Olbermann fails because of poor ratings and because he ends up pissing people off with his arrogance. People keep giving him a chance because he's highly intelligent and well liked by liberals. It just never ends up translating to anything profitable.
Keith was great at sports. His intelligence and love the game gives him a lot of knowledge when talks. I remember the world series he did with Bob Costas. That was the best teaming ever. Those two guys had such great appreciation and knowledge of the game and it's players at the time and as well as the historical perspective. That was before any of political shows, and I didn't even know his political leanings. I think baseball is where he has the greatest knowledge and most to offer. I don't think it matters how popular his show is, because he seems to have problems working with others. I think that was true at every job he's had. So at some point, I imagine he'll burn too many bridges to keep working on this sports show. I don't care about his politics, he's great at sports shows especially baseball.
As far as not working well with people... there's a reason this show is in NY, and not on the main ESPN campus (I think Olbermann is banned from the bristol campus for life). He's isolated himself pretty well... away from the main people he could have conflicts with to get him off the air. Only thing that could potentially lead to badness is his show's content. He is listened to... and his opinion on sports matters (no matter what people like/dislike about his political view) usually is respected and well-stated. He's a baseball historian... by far his favorite sport (don't expect him to go all nuts over the NBA). You could tell his appreciation for the history when he called out the Red Sox for basically presuming that guys like David Ortiz and Pedroia were locks for the HOF (People love to say "future HOFer" as if anybody who made an all-star team is in consideration). This all happened on the night they "honored" Mariano Rivera by having him get gifts from the "Red Sox own future HOFers!" He was quick to point out that JEFF BAGWELL, somebody with better numbers than Ortiz, will likely fail to get in (for whatever reason), and people shouldn't presume anything about a career DH with offensive #'s that were accumulated in part during the steroid era. Also he thought declaring Pedroia a lock, at this point, was absolutely nuts... and he'd be right.
