James Dolan, Billionaire Owner of the New York Knicks is Singing the Blues, Literally

Blues is the music of pain, an amalgamation of spirituals, slaves’ field hollers and work songs, an art form predicated on leaning into suffering and, in turn, finding release, be it in the Mississippi Delta or the slums of Chicago. To trace the history of the blues is to trace the history of black culture.

James Dolan, the billionaire owner of the New York Knicks and son of the founder of Cablevision, is singing the blues. He’s performing at City Winery in Tribeca with his band JD and the Straight Shot, which, according to the band’s website mixes “blues, folk, and Americana styles into a timeless American music sound of their own.”

If you were to take a strawpoll to find the least popular man in New York City, Dolan would undoubtedly crack the top dozen or so. Since he took control of the Knicks in 1999, the team has been a demoralizing, soul-crushing strain of bad. In the previous year alone, the Knicks banned a beloved former player from Madison Square Garden, had their starting point guard vanish before a game without explanation, and have moved heaven and earth to alienate their two best players, Carmelo Anthony (a sure-fire Hall of Famer who inexplicably wants to be part of this team) and Kristaps Porzingis, a 7’3" titan of sport and the love of my life. Dolan has been the sole constant for perhaps the worst 18 years in franchise history, overseeing 12 coaches and 834 losses during that span, with his face permanently twisted into a frown. And, oh will you look at that: Dolan is performing on the night of the NBA Draft. Nero fiddled while Rome burned, but in the eyes of Knicks fans, he’s got nothing on Dolan.

Those eagerly awaiting a gross spectacle of a concert, though, would be severely disappointed — inside of City Winery, no one seems to know or especially care about Dolan’s day job. Sure, there are Andrew, Ryan, and Josh, three impressively goober-ific Knicks fans who learned about the concert on Barstool Sports (a sports website for the racist illiterates amongst us), but by and large, the performance remains good-natured and Knicks-free.

On stage, Dolan cuts a joyful if shambling figure as he paunchily bops along to his songs in a shiny red velvet jacket. Supporting JD are the Straight Shot: two guitar players, one of whom is Aidan, Dolan’s large adult son; a violinist who plays with the verve of an entire orchestra; a standing bass player; and a drummer who intermittently dons a suit of rattling trash for added percussive effect. Two hecklers — “I want a refund!” shouts one; “Your singing voice is terrible! How did you get a job in a band? You’re just bad!” his friend yells at James Dolan, as security escorts the two from their seats — fail to phase the fivesome.

“I very rarely play New York because I can’t escape the sports fans,” a sweaty, happy Dolan says after the show, “but tonight was great, and the rest of the country is great, and Europe is even better.”

This isn’t to say that Dolan’s music is good. It isn’t. He sings like he’s trying not to cough, and it's possible he can’t play the guitar. Worse, his songs belie his status as a cosplaying bluesman; most of his lyrics simply summarize current events or books that he’s read, as if he were presenting a 10th grade English class project. The sheer earnestness and naïveté of it all is hilarious, especially coming from a 61-year-old man.

“Our songs tell stories,” Dolan explains, “and they’re the stories that I know and the stories that I’m sure of.”

His set is a mixture of songs from his previous albums, Ballyhoo and Where I’ve Been, as well as ones that he’s working on for his third album, which is slated to come out next fall. “Moonlight” is an aggressively glum unreleased song about Pygmalion, an ancient Greek dummy who fell in love with a sculpture; the titular track of his forthcoming album,“Good Luck and Good Night,” is a smug acoustic ballad (an apt description for nearly all his songs), warning of the dangers of fake news, which would be fine if not for the fact that you donated 300,000 American dollars to Donald Trump and that this is all your fault, James. Let’s not forget the manic Adderall-bender of a song that Dolan uses to close his set, in which he yelps about receiving a handjob while operating a motor vehicle; the thought of it alone makes me want to tie rocks to my feet and walk into the ocean. His true piece de resistance, though, is “Under That Hood,” a plodding retelling of the story of Trayvon Martin, written with all the nuance of a 13-year-old on Tumblr telling you that I just don’t see race, man.

Nothing in his pocket but candy and a pop / Made him different and why'd he get stopped,” drones Dolan, making a very Concerned Face. “Color of his skin or the hoodie on his head / Ain't no reason for the boy to be dead.”

Makes you think.

Still, while Dolan is an easy target for snarky blogger types, it’s undeniable that he and his audience thoroughly enjoy the show. Naturally, Andrew, Ryan, and Josh have a good time because, as they are eager to boast, they were very, very drunkbut the wine-sipping Olds who populate most of the crowd raucously applaud at the end of each song and even, at times, sing along. Everybody is laughing and everybody is smiling. In the end, really, that’s all that matters.

“We loved it!” enthuses Leslie, a tourist from Australia who’s at the show with her husband, Jeff, and has no earthly idea who the Knicks are. “We just found the show by googling ‘live music in New York’ and luckily it was really top-notch.”

Like all great art, JD and the Straight Shot's music reflects life, particularly “Violet’s Song,” a tune-adjacent rendition of August Osage County’s Sparknotes page. Ostensibly, Dolan’s taking on the persona of Violet Weston, the play’s matriarch, but he could just as easily be singing about himself, pridefully, steadfastly holding firm amongst the ruins of his own making — not that this level of metadiegesis is at all purposeful. 

“Look around, you will see / there’ll be nothing left but me,” Dolan croons, as Knicks fans worldwide beg him to sell the team. “It’ll never break me down.”

If he were Nero, he’d smile.