You said, in part: I still wonder if Bush's main weaknesses is being to nice to those who want to destroy him.
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President Bush is looking to history. Cheap (even if true) shots at Ann Reynolds and stupid Democrat comments gain little if anything in the short term, and offer fuel for historians to attack Bush down the line. He is denying them that, just as he did when Clinton's portrait was dedicated, for example. One can argue that President Bush is not assertive enough, but ultimately he gets most of what he wants. If anyone doubts that, just look at the reactions of democrats to him. If he were totally ineffective do you think the dems would care about him?
It's one thing to not say negative things about someone who died, but he has given the Clintons, Kennedys, and Richards more respect and kindness than they deserve, and it's let them continue to get away with trashing him and his agenda.