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Not sure why it didn't work the first time.
I find it really funny how the memory of arrogance uses a CHAAAAAAAAAAAAARIZAAAAAAAAAAAAARD and you're meant to humble it by taking it and the Moltres down with the funny pebbles. Despite my bitching, I do like some of the memory fights in this game when they feel intuitive rather than janky. If this was Empire for instance both the Charizard and Moltres would have heavy-duty boots and Octavius would still force you to beat both to get a reward or important points.
