The only way to ask this question is to make it relative. The real answer’s probably that it’s either always or never a good time to be James Dolan. On the one hand: Rich, powerful, has a lot of fun toys. On the other: Very easy to make fun of.
In a lot of cases, these two sides of Dolan’s identity show up on the same coin. He got his band to open for the Eagles, which was probably a lot of fun. That band is also the thing that erodes any last inclination to take the guy seriously. Plenty of shitheads own sports teams and/or big arenas. Only James Dolan used those to make the Eagles and ZZ Top associate themselves with what reviewers call Dolan’s bad karaoke. At least to an outsider, nothing captures James Dolan’s earthly experience like JD & the Straight Shot.
Right now, though, two of the three things in James Dolan’s public life are doing well: On the MSG side, the Sphere is a phenomenon, one of the highlights of Las Vegas. On the basketball side, the Knicks have won a playoff series three years in a row, the first time this has happened since before 9/11. On the hockey side, the Rangers went from winning the Presidents’ Trophy to missing the playoffs, and then right as their season ended, a report came out about an Artemi Panarin sexual assault settlement. MSG: Good. Knicks: Good. Rangers: Bad.
Last year was when times were really good for Dolan. Last year, the answer to this question was easy. The Sphere was even newer, the Knicks were better, the Rangers didn’t stink, and nobody’d heard about Panarin yet. It was a James Dolan sweep! Maybe this is the end of a good Dolan run, then? The thing about the Knicks’ accomplishment is that it only looks good in contrast to how bad they’ve been this century. Get walloped by the Celtics, which is probably what will happen, and the veneer cracks.
As of today, I’d still call things good for Jimmy D. Two out of three enterprises succeeding is frankly much better than things are going for me. Although: I just looked for tour dates for JD & the Straight Shot and I didn’t find any. Maybe they’re waiting for the Grateful Dead to finish their residency at the Sphere.
P.S. JB Pritzker getting presidential buzz has to be a good sign for Dolan in the public eye. Pritzker is Illinois’s answer to the J-dog.
**
