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Ok lets talk about Ash and his challenging of the leagues.
>Kanto
He was a newbie, of course he didn't do well.
>Johto
While his Johto team was weak he did use his older, stronger Pokémon from Kanto and the Orange Islands to make up for that. He also managed to defeat his rival.
>Hoenn
He intentionally gave himself a handicap and still managed to make more progress than his previous two leagues
Sinnoh
>Stronger local team, no handicap and made it all the way to the semi finals. He only lost because his opponent had a team of legendaries, who he still did a better job against than anyone else in the entire league.
>Unova
He did horribly here but I blame the rushed "lets get to N already" writing rather than Ash's skill. He'd finally caught enough local Pokémon to mix up his team without using his older Pokémon so if they'd cared about this arc Ash could have done really well.
