I find him unwatchable. He had an almost identical rant complaining about Hillary and Geraldine Ferraro. It looks like he's about to cry in both rants. He makes a decent enough point, but christ, does he really need a 10+ minute rant directed right at Hillary, as if she were watching it?
Whether she's watching it at that moment or not, she certainly will at some point - any candidate needs to be aware of precisely what the media is saying in order to deal with it effectively, especially "mainstream" media like MSNBC that caters to the crowd she's trying to get to nominate her (liberals/Democrats).
As for Olberman himself, he's a sportscaster-turned-op/ed guy and doesn't pretend to be anything but. He's not
a standard "journalist," and anyone expecting him to be so will be sorely dissappointed in his schtick. However, if you watch him in the spirit that others watch "Mr. War on the Middle Class," then you may appreciate what he says.