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Might be an unpopular opinion but I feel like Ash's first league victory (in a league that is also from the games) should be a culmination of all of his journeys, not just his very latest journey.
Hoenn and Sinnoh were the last times this could have happened I guess, with Ash's past friends and rivals showing up more commonly in gen 3, and ash using old reserves in gen 4.
In Unova his failure was obvious and I was actively against the idea of him succeeding in XY and SM. If he wins in a majorly self-contained generation it just feels kinda cheap imo.
Either way they have to market the current characters and games, I guess I can't complain
