Richie, however, team Rocket wore out pikachu before the battle and Ash was forced to use Charizard, who refused to battle.
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If you are following the anime/show then no... you are suppposed to be beaten by some dude (forgot who sorry) if your not following then you can beat the indigo plateau
If you're talking about the anime, he meets Richie in what i think is season 2 at the indigo plateau.
you have to get trough victory road
You can't
Lorelei leaves the indigo plateau to defeate rocket grunts in icefall cave above the waterfall.