I agree, I've always like Bill Simmons, especially his writing.
Some of his Podcasts were pretty good also, I remember the Football ones with Mike Lombardi and the Basketball ones with Steve Kerr being especially good (too bad they are now both employed for teams).
When he was on the ESPN Basketball broadcasts, he was OK, but that is not really what he is one-of-a-kind at. It is his writing especially that can be sublime in some cases.
This isn't really going out on a limb much, but I've completely convinced either he or one of his staffers reads Patsfans.com occassionally. A couple of years back, there was a very off -the-wall thread that was absolutely not something that was obvious or timely and I had never seen anybody write on this weird subject before. A day or two later, he addressed this exact subject in one of his mailbags, although he said something like ("I received an E-Mail on (weird subject).....", and then he addressed it). I noticed because I had brought up the weird subject in the thread, but I hadn't E-Mailed him. It could have been a coincidence, but again it wasn't anything timely or obvious and I had never seen anyone else talk about this weird subject.
That was the most obvious example. However, during Deflategate he seemed so knowledgable that I wouldn't be surprised if he or one of his staffers were reading some posts by many of the knowledgable people here.
It wouldn't be shocking, he is a Pats fan also.