A Short Course In Trumpology

The media needs a translator. When Donald Trump speaks, they don’t understand a word he is saying.

Jeff Cunningham
10 min readJun 4, 2017
Donald Trump at his home, Mar-a-Lago, in conversation with the author

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

Why Does He Do These Things?

Donald Trump is a formidable gamesman, a talent more often associated with chessboards and blackjack. To some Americans and many global leaders it is a disruptive feature of the ordinarily well-scripted Oval Office. The fashionable response by journalists and Beltway elites to our 45th president is to condemn or dismiss. For the sake of argument, it would be more helpful if first tried to understand.

It wasn’t the Russians.

To decipher Trump, start with his predecessor, who 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, life under the 44th president 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 far away. The people showed their eagerness for such a move by granting Trump the presidency in 2016.

Obama’s melt in your mouth smoothness casts a harsh light on Trump who can seem rough edged and agitated. Although reality TV should have made Trump a natural, he hasn’t found his footing. These still might be rookie days, as 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. 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 thrust and parry and the effect is to cast him as a knight errant who lurches forward then retreats, picks fights against too many enemies, natural and self-inflicted.

Trump Watch

I’ve known Trump for over 20 years now and so I have a somewhat unique 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. 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. But he wasn’t known for making outlandish requests that were illegal as well as reckless.

The Gambler

His good qualities aren’t easy to discern. 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 ahead.

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.

The bottom line, 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.

Advanced Trumpology

Before he became a reality TV star and the President of the most powerful country in the world, Trump was rebuilding his real estate empire after a nasty recession in the early 90s. I was Publisher of Forbes Magazine, that arbiter of the nation’s wealth. We attended football matches together, dined on my company yacht, and I would fly chief executives of major companies to his parties at Mar a Lago, his Palm Beach home (a 1997 New Yorker profile nicely captures it).

What did I observe during those occasions? Titans of the universe making nasty comments about Trump before he arrived; then, as he entered the room he turns on the charm, flatters and acknowledges their great achievements, places a great big bearhug around their shoulders, winking at me as he closed deal after deal with those who made the fatal mistake of underestimating him.

In Trump’s world, you are either a friend or an opponent, and his playbook is apparent to anyone willing to watch objectively from the sidelines.

The Bluff

“Appear weak when you are strong, and strong when you are weak” — Sun Tzu

In 1997, Trump called me looking for a sit down with Forbes to talk about our upcoming Forbes 400 Richest Americans issue. His big move was to secure a spot on the list. It would silence critics who claimed he didn’t have the financial stake to compete. A few weeks later he was at the Forbes townhouse sitting on the living room couch and starting things off by telling the editors how rich he was. He hit them with his favorite gambit, making a stratospheric claim — that his wealth was north of $3 billion.

This was about the time the journalists lost the battle.

The editors clearly weren’t biting. They are a skeptical lot by nature, and it was undeniable. How could he have dug himself out of the hole in such a short time since declaring business bankruptcy? But he said it was so and PriceWaterhouseCoopers backed him up. Editors hate to be wrong a lot more than they enjoy being partially right, so they hedged and gave his net worth a huge haircut. That’ll show him.

But they put him on the Forbes 400.

What they did not know is that Trump cared only that he was on the list. It meant he could parlay that single fact into a sterling balance sheet and he moved swiftly to buy trophy properties in a down market. Soon he was back, larger than life, richer than ever, plotting his next big move. We now know what it was.

Bluff with bravado, incredible timing and audacity, and voila, you have the art of the comeback.

The ‘Tells’

With Trump, his reflex for diagnosing his opponent’s state of mind during a negotiation is as deft as a surgeon feeling your pulse.

Trump can read your personal balance sheet, what you need to win, what makes you happy or sad or popular or humiliated, and knows these things before you do.

If you ever go mano a mano with Trump, keep an eye on the “tells.” In practical terms, pay attention to his actions and who he deploys to get things done, not necessarily his pronouncements.

To use an old fishing expression, Trumps throws a lot of chum in the water. We have all witnessed him saying one thing and doing another, or his people will do yet a different thing before he says something else. It can seem very confusing and the media calls it “chaos.” To me, it’s just code for keeping your opponent off balance, and the code breaker is Sun Tzu:

“The general is skillful in attack whose opponent does not know what to defend, and he is skillful in defense whose opponent does not know what to attack.” — Sun Tzu

Head Games

President Enrique Peña Nieto of Mexico could have simply ignored Trump.

Instead, he let him get under his skin with the comment “‘they will pay for the border wall.” Now Nieto faces a difficult set of outcomes: capitulation, which is political suicide, or an economic enemy in America, which is unacceptable.

How did this impressive young politician and leader of such a great country find himself playing ‘rope a dope’ with an untested American president? This favorite Trump gambit is, again, right out of Sun Tzu:

“If your opponent is temperamental, irritate him. Then build him a golden bridge to retreat across.” — Sun Tzu

Nieto will play for time most likely because he is on an uncomfortable ledge. He is practically imploring Trump to offer Mexico a way back and Trump, of course, knows this. There will be a solution and it will have two terms, America will look like a winner but in a way that makes sense for both countries. That’s how a dealmaker thinks. Your first move is just an opening feint, but your opponent mistakes it for war and overreacts.

If you find this too crazy to imagine, you haven’t followed Trump’s life story. Read how Trump the minor developer became Trump the superhero while launching his reputation and restoring a historic landmark in New York’s Central Park at a time the city was falling apart, and his relationship with New York’s powerful Mayor Koch was frosty as the Wollman Ice Rink.

Trump L’oeil

There is an old George Burns routine, “it’s too bad the folks who really understand what the country needs are too busy cutting hair and driving taxis to do anything about it.”

If Trump seems bipolar at times, it is a job requirement. He has to make peace short term with the populist urges that propelled him into office like George Burns’ barbers and cab drivers, only now it’s factory workers in Saginaw and murder rates in Chicago. But he also has to think about some very adept long-term moves that will help him run the most powerful country in the world. This is pure cognitive dissonance and, to make it work, Trump needs to pull off a visual illusion worthy of Houdini.

For those not schooled in American history, Trump’s populism, some call it America First nationalism, is a very old Democrat tune. FDR turned it into his campaign theme in 1932: “These unhappy times call for the building of plans that…put their faith once more in the forgotten man at the bottom of the economic pyramid.” It took the start of WWII to get us worrying again about the rest of the world.

While the populist sentiment is very important to Trump’s American heartland voters, it is of much lesser consequence than the other mandate, which also has a two-year time stamp. It is the miracle-gro for our economy and is the reason I am optimistic that under Trump, America will become more global and more outwardly focused.

The Scorecard

What gets you into office doesn’t keep you there, as politicians find out to their — but no one else’s — surprise.

Trump knows the metric on which he will be judged, and the one he judges himself on, will be growth and that means firing up global trade, no matter what anyone calls it.

But he can’t do it like the establishment elites that came before. He owes his constituents the pleasure of demeaning the treaties and trade agreements and punching a few of the key partners in the nose. After which he will have the political cover and the leverage to launch a robust, if stealth, internationalism, one that can propel us in a way that is transformative. That is my thesis based on watching Trump over the years, recognizing at heart he is a centrist (and a former Democrat), an ardent businessman who uses common sense as his litmus test.

The Trump Doctrine

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

There are too many variables to throw out predictions without strenuous caveats.

Start with the cornerstone of the global pivot — undo the Obama damage to former friends with global benefits. Tell the established countries to show some respect, and pay their fair share. Focus on a few bad guys who really matter as we can’t afford the luxury of too many enemies. Then sort the things we can win from the things that are hard if not impossible to do in a four-year term. He is a builder first and foremost, and he knows ambition will be disciplined by time and budget.

Driving higher and broader global business growth is the only choice Trump has if he is to move a nearly $20 trillion economy. It buys him the kind of recovery that even journalists would be inclined to applaud. But he is running out of time, politically speaking.

The long term game plan is what one of the world’s greatest geopolitical strategists would have suggested, a strategic “rebalance of power.” When the story is written, I believe the “Trump Doctrine” will follow Metternich’s counsel, only tilted slightly in America’s favor.

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