I enjoy reading his columns, but not as much as I enjoy his podcasts. I think he's really good at getting interesting guests and letting them have a free-wheeling forum to just talk about sports stuff.
I think because of the podcasts he's gotten a little lazier with the columns. But I like the podcasts more, so I'll take that trade off.
I do have a few problems with his writing, but not enough that I'll stop reading.
1. I dislike how definitively he states things. Then, when wrong, (which most people are, by the way, not just hated experts) he just chalks it up to being a self-acknowledged "idiot," but then goes on to make other definitive predictions. To be fair, this is the case with pretty much everyone (fans, talking heads, etc.), but he seems smart enough to know better.
2. I really hate that he "learns" lessons, then either a. ignores them because he thinks they no longer fit, then it turns out he should have listened to his lessons, and uses that as proof of his lessons, or b. decides that he doesn't need to actually follow through on lessons because he's a "fan." As an example of "a." see all of his gambling "rules." As an example of "b." see his "5-year post-championship no-complaints" rule. I actually like this rule, but it took him only a couple of years to figure out why it shouldn't apply to him, which, in his writing, is okay because he's just a fan.
3. Related to above, I think he's having a very hard time straddling the line of "fan" vs. "commentator." It's difficult, but I don't think he's doing the best job of it either; he's basically trying to have his cake and eat it too. He's always talking about not being crazy and overreacting, then goes crazy and overreacts, but, at the time, truly thinks he's not overreacting, then a few weeks later will acknowledge that he overreacts but that it's okay and forgiveable because he's a fan.
4. Not exclusive to him, but rather an epidemic in ALL sports writing, is how sports writers force reality into their own pre-written narrative structure, regardless of how well it fits. This in particular was my biggest problem with his Book of Basketball. Now, I really enjoyed the vast majority of it, but I really could have done without the whole "secret" premise, as well as his discussion of how he'll have to re-work some of it with Kobe's post-book success. This is how a lot of people's minds work, especially with regards to sports, but it still drives me crazy with him. Essentially, he adopts the premise that all championship teams must embrace the "secret." The flipside of this is that players and teams that don't win didn't win because they don't possess the secret. Unfortunately, the logic is entirely unprovable and cyclical, and instead of analyzing all championship teams vs. non-winners and then figuring out the common thread (if any), he starts with his conclusion, and then actively FINDS the supporting evidence in championship teams and FINDS the lack of evidence in non-winners. Lazy. Completely arbitrary. EVERY sports writer does it, and it's stupid. Because now, he's essentially locked into describing how Kobe, WHO HAS PLAYED EVERY SINGLE GAME OF HIS CAREER THE SAME EXACT WAY, didn't have the secret, then suddenly now does (maybe Pau brought it with him? Maybe that has something to do with it?). I hate it, and almost all writers do it, regardless of how things actually played out.
-aside-
The above, however, is true for almost all sportswriters, so while I hate it when Simmons does it, it's unfair to really hold it against him too much. However, I want to point out that this is one reason I think Hollinger (gasp!) is one of the better and more interesting writers, simply because he lets the games unfold, then tries to explain why things happened the way they did based on what actually happened, and not based on what he expected to happen going in.
For example, in the Celts/Lakers finals, there were basically 2 stories that were going to get told afterwards, regardless of what actually unfolded on the court. If the Lakers won, it was because Kobe's figured it out and he's a winner. If the Celts won, it was because they were a smothering, defensive team and because Kobe hadn't quite figured it out. Of course, the reality was that the Celtics played incredible defense, good enough to win, but their OFFENSE failed, and Kobe played THE EXACT WAY HE HAS HIS ENTIRE CAREER, namely shootig a LOT, regardless of how well he's shooting, and allowing his big men to quietly be ridiculously efficient. But guess what, the story was already written one of two ways, the writers were just waiting for the outcome to plug in the formula. Hollinger, to his credit, tries to avoid this; he's the only one I can think of that really does that on the national stage.
So, after seeing the above, why do I like Simmons? Sadly, he's still among the best sports writers, despite the above flaws; that's how bad most are. Additionally, he has a few things that I still truly look forward to and enjoy:
-I always like his quit-hitting Friday Football previews. Usually quite amusing.
-I always like his NBA previews where he picks a movie to quote and applies those to predictions. Again, amusing, and this is one of those columns where everyone knows most of those predictons will be wrong, but it's fun.
-Trade Value Column
-NBA draft running diary.
All are pretty much more bankably entertaining than 99% of everything else out there about sports.