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Lenora was the only gym leader I lost to in recent years. Retaliation just kills me, man. If you count when I was a kid, I'll throw in Whitney, but these days she's a walk in the park.
In the 2nd gen, Whitney, because I always used Quilava. Overall, Clair, because I never have a type-effective pokemon for her. 2nd gen remakes, I say Bugsy. 1st gen was Misty in Yellow because Pikachu has bad defense. 3rd was Norman with his Vigoroth. 4th was Crasher Wake if his Floatzel could out speed me. 5th is the 1st gym, just because I insist on soloing it with my starter pokemon. Overall, I'd say the elemental bros, for the reason mentioned before.
I've only played one of the main pokemon games, (it was white version) and i'd have to say Lenora or Elesa. Lenora just spammed me with her stupid Watchog's stronger moves, and Elesa kept spamming me with moves that cause parlyz. I bought 99 parlyz heals after my third time losing to her.
Like a lot have mentioned Whitney back in Generation 2 was actually quite interesting to battle, with her Miltank's Rollout technique. I actually found her to be the most problematic out of all the Gym leaders because of this and lost the battle on the first attempt. Once you knew her strategy though it was pretty simple to change your strategy accordingly.
on my first play through of Sapphire I remember struggling against Tate and Liza... the Double Battle they spring on you totally threw me off! and if, like me, you have a particular fondness for the move Earthquake, their Levitators (plus Xatu with its flying typing) are a bitch! My poor Camerupt ('team leader' on Sapphire) got totally screwed over!!!
Clair with her Kingdra. Even for a late gym when your pokemon are decently leveled, this is one gym that is hard to get through. Full Restores are so annoying in this battle as well.
Sabrina in Yellow. I always fight her before Koga, so I'm at a Level disadvantage there. Plus Psychic has no true Weakness, and Alakazam has huge Speed and Special. Nowadays I always use Gyarados because he can survive a Psychic and use strong Physical moves to bring Alakazam down.
Another one is Tate & Liza in Emerald, mainly because of the level jump, and they have something to hit all three starters with
The Hardest for me was actually Misty, though Whitney comes a close second. This is presumably so because i almost never choose bulbasaur as my starter though.
In my opinoin Norman was the easiest of the Normal type gym leaders to beat, well for me at least. Though Slaking was a bit difficult to deal with. Truant however ruined his chance to be a total nightmare.
I just ran into Whitney the other day thinking people made too big a deal out of the Miltank. It rolled over my 6 pokémon with infatuation/flinch and drank its own milk whenever the bulky cow got below 50. I got so mad. I didn't have any heals, revives or an appropriate switch-in. Second time around I spammed Smokescreen, Geodude got rock smash and wore it down. Never have overcoming a gym leader felt like such an accomplishment, I didn't take a breath throughout the whole battle.
Whitney and her goddamn Miltank were such a pain in the ass in the original Gold and Silver. She was easier in HeartGold/SoulSilver though. I'm ashamed to say this, but I thought Cilan was pretty hard. That fucking Pansage kept annoying me until I discovered a girl in the Dreamyard would give me a Pansear if I asked her.
Clair from Pokemon Gold and The Platinum iteration of Fantina. Clair in GSC (and HGSS) is hard because it is difficult to train for her battle. The level scaling is horrid in that game and it made her Kingdra difficult to defeat.
Fantina in Platinum is also another tough one. At that point in the game Mismagius is one of the strongest Pokemon that you will face. Shadow Ball being special in Gen 4 makes Mismagius a huge threat. She can take out most Pokemon you have at this point in one or two hits. I really had a tough time beating her.
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