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25 January 2017updated 29 Jul 2021 11:52am

You Should Feel Sorry For Donald Trump

Here is a man who is obsessed with respect - so the most wounding emotion you can give him is pity. 

By Tom Cowell

To everyone on the Left and the Right who see Donald Trump for what he is – a blowhardy buffoon, blessed with brilliant salesmanship but all the substance of a wheezy bed bug – this post is for you.

In these dark times, I want you to think one soothing thought.

Donald Trump is screwed.

Yes, he is riding high today, and it is excruciating to watch. But comfort yourself with this fact: for the next four years, we will watch the largest ego in the world disintegrate. Picture the hypnotic, slow-motion demolition of a (failed) Trump casino.

I’ll explain.

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Trump’s quest for the Oval Office was not about his ideas. It was about his demons. Trump’s defining psychological trait is his fear of humiliation. Smart observers mark the exact moment Trump’s dilettantish dreams of the Presidency became genuine. It was the White House Correspondents’ Dinner of 2011. With Trump in attendance, both comedian Seth Meyers and President Obama coated Trump in layers of insults, like satirical bukkake. He was utterly humiliated in that room. The most powerful and most celebrated people in the country laughed openly in his face, and Trump’s resolve to run suddenly bloomed, under the heat lamp of elite ridicule.

This pattern repeats itself in everything Trump does. Fear of ridicule is his trigger to action, and it explains most of the man’s vast weirdness. Beneath every boast, every grand gesture, and every paranoid outburst at imagined slights, it’s the same thing: they’re all laughing at me. How dare they laugh at me?

This sensitivity probably imprinted onto Trump at an early age. It was not easy to be the son of Fred Trump, a cold, workaholic real estate developer, who filled his son’s head with appalling ideas of what it means to compete. Donald shared memories of his childhood with his Art of The Deal co-author Tony Schwartz, and Schwartz told a PBS documentary that “the way the game got played in [Fred’s] household was, if you did not win, you lost. And losing was: you got crushed. Losing was: you didn’t matter. Losing was: you were nothing.”

It is never wrong to humanise people, even the worst of your political opponents. We can all empathise with the emotional violence of Donald’s childhood (privileged as it was). The fear of failure and embarrassment before the patriarch Fred Trump must have been debilitating. And Trump was apparently singled out for the toughest treatment. He was the only one of his four siblings to be sent away boarding school at the extraordinarily austere New York Military Academy, located just a few miles from West Point. It must have felt like a kind of banishment. And perhaps that symbolic rejection is at (or near) the root of his crippling insecurity.

And in the annals of world politics – which feature quite a few insecure people – has anyone even come close to the insecurity of this man? To put it in perspective, Trump is only the 45th President of the United States. It is the single most powerful office ever created by human civilisation. Only 44 others have successfully earned the title, despite being coveted by many thousands of the most gifted, brilliant, ruthless, and cunning men of their age. Trump won first time out, never having run for any lower office. In the glow of this astounding feat, did he have peace? Was there balm for the wound in his soul? Of course not. He raged about the crowd size at his inauguration, which was not quite the largest of all time. What is behind such bafflingly bathetic behavior?

I sincerely believe Trump ran for President to finally defeat his humiliation demons. By beating the establishment at their own game, perhaps he could finally put his ego beyond the reach of social stigma. Surely, at the apex of power, “they” – the opinion-makers, the intellectual class, the old money, the deep state… whatever you call them – would be forced to respect him.

He won. He has the office. But did seizing that prize earn him even a crumb of serious acceptance? No. It absolutely has not. His incumbency will not change the disdainful elite consensus on Trump. The jury stays in. To the people who really run this country, Trump remains a tacky, dim, clownish braggart, undeserving of respect. And now, burdened with actual responsibilities, Trump’s exposure to humiliation has ballooned. Every day he will have to confront unpleasant trade-offs. Every day he will be backed into corners. Every day there will be climb-downs, reversals, legislative defeats, and judicial snubs. He will have to confront what he has tried to ignore his entire life: his limitations. And because Trump’s adolescent mind processes limitation as humiliation (“if it’s not the biggest, best, tremendous-est, then it’s not acceptable”), he is in for a terrible four years.

Trump’s political triumph will expose him to psychological defeat, and that is – in literary terms – a tragedy. It’s not a Shakespearean tragedy, but it’s mid-level Ibsen.

So if you oppose Trump, and really want to piss him off, consider this. There is one positive human emotion you can direct toward this man that will infuriate him above all others. And that is pity.

We pity you, Donald. We sincerely do. It must be truly awful to be you.

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