The Awkward Moment I Stopped Hating Trump, And Began To Feel Sorry For Him.

As Election Results Continue to Roll In, Let’s Reflect On What Drives Donald Trump’s Behavior.

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Donald Trump emerges from the motorcade. He looks across the divided Manhattan landscape of red and blue. A city block full of people that easily represent the divide he has caused across the country.

It is blocked off by barricades to prevent the protesters, and the counter-protesters from getting violent. Trump eyes his supporters and then scans the crowd. Against the advice of the agents, he walks towards the “Never Trumpers,” holding signs. He reaches into his pocket, and quickly pulls out a small firearm. Without emotion, he shoots a young woman in the chest. His confused security detail immediately jumps on him to protect the president and shuffles him away in the motorcade.

Despite the best efforts of police and first responders, the woman is pronounced dead minutes later. Donald Trump, the 45th President of the U.S., just committed murder. In broad daylight. In the middle of Fifth Avenue. And will get away with it.

Now, this scenario is not something I made up, like some weird fan fiction. Being able to murder someone on Fifth Avenue is something the President, himself, readily admits he can carry out. I just added a bit of texture, to show the sad and graphic reality of what he was bragging about. Of how it may live in his head with a narcissistic glow. His ability to shoot and kill an unarmed citizen, who presented no threat, and get away with it.

When Trump first made that revelation, it seemed ridiculous. But more recently, it seemed scarily accurate. He proclaimed that even with a cold-blooded murder, his supporters would still stand by his side.

To get to the heart of this, we must first consider the source. Donald Trump is not the most self-reflective man on the planet. Rarely, does he do things that don’t directly benefit him. His organizing principle is establishing divisive political discourse. To keep things simple, he does not allow his cognition to deviate from “Greatest,” “Terrific,” and other words that represent his limited and easily digestible set of fall-back hyperbole.

But what he lacks as a poetic orator, he makes up with his deep understanding of what he means to people and what his station presents. He is a grifter, a showman. And instead of us looking at his statement of getting away with murder as a chest-beating sign of superiority, it comes through more clearly as a cry for help.

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Imagine being in the position of Donald Trump, who, in his mind, fits into a polite society different than anyone else. For many of us, we live within the law-abiding confines. We are not land barons, dictators or have a title attached to our name that puts us above the law. We don’t have fixers, or friends in Washington. Our name is not on water bottles, or worthless chunks of meat. We do our best to be our best, not just for us, but for the world.

But Don doesn’t have the same outside pressures applied to him in this way. And that is not a gift to celebrate, but a burden to carry. If you don’t have the guardrails of morality, religion or society to keep you in check, and you have both white privilege and economic privilege, that carte-blanche cocktail can be dangerously intoxicating.

The question becomes: If the law doesn’t apply to you, then what does? How do you keep yourself in check to be a law-abiding, compassionate citizen when your acts go with consequence? Especially when your family life at an early stage was not one of love, but one to prove worth. Where emotion was weakness, and empathy was emotionally beat out of you. Where the best businessman Donald could conjure for his father was a ruthless, unfeeling autocrat. That is how he won favor with his dad, and how he still wins favor today with his base.

The Presidency was the ultimate status symbol. More elegant a bounty than a provincial Manhattan gilded apartment or his name on a hotel. And merely attaining that was the goal, not to actually do something once it was conquered.

He ran for office to prove something to his dead father, and that is the saddest part of it all. Because Fred was the only person who Donald ever respected and put above his own needs. Everyone else, seems to be a pawn, a distraction, a physical release, or a means to an end.

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Donald Trump carries a privileged burden none of us can relate to. We look at the forces of society. We look at our own character, or our own religion. We look at what is polite, what is the law. Those boundaries force us to develop a moral persona to stay within the confines of what’s right.

Donald’s transgressions happen in plain view. The law does not apply to him. Conventional morality does not apply to him. Sexual harassment, or traditional family roles do not apply to him. In his mind, he is above it all.

And among his base, it’s true as well. And he knows it.

He gravitates towards the parts of the Presidency that serve him best. The soapbox to denounce enemies and lift up allies to present his truth.The blind faith of his staff that he manages with the same fear as his business. The ability to mandate, without discussion or compromise. He is a warlord of words, lashing out at others in an attempt to ease his own pain.

It never works.

If we allow our eyes to see, Donald Trump is another scared child who wanted to prove himself to his overbearing father. The confused kid who would see his mom sleeping, all around his apartment. He would take care of her, when it should have been the other way around. Early on, he created walls. And sadly, that is the figurative way he deals with basic human emotions.

How sad for Donald Trump that he grew up this way. Forgive him for a second, and think about that. All the wealth and power cannot make up for a flawed and unloving family. I imagine in those quiet moments, when humanity creaks the door open, he must talk to his father. Asking if being President finally made his dad proud.

Yet, what is apparent is that Donald Trump is not happy. I am not sure if he ever was. And every gift and advantage he has been given, is not enough to change that. Every woman he grabs, every business he unveils, and every voter feverishly screaming his name at a rally is not enough. Nothing will be enough.

Donald Trump wants to go back in time. He is buoyed by his supporters who wish the same. And even as the leader of the free world, Donald Trump cannot make time go backwards.

Yet, he tries. Look at the tweets, the news conferences, the schoolyard fights and name-calling he has taken to the public. Donald just relives that fire, over and over. From childhood to the Oval Office, his life has never been enough. He spends it living in anger, in isolation, rather than looking at and accepting the gifts that are right there before him. The gifts many of us could only dream of having.

We all may debate the character of his family, but they are his family. His relationships are different. And yet, he continues to socially distance himself from the happiness they could provide, in service to how he can weaponize them for his own agenda, ultimately in service to his dead father.

Warped, right?

The code of Donald Trump is unlike any President before him. The ultimate power has presented ultimate consequences. When you feel the law does not apply to you, you don’t bother trying to understand it. You simply do as you please and allow your fixers to adjust. On those occasions where a line is crossed and threats are not enough, a check and an NDA become the only consequence.

That’s why Trump thinks the Coronavirus will simply go away. Because everything unpleasant within his world does that. He is trained to believe that whatever does not serve in his favor can be wished (or paid) away because of his station.

Yet, nature is different. It will not accept payoffs. Nature will not take a stack of cash from a shell company and make it go away. And voters are not like business people. The office of Presidency is to serve the people it represents, not the other way around. That is why he never has reached beyond his base. The strong allegiance from that group is like running a business for him. They stick with him no matter what, not for fear of losing their jobs, but for fear of losing the issues that matter to them.

And when Trump does not have complete buy in, that frustrates him. And frustrated Trump, who cannot “fire” those who don’t fall in is even more angry. And if we easily connect the dots, we know Trump can survive anything, except maybe himself. And the most open secret in politics is that Donald is the only person who can take Donald down.

Sadly poetic.

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All of this makes us angry. And the angry expression of his internal struggle is on full display every day in how he treats others. The mockery, the open defiance of what’s right. But most of this is externalizing the pain inside, so others feel as bad as he does.

This is not an excuse for his behavior, but another looking glass to help understand these behaviors. It is hard to judge rational thought, through the eyes of an irrational person.

Mary Trump recently said in her book that the country has fallen into the same dysfunction as the Trump family. It makes sense, as that is all he knows. Dividing, demeaning is how he got to where he is today. There is no debating whether that strategy is working for him, especially among his base. Donald wants to bring America back to a time when his father lived. That is the basis of making it “Great Again.” His attempts to lily white our streets, to shut off others from the American Dream, to dictate the love that is allowed in this country, and to decide what a woman can and cannot do to her body, are more precisely what he means.

Making American Great, is fundamentally in service to someone who had died over 20 years ago. And many of us, who see with open eyes, are paying the price.

I don’t love Donald Trump as a President. I don’t love Donald Trump as a person. But I don’t hate him either, at least not anymore. I just feel sad that anyone should go through life with so many gifts, and never know how to use them. To never break free of the box his early life put him in, and the constant need to prove himself.

As Mr. Miyagi said in the Karate Kid, “There are no bad students, only bad teachers.” Whether that is an absolute truth or not, it is easy to see how the teacher influences the student, and can lead them down a path that can have devastating consequences. Fred ruined Donald’s life, and he is doing the same to his own children.

Sadly, he surrounds himself with people unable to see the beauty of others, who cannot let citizens live in their own skin, with their own values, loving who they want to love. He creates Straw Men, pushes and divides. He creates borders, and enemies of those outside of the wall, never questioning whether it is right or not. Because, all his life he never had to. And when your heart goes dark, there is little room for light. Little room for happiness.

And happiness is something we all deserve, whether you are broken or not. I hope one day he finds it. But I don’t think the office of President is where we should be teaching that. It should not be on the taxpayers dime to help him work out his own demons. We should not co-mingle our country’s future with the healing of deep psychological scars of our President.

The office is many things, but not that.

And if there is a path out of it in his remaining years on earth, he will find it once he leaves the public sector, and focuses on things that matter. But without that quiet revelation, sadly, things will persist for his remaining years. And in the name of compassion, and the world’s love of redemption, I hope he does find happiness.

Because, I feel sorry for what this man carries in his heart. And would never wish that weight on anyone.

Co-Founder Cast Iron LA agency. Webby Judge. Satirist. Contributor to FastToCreate, AdWeek, HuffPo, Digiday and others. I fight fire with humor.