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I have to say, the lead in to the last Brandon battle, and everything else surrounding the end of the season, all seems very final somehow. By this point they were hinting at Ash traveling to Sinnoh, and obviously they weren't going to not have an anime for Diamond and Pearl's release. But I do wonder if at any point during AG, they considered retiring Ash, with a non-League win being the cap to his on-screen career. Like Misty or Tracey, he could've returned for cameos or to help guide the new protagonists similar to how he did May. Obviously that didn't happen. I'd imagine the temptation to end Ash's part of the anime must have come several times in the 26 years he was the face of the franchise though.