James Dolan, Donald Trump and the Power of the Dark Side

You know who Donald Trump is. But, unless you’re a New Yorker or a basketball fan, you might not know that James Dolan is the tremendously unpopular owner of, among other things, Madison Square Garden and the New York Knicks.

Dolan, who is widely considered the worst owner in all of professional sports, is currently enjoying a moment in the media spotlight here in New York because he recently had Charles Oakley, a beloved and iconic ex-Knick, forcibly removed from his seat in the stands at a Knicks game, for really no good reason at all. Oakley, a giant who in his flat-topped heyday was literally the baddest man in the whole NBA, was unceremoniously wrestled to the ground by about nine anonymous white guys in suits, eventually being handcuffed, arrested and booked on some silly misdemeanor charges that amounted to nothing. What it boiled down to was that Dolan doesn’t like him because he’s been a vocal critic.

Superficially then, James Dolan and Donald Trump seem to have enough in common to garner some comparison. Notably, they both own gigantic buildings in Manhattan and don’t hesitate to have henchman use questionable levels of physical force to remove people they don’t like from public events. What’s more interesting though, is that both men are stupid and mean.

In and of itself, that wouldn’t be so interesting, except that, by any objective standard, they are also outrageously successful. And their ongoing success literally flies in the face of everything I’ve learned about what it takes to succeed.


When you read about guys like Warren Buffet, Bill Gates and Steve Jobs, it’s easy to develop the comforting notion that, at the end of the day, the best and the brightest win in the game of Life; that certain admirable, inimitable traits — leadership, intelligence, grit, wisdom, courage, creativity, insight and so on— pave the only true path to success. These are not easy skills to master, mind you. And they are very virtuous ones to boot. So those who do so deserve success, or so the thinking goes.

It’s not a myth either. There is a virtual pantheon of innovative, successful entrepreneurs and leaders who fit this basic mold. Mark Zuckerberg, and Elon Musk are two of the most prominent, recent incarnations but pretty much every CEO in what I’d call the New Economy — that is to say companies that were born of the Internet — adheres to the tenets of this meritocratic worldview. And no one can reasonably argue that these people are not shaping the world. None the less, there is some mythologizing going on here.

There is a well known narrative arc that is recurrent through all of mythology. Joseph Campbell called it the Hero’s Journey and it was used by George Lucas as the basis for Star Wars. It’s also pretty much the storyline of every Disney movie and superhero story ever made too. If you’re not familiar with the concept, it reads something like this; Anonymous outsider-underdog with a heart of gold and a special ability embarks on an epic journey. Along the way he must overcome all the doubters, haters, and an assortment of challenges until, aided by some allies he meets along the way, he ultimately emerges triumphant and transformed. The hero is born.

You can easily drop Steve Jobs (or, come to think of it, Barrack Obama) into this arc and — boom — you have the basic outline of their accepted biographies. And nerds, geeks, artists and dreamers, that is to say, people like me, eat this shit up. Because the message is that we can win. In fact, the implicit message is that we are destined to win.

It’s fun to be a part of. Everyone entrepreneur I know is training themselves in things like meditation, yoga, nutrition and mindfulness. All of that stuff was totally fringe just 15 years ago. Now they talk about it at Harvard.

But as Donald Trump and James Dolan defiantly exemplify, Enlightenment values and the mastery of noble virtues do not represent the only path to success.

These guys, with their inferior intellects, poor tempers, mediocre ideas, and laughably-low EQ’s… They should not be able to beat us at a game as complex as business. And yet they do.

But how?


Call me naive. It’s fair because in retrospect I have been for quite some time. I got so wrapped up in my own little Hero’s Journey that I completely lost sight of the fact that, not all that long ago, business was considered anathema to idealism by pretty much everybody I knew. If you grew up in the 90’s, as I did, you’ll remember that “corporate” was synonymous with “evil” or “greedy”. And the term “CEO” evoked images of guys like Dick Cheney and Kenneth Lay.

There’s a reason Google, founded in 1998, chose the motto “Don’t be Evil”. Back then, the default assumption of young people was that all businesses were, necessarily, evil. And the idea of someone like me — a liberal arts grad who studied sculpture — founding a corporation and becoming a CEO wasn’t even absurd — it was just a non-thought. Like, it simply never would have crossed anyone’s mind as a possible outcome.

Business was for guys like, well, Donald Trump; prototypical, old-school alpha males. White guys, with rich dads. Cutthroat competitors who wore black suits and fat ties and would do literally anything to win. And the CEO, presumably, earned his position by emerging from some decades-long Darwinian tournament that guys like me would never, ever enter in the first place.

Here in 2017 though, in my idealistic little corner of the business world, no one ever talks about those guys anymore. We’re a very studious lot, mind you, we just conveniently ignore the existence of people like Trump and Dolan when it comes to studying business, even though their ongoing success is undeniable. It’s like some sort of collective denial took hold and we didn’t even know it.

Perhaps the assumption is that sooner or later, they’ll simply be Disrupted away, like dinosaurs. So why waste time worrying about them? I think it’s more likely though that we ignore them because their existence makes us uncomfortable. It threatens us.


When Trump won the election — that is to say when I could no longer write him off as a joke or a loser — I was forced to ponder him sincerely because, like many millions of people throughout the world, I was experiencing a psychological dissonance, which is acutely uncomfortable.

The reality I witnessed on Election day suddenly felt incongruous with the one I’d constructed in my mind and lived by for the preceding decade or so. And so, in simple terms, I was in shock. I literally couldn’t understand what had happened and, in order to get my sense balance back, I would have to come up with a new theory that accounted for Trumps and Dolans.


What I came to is that there really is a Dark Side.

Empathy, creativity, wisdom and vision are indeed very powerful. Wielded artfully, they can transform reality itself. But there’s always a yang to the yin. I had failed to appreciate that greed, ruthlessness, deceit and fear are just as powerful — maybe even more so because, as any kid knows, to destroy is much easier than to build.

In business, as in life, as in all of mythology… the struggle between the l, referred to by Joseph Campbell as the hero’s journey.ight and the Dark is real and it’s eternal. It can not and will not end because like night and day, the one simply can not exist without the other.