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4th Gen The strongest one???

Definitely Sabrina in the rematch. That retarded Wobbuffet was a huge pain with CounterCoat, especially when backed by Full Restores.
 
It Was Whitneys Miltank It Alwaya Use Attract +Rollout to Defeat Me
 
Almost everyone can agree that Whitney's miltank is by far the only challenge I had
 
In the GSC days it would have been Whitney with her Miltank and rollout absolutely dominating my Quilava but in HG/SS it would have been Claire with her Kingdra as i used to teach Typhlosion Thunder Punch to take out Kingdra and since they weren't available at the Department Store in Goldenrod anymore i struggled a tad

Hurray! A fellow PWD Fan.

Ontopic: I really hated Whitney and her Miltank. More so back in gen II. And Claire's Kingdra. That sucker had some really high power, and to top it off, she always used a hyper potion on that thing ..
 
I think the only leaders I had any problems with were Blue and Chuck. I went through the whole game with the Sinjoh Ruins Dialga, so the normal threats like Whitney could hardly touch me.

Chuck, however, had type advantages over Dialga and my other main Pokemon, Typhlosion. By the time I reached Blue, I had relied so heavily on Dialga that the rest of my team was significantly underleveled, and I didn't get coverage on the entirety of his mixed team.
 
Whitney is obvious. Her Miltank for that point in the game is uncool. However, my vote goes to Clair because of her Kingdra. Which was even more uncool.
 
In terms of the Pokemon that I used in the game, Chuck or Whitney would be the hardest Gym Leaders for me in Johto. It was always just how strong Chuck's Pokemon were, and there aren't very many good places to train your Pokemon so I was always very weak to the point of him beating the pulp out of me. Whitney is just plain unfair. That Miltank always kept spamming that Milk Drink move or something. The Clefairy was very annoying as well because my Pokemon always got attracted to her Clefairy, which really could destroy my whole team, since I can never find female Pokemon.
 
Whitney wasn't all that hard for me honestly. My Sandslash usually destroys Miltank with Dig. I'd say my toughest time was Clair since it's near-impossible to get Dragon moves by that point in the game.
 
Clair.Her Kingdra is strong and it takes me about 4 battles before I defeat her.
~Sorry for the bad English.
 
I didn't have a huge amount of trouble with Whitney, probably because we share the name and she went easy on me ;) I have no idea why, haha.

Well, yesterday it took me over 20 minutes to beat Pryce in one battle because it came down to his Dewgong and my Quilava. He kept using Rest and didn't have any Water-type moves so he couldn't kill me. >.> I only had 2 Fire-type moves, Swift, and Quick Attack, so it took quite a while for me to wear him down.
 
If Sneasel was obtainable in HGSS pre-Kanto, this answer would be different, but, I didn't like any of the Ice-types available before Blackthorn City, and none of my Pokemon knew Ice Beam, Blizzard, and none could take a strong Dragon-type with manageable health left. Needless to say, I wasn't very well prepared heading into Clair's gym. It took me a long, long time to get past that part of the game. I think I spent a week or two without playing it out of pure frustration. n__n;
 
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