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In short,
>Losing ensures an easy way to continue the series indefinitely, since Ash is an icon of a character and throwing him away would be utterly retarded
>Kanto also has the benefit of having some artistic merit to the writing since Shudo did care about what he wrote. It's actually pretty impressive how they had the guts to let him lose at first.
>The significance of Johto was defeating Gary
>Every League introduces a character right before it that will be the one to defeat Ash (ie. Richie, Tyson, Tobias, Cameron)
>XY introduced Alain far earlier independently of Ash's adventures and built him up
>Letting Ash come so close was intentional, they wanted the victory to be saved for the 20th anniversary Gen
>Unfortunately, the more slice of life tone of SM and amateur League of nobodies softened the impact of Ash winning compared to the shounen XY and each previous series
>Ash vs Gladion doesn't feel like a Championship match, it's 3v3 and has some bullshit like countering Counter
>Ash vs Kukui is fantastic for many reasons, but it's unfortunately also softened by not having stakes since it's a commemoration match and Ash already has the title
But he counts as a Champion now, and because it's for a new League, he still seems like the underdog in comparison to established characters like Lance, Steven, and Cynthia. But his entirely new team storming the competition feels unearned as a result.
