Character types

Bill Clinton was, of course, a band guy. The off-center outsider at High School with a special talent that freely moved among the cliques.

G. W. was a frat boy. Nuf said.

Obama's formative experience was being a "new kid". That means that his special gift lies in figuring out what people want, and then reinventing himself to become that thing. If you watch childhood dynamics, the first people to reach out to the "new kid" in a grade school are always the misfits and the losers, so it should not surprise the people on the left as they find themselves left behind as Obama moves into more elevated circles.