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Got one! Ev training a level 1 Bagon all the way to a Salamence at level one hundred. I didn't even use a Rare Candy even once on him. It took several days, but I finally got the now trump card of my party.
Going up against Palmer in my first Diamond game. Couldn't ever beat him no matter what i tried.
Playing a new game i defeated him first time thanks to a Garchomp earthquake on his Milotic
My toughest challenge so far was beating Cynthia's Garchomp... I haven't really bothered with the Battle Frontier yet, though, so the Frontier Brains might end up being harder...
Those Frontier Brains are quite a pain, but Darach was the worst... The last turn was decisive: the Pokémon that attacked first would win. But I won in the end. XD
Hm. Hardest challenge so far would be beating cynthia again. My pokemons were horribly underlevelled when I beat her the first time and I stupidly did the stark mountain quest which made everyone in the Elite 4 even more powerful. I finally beat her though, and now my Dragonite can whoop everyone single handedly. :'D