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Whitney - I HATE her Miltank. It's like, 30 turns later she's about to finaly die, and then she uses Milk Drink and fully recovers in two turns!
Lt. Surge - Double team. Nuff said.
Jasmine - Not only because the whole cross the ocean thing but because of her Pokemon. It took me like 5-10 restarts before I managed to get Sudowoodo to critical hit Magnemite with a Low Kick and then Steelix took forever to kill, thank god for my Vulpix. :)
That just about sums it up. If I recall, it took me more than 10 tries to beat this on my first run-through of Pokemon Silver. Rollout + Milk Drink + Attract = EVIL (If you don't have a Machop, prepare to be stuck for hours)
Definately Brock. Honestly, I can't believe he is a ROCK TYPE EXPERT yet refuses to understand the fact that ROCK TYPES ARE VERY WEAK TO GRASS TYPES. He doesn't seem to have any form of counter strategy for them at all. I mean, Whitney has her Girafarig for fighting types, Koga has Weezing for ground types but Brock. . . just isn't good enough.