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By the end of DP, everyone WANTED Brock gone, because he had worn out his welcome. Same with Misty by the end of Johto. I'd rather the supporting characters get closure than wear out their welcomes like MIsty and Brock did.

Have him to go to Kanto with Lillie and act as a mentor figure (her Brock) for her journey

Ash has yet to show any signs of being regressed in the SM series though. The few battles there have been show no indication of his battle skills having suffered.

That's not really accurate though, at least not for Iris, Serena, or Lillie.

An interview with an old director suggests that they're aware of that and don't care. Second Interview with Masamitsu Hidaka - Many Interesting Points! - PokéBeach / Pokémon TCG, games, and anime news! That guy is no longer working on the anime of course, but it does provide insight. He, at...

Win or lose, Ash still won't be a Pokemon Master. Winning a league is just a stepping stone, not the end goal. We don't even know what a Pokemon Master is, and likely never will. It's an intentionally vague goal designed to keep the anime going for as long as necessary. The reason they don't...

Pokemon Generations was just a bunch of random scenes with no context behind them unless you've played the games. It was supposed to be "untold stories", but most of it was just stuff we already saw in the games, or stuff that was done better in the main anime. Why do they keep Link as the...

Lillie might actually have a chance considering that the games seem to have set her up to return at some point in a future game, and she's clearly of greater importance than the other classmates in the anime, having the most screentime and focus of them all. The rest, I doubt they'd even appear...