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It's a very hard task.
How can you campaign against hope and change?
When every comment or critique you make is taken the wrong way?
Obama was formulaic, streamlined, strategic like a sports team.
But he had to work at no drama - for there to be - no drama.
Hillary is used to being damned if she does, damned if she doesn't. She was probably trying not to get accused of being too "bossy" with her campaign staff. I'm sure she was just trying to do the best job she could. She went after experience and knowledge issues - not the "he's not one of us" issues Penn suggested. She pointed out what many of the Republican attacks would be, and the polls did show McCain and Obama neck-in-neck before the economic crisis.
I think part of the reason Obama wants Hillary to be Secretary of State is because he knows just how talented, intelligent, devoted, knowledgeable and capable she is (and how during the campaign they didn't give her enough of the respect she deserves).