mehmeh1
Not thinking twice!
The idea of ash winning a league has been entertained a few times by most of the fans, but after the kalos league, many, me included, lost most if not all hope for him ever winning, as it felt like an unbreakable rule back then. However, with the SM player becoming the very first champion in alola, marking a special occasion in the region as a whole, there was a bit of hope for ash to win, but it still had an astronomically low chance of happening. However, last week an event that should NOT be understated happened: Ash caught a mythical, a tier higher than a "simple" legendary (in rarity, not power), thus breaking one of the biggest "rules" of the anime, one that was pretty much as enforced as him not winning a league, opening up the possibility that it could happen. I still doubt it will happen, because it's the pokemon anime, but it is a legitimate possibility now. Also, in-universe there aren't many trainers that would be much of a threat for ash in alola, with kukui and gladion being the only ones so far, and ash is all but guaranteed to end up beating the latter in the league, leaving kukui at a 50/50, unless they end up making guzma the one who beats ash, which could be a thing that happens tbh.