The whole thing with the WON is weird, because it shouldn't be a surprise. People subscribe to Dave because he says what they want to hear, and then they vote on the awards given out by the guy who tells them what they want to hear, so they parrot back what Dave's told them, because it's what they want to hear. And it becomes this weird loop.
Dave says "X is the best"
Subscribers say "X must be the best, Dave said so" and vote for it
Then it wins, and Dave says "See, I was right, the subscribers voted for it"