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I watched the piece that prompted Glenn's criticism and, quite frankly, didn't get from it that Olbermann was flip-flopping on this. I suppose one might get that impression from (1) the way he questioned Dean and Markos; and (2) the fact that he didn't take this opportunity to renew his criticism of the bill. I saw the piece as more of a "let's hear what these guys think", instead of "let's hear what Keith thinks". Interestingly, both guests were not drinking the kool aid about some secret Obama plan and were critical of Obama's handling of this issue. And Olbermann had no one on his show to argue that Obama was correct. So, I think Glenn's criticism of Olbermann is overdone and not necessarily valid.
Having said that, I think Glenn's take on this entire issue (sans Olbermann) is spot on. And I too am getting a little concerned about Obama's apparent willingness to compromise with what can only be described as fascist attitudes.