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Brock even with a charmander is easy because once you learn metal claw it's over. Sabrina will be easy once I get my Haunter :D and a lot of potions... I'm still deciding if I want jolteon or vaporeon.. My trainer card is what I'm aiming for.. The marowok isn't for sure I might find a HM slave instead.
Ruby -> Wattson
REASON: I had to use Ember a few times and that was doone
Emerald -> The flying leader
REASON: I had a whole lotta training before. Thought her PKMN were stronger. Didn't know she uses flying. Altaria was sort of a pain, though. Emerald was a pain... Had to level up 5 more levels for Altaria
LeafGreen -> Erika
REASON: I didn't use squirtle at that time, had my Pidgeot handy.. Err.. eheh... She was my best Pokémon. Shared my best memories. I'm still dreaming of my lv.100 Pidgeot, Jauna, coming back...
I'd say that the easiest Gym Leader was Misty. No matter what Pokemon I had with me, she was always so freaking easy to defeat. I can't say the same when I played through Blue Version as a 7 year old, though. XD
Well, like everyone else I have to say Erika was easy as pie. :U Fire types of course being most helpful. Also Blaine's gym seems very easy, I can't remember exactly what pokemon I had in my roster that helped so much but I just know that gym was a total breeze~