How Donald’s Deep Insecurities Damaged Our Democracy

A Donald has already begun explaining to us all why his impending electoral beat down at the hands of one Hillary Rodham Clinton is not his fault. The game is rigged, he howls. Malignant forces that wish the American people harm have lined up against him to prevent A Donald from saving the world. A nefarious globalist consortium of international bankers and media executives (I wonder what he means by that? Hmmmmm…) is conspiring to steal an election that is rightfully his. It’s the Elites, he tells ya, the Elites.

This sort of talk is not new, just as very little about Donald Trump is original if you look hard enough. The GOP has been playing this hit for decades. From Richard Nixon to Ronald Reagan to Newt Gingrich to Sarah Palin, Republicans have long told their base that the Elite is the real enemy, those snobby coastal types that peer down from their ivory towers upon the huddled masses of “real” Americans. They want what’s best for them, they swore. We want what’s best for you.

Most commentators have scoffed at Donald’s assertions that he is not one of these so-called Elites. He grew up in the lap of luxury in New York City. He went to Wharton. He flies around the world in a private jet that literally has his name emblazoned across the fuselage in gold letters. How can this man possibly understand the fury a “real” American has for elites?

The answer to this question gets to the heart of what fuels Donald Trump, and why political punditry constantly underestimated his appeal to the heartland and the heartland’s appeal to him. To understand it, you have to delve into the peculiar dynamics of the five boroughs of New York City and the bizarre social hierarchy of the mega-wealthy.

The specter of Fred Trump, Donald’s father, has already loomed large over this campaign. He was a real estate magnate in New York who generated enough wealth to gift his son a head start in life. Without Fred, Donald is a nobody. Any suggestion that he is not a “self-made man” who did well in life sends Donald into a tizzy. The mere mention of the $14 million in loans he received from his father during the first debate sent Donald into an emotional and mental breakdown that continues to this day (Seriously: Any post-mortem of how HillDawg won this election that doesn’t include that moment is incomplete).

What has gone mostly unexamined, though, is the specific nature of Fred’s business. Yes, he was a real estate developer in New York City, but that doesn’t tell the whole story. Fred built his fortune building and managing affordable housing complexes in Brooklyn and Queens. His clientele were not the rich, famous, and classy that his son would later attempt to appeal to. They were (White. See the metric shit ton of civil rights lawsuits) working class families in the outer boroughs of the city, far from the glitz and glamor of the skyscrapers in Manhattan.

Back then, Manhattan was where the fashionable crowd lived, away from the “bridge-and-tunnel” folk of Brooklyn and Queens who lacked the social graces to attend Manhattan’s high society parties. Manhattan is where the powerful came to play. Manhattan was home to the Elite.

From the moment Trump completed his Ivy League education, Donald dreamed of crossing the East River into the bountiful bosom of the famous skyline that haunted his illusions of grandeur. “He had enormous insecurity about his place in the world,” biographer Tim O’Brientold Buzzfeed earlier this summer. “I think he saw Manhattan … as the only place he could get those establishment blessings he really wanted. It’s almost an unfillable hole for him.” He wanted to be seen as a big shot, a player amongst the titans of industry.

Over the course of the ’70s, ’80s, and ’90s, Donald failed in his endeavor to break into the elite ring. He made no friends or allies over a lifetime of trying to get in with the in-crowd. The profound lack of testimonials to his business acumen and personal virtues by anybody who doesn’t share his last name, as well as the paucity of campaign donations he is receiving from this very crowd, the deafening silence from those he spent decades attempting to impress, speaks to this failure. Donald himself even admitted as much in a Washington Post Interview earlier this year. The man has no friends.

The coverage he received by the various tabloids and magazines of the day also demonstrated this lack of social success. As the editors of the now defunct Spy magazine would later say in an NPR interview, he embodied a certain “vulgarity” that was off-putting to the elite socialites of his day.

We know by the odd hours of his social media indulgence that there are things that keep Donald up at night. I imagine this rejection was one of them. Why didn’t they like him? Why didn’t they respect him?

In retrospect, there were many reasons. Donald insisted on tacky, ostentatious presentation. He insisted on proclaiming his primacy, his intelligence, his superiority. He insisted on taking his mistress on a family vacation and putting her on the cover of the New York Post. He insisted that he was a stellar businessman, when by almost all objective measures he wasn’t that good at business. He insisted upon his generosity, when he was notoriously ungenerous. And above all, they just plain didn’t like him. He carried himself like a poor man’s caricature of a wealthy man, not with the grace and decency that was expected of a card-carrying member of the Elite.

He was respected as a businessman the way that Dr. Phil is respected as a therapeutic scholar. And, in keeping with the grand tradition of Dr. Phil, he took his talents to the only arena where he could truly sell an audience on their existence: television.

It’s worth remembering that, prior to The Apprentice, Donald Trump didn’t have much of a profile outside of New York City beyond beauty pageants and Home Alone 2: Lost in New York. He was seen, for better or for worse, as a quintessential New York figure, a figure of NYC kitsch like Times Square or “I ❤ NY” shirts that New York itself didn’t much care for.

So a reality show that depicted Donald as the ultimate Big Boss, the jet-setting, wheeling-and-dealing tycoon straight out of a cartoon and into primetime on a broadcast network was mutually beneficial. It granted the show legitimacy if the host of a show where contestants competed to prove their business sense was himself seen as a successful businessman, and it helped calcify Donald’s brand across the country. That brand would later become a central tenet of his business, as he licensed the Trump brand to numerous properties and productsbig and small.

The Apprentice was a hit. Millions of people watched it. But it still didn’t earn him the respect of the elite whom he had crossed the river all those years ago to impress. He still wasn’t invited to their dinners, events, and parties. Despite his newfound television fame, he was still seen as a clown.

So he tried to become a political player. He had long teased senatorial, gubernatorial, and presidential runs. George H.W. Bush’s advisors even briefly considered him as a running mate. But his first “serious” foray into political life was his birtherism crusade.

The connection between Donald’s current base of support and those who felt empowered and enabled by Donald’s public assertions that the first black President of the United States was illegitimate has long been established. The narrative of the relationship between Trump’s embrace of birtherism and his current political run often includes the public humiliation Donald received at the hands of President Obama at the 2011 White House Correspondents’ Dinner (while some have questioned this version of events, there was a telling moment at this year’s dinner when Obama tipped his awareness of what the 2011 jokes did to Donald: when questioning why Donald wasn’t at the event, Obama quipped “We had so much fun the last time,” perhaps the most gleefully vicious public moment of Obama’s presidency).

That Correspondents’ Dinner is the living embodiment of the elite that Trump has wanted to be a part of for so long. Anybody who’s “anybody” is there. Journalists, media, powerful politicos, beautiful celebrities, and this time Donald was invited. His mood-shift as the President and host Seth Meyers relentlessly ridiculed him has been well documented, as well as his sullen exit from the festivities shortly after the performances ended.

Yet Donald remained popular with a certain base in the Republican Party, a base didn’t much give a shit what the likes of liberal presidents and smart-ass comedians had to say about him, a base required to win the party’s presidential nomination. So candidate after candidate in 2012 made the pilgrimage to Trump Tower to earn his blessing. That distinction eventually went to eventual nominee Mitt Romney (while I appreciate Romney’s virulent rejection of all things Trump this time around, I would love for him to acknowledge his part in all this). After a joint press conference announcing Trump’s endorsement of Romney in Donald’s Las Vegas hotel, the Romney campaign proceeded to pretend that he didn’t exist, ignoring his calls, rejecting his offers of help, and laughing at him behind his back.

Just when Donald thought he was in, that he had finally made his way up the stairs into the ivory tower, he once again found himself on the fringe.

So now we have a strange paradox: Donald is a rich man who was truly rejected by the elite class. But he is still a rich man who has always been rich and lacks the knowledge or empathy or curiosity to truly understand what it’s like to be an ordinary person.

Another paradox lies at the heart of Donald Trump’s being: He is deeply insecure, but thinks he’s the smartest guy in the universe. He believes that he is wildly intelligent, but is wounded by those who don’t recognize it.

Most political pundits did not think Donald would ever run for President. The Buzzfeed profile “36 Hours on the Fake Campaign Trail With Donald Trump” tickled serious-minded folk everywhere who wanted to gawk and chortle at the Trumptastic sideshow. Throughout the piece is the “din of guffaws” that swallowed Donald everywhere he went and a “fading relevance” that certainly provided Donald with his fair share of existential dread.

And yet, buried in the middle of that piece, lies a prophetic utterance by a long time Trump confidante: “If you have no education, and you work with your hands, you like him. It’s like, ‘Wow, if I was rich, that’s how I would live!’ The girls, the cars, the fancy suits. His ostentatiousness is appealing to them.”

Since declaring his candidacy last June, Donald has made headline news on an almost daily basis. His primary process was defined by near endless, breathless coverage that focused far more on the phenomenon than on the man. Despite his outrageous, atrocious public statements, journalists more often focused on the circus rather than the substance of his campaign.

“Finally,” Donald must of thought. “I got ’em. This is it. This is how they know I’m to be taken seriously. Look at my rallies. Look at my movement. Look at my coverage. I’ve made it. I’m in the ivory tower.”

He found himself on, as he would put it, all the shows. Credible highbrow political types discussed him on their highly-rated, highly-respected panels. And they were no longer laughing.

That coverage has since turned. That which once gave him life has poisoned him forever. Coverage of Trump has become a deluge of negative press. A well-deserved deluge, but a deluge nonetheless. The man has been called out for being what he is: unintelligent, incompetent, belligerent, incoherent, intemperate, fascistic, vulgar (yet again), crude, and ultimately, sexually predatory. These traits have come to define Donald Trump, and deservedly so. It’s how he will almost assuredly be remembered.

At 70-years-old, Donald must see this election as the last straw in a long line of indignities suffered at the hands of the elites that have always rejected him, denied his brilliance, and not given him the respect he feels he richly deserves. All the wealth in the world could not fill this hole in his heart. As the presidency slips through Trump’s tiny baby hands, so do his chances to be taken seriously.

The elites kept Trump from the high-society parties in Manhattan, and now Donald thinks they’re keeping him from the White House. Trump sees these grievances reflected in the screaming masses that have been thrown red meat by right-wing ideologues and pernicious politicians for generations.

So he’s taking the opportunity to strike back at that ivory tower, to air his personal grievances with the forces that, as he sees it, have kept him away from the keys of power — the kind of keys that can’t be bought and branded with your name in gilded gold. Donald believed those keys would have unlocked an inner happiness and serenity that alluded him all these years. Now they’re gone forever, inexplicably lost to a man with no capacity for self-improvement or reflection.

This is A Donald’s last stand. The long-standing traditions of the legitimacy of our democracy and the peaceful transfer of power are secondary to him. They probably haven’t even generated a passing contemplation in the midst of his wild thrashing ego, flailing to and fro like a wounded dying animal. All that matters to Trump is his singular, quixotic quest.

I wonder if Donald still sees himself as that young man in Brooklyn in 1968, gazing across the river at the pretty lights atop the big buildings built by big businessmen with big, beautiful, buxom wives, smoking cigars in the backrooms where it all happens, making deals and telling jokes that only they could ever understand. It all probably seemed so attainable then. But now those lights are fading away, that river feels like an ocean, and the dream is dying.

The tremendous psychic damage on our national consciousness far outsizes its cause, the broken ego of one lonely man. This won’t end well for Trump. He will not get what he wants. But it is left to us to pick up the pieces.