I mean, I'd like to say there's some racial factors here. I think he's normally pretty objective so it enables him to gather some really good insights into certain things like the James Harden trade to the Rockets. But then again he kind of followed Morey quite a bit from the Boston connection/obsession. He's unapologetically a Celtics fan, an organization that Morey has connections with. Also the MIT thing. ... Hmm.. So I guess he's biased. As you say, the intellectual aspect is incredibly entertaining for me when I hear him talk. He's very efficient with his wording and is great for a fan like me. Jalen Rose brings a practicality aspect to that intellectual discussion, talking about the on-court skills and what aspects of a player's game is worthy of discussion. It takes a special mind to put together this kind of thing, and it's just objectively better than most of the other talk shows I can watch. I do hate it when I have to hear about football for like more than half the show on Grantland. Ever since it's become a political playground, I'm not even wanting to get into that sport. NBA has been doing much better.
I still love Simmons, but definitely do an eye roll every time that something totally unrelated makes him say "oh yeah, that reminds me of the '03 Patriots" or "that makes me think about the time that Robert Parish..." or "yeah that's like the time that Paul Pierce made that shot..." It almost always has nothing to do with Boston sports but he can't help but bring it up at any opportunity.
In that same podcast he did about a 10 minute segment pretty much talking about how guys were getting fired for not drafting Luca, the Pierce firing in Atlanta started it off and he had prepared for it. If he had actually won a playoff series yet I could maybe go for it but he has 1 playoff appearance.
He jumped the shark years ago. Podcast still mildly entertaining at times however. The Ringer website is crap now, not having any writers and just linking to podcasts all the time. Lazy.
I'm curious how many know where the name Grantland comes from? If not, given your post, I thought you might find it interesting.
Bill Simmons can still be funny, when he does his homework and is paired with other talented, intelligent people. I enjoy "The Rewatchables" podcast. I also think his "Book of Basketball 2.0" deep dives were pretty interesting. He clearly researched his topics and he got into a level of detail with past players that most sports journalists do not bother with. He is best when he doesn't try to maintain his college dude persona of his younger days. Sometimes it feels a little icky when he tries to talk about actresses in the Rewatchables. He is like "OH YEAH," and everyone else is like "ewww." Dude, you are 50 years old, nobody wants to hear about your horny thoughts anymore, even if you are talking about your past self. I mean in principle, these women are also 50 years old now, but somehow it still seems a little off to hear his randy thoughts about an 18 year old (even if from the past). I also think his music takes are weird, like an old man trying to stay hip. But whatever.
Listened to him and Russillo and they both agreed that Houston fans should be pissed that now everybody likes Hardens game, when he has not changed his game at all. Was surprised they admitted that and it was pretty matter of fact.
Both of these out of shape middle aged bozos who probably never spent a day in a gym in their miserable lives deep hatred for Harden is hilarious.