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Hardest Gym Leaders?

Fluttershy ♥;481524 said:

Oh god how did I forget Koga in Yellow :C Also Sabrina. Whoever decided the Gym Leader's maximum levels needed to leap straight from the low thirties to fifty was just mean. And it didn't really help that my main strategy for both was "screw it, just use Pikachu".
 
GSC Whitney/Clair
RSE Norman/Tate Liza
DPPt Candice (Try Torterra...)
HGSS Whitney/Clair/Blue
BW Elesa/Iris
 
GSC Whitney/Clair
RSE Norman/Tate Liza
DPPt Candice (Try Torterra...)
HGSS Whitney/Clair/Blue
BW Elesa/Iris

Liza and Tate are especially hard if you try to beat them with a Ground-type, but I don't remember how much trouble I had with them. However, I remember that the trainers at the beginning of their gym are easy. Those Kirlia only know Psychic and non-damaging moves, so I easily beat them with my Mightyena.
As for Blue, I don't remember much from Gold and Crystal, but he surely was very hard even in the old Johto games because he's universal.
Candice was hard for me because I have a Torterra too (But the Medicham... I expected Weavile), and Crasher Wake... Yes, Ice again.
And Whitney... Defeating her in Gold was a coincidence consisting of burning the Miltank and then her missing when I only had one Pokémon remaining.
 
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Whitney was most certainly one of the most troubling for myself, for I shall fall within the camp of good people that have found the Rollout attack and various other factors of her Miltank to be quite the euphemistic annoyance. Winona also always posed a problem to my team for whatever reason, but perhaps that may simply be attributed to the fact that my younger self focused more so on his starter than he did the rest of his team.
 
Winona also always posed a problem to my team for whatever reason, but perhaps that may simply be attributed to the fact that my younger self focused more so on his starter than he did the rest of his team.

I forgot about winona. Because I chose Torchic/Treecko pretty often, her pokemon were hard to deal with. And her altaria... That thing knew Earthquake. I think I finally managed to beat it using a swablu to put it to sleep with sing, then using a revive on my Blaziken, and hopefully defeating it with rock tomb. But... man, she was tough.
 
And her altaria... That thing knew Earthquake. I think I finally managed to beat it using a swablu to put it to sleep with sing, then using a revive on my Blaziken, and hopefully defeating it with rock tomb. But... man, she was tough.

Oh indeed, the aforementioned Earthquake caused a great deal of trouble for myself as well regardless of the starter, for such odd reasons. I cannot recall my own strategy for beating her, but it usually switched between either brute forcing her or extensively spamming items with outpours of hope and determination. Not the wisest strategy, but apparently it was successful to a general extent.
 
Cilan((I forgot to unbox my monkey), Burgh((before I caught a Darumaka)), Elesa and Skyla. The rest were easy. Iris was pathetic, but I did battle her in Winter so I got a level 34 Tsunbear to 42 trained before I fought her.
 
R/B/Y Misty (Friggin' Starmie)
G/S/C Whitney and Claire (Miltank and Kingdra are royal pains)
R/S/E Flannery (Unless you started with Mudkip, GOOD LUCK fighting her damn Torkoal)
FR/LG Koga (He just looooves making his Muk Minimize and Acid Armor.
D/P/Pt Maylene (Catch a Ghastly, or her Lucario will steamroller your whole team)
HG/SS Chuck (Double Team and Focus Punch make me wanna cry)
B/W Clay (YMMV, but his damn Excadrill kept landing critical hits on my Pokémon like crazy, and it didn't help that my team was underleveled)
 
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I competely demolished Clay with my Scraggy. She killed everything with newly learned Brick Break and didn't go below 3/4 heath. And she was underleveled.

((and Moxie helped but...)))
 
Elesa didn't use Volt Switch on me until she only had one pokemon left. :U
 
Really? Volt Switch was the only move she used on my until she was down to her Zebstrika only. I beat her first time.

Gym leaders which have given me problems in the past have been Clair in HGSS and Chuck in HGSS. There are no places to level your monsters in that game. :(

In the most recent game, I had to fight Aloe and Clay twice but, that was really the extent of difficulty they gave.
 
Red/Blue: I guess "hard" is a relative term here, since everything in Red/Blue is pretty easy, but... way back when I first got the game Misty was kinda hard, mainly due to having to fight a Starmie with a bunch of random unevolved wimps that (unless you overlevel like crazy) are pretty much guaranteed to be at least a few levels lower.

Yellow: I can't remember. I know I actually found Sabrina easier in Yellow than in Red/Blue, since all of her Pokemon were from the super-fragile Abra line and never used anything but non-damaging moves and Psywave (which was horrible in R/B/Y, since it could do as little as 1 damage sometimes...), but I can't remember if any of them were hard.

Gold/Silver: Whitney--same problem as Misty in R/B but much much worse, since instead of just Bubblebeam you have to worry about Attract, paralysis, the thing healing itself with Milk Drink, and of course Rollout doing ludicrous amounts of damage if it didn't miss the first few times. Clair was pretty hard, too.

Ruby/Sapphire: Wattson was always insanely hard unless you decided to be really cheap and load up on Ground-types, and even then he put up more of a fight than most Electric gyms do against Ground-types (Sonicboom is actually still dangerous this early on in the game.) Norman and Winona were pretty tough as well. Roxanne's Nosepass was sometimes pretty hard too, depending on what Pokémon I had at the time.

Diamond/Pearl: Can't remember too well, as I've only played through Diamond once and it's been a few years.

Platinum: Gardenia's Roserade was hard for basically the same reason Misty was kinda-hard and Whitney was hard: strong fully-evolved Pokémon, but fought at a point when you don't have anything even close to that. Wake and Candice were probably the hardest in the game, though... and Volkner might have been hard if I hadn't had two Ground-types with me at the time.

Black/White: Clay was the only one I hard a hard time with (everyone else I beat in one try; Clay took three.) Out of the rest, Burgh and Elesa were probably the hardest, but they weren't really hard at all... just harder than the rest of them. In most of the later gyms, I actually had more trouble getting through the random trainers than I did beating the leader...
 
Hey, those people gave me the hardest times when battling them despite any differences or similarities. I'm just stating that they were the hardest for me in that particular game(s).
 
Really? Volt Switch was the only move she used on my until she was down to her Zebstrika only. I beat her first time.

Actually I took her on with a Scraggy and her Emolgas were too busy Aerial Acing me, so that may explain the lack of Volt Switches. :v
I honestly didn't find a single B/W gym leader challenging. I think I struggled a bit with Cilan and Lenora, but only because I was horribly underprepared.
 
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