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Alain is why I said "almost certainly".Well to be fair, it has happened before that Ash meets someone it looks like he's supposed to defeat despite losing constantly, only to never win against him. *ahem* Alain *cough*.
There are some big differences, though. As Panky mentioned it's always been anime-exclusive characters who stop Ash from achieving his main goal.
Things have also changed since XY in regards to them letting Ash's story line actually progress. He won a league, hasn't reset (as a trainer, at least) and is catching stuff like Dragonite out of the box.
Sure, it's possible an anime-only character will knock Ash out of the tournament then beat Leon, but it seems unlikely and it would be a waste of the momentum letting him win Alola brought to the character.
Edit: I want to go into a bit more detail on what I mean by "momentum". Ash got trending on twitter twice in the last half year (winning Alola and then capturing Dragonite) with the former even getting articles on mainstream news like Forbes. The talk about wanting episode 1 to go viral shows they're tracking that sort of thing. Ash's "stock" as a character is at a peak; he's getting positive attention en masse for the first time in a very long while.
Honestly, I'm still not convinced they aren't planning to have Ash dip out of focus in favor of Gou after this series. Maybe keep him around in more of a Brock role with Gou getting the main attention?Ash may be a good trainer, and the protagonist, but this is the World Champion we're talking here. If Ash beats him, that might as well be the equivalent of Pokemon master right there.
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