9. Dawn - Sinnoh, Ash's travelling floozey
Dawn winning the Aqua Ribbon.
Anyone who's read Katsuya's Amazing Race 2 would automatically jump to the conclusion that I hate May. Well I don't, in fact, Misty got really boring towards the end of Johto and I came to the conclusion that May - with contests, rivals, and a brother - became a far more interesting character.

Dawn on the other hand is an overconfident, spoiled little brat. She thought that just because she was 10 (which is far to young to be sending children out on their own where scary shit like Ariados can come and get you. I mean, seriously, those things are huge fucking spiders) and ready to go out into the world, that she'd start winning contests like that. Thankfully, the anime is now far more story-driven and more 'realistic' as to what you'd expect a 10 y/o to achieve, and after being so on top of the world about everything, she gets hit hard by the fact that most coordinators are better than her... and of course she gets all emo about that after losing her 2nd contest in a row. More reason to hate her.