Reagan = Governor of California
Bush = VP of the most popular president in decades
Clinton = Governor of Arkansas
Bush = Governor of Texas, definitely appeared to be an outsider despite his elite family connections
Obama = Gave the appearance of being an outsider
I'd say all of those except Bush 41 came off as being from outside the establishment.
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Congratulations to SuperNiceDog, Guru Winner, who was smart enough to pick
your 7 time champion, Link.