So James Dolan inherited the corporation that owns the New York Rangers, New York Knicks, and Madison Square Garden. Thanks to his colossal inheritance, he's still a billionaire even though he's grossly mismanaged the sports franchises, and he's presided over some ventures that lost hundreds of millions of dollars (I cannot think of any other New York businessman who inherited Daddy's billions and remain billionaires despite their overconfident blundering).
He is famously thin-skinned, combative, and vengeful. He gave Knick fans lifetime bans from MSG who wore anti-Dolan shirts to the arena. After Oakley publicly criticized Dolan for a decade of horrific trades/contracts, Dolan sent security guards to Oakley's seats during a game and had him forcibly ejected from the arena (Oakley lost his shit and lawsuits ensued).
Speaking of bankrolling promoters... Dolan surrounded himself with superb musicians, formed "JD and the Straight Shot," who opened for the fucking Eagles (!!!!!!) -- and his band has been on numerous late-night shows. He was on Fallon, which should tell you everything you need to know about the integrity of a network choosing its musical guests.
Anyway, I really wanted to link to a couple YouTube videos, but they've suspiciously disappeared from the website. The Fallon appearance is gone. Another video that is scrubbed from the internet was shot by a fan when Dolan was playing City Winery in New York. Between songs, a frustrated fan starts yelling, "I want my money back!" and later, "You have a terrible singing voice!" Then there was an awkward silence as the fan is ejected from the venue, and then as the room is still murmuring and buzzing, Dolan saying energetically to the crowd, "Hey, do you guys like Johnny Cash?" It was glorious. I wish I had saved it.
There are only a few videos of him on Youtube, and they have comments disabled.