James Dolan Is The Donald Trump Of Sports Owners, And His Thin Skin Is Showing

Imagine waiting 53 years for your team to win a championship, only to learn the owner is an even bigger asshole than before the team won. 

Such is life for New York Knicks fans, who have the unfortunate displeasure of being owned by James Dolan — which is the equivalent of ICE owning a taco truck.

The New York Knicks finally brought home an NBA championship, and James Dolan’s organization celebrated by giving some assistant coaches empty ring boxes and emailing employees a promise of free championship rings that turned out to be a phishing test. That’s right. Some employees clicked a link expecting to select their championship jewelry and instead got assigned mandatory cybersecurity training. Congratulations on the title, y’all. Now report to detention.

*** Even Trump was like, “Damn, Dolan.”

Because on the boorish scale of objectionable, rude, and unprofessional behavior, Dolan has reached Trump administration levels. He should really look into 

To be fair, Madison Square Garden says more than 275 people will receive championship rings or jewelry worth a combined $3.7 million, and the company apologized for using the rings as bait. But good Lord, could this man let people enjoy something without turning it into a hostage negotiation? The Knicks win their first championship in more than half a century, and somehow the celebration comes with a side of corporate humiliation.

It’s a total Trump move: to humiliate the people around him, those who depend on him to do right by them. Despite having more money than most people can dream of, they still aren’t happy unless they are smashing the hopes and dreams of those who depend on them. 

They are the Ramsay Boltons of King Joffreys.  

They confuse criticism with disrespect, loyalty with submission, and having power with being universally adored. They have the resources to enjoy lives most of us couldn’t imagine, but they remain preoccupied with the people who hurt their feelings.

And everything hurts their feelings. Everything. 

Dolan is what happens when you give a man billions of dollars but never teach him how to take an L. The man owns one of the most famous basketball franchises in the world, Madison Square Garden and an entertainment empire. And yet, somehow, he keeps finding time to put himself in the pettiest beefs with basketball legends, cultural icons and regular-ass fans who have committed the unforgivable sin of not kissing his ass.

Just ask Charles Oakley.

In 2017, the former Knicks enforcer and beloved franchise legend was forcibly removed from the Garden during a game and arrested following an altercation with security. Dolan subsequently announced that Oakley was banned from the arena. The ban was eventually lifted after the two met with NBA Commissioner Adam Silver, but the damage was done.

Oakley played a decade in New York, helped the Knicks reach the NBA Finals and embodied the toughness that made those teams beloved. He was part of the franchise’s identity. And Dolan’s response to a very public dispute was to turn a Knicks legend into a trespasser in the building he helped make special.

And then there was Spike Lee.

The Oscar-winning director is practically a Knicks institution. He’s been sitting courtside for decades, spending a reported fortune on tickets and showing up in Knicks gear like the team’s unofficial cultural ambassador. But in 2020, Lee got into a dispute with Garden security over his use of an employee entrance he said he’d used for 28 years.

The Knicks insisted Lee was violating a new entrance policy. Lee said he was being harassed and announced he wouldn’t attend another game that season. Let that sink in. One of the most recognizable Knicks fans on the planet was publicly feuding with the owner over which door he used to enter the building.

Dolan couldn’t simply resolve the disagreement and move on. He couldn’t stand that a Black man who makes films that usually center Black actors that are highly recognizable, yet none of us know their names, was walking through a door that he hadn’t approved. 

Fine, I made a lot of that up, but still, what is this man’s name without Google-ing:

Told you. 

Back to Dolan, I hope he’s consciously edging towards his villain arc, because if not he’s going to be confused when he gets there and tries to figure out why he’s dressed like Gargamel. But the funny thing about Dolan isn’t that he’s joining fights with Knicks legends and cultural Black icons, much like his godfather Trump; he’s creating them. 

The security guards harassing Oakley did so at Dolan’s insistence or with his consent. He implemented a new entrance policy to thwart an icon from having to walk through the throngs of fans to get to his set. These aren’t actual problems; they’re imagined catastrophes like the massive hoard of Mexican rapists that are coming over the borders by the millions, or the influx of immigrants who will do anything to remain undetected but somehow seem to vote every November.  

In 2021, a fan wearing a “Ban Dolan” T-shirt was ejected from Madison Square Garden. The shirt’s designer, Frank William Miller Jr., later said he was banned from every venue owned by Madison Square Garden Entertainment. In March 2025, Miller said he was escorted out of Radio City Music Hall while attending a concert with his parents.

MSG said Miller had made threats against an executive on social media and sold merchandise the company considered offensive. Miller denied threatening Dolan. But even with that dispute acknowledged, the optics are ridiculous. A billionaire entertainment mogul and a T-shirt designer have been locked in a controversy that followed the designer to a concert venue years later. Imagine having enough money to buy your own arena but not enough emotional stability to let someone wear a shirt that makes fun of you.

Dolan can buy the building. He apparently cannot buy a sense of humor.

And that’s what makes him the Trump of the NBA. Trump has spent years treating personal slights like national emergencies, publicly attacking critics and using his power to punish people he believes have disrespected him. Dolan’s arena empire gives him a similar ability to make criticism feel like a punishable offense. Neither man seems to understand that being powerful doesn’t mean being above ridicule.

They also demonstrate one of the great truths about rich people: Money can buy access, influence, and an army of people paid to tell you you’re wonderful. It cannot guarantee that anybody actually likes you.

Dolan has spent years making enemies out of people who should be his greatest allies. Oakley represents the franchise’s history. Lee represents its culture. The fans represent its lifeblood. The employees represent the people who keep his empire running. Yet again and again, the story becomes less about the Knicks and more about Dolan’s apparent inability to let anything go.

Apparently, billionaire skin is about as thin as the Washington Wizards’ chances of making an NBA Finals. But if I may borrow Dr. Cheyenne Bryant’s imaginary doctorate for a minute, I’d say both Trump and Dolan share one thing in common: They want to be loved. They got rich, in part, because they believed money could buy them the one thing they desperately crave but can’t seem to earn — genuine affection. And the wild part is that it’s never enough. There’s always more money to steal, more fees to charge, more knees to bend, and more rings to phish — I mean, kiss.

And if you take nothing else from this story, remember this old adage: Money doesn’t un-lame a lame.

Because that’s really the only lesson here. 

***Trump never said this.

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