I first began to think well of Howard Dean after being hit in the head with a "Dean for President" tortilla.
It was the 2003 Bay to Breakers, and it's traditional to have a tortilla toss as the runners all queue up at the start. (Flour tortillas are fine, but the corn ones kind of hurt when they land.) Dean campaigners were well-represented at the event, and one way they made their presence known was by tossing tortillas that had been painted with the Dean campaign logo.
I found myself admiring the unorthodoxy of his campaigners, and as I came to know more about him was impressed by his unorthodoxy as well. He wasn't about politics as usual. He seemed to be about effective politics, connecting people and taking positions that made sense on their face, without so much regard for the complicated web of powerful political interests that so typically set politcal agendas. (For example, I appreciated how he understood the power and promise of technology as a social medium, and took stands on regulatory issues that demonstrated this enlightenment.)
This willingness to buck convention I think will serve him well as the new DNC chair and be just what the party needs. As it was a very typical Democrat could not win the last election. If the party is to survive it's going to need to find new ways of making its politics relevant to more people. I think he's just the guy to lead the way, someone unafraid to try the new things necessary to do it.