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For me it depends on which version. In the originals (Yellow) I always had problems with Lt. Surge. If his Raichu's Thunderbolt didn't take me out, Slam did. Even though Slam isn't only 75 accuracy, it always hit me. Very annoying.
The remakes, I'd probably go with Misty, when unprepared. Even Bulbasaur is weak to that Confusion. It doesn't help that her Pokémon are so quick.
For me personally, Misty's gym was always the hardest gym to beat. I always chose Charmander or Squirtle but never bulbasaur. I remember the first time I played red I had no idea what to do So I had a Blastoise lv 70 by the first gym and a Pidgeot lv 67 so the gyms were easy back then. Lol.
Ugh, Misty and Sabrina are by far the hardest gyms for me. When I played through LeafGreen I had Pikachu and Oddish and after a few tries I eventually got it. But right now I'm playing FireRed and I traded my Bulbasaur to LG for the pokedex and my other game boy broke so it's stuck there, and I've played through 6 gyms without a starter. But anyway, I never have strong enough pokemon for Sabrina. She always beats me at least 3X before I can even damage her pokemon. :X I voted for her because I have the most trouble with her. My five pokemon are all in their 40s and can't beat hers at all. It sucks.
For me, it had to be Koga, the 5th gym leader. if i had a fire or flying type, i could kill him pkmn in one hit, but if i didn't, he had those poison type moves that would eventually kill my whole crew
I agree....Koga was the toughest. I think he was the only gym leader I ever lost to in fire red. I beat him on my second try though. My team couldnt deal with poison very well :/
I never found Misty hard. I did hate Sabrina though. Most of the pokemon I would have by that point all seemed to get outsped by her and had horrible Special Defense. Koga was never really an issue for me, because whenever I finally got around to fighting him my pokemon were leveled up fairly well as far as I can remember.
Misty is really hard for being the 2nd Gym leader, all other werent all that hard.
If you picked Charmander though, Brock was already pretty tough, misty even more.
And since there were no dark types in the originals, Sabrina could be pretty hard to beat too