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Honestly I don't get why you guys are investing so much into Ash winning the league this time. I guess it's different for me because I've only been watching on and off since like a decade ago only came back fully for XY (marathoned what I missed though).
For me it's more of a "cool if it happens, whatever if it doesn't" thing. It's kinda funny, I can think of kid's shit like Sonic SatAM which had ridiculous cliffhangers which annoy people but faded from memory, but the three things I can think of where they made a legitimate ending and people are mad as hell to this day: Harry Potter, Digimon Adventure, and recently Naruto.