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I honestly think at some point they got it in their heads that they either couldn't work with an Ash winning something, or that fans didn't want it. ...I've never seen it said outright but I feel some of the talk with voice actors in Japan implied some disconnect. And writers get odd ideas...

Eh, it was probably more humiliating to lose by way of disobedient Charizard, though the battle with Cameron is just a mess in general. You ever watch it, the pacing's all off from how a battle should be.

You mean Break Pikachu and Break Swellow

I'm willing to give something like Ash v Alain a slide, partially as they did seem to want to explore that a bit aftewards, but I'd say the Ash v Elesa and Hau fights are very much among the worst of the worst. One is so stupid that I don't think Ash has ever topped that, and he's been around...