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I honestly do not have a problem with Ash losing against Leon as long as the match is pretty close. I mean Leon is the freaking world champion (Until next gen at least). Going toe to toe against the strongest ever and losing by by an inch is not terrible. But to be honest, I'm afraid of what it would mean for Ash to beat the strongest trainer in the world. I don't want him to retire as a childish retard. I want him to go back to his old personality before leaving forever. I can't bring myself to say goodbye to this Ash and pretend he is the one I grew up with. That's far from the closure I've always wanted