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[All Gen] Hardest Gym

Bugsy. I started with Chikorita though, if that has any impact on it. I just had the hardest time with this gym.
 
Whitney surprisingly never gave me a ton of trouble, neither in HGSS or back when I played the original GSC games. Clair, however, gave me a significant amount of trouble both times, and surprisingly I also think I had to challenge Chuck more than once in order to beat him. Tate & Liza gave me a lot of trouble consistently in RSE, though, so I will definitely go with them! Another honorable mention goes to Maylene, who crushed me the first time I played Diamond.
 
I remember having a hard time with Sabrina in Blue, because back then no type was effective against Psychic, and Sabrina and Koga is where gym leader levels spike up in the game. Of course, you can go beat Koga first and then go to Saffron (actually I think that's the supposed order), but RBY was largely non-linear so you could do the Saffron quests and Sabrina first if you so wished.
 
There have been plenty of situations and times in which I've struggled against a Gym Leader, the most difficult would be Whitney in GSC specifically. It was just the set up of Rollout and Milk Drink that was just so difficult to break, especially if you didn't have a type advantage such as Machop.
 
Tate and Liza immediately spring to mind. I guess the frustration I built while trying to beat them in Emerald was pretty strong if I can't think of any other Gym Leader lol :) It got to the point where I actually had to catch a new Pokémon (Sharpedo with Crunch) to beat them cause no matter how much I levelled up my party it just wasn't happening lol. I think the fact that they were a double team had a lot to do with it, their combinations were just too powerful lol :)
 
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