2nd Gen The Hardest Ones

In Gold, Silver, and Crystal(especially Crystal for me), there were some of the difficult trainers I've ever battled. Here's a list of the most undefeatable people in Gen 2:
---
-Koga: Koga is the Poison-Type Elite Four is the 2nd one you encounter in the Indigo Plateu. He's a pain in the butt if you have Grass-Types like I did. His signature Pokemon, Muk, is the hardest to faint due to the fact that it carries Black Sludge and always raises it's Defense. I reckon you train your Grass-Type starter(if you even got Chikorita) to Level 73-80, enough to be him while still having Revives and Full Restores.
-Bugsy: Bugsy is the Bug-Type Gym Leader from Azeala Town. While he is not that difficult, his Scyther sure is a tough act to end. Bugsy's Scyther is the strongest Pokemon in his team and just like with Koga, if you have a Chikorita(or in this case Bayleaf) or any other kind of Grass-Type, well, let's just say your gonna be on one heck of a Pokemon ride. Be sure to carry a Fire-Type if your Pokemon aren't strong enough.
-Chuck: Chuck is the Rock-Type Gym Leader from Cianwood City. From what I heard, he is the most difficult gym leader of the others(the rest of the Johto Gym Leaders). The only reason he's hard is because your either using the wrong Pokemon(which I reckon using either Grass or Water-Types) or your Pokemon are low-level.
-Red: As we all know, Red is the original Gen 1 trainer that we get to play as....in Gen 1. He has all the first gen starters, level 83 Pikachu from Pokemon Yellow, a Snorlax, and an Espeon(Lapras in HG/SS). Of course, just like Silver, he has a Type Advantage. If you have a Meganium, Red's Charizard will burn it down. If you have a Typholson, Red's Blastoise will put hose it down. And, if you have a Feraligatr, Red's Venusaur will absorb the it's HP. Pretty easy to understand. Remember to switch Pokemon.
That's all that I know of. Post the most difficult Gen 2 people you've ever fought here.

Whitney's gosh darn Miltank gave me a lot of issues at first until I got the female Machop.

I never found Red to be all that difficult but I'm a very OCD player and tried to ensure I had a balanced team for every situation.

I would say the dark-type elite 4 member. Forget her name at the moment. I had some issues with Whitney and her Miltank as well until I figured out how to beat her. Back before I knew games had internet help.

Whitney...

Other than her, I remember in Yellow Version I had a lot of trouble getting past Brock with my Pikachu, and for some reason even Misty's Starmie gave me a hard time... which is a little embarrassing.

I think Gen II's Elite Four is pretty balanced - moderate to difficult, not easy but not terribly challenging either. If Koga gave you issues then I would hazard a guess your team isn't balanced. A fire type or psychic type will wipe the floor with him.

Pff, Red was easy street. Now, a REAL hard trainer was that young wippersnapper Joey. He'd give me trouble every time. It was almost as if his Rattata was in the top percentage of Rattata.

Hikari Takahashi said:

Whitney...

Other than her, I remember in Yellow Version I had a lot of trouble getting past Brock with my Pikachu, and for some reason even Misty's Starmie gave me a hard time... which is a little embarrassing.

Click to expand...

Thats right. :)

Whitney and her Miltank as well as Morty and his Gengar gave me the most problems

Whitney's Militank... need I say more. Rollout was the bane of my existence. lol

I don't recall too many problems with particular trainers. Whitney wasn't too bad the first time, though I ended up turning off my game after teaching my starter Scary Face in the battle and not being happy with what it did (this is why I really like the addition of move descriptions!). When I faced Whitney again, I had more difficulty with her Miltank. I recall some challenges with Morty's Gengar, though nothing too serious, and then some difficulties with Lance. (Using an underleveled Totodile with a terribly moveset as my only Pokemon didn't help things.)

I built a team at some point during Kanto (still terribly unbalanced, but at least better than just Totodile), and while I expected to have problems with Red, I found him (and the rest of Kanto) pretty easy.

The area where I really had issues was the ice puzzle area in the cave between Mahogany and Blackthorn. It took me a while to figure out the first patch of ice (though the rest weren't too bad).

Red was piss easy with Mewtwo. I'd say probably Morty and Clair gave me the most problems.

Whitney for me. After i beat her i really wanted to be able to re-challenge her and beat her over and over again because she frustrated me so much.

Also Koga and his Muk. didn't have much issue with original gold version but HG/SS whenever i faced him he'd usually give me a hard time with minimize spam + leftovers + toxic.

Whitney was one of the hardest trainer ever. ^^
I can good remember how i lose so often in my first time i played pokemon. xD
What i wonder is if i was 7-9 years old it take months if i complete the game, but now i take only 1 or 2 days to complete a pokemon game. lol
I really miss the old times.

Red still maintained to be the hardest for me while the rest is okay. His Snorlax is the most frustrating one in his team for me.

GiovanniViridian said:

Red still maintained to be the hardest for me while the rest is okay. His Snorlax is the most frustrating one in his team for me.

Click to expand...

That is true.

Whitney's Miltank was initially caused me problems, as did Koga's Muk and Red's Snorlax. I'm not sure they were 'difficult' per se, but they were definitely frustrating.

Clair and Lance were relatively difficult in my first run of Gold. I didn't consider weaknesses to the more uncommon types back then, so their dragons were pretty effective against my brute force style.

Of course Whitney's Miltank, considering that I always used to pick Cyndaquil as my starter. My poor Quilava had no chance. xD

Other than that, I'd have to go with Lance simply because there weren't enough trainers in Johto to get my levels on par with those of his hax Dragonites. :(

I'm going to be a Chatot here and mirror what 90% of others have said and say that Whitney's Miltank was one of the hardest things to defeat. That and Bugsy's Scyther when I decided to choose Chikorita as my starter. I didn't have any Pokemon that were super effective against bug-types at that stage of the game so I was pretty screwed for awhile there.