Why Does He Do These Things?

Donald Trump is a formidable gamesman, and to a number of Americans and the media he is a disruptive presence in the ordinarily well-scripted Oval Office. The fashionable response to our 45th president is to condemn or dismiss.

For many who didn’t care for Barack Obama, life was like living near train tracks, you got used to the rumbling and then stopped hearing it. It’s called a trance in medical circles or by those who make a living selling marijuana. But given a choice, a number of people wanted a new home. They broke the trance by signing a new lease with Trump.

Obama’s melt in your mouth smoothness makes Trump look rough edged and agitated, not to mention to some, deplorable. Although reality TV should have made Trump a natural, even giant talents such as JFK had problems with the media. Walter Cronkite blew up at him during the campaign for demanding to reshoot a botched interview, a moment the news anchor never forgot (see my article on Cronkite).

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

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 stories and campaign rhetoric. People will ask, but what about the tapes and those stories? I don’t have a good answer, except this: if someone video taped all our lives, we would all be thoroughly embarrassed. Whether the peccadilloes of a big life disqualify someone from the presidency, is for everyone to judge for themselves. I adore and admire MLK, JFK, FDR, and of course, Winston Churchill. While their failings may not rise to Trumpian proportions, you can be sure if judged by today’s moralizing sympathies, all of them would be thrown out of office or investigated. The Puritans of New England would have thrown them out, too. They preferred shaming and banishment for anyone who insulted their standards, and as a result, they lost innovators along with the heathens.

On a positive note, from everything I saw and all the people and Forbes writers who knew Trump (one ghost wrote his autobiography) I would add he is often unfailingly generous to his people and loyal to a fault, particularly when someone is down and out.

These qualities aren’t always easy to discern. His antics can 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 Obama smooth and part Bill Clinton charm, he is likely to continue to have a bumpy ride ahead.

The bottom line, to understand Trump, we should be looking at him as a complicated president. He 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, gaming the ref, and planning the next move.


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.

Did I Help Trump Get Elected?

“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. The editors put up a protest, they didn’t care for him, said he was a washed up bullshitter. I said, hey, what have we got to lose and anyway, he’s news.

A few weeks later he was at the Forbes townhouse sitting on the living room couch, with Malcolm Forbes, jr. in attendance, and he doesn’t waste a moment. He starts off 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. They thought this was about a number, because they were listening to him. If they only watched, they would know it was about an achievement, a symbol.

Editors are a skeptical lot by nature, and it was undeniable, there was no way he could have dug himself out of bankruptcy in such a short time? 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, call it one billion. Boom. That’ll show him, they thought.

But it was enough to put him on the Forbes 400. Once Trump was back on the Forbes list, it meant he could parlay that fact into a sterling balance sheet and he moved swiftly to buy trophy properties in a down market.In a major respect, that brought him back from bankruptcy and changed the trajectory. It lead to a restart on his fortune and empire building, which of course, led to his reality show, and that led to you know what. And I sort of helped make it happen? Who knew?

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

Head Games

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

To use an old fishing expression, Trump 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. The best way for a foreign leader to get a deal going with Trump, and keep him off balance, is play a round of golf or invite him to a state dinner. Ignore the protestors, they’ll protest something else tomorrow, but by then you have a deal.

During the early days of the Trump administration, President Enrique Peña Nieto of Mexico should have simply ignored Trump. Realizing politicians aren’t good at ignoring a comment they find insulting, I would not expect him to take this advice. But we would ignore a barking dog or a vicious snake, right? And Donald Trump on stage or in front of a mic or tweeting is not as far from that as you might believe.

Instead, Peña let the ‘machismo’ get under his skin when Trump shouted, “‘they will pay for the border wall.” That was time for a tete a tete, not a bullfight. It left Nieto with a difficult set of outcomes: capitulation, which amounted to political suicide, or an economic enemy in America.

How did such an 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

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 Trump Doctrine

What gets you into office doesn’t keep you there, as politicians find out to their — but no one else’s — surprise. This is my thesis based on watching Trump over the years, recognizing at heart he is a centrist (and a former Democrat).

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

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.

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’s got to be careful about two assets, time and political capital. A builder would call that finishing the project on time and on budget.

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 stealthy and strategic international reset that will be as orderly as the chaos that is around us now.

The secret to Trump is not to listen, just watch.

The views expressed in this article do not necessarily reflect those of Thunderbird School of Global Management or Arizona State University as a whole.

Author’s Bio

Jeff Cunningham is an advocate for enlightened global leadership, which he calls the most valuable natural resource in the world.

He is a Professor at ASU’s Thunderbird School of Global Management and was the former publisher of Forbes Magazine, startup founder, digital content CEO, and ran an internet venture capital fund.

He travels the globe in search of iconic leaders. As an interviewer/host, he created a YouTube interview series, Iconic Voices, now co-produced by @Thunderbird, featuring mega moguls from Warren Buffett to Jeff Immelt. His articles on leadership have been featured in the Arizona Republic, Forbes, Chief Executive Magazine, Board Member Magazine, LinkedIn and Medium via JeffCunningham.com.

His career experience includes publisher of Forbes Magazine; founder of Directorship Magazine; CEO of Zip2 (founded by Elon Musk), Myway.com, and CareerTrack.com; venture partner with Schroders. He serves as a trustee of the McCain Institute and previously as a trustee of CSIS and Middle East Institute, and as an advisor to the Nobel Peace Prize Committee.

He has also been a board director of 10 public companies.

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