A Short Course in Understanding Trump

When Donald Trump speaks, the media and his opponents don’t understand. Whose fault is that?

Jeff Cunningham
5 min readJun 11, 2017
Chatting with Donald Trump at his home, Mar-a-Lago

“In the midst of chaos there is opportunity.” ― Sun Tzu

Why Does He Do These Things?

Donald Trump is a formidable gamesman, a talent usually associated with chessboards and blackjack. To some Americans and many global leaders it has become a disruptive feature of the well-scripted Oval Office. The fashionable response by journalists and Beltway elites to our 45th president is to condemn or dismiss. For their sake, like any problem, the solution begins with understanding.

It wasn’t the Russians.

To decipher Trump, start with Obama, who could put on a performance like a broadway pro. Obama played to the media so convincingly skeptical journalists fell into a trance for eight years and forgot what was bothering Americans.

For many who didn’t agree with Obama’s politics or methods, life under him was like living near train tracks, you get so used to the rumbling you stop hearing it. But given a choice, what you really wanted was to move. The people showed their eagerness for such a move by granting Trump the presidency in 2016. How else can such a sloppy primary and tortured candidacy that ends up in the Oval Office be explained?

Obama’s melt in your mouth smoothness casts a harsh light on Trump. He seems unsure about his role and his expression is all over the map. Although reality TV should have made Trump a natural, he hasn’t found his footing under the glare of presidential Klieg lights.

These are still rookie days however, and even giant talents such as JFK had problems with the media early on. Walter Cronkite once blew up at Kennedy for demanding to reshoot a botched interview, a moment the news anchor never forgot (for more on this, see my article on Cronkite).

Cronkite interview with then Senator JFK

What saved JFK’s place in history among many other things was style, as anyone who watched can confirm. Trump’s style is so different it’s really not fair to call it by that name.

It is primal instinct.

Trump Change

He ran as a change maker and was elected as one. But he doesn’t effect change through his team, but prefers his hand on the tiller at all times. And he likes the limelight and the credit. This paints a target on his back and doesn’t provide cover to change his mind or the message. The result is he shifts gears each time something untoward happens.

The world is too chaotic for this kind of thrust and parry game. The unintended effect is to cast him as a knight errant who lurches forward then retreats, picks fights against too many enemies, natural and self-inflicted. He will envetually bow to political expediency, but not before the ring is splattered with blood, his, his opponents, and in many cases, his staff.

This kind of behavior has to abate if he is to be effective as our 45th president.

What Is He Really Like?

I’ve known Trump for over 20 years now and so I have a somewhat different perspective. We palled around at football games, occasionally met in his office, had dinner parties at Mar-a-Lago, and long chats on boat trips. These experiences have left me with some distinct impressions and although I cannot say with certainty who Trump really is, I am certain he is not what his press says.

I never saw a moment, offhanded or in humor, that suggests he is anything but a supporter of inclusivity, women, minorities, and immigrants, despite the campaign rhetoric and despite the locker room stuff, which I presume is real. I would add he is often unfailingly generous to his people and loyal to a fault, particularly when someone is down and out.

That may explain the “I hope you can let this go, Flynn is a good guy” bombshell Trump dropped on former FBI director James Comey. In business, Trump often asked for and did favors for friends. He may believe he can get away with that, and perhaps he can, but it isn’t the right way to go about the job or helping Flynn, for that matter.

Trump L’oeil

His good qualities aren’t always easy to discern, and not just for his wives. Trump’s antics make him a difficult man if you are a believer and a convenient foil if you aren’t. Unless he finds a hybrid approach that is part smooth Obama and part charming Bill Clinton, he is likely to have a bumpy ride.

The Trump obsession by the media and the Beltway elite is entirely understandable. The media isn’t making any money unless Trump’s name is in the headline. But we have too many things that need our attention, and the clamor around the presidency is a distraction we can’t afford. I know a head of state visiting us in New York who said he could not watch American CNN news because every comment was about Trump. He switched to BBC.

How Does This End?

To understand Trump, we should see him as a complicated president. Dismissing him or dissing him doesn’t solve anything. Some say, “well, he deserves it.” Maybe, but the country does not deserve a distractingly hateful war of words, which is how the media and opposition retaliate. He makes his political enemies howl with laughter but America’s enemies aren’t howling, they’re plotting.

Leave it at this. Trump is a bit of a black box and a poker player. Every time he makes a move that seems inscrutable, he’s not looking for votes or counting poll numbers. Trump is just being Trump, raising the ante, messing with his opponents, and planning the next move.

He’s unlikely to become a nuanced communicator. So start by paying attention to more of what he does and spend less time parsing every utterance, and heaven help us, every tweet. We will all be much better off.

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