I've never been one for team sports, preferring running, swimming and the like.
But I have read and will read anything written by Bill Simmons. The man is one of the great writers of our time. He's the Stephen King of sports writers, a guy who keeps pumping out solid, often great stuff that transcends his genre.
I don't follow football, but I read Simmons' picks during the season. I don't follow basketball, but I read his trade value column every year. Why? Because
-the guy explains it in an interesting way
-puts it in the proper perspective like you said
-links me out to great, great stuff I never would have found otherwise (like the greatest YouTube video ever: http://sports.espn.go.com/espnmag/story?section=magazine&...)
-is now living a bit of a glamorous, interesting life that's fun to experience vicariously
-can write like the devil
This is a guy who took a week to review the Karate Kid trilogy in detail instead of filing regular columns one summer.
http://espn.go.com/page2/movies/s/simmons/020830.html
And yet he attended a funeral for a young athlete who died senselessly, and wrote a "serious" piece that was moving, humble and very honest: http://sports.espn.go.com/espn/page2/story?page=simmons/0803...
There are writers who excel at structure, writers who are idea guys, writers who can nail little details, and then there are writers who simply have more firepower than the average man. They can write more, faster, and with more panache than 99% of the folks out there. It won't all be good, but it'll all be interesting. Simmons has a lot of firepower.
Which, to get back on topic, is why it's INFURIATING, that he's cranking out 3-4 podcasts a month and only 1-2 columns at this point. I simply can't listen to the podcasts. They don't fit into my schedule at all, in any way. I don't have an hour to stare at my computer while it plays an audio stream. Bring back the columns.