One of the biggest factors in the 2000 election was the way Al Gore allowed the media to form his image while Bush cultivated a more friendly relationship with them. Howard Dean, like Ronald Reagan, doesn't seem to need the media and deals with them on his terms, as in this exchange from Larry King tonight:
Larry King: "Will you run to the center as the election gets closer?"
Howard Dean: "Larry, I am in the center."
Not being pigeonholed is half the battle.