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Considering how many former Clinton staffers Obama has picked for his administration, I think that we need to take a good look at the people who are a level or two below them, the deputies and undersecretaries who will do the day to day operational work and presumably replace them someday if and when they leave their jobs. I'm trying to stay hopeful that Obama's decided to start out with experienced hands who know how DC works even if they don't necessarily reflect his policy ideas (which I suspect are still very much in the process of being formulated), to make for a smooth transition and first year or two, with the idea of grooming the staffers just below them to take over their jobs eventually. They might need some political seasoning--including himself--before they're ready to take on the system. Pure speculation on my part, but if I was Obama it's something that I might consider doing.
We'll see. OLC is pretty high up, though.