I see some of the same criticisms of KO that Howard Cosell used to get back in his heyday. Too New York, too pompous, too ... intelligent. Cosell was way ahead of his rivals back in the 1960s, asking tough questions and taking on hard issues. Olbermann is similar to Cosell in the way he delivers his message, too. Cosell could speak extemporaneously, wthout a script, and time everything down to the final second before breaking to commercial. Olbermann has a staccato delivery that is remarkable, if only for the amount of words he crams into every rant. He rarely slips over a word.
Cosell hated the newspaper columnists who attacked him. He returned fire with heavier artillery. Critics mocked him but no one denied he wasn't interesting. Same goes for Olbermann. I think we should enjoy the time he has for this show, the two or three years before he implodes once again. In a vast wasteland of smugness, KO is trying to give the public what it wants, regardless of what the big shots in sports think.
KO is also socially awkward, introverted in real life, very similar to Cosell, who had few friends outside of his immediate family.