms race? Bring it on, sayeth he, those
loser countries will be eating our atomic dust: “We will outmatch them
at every pass and outlast them all.” He’s a swinging dick and an alpha
male, a maker of deals and a builder of buildings—why, the Manhattan
skyline is simply crammed with his erections! And since we’re on the
topic of erections, he isn’t one of those pencil-necked sissies who need
a woman to sign a permission slip before he’ll try to hold her hand.
Hell no, he grabs pussy first, asks questions later. Is a masher of the
type that’s supposed to have died out generations ago.

This isn’t to say he’s devoid of romantic feeling. Who could forget that
series of impassioned tweets from 2012 in which he urged Robert
Pattinson not to take back the cheating Kristen Stewart. (Had Pattinson
been his fella, he wouldn’t have treated him so shabbily seems to be the
message he’s trying to convey.) There is, too, the wistful, teenage-girl
note that creeps into his voice whenever he talks about Vladimir Putin.
“Do you think Putin will be going to The Miss Universe Pageant in
November in Moscow—if so, will he become my new best friend?” Does
Trump secretly long for the brutal quasi-dictator to take him in his
arms, crush him to his chest, make him dream again?

And then there’s Trump’s temperament, which is, and not to be a traitor
to my sex, on the womanish side. He clutches to his dignity as
tenaciously as a dowager to her pearls. Never does he let an insult roll
off his back. Make a dig about his hand size, for example, and he will
(in fairness, rightly) perceive it as a dig about his manhood. Could the
Donald’s Donald be merely a Don? Not to hear him tell it: “My fingers
are long and beautiful, as . . . are various other parts of my
body.” Touchy, touchy.

It was in 1961 that Bruce said the 10-letter word onstage, got arrested
for obscenity. His life was ruined, but it was the making of him. He’d
always been more than a guy in a rented tux telling jokes to drunks.
Suddenly, though, he was a rebel with a cause—Amendment Numero Uno. He
refused to be silenced, endured bust after bust, so that we might speak.
And, five years later, his martyrdom would be complete when he died in a
bathroom, fat, naked, a needle sticking out of his arm. The Christ who
said cocksucker.

If Trump were really smart, he’d have done the same. Not the
dying-next-to-a-toilet thing, the losing-in-order-to-win-big thing.
Trump feeds off the ardor of his fans, and his best chance of retaining
that ardor lay in defeat in a squeaker. Then he’d be able to claim that
he was the man who could be, nay, should be, king, and spend the
remainder of his days shaking a Byronic fist at the “rigged” system,
the ideal situation for someone who is, by nature, an outsider and a
rager. Instead, he pulled off the upset. Now he’s on the inside of the
inside, in a job that requires, above all else, calm reflection and
sober judgment. No longer can he say whatever kooky little whacked-out
thought that pops into his skull. Not without bringing down a world of
shit, anyway (see: Obama wiretapping tweets). And, oh yeah, he’s going
to actually have to deliver on his campaign promises or risk hurtful
comparisons to Crooked Hillary. And from there it’s only a short jump to
the most painful scenario of all: the crowd’s love turning into hate,
the cheers turning into jeers.

He’s president of the United States. It’s his nightmare. Our worst
nightmare.

2014

Losing to wind next to his helicopter in Scotland.

Photo: By Michael McGurk/Alamy.

January 26, 2017

Losing to wind at Andrews Air Force Base in Maryland.

Photo: By Nicholas Kamm/AFP/Getty Images.

December 1, 2016

Losing to wind as he heads to Indiana.

Photo: By Timothy A. Clary/AFP/Getty Images.

February 23, 2012

Losing to wind while he’s in Scotland to discuss bankrolling an anti-wind-farm campaign in order to fight an off-shore development near his luxury golf resort.

Photo: By Danny Lawson/PA/A.P.

December 6, 2010

Losing to wind in the presence of Tom Brady.

Photo: From Boston Herald/Splash News.

January 20, 2017

Losing to wind while waving.

Photo: By Rob Carr/Getty Images.

July 2, 2014

Putting up a good fight but ultimately losing to wind in Scotland.

Photo: By Michael McGurk/Rex/Shutterstock.

2014

2014

Losing to wind next to his helicopter in Scotland.

By Michael McGurk/Alamy.

January 26, 2017

January 26, 2017

Losing to wind at Andrews Air Force Base in Maryland.

By Nicholas Kamm/AFP/Getty Images.

December 1, 2016

December 1, 2016

Losing to wind as he heads to Indiana.

By Timothy A. Clary/AFP/Getty Images.

February 23, 2012

February 23, 2012

Losing to wind while he’s in Scotland to discuss bankrolling an anti-wind-farm campaign in order to fight an off-shore development near his luxury golf resort.

By Danny Lawson/PA/A.P.

October 21, 2012

October 21, 2012

Losing to wind while he talks to Patriots owner Robert Kraft before a game.

From Splash News.

June 9, 2008

June 9, 2008

Losing to wind at the house on the Isle of Lewis, Scotland, where his mother was born before she immigrated to the United States in 1929.

From PA/Alamy.

January 26, 2017

January 26, 2017

Losing to wind while boarding the Marine One helicopter at Joint Base Andrews, Maryland.

By Jonathan Ernst/Reuters.

January 6, 2017

January 6, 2017

Losing to wind while leaving One World Trade in New York.

By Timothy A. Clary/AFP/Getty Images.

December 6, 2010

December 6, 2010

Losing to wind in the presence of Tom Brady.

From Boston Herald/Splash News.

January 20, 2017

January 20, 2017

Losing to wind while waving.

By Rob Carr/Getty Images.

July 2, 2014

July 2, 2014

Putting up a good fight but ultimately losing to wind in Scotland.

By Michael McGurk/Rex/Shutterstock.

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