Bill Simmons

While Bill Simmons started out as the casual fan getting a voice through a huge sports media mogul, he has turned into part of the machine, like it or not. He has always been on a collision course with his employers at ESPN, but the timing of everything makes it difficult to feel sorry for him.

Simmons is no longer the guy sitting at home and watching television, flipping between NBA games and dishing out an interesting perspective dosed with pop culture references. He’s the godfather of Grantland, one of the guys behind ESPN’s 30 for 30 and less and less of a writer. And as a writer, his schtick has grown quite tiresome to many who followed him since his early days.

There’s also Simmons the podcast guy and the studio, pregame, postgame guy. His podcasts are considered to be quite successful, his TV appearances? Not so much. There comes a point when trying to build some bigger than life theory on every event in regular season basketball and beyond is a bit too much. There comes a point when The Wire, Teen Wolf and other shows/movies Simmons constantly brings up become a bit too much.

In one of his final burst of Simmonism, he mentioned having a hard time figuring out what to do on May 2: Attend the game between the Spurs and the Clippers, or fly out to Las Vegas and watch Manny Pacquiao lose to Floyd Mayweather. No longer the sports guy off the couch, it’s harder and harder for the common man or sports fan to feel sorry for Simmons, even if the whole him against ESPN thing is about Simmons not laying off Roger Goodell, a person very few people actually like, even the guys paying him more than $30 million a year.