The Podcast That Isn’t Afraid of James Dolan

Photo: Wondery

Long-suffering New York Knicks fans caught something resembling a break this year: For once in a very long time, the Knicks are pretty good again. Powered by an electrifying Jalen Brunson, the team made a solid push into the playoffs this season, ultimately falling to the unmovable wall that is the Miami Heat’s Jimmy Butler.

Now that the season is over, a familiar smog descends on the franchise. Whatever hopes may flourish in the offseason about this being the start of a genuine ascendance, it’s still the reality that nothing about the broader conditions informing the Knicks’ long-suffering state has fundamentally changed. Specifically, the team remains under the ownership of James Dolan, the media-empire scion and wannabe blues musician who inherited Madison Square Entertainment from his father, Charles, over which he continues to rule with an iron fist.

The mythology of Dolan and his persistently troubled reign over the Knicks has been chronicled for ages, including by this magazine. But even as he has become a permanent fixture in the ownership role and New Yorkers’ hatred toward him has curdled into a kind of foundational civic spirit, new and crazy stuff always seems to be happening with the guy. If it’s not having a Knicks legend forcibly ejected and banned from Madison Square Garden, then it’s pioneering surveillance-state-level facial-recognition technology to further enforce his will over his stadiums.

So it’s prudent to revisit the Dolan story every once in a while just to lay down all the bizarro threads in one place. One such effort is Wondery’s Reign of Error, a five-part audio miniseries stemming from a collaboration between Campside Media — the podcast studio behind formidable investigative pieces like The Evaporated, Chameleon: Wild Boys, and Suspect — and Smartless Media, the new audio studio spun around the Jason Bateman–Will Arnett–Sean Hayes celebrity hangfest resulting from the gobs of money they’ve received as part of a lucrative Amazon Music deal.

In a departure from Campside’s usual stuff, Reign of Error is a chattier, bouncier, more overtly humorous affair. It’s closer to the core Wondery model of nonfiction production in which a performing host — usually a celebrity, sometimes a comedian — is grafted onto a previously reported narrated spine (see Fed Up, among others). In this case, the Campside team sourced the public-radio veteran David Greene for the role. A former Morning Edition host who left NPR a while back to try out new things in the audio space, Greene is currently the host of KCRW’s Left, Right & Center and recently led In the Moment, an interview series published by Religion of Sports back when the Tom Brady–co-founded media company was still dabbling in the podcast business.

Reign of Error is a bit of a different beast for Greene, who gets to play around with his humorist chops. But as Josh Dean, Campside co-founder and Reign of Error executive producer, tells me, the team went through a long list of people before landing on Greene, who seems to be completely fine with that.

I heard you had some trouble finding a host for the show. How many people did you plow through before getting David?

Josh Dean: Well, for obvious reasons, I can’t literally name names. But I can say we reached out to at least one former NBA player, one late-night comedian, one New York City–based actor, and one semi-retired sports broadcaster. Man, we had so many conversations with people who were like, “Yeah, can’t stand the guy, but no way.”

And not once was the reason “I have nuanced feelings about this person.” It was always “I want to be able to go to Madison Square Garden. I don’t want to tell my kids we can never go back to a Knicks game.” In the case of the broadcaster, he’s a freelancer now, so there was a fear that some of his relationships in the league might be endangered.

Anyway, we got really down the road with someone who backed out at the last minute, and that’s when David came along.

David Greene: Yeah, I wasn’t the first call. I don’t even think I was the ninetieth. They called me and were like, “Full disclosure, we’ve asked so many other people, but no one wants to do it because they don’t want to be banned from the Garden.” At first, I thought they were joking, but knowing what I did about Dolan, I mean, it’s a thing.

I guess they decided to try a journalist and someone who maybe would see value in telling this story and have a blast doing it even if it meant never being able to go to the Rockettes again. But I was down to do it. There have always been a sports fanatic and a wannabe comedian living in me, and it sounded like exactly the kind of project I wanted to try since leaving NPR. Giving up the Garden would be huge, but it’s also a badge of honor.

It’s crazy to me how many people are afraid of being banned from the Garden. Everybody hates Dolan but is afraid to piss him off. It’s almost as if the Garden were the reason he still has friends.

Dean: Exactly! If we put aside the anomaly that’s happening right now, where the Knicks are actually winning a few playoff games, the Knicks have been consistently terrible for the last 23 years yet they keep selling that place out. I underestimated how much celebrities still want to be seen courtside.

It’s completely baffling. And it really does feed into this question that’s kind of driving the series: Why won’t this guy sell? He doesn’t seem happy to me. He could probably sell it for a record — $6 billion at least. This is a guy who produces a low-tier basketball team in the world’s most successful media market with a rabid fan base that hates him passionately. No one wants that. Except Dolan, for some reason. It’s like he wants to keep stepping on the rake again and again.

He has been a known quantity for a very long time. Where did this project come from, and why did you want to tell Dolan’s story now?

Dean: I had actually written a story about him for Bloomberg Businessweek a few years ago, and that was on my mind when Smartless reached out to us to develop projects. I had thought I knew everything about him, but when I was reporting that story, it occurred to me I’d never seen all the pieces assembled in one place. So many more things have happened with Dolan since then: all the facial-recognition stuff, being at war with the City Council and the New York State attorney general, politicians threatening to take away his tax breaks.
We do serious journalism here at Campside, so we went into this project not only to tell the story of this absurd man but also, like, maybe to try to tip the scales and maybe liberate the Knicks in the world. We’re also hoping to make something people who aren’t sports fans would listen to — he’s just so interesting as a character. He’s almost scripted in that he does exactly what he shouldn’t do every step of the way. Every time there’s a decision to make, he makes the wrong one.

Were you banned from the Garden for writing that piece?

Dean: I haven’t tested it yet, but I’m pretty sure I’m banned now. I should probably try it for publicity on this show.

Did anything new come from the reporting that surprised you?

Dean: I’m not sure if there’s anything revelatory here, but I was struck by how it almost all goes back to how he always wanted to be a musician, having a moment of rebellion, getting caught up in drugs and alcohol, and essentially being pushed into the family business.

Again, for the Dolan scholars out there, nothing here is new, but I didn’t truly comprehend how much Jim actually stood up to his father. I knew they had butted heads in the past and that their relationship seems to be good now. What I didn’t realize was how the story was of him vanquishing his father. And of course, with the power dynamics of wealthy families being what they are, there’s this element of him just holding on to the Garden because selling would feel like an admission of failure.

The thing about Dolan being a wannabe musician is one of the more prominent aspects of his public story. What do you think that reveals about him?

Dean: I think it just means he’s never going to be satisfied. Whatever needed to happen for him to realize a music career just didn’t happen, so he was pushed into the family business and succeeded wildly.

Honestly, it’s hard not to think about the absurdity of that.

Greene: Totally absurd. But it’s also something you can latch on to, right? Who among us can relate to James Dolan in any way when it comes to being that wealthy and powerful and crazy? But we can relate to having dreams, having goals, wanting to do a thing you feel you cannot do.

You know, I’m a karaoke addict even though I’m a really bad singer. I like going to karaoke bars and picking the one or two songs I can actually be respectable onstage with, and there’s a kind of culture in it that’s pretty supportive. You’re allowed to be yourself and authentic. So with Dolan, I think that music is like his safe, innocent space.

Do you think he’s a good businessperson?

Dean: You know, it would be hard to argue that he’s not by the metrics of stock price, how much the Garden sells out, returns to shareholders, and the value of his equity, things like that. Now, could anyone have run Madison Square Garden and made it successful? There’s probably some amount of it being that hard not to be successful in that business.

But he did buy the Beacon Theatre, Radio City Music Hall. He bought the old Forum in L.A. He’s expanded the empire in ways that weren’t as obvious, and I think they’ve all been wildly successful. So I think we could definitively say he’s at least a quite good businessman. He’s just terrible at this one specific thing.

He also seems to be betting the farm on that giant concert sphere in Vegas. Part of me thinks that may be the end of the empire.

Greene: Oh, we get into the spheres. It’s some of the funnier moments on the show. I think you’re going to find a lot of our sphere reporting is fairly new: how it came about, where it was tested. It takes us beyond Las Vegas. Our story doesn’t really end on the spheres, but you do understand the strangeness of this guy who’s looking for the future of entertainment in something that’s globe shaped.

Dean: Yeah, the sphere stuff is something we feel might actually end his reign at the Knicks, and we get into it on the show. It’s a billion dollars over budget. It’s entirely possible that it’s going to fail spectacularly and he’ll have to sell the Knicks to pay off investors. Or who knows, maybe it’ll be a spectacular success and everybody’s like, This guy’s a visionary, we’re all gonna watch concerts in spheres now.

Do you think the Knicks will ever be free of Dolan?

Greene: I mean, that’s part of the mission of the podcast. Even if the Knicks go out of the playoffs — and I doubt they’re gonna end up beating the Heat, just given where this series is going — maybe there’ll be some lesson in here that Dolan will learn that the more he stays out of the way, the better this team can be. I give that like a 0.01 percent chance of becoming reality, just given Dolan’s history.

But who knows? Maybe he becomes so obsessed with spherical entertainment that he gets out of the way and lets this team be what it is.

If you could meet Dolan in person, what would you want to tell him?

Dean: I think my message to him would be “You don’t have to do this.” If I could remove the cross or burden he’s carrying, which is owning the Knicks to impress his father or prove the doubters wrong or whatever, he doesn’t have to do it. He can tour with his band and own spheres and make 6 or 8 or 10 billion dollars selling the Knicks. And then no one will yell at him on the street anymore.

Are you two Knicks fans?

Dean: No. I’m from Maryland originally, and there’s no team in Maryland. I live in Brooklyn, and my kids are Nets fans, so if I had to pick a team, I would say the Nets.

Greene: I’m a die-hard Sixers fan. And I’m all Pittsburgh: I’m a Penguins fan, so I hate the Rangers.

Wait, you’re a Sixers fan? Is that why you’re hosting this show?

Greene: I mean, as a Sixers fan, whatever causes the Knicks to be terrible for a sustainable period of time is great for me. I’m thrilled with that. So even if all this ends with Dolan continuing ownership and staying involved in the Knicks, it’s still a good outcome for me.

So this is just Schadenfreude for you.

Greene: Basically.

The Podcast That Isn’t Afraid of James Dolan