I love the Boston teams as much as anyone, but Simmons ranks up there with Dane Cook and Ben Affleck as Boston celebrities/ national media figures that make me wish I was from Chicago or Toronto.
He can be an excellent and worthwhile read when talking about select subjects (like the NBA) and I won't be surprised if his Basketball Book is good, but he has collossal blind spots and sounds as dumb as anyone when caught in these subjects. The podcast where he mentions Zach with Dave Dameshek (a wannabe poor man's Adam Corolla) he spends a good 40 minutes spouting pure bullshit about the NHL. His hesitation on whether Minnesota should have and NHL franchise discredits any opinion he has on the subject. The fact that he leaves out the Bruins as one of his teams puts him right down there with the other 70% of Boston "sports fans" who only start caring when the team's won a championship. His weekly chats with JackO can be entertaining but he and his college buddy basically bring nothing new or intelligent to the Red Sox/Yankees discussion except when either of them have a hystrionic meltdown.
The ironic thing about Simmons is the transformation he's undergone from the days when I first read him on Digital Cities. His whole act was writing from the fresh perspective of a fan with a knowledge of pop culture, something that Deadspin and thousands of others have imitated, but by the end of the decade turns into the very same kind of privliged, lazy, uninspired sportswriter he wasn't when he started... only with the half the intelligence and ten times the column inches. He's almost turned into one of Tom's Gregorian Monks who've gone to Hollywood and ended up completely ruined by it.
While his discussions with Klosterman and the former ombudsman and his boss at ESPN on the changing media landscape were probably the best podcasts he's done, I'm still blown away by the grudge he still holds towards The Boston Globe for not hiring him straight out of Holy Cross as a columnist. He instead starts on AOL, then moves to ESPN, then writes and produces for a network late night talk show and is now as prominent as any Globe columnist except Bob Ryan... seems like a pretty good trade off to me. He's made comments in the past blaming him not getting hired because he's a white male. I bet he has pictures of Michael Holley and Jackie McMullen pinned to a dartboard at the Sports Guy Mansion.
Simmons is just a spoiled rich brat who habitually throws temper tantrums and lashes out at anyone who crosses him or doesn't bend over backwards for him. Like Peteski's suggested, some 'too-cool-for-school comedians' must have justifiably made him feel dumb once.
