>>53521208He couldn't even beat Ritchie lol.
Realistically in the context of the ashnime the best way to end him would be:
Sinnoh: loses to Tobias. (Objective loss, no way he'd beat him).
No reset after DP, in BW he reaches the top 2, except it's a proper league. Loses to Bianca in a very very tight 6v6 - the delicious part of ashnime league tournaments.
Play Bianca up as Ash's main rival, have her win the Unova league. (Have Ash win against Iris in the semi finals to show Iris's ambitions in the Pokeleague).
In Kalos, Ash wins against Alain, but loses against E4 Malva - then the Team Flare thing happens - Malva escapes but takes Alain and Mairin under her protection, the 3 of them go underground rogue)
Alola has no leagues but during the whole season Ash trains hard to be able to fight E4s on par, Ash trains wirh Ultra Beasts. We get a short arc of Iris temporarily joining Lance's G-Men to show her growth in power towards Unova Champion, Bianca as BW Champion gets beaten by Iris in a tie, but still passes the title to her. Bianca herself goes to establish PokemonWorld government control in the Distortion world.
Also a cameo of May marrying Drew and their wedding in Alola.
The subtly implied relationship in BW between Dawn and Cynthia still isn't confirmed but we see them hanging around a lot together with matching rings on their hands, they hang around as a couple but nobody except for Brock ever catches onto what's going on with them (becahse everybody except for Brock is romantically dense in Pokemon).
In JN, Ash gets into the M8, and the same scenario repeats except he relies on reserves way more, bringing back all of his aces.
Manages to win with bullshit hackery even at his best but the best Champion is still Cynthia as opposed to Leon (who is 3rd place). Giselle is 4th place (Alain doesn't participate, we get Giselle instead of him in the M8).
*SM and JN have no artstyle changes from XY.
This is the only way it would have worked realistically.