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Hm.. That's a tough one.
All of the gym leaders were so easy for me to topple over.
Maybe.. Jasmine? Because she used steel type, and by then I usually had a Typhlosion. :/
Hmmm, some were easy, other were tough, it depends on the Pokémon I have at the time.
But the last easy challenge I had was beating Brock at Fighting Dojo. Come on!
Relicanth, Golem, Onix, Omastar, Kabutops and Rampardos! Magical Leaf on them!!!!
Easiest? Probably the entire kanto region leaders (excluding Blue), since you're pretty well leveled at that point in the game.
The hardest was definitely Whitney (Because of Rollout + High HP and Defence) or Jasmine (If you didnt start with Cyndaquil)