DONALD TRUMP


Spoofing Trump’s presidential candidacy is starting to feel like blood sport for the chattering classes. Yet we need to take a step back to understand why Donald Trump is universally described as an “American original” and whether there is more here than a florid, hard driving, self-promoter.

To veteran Trump watchers, calling out Trump’s little known reputation for loyal friendship might seem like I’m applying for a job in his latest TV series. After all, this is a man whose life’s work has been portrayed as code for pungent cliches of avarice, luxe indulgence, too many marriages and too many TV shows. Yet the backstory behind Trump is the reality of his loyal friendship and it is the stitch that holds together the bravado, egotism, and bravura.

For those whose awareness of Trump is limited to episodes of The Apprentice and scratch their heads about his presidential run, I do have a few insights. It may not whet your appetite for a campaign contribution but might explain his continued rise in popularity and why he will be in the running if not in the White House.

General Douglas MacArthur famously said “in the evening of my memory, always I come back to West Point” and that is precisely where my first memory of Trump began.

The Forbes Highlander

It was September 1997 and Trump was a guest on the Forbes yacht, The Highlander, a 151′ luxury cruiser, on its way to a West Point football game together with friends and numerous celebrities (Don Hewitt producer of Sixty Minutes, Lady Margaret Thatcher, Colin Powell, and of course, the four Forbes brothers). I was publisher of Forbes Magazine, which granted consigliere status for the family owned media empire.

It was late in the first quarter and West Point was ahead when it started to rain, and Army football not being a sport for the faint of heart I picked myself up off the bleachers and walked over to the Military Academy’s fine weapon and war museum. Trump was thinking the same thing, and we joined forces, touring the weapons and suits of armor and afterwards stepped outside for some fresh air. Trump was in his Saturday informal best, a baseball cap and a New York Yankees jacket, the kind that pinches your waist line and exposes whatever you have going on in the bottom drawer, so you get the picture. There we were, looking to anyone else like two regular guys talking football and business. Every day stuff.

West Point football game at Michie Stadium

Donald had just published his second book, The Art of the Comeback, with co-author Kate Bohner, ex wife of Michael Lewis, and one of our Forbes reporters of whom my editor Jim Michaels said: “The girl can write like nobody’s business.”

The books’ jacket describes Trump’s story as “when many real estate moguls went belly-up in what he calls the Great Depression of 1990, Trump reveals how he renegotiated millions of dollars in bank loans and survived the recession, paving the way for a resurgence, and outsmarted one of South America’s richest men for rights to the Miss Universe pageant.” So by this time he was well known, even famous, and on one of his many career upswings.

Newburgh is a tired, industrial suburb as well as the home town of West Point, and not many realize it is more simpatico with Harlem than with rural Orange County in upstate NY where the campus is located. Which is why a small group of teens, mostly African American and Hispanic, were milling around. They noticed Trump and hurried over with knowing smiles and energetic eyes. They were about to meet a real celebrity. I was merely the innocent bystander, barely accorded a nod from the young boys, and rightly so. But Trump had other ideas. When they asked for his autograph, he replied, “This is Jeff Cunningham. He’s much more famous than me, so you have to get his autograph too.” So I dutifully signed their baseballs and then he did the same. I always wondered years later what they thought when they looked at the baseball prominently displayed on their brag wall and wondered about the Jeff Cunningham autograph next to Donald’s?

Trump has a special way with people that few would guess as he’s firing someone on his TV show. He likes fame as everyone knows, but if someone is around who’s not part of the action, he feels a need to share it so no one is left out. That’s just how he gets his kicks and it’s why people stick with him throughout their lives if they can. He knows when to sublimate his ego and when to stroke theirs. He knows how to have fun and how to make it fun to be around him. It could be instinct or a cynic would say it’s just a flair for salesmanship, but I have seen it so many times I recognize it as something apart.


Several years later I called Trump and asked him for a favor, could I bring a group of honchos for dinner to his palatial Palm Beach home, Mar a Lago, formerly the home of Dina Merrill and her mother, Marjorie Merriweather Post.

“Trump solo” refers to a New Yorker profile of this trip and our evening with Trump. I was a source for the New Yorker profile, which nicely captured the sizzle of the occasion:

“The only formal event on Trump’s agenda had already got under way. Annually, the publisher (Jeff Cunningham) of Forbes invites eleven corporate potentates to Florida, where they spend a couple of nights aboard the company yacht, the Highlander, and, during the day, adroitly palpate each other’s brains and size up each other’s short games. A supplementary group of capital-gains-tax skeptics had been invited to a Friday-night banquet in the Mar-a-Lago ballroom. Trump arrived between the roast-duck appetizer and the roasted-portabello-mushroom salad and took his seat…at a table that also included les grands fromages of Hertz, Merrill Lynch, Countrywide, Sprint, Fannie Mae, AT&T, CIT, Chase Bank, and the owner of the New Jersey Devils.”

The backstory, which I managed not to spill to the New Yorker, was that earlier in the evening one of the CEOs said to me, “if Trump is coming to dinner, I’ll be leaving early. I’ve had it with him.” Then another CEO said, “sure he paid off his debt. At fifty cents on the dollar.” So I promised both I would understand if they departed. There was no question about Trump’s attending of course, this was his home, after all. During the cocktail hour, the maitre d’ came over and told me that Mr. Trump’s plane was about to land.

Air Trump flight to Mar a Lago

As the evening festivities wore on, Trump got up to welcome my guests and he then offered a few remarks about business which were quite hilarious and got everyone going. He went on to point out the long relationships he had with everyone assembled, mentioned anyone worth mentioning, flattered all the spouses, and then hopped table to table graciously glad handing like an old pol. A few minutes later I felt a tap on my shoulder — it was the two CEOs who told me they would be leaving. Instead of having their hats and coats, Donald had his arms around them and looking for all the world like a band of brothers. One of them said to me, “What can I tell you. He’s a great guy, the greatest salesman in the world, I can’t believe I’m doing this.”


“Fame is an asset and having the right kind of sustainable fame could be wealth generating in the same way as having a billion in the bank.”

Then it was his turn again. Trump called me and asked for a meet and greet with the Forbes editors. It was Trump asking after all, so I wasn’t going to inquire what it was about, I just put it on the calendar and arranged for the meeting in the Forbes townhouse adjacent to our headquarters building on lower 5th Ave.

Trump had really turned things around in his real estate empire after problems with Atlantic City and other properties became widely reported. He is a huge risk taker or at least was in his early days, and timing is everything in his case. But the good results he was finally showing weren’t turning into good news yet in the minds of the media, who as the saying goes, love to take you up almost as much as they love to take you down. And being down on Trump was good business for magazines and newspapers, and so the writers weren’t in any hurry to change their minds.

In real estate as in Hollywood it’s perception that matters. The final arbiter of wealth in those days was the Forbes 400 richest list of Americans. This was something of a who’s who for the real estate community and they tracked the comings and goings of the wealthy like a bettor reads the Racing Form, and Trump was no longer on the list.

When Malcolm Forbes (he was crazy about Trump, by the way) first launched the idea of the Forbes 400 (so named because Mary Astor’s Waldorf ball was limited to the top 400 people in New York society), editors roundly criticized the idea as unrealistic. They claimed the wealthy have their assets tied up in private investments and so no one could really accurately measure them. They would look like fools, even be laughed at by their peers. Malcolm didn’t mind being laughed at as long as it came with a price tag in his favor. Editors may have huge followings and be seated at the best table at the 21 Club, but in fact they are middle managers in a media enterprise, and their role is that of a drama critic not an acting coach. They aren’t there to solve problems, just to give the thumbs up or down. Only Malcolm would have none of it. He knew a great idea when he saw it, even if it was his own. So he presciently pointed out to the editorial pantheon that after the first issue was published, we would hear screams of errata and then we could actually use that (the first instance of crowd sourcing data analytics) and make improvements next year and so on until we got it right. The Forbes 400 became the magazine’s most profitable product, and ultimately, the swimsuit issue for the wealthy.

The fact was that by late 1997 Trump had earned the right to be back on the Forbes 400. That’s why he called me. He wanted the meeting with the editors to prove it, or more transparently, to show New York real estate community. During our meeting, he brought out a signed document from his accountants that supported his claim to several billion net worth and passed it around like a straight A+ report card. The editors politely nodded and then whispered there was no way they were going to accept this as proof. When the issue came out, Trump was on the list but at a fraction of his claim. But he was back.

Trump recognized long before anyone else that fame is an asset and having the right kind of sustainable fame could be wealth generating in the same way as a billion in the bank, maybe even better. Because a billion is a commodity but fame has far-reaching significance, particularly in international circles, and it can be recycled endlessly.

Trump’s magic touch is that he knows how to make money and to make fame and make money through fame. He has a unique gift of putting himself in the limelight, and regardless of how questionable the circumstance (how many of us questioned Apprentice when it began), he knows that at the end what survives is his name and that everyone wants in. He was the guy who turned real estate into a consumer product.

“I don’t care what you say about me, as long as you say something about me, and as long as you spell my name right.” — George M. Cohan

In Trump’s case, he would add, and get my net worth right.


It’s the early summer of 1998. I just returned from my annual trip to Asia. Two weeks before leaving I had handed in my resignation to the Forbes because despite having the best job in publishing, I felt the internet was a better bet. I was also not on the greatest of terms with one of the Forbes brothers and one thing you learn in a family company, you don’t make enemies with people whose name is on the business card three times (i.e., their name, the company name, the building name). You walk away quietly and hope they don’t throw anything at you.

I visited a few of the people I had come to know over the years to get some advice on the next chapter of my career, some of whom were generous with their time and advice. Mike Bloomberg comes to mind, who met me in his office across from the bullpen that was Bloomberg’s reporting floor before he became New York’s Mayor. Bloomberg asked me about my interest in getting involved with his magazine, but I had the desire to move beyond the print world at that time. Another was Michael Milken, the famed financier and philanthropist, who offered me a job as CEO of one of his Knowledge Universe portfolio companies.

Trump was the third loyal soul. And if you think about it, these incredible people, all billionaires many times over now, have a gift that is often missing in those people we think of as our ‘friends’ and from whom we expect help when we really need it. The social climbers and LinkedIn wannabe’s  forget we ever existed during those moments our star seems to fade. Not Bloomberg, Milken, or Trump however. Perhaps it’s one reason these bigwigs got so big.

We met in Trump’s office which isn’t one of those ego inspired outer room/inner sanctum corporate mansions in the sky that is often the case of the hot shot CEO. In fact, it’s a serviceable, practical room where he doesn’t try to impress. Ironically, it reminds me of Warren Buffett’s office. Big enough to capture the details, not too big to lose track of them.


“Real people understand intuitively he’s a good guy and believe he has their back more than any other politician, and it is likely they are right.” 

We talked for an hour, and he simply said any time he could do something for me or be a reference, to give him a call, and he meant it. I asked before I left, because his last market defeat came when the market crashed and things were going so well it felt like he was tempting fate again. “What will you do if the market craters.” In his fashion, Trump said, “if the market crashes I will too.” He doesn’t worry about rises and falls and doesn’t fret over trying to game the timing, just how to keep going and get back on his feet when they things turn south.

IMG_0332Donald Trump is not someone often underestimated except when it comes to his potential on the political stage. Who knows if his ambitions lie in political office or only in what politics can do to burnish his credentials, which is the last refuge of the rich. As the Google Trends chart above shows, running for President may be turn out to have its own rewards, as it has in the past election cycle.

Either way it goes, Trump is not to be counted out nor should his influence on the average Joe be ignored.

Real people understand intuitively he’s a good guy and believe he has their back more than any other politician, and it is likely they are right.

So the $64,000 question – actually it’s a billion dollar question for 2016 is whether the Donald prevails and goes onto the general election. It’s a long shot to be sure. But Donald is no longer on a mission, his life is a sequence of miracles at least from a business perspective, so that he’s reliably on a journey.

Newton’s second law of thermodynamics says that an object in motion tends to stay in motion due to the pressure of force. With Donald, the force is always with him.