In the anime, How come Ash never won a championship until Sun&Moon?
Ash must've been on a bad track because he lost in Kanto, Johto, Unova, you get it.
Go never caught the whole national pokedex, And in Sw/sh (anime) Hop never existed.
Be amazed by childrens existential crisis.
Answers
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I believe that he won and fought in Pokémon battles from Kanto to Kalos. It didn't took long until he became champion. Ash made new friends while he was on a journey to become Champion.
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You see, there's something called "plot armour."
Meaning he has to lose at the last moment until they make as much money as they can or get tired. And then he starts all over again, a ton of people watch the new series, and a ton of money is made, he loses at the last moment, everything repeats. There's no in-canon reason for him to be so bad after three regions.
They did seem to get tired after doing it for 7 generations, though. Now we can watch a different person go on a different journey.
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Hop was at the masters 8 tournament
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i know orange island Leyte doesn’t really count but still that’s there
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