1) Lance: Definately at the top of the food chain in all Pokemon games. Cool in every sense of the word.
2) Steven: Modest and quiet. Still a damn powerful trainer, second in level to Red, but superior overall.
3) Red: His "..." is the coolest thing ever uttered in Pokemon games. Ever
4) Clair: Maybe it's because I'm obsessed with her ti....uh, titanic dragons ;/
5) Will: Pretty cool, least memorable Elite 4 though.