>>46021252Because his end goal is literally made-up bullshit with no real definition, and retiring him is impossible without also retiring Pikachu as the mascot. Never mind the two are one of the most iconic duos in all of Japan and that the ones running the anime literally liken him to Mickey Mouse, ergo a timeless character that's destined to stick around indefinitely.
But say none of that applied, and Ash was set to be retired. Pikachu's still vital, so they're going to give the next protagonist a Pikachu, but then that begs the question of "why not keep using Ash in order to save time, money and effort" in regards to character design, writing, voicing and all, because at the end of the day, the Pokemon anime is still a weekly toy commercial that's been ongoing nearly nonstop since it first aired.