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2nd Gen The Hardest Ones

I definitely Remember Bugsy's Scyther and Chuck.

i agree 100% Chick being the absolute hardest. I remember still having water type Pokemon and still being a close match. After that, the rest of the Gyms weren't so hard. Dragon gym was a little confusing. But not so much.

I really hated grinding Pokemon after level 40. It was such a drag.
 
whitney is the toughest especially his milktan in heartgold . Its ability is giving me hard time for all my pokemon . Especially that rollout attack & stomp attack . Whenever i use onix it use attract . Its so annoying . Red is not that much tough to me .
 
i think the hardest fights for me in all the games have been lance, red, and that dude with the hydregon at the end of black2/white2.
 
Chuck? Come on, guys, he was the easiest Gym Leader apart from Falkner imo.

Whitney's my biggest struggle. That stupid Miltank of hers got me raging a lot. Bugsy's Scyther is a pain to kill. My tactic is to Confuse Ray with Zubat, then unleash Flame Wheels and Wing Attacks until it dies.

Now i might sound like an idiot to you guys, but i never got to face Clair. Ever. Gym Leaders that are a challenge to everyone usually end up being a breeze for me, but what do i know.
 
whitney for life
it unleashes a rollout at full hp and you can see death coming
chuck was easy for me, as i always used kenya the fearow as one of the higher-level pokemon of my team (boosted exp made it easy to train)
i don't remember red being too hard in my crystal one-heal-per-pokecenter-no-mart run, and all my pokemon were high level 40s at the time ahaha
 
Whitney wasnt that hard for me to be honest, if you are using cyndaquil you can smokescreen so rollout misses, if you are using totodile just charge up rage with clefairy's doubleslap and smash miltank, if you are using chikorita i dont even know how you reached that far that thing sucks but maybe just spam X attack in clefairy? idk

The hardest one for me was Chuck's poliwrath agaist my Typhlosion, i didnt have any other trained pokemon since thats how i replay most games, only leveling the starters so i can go through it faster, but Chuck was pretty hard to beat, yet again i had to spam smokescreen, he killed me and I used growl and other stat lowering moves with my other bad pokemons, then had to revive Typh again and then kill it.
Besides that all the other gyms was spam attacks and win
 
Clair and her Kingdra the amount of times i lost before i won the first time i played
Pokemon Crystal was horrendous
 
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Whitney. No one is tougher than Whitney for me. Morty comes a close second, and Lance is third.
 
Bugsy's Scyther in Pok?mon Silver Version gave me so much trouble when I first went through the game specifically due to Fury Cutter. Gah!
 
Falkner wasn't bad, though his Pidgeotto's mud-slap made the battle closer than I would have liked
Bugsy was a breeze, since Cyndaquil is my preferred Johto starter
Whitney is known for being tough, but I always got the trade Machop in Goldenrod and never had any trouble with her
Morty was the one that always have me the most trouble. Even with a properly-leveled Pokemon that was immune to ghost-type attacks, curse and spite could cause real trouble
Chuck was really hard on me on my first playthrough of Silver because I hadn't been thinking ahead and didn't have either a flying or a psychic type anywhere near leveled up enough to be viable, but in Crystal I made sure to have a decently leveled psychic and had no trouble with him
Jasmine was tougher than it seemed like she should have been for having decently leveled Pokemon with type advantages, but still not that bad
Price was no problem
Clair wasn't bad for the most part (yay Lapras), but her Kingdra was pretty obnoxious, given its balanced stats and dragon being its only weakness.
 
Falkner wasn't hard because I caught Geodude nearby
Bugsy was a breeze because of that too.
Same goes for Whitney.
All Morty's pokemon were part poison type and my Graveler knew Magnitude when I fought him, so It wasn't hard too.
Chuck wasn't really hard because I used combo of Gyarados and Meganium.
Jasmine was hard because I thought that Ground is NVE against Steel. why i was so dumb
Price gave me some problems, but not much.
Clair... why did she almost always one-shot my pokemon
Will, no problemo.
Other 3 of Elite four gave me problems, since my team had only 3 pokemon and was very unbalanced.
Lance... what did i do to deserve this
None of Kanto gym leaders gave me problems. Even Blue.
About Red, I was TERRIBLY underleveled when I fought him... Hardest trainer in the game. I rebalanced my team a bit around this point though.
 
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