I mean let's look at it this way. The guy was a nobody they signed off the street because his column was funny. Years later he's been one of the most powerful people in the company. That's worthy of respect.
He's ambitious enough to be directly responsible for two of the best things ESPN has ever done which is 30 for 30 and Grantland.
I've read his book of basketball. He knows more about basketball history than anybody in ESPN knows about anything in any sport, except maybe The Schwab before he was let go. That alone makes me respect anything he says when it comes to basketball. I agree his knowledge of football is not much more than a typical knowledgeable NFL fan.
I could see why people think he's smug and has a big ego, but frankly, ESPN is filled with so many of those guys, it's refreshing when there's a great writer with a sense of humor who knows more about the game than 99% of people. Another thing I like is that he "gets" the intangibles in sports. Nothing pisses me off more than the Bill Barnwell advanced stat geeks who try to act like momentum, "IT" factor, and the mental/will power part of the game doesn't exist.