I think Gore needed the Clinton machine because of a lack of personality (at the time). As much as we want to be optimistic and think that most of America votes on the issues and does there homework, we know that Bush won because many thought they "could have a beer with him" and Gore... not so much. Of course we all found out that once Gore got out from the shadow of the Clinton machine that he really did not need it after all. But it was too late. So as far as Obama is concerned, his personality, along with all his other traits and qualities, did not need it. Everytime, with possible exception to that final rally in FLA, felt forced. And while Bill and Hilary, deep down, are happy, I believe that there will always be alot of resentment there.
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