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One of my newer game headcanons is that any rival who has winnable matches (as in if you lose to them the game just continues on without forcing you to beat them) then they won those matches (or at least some of them in the cases of Blue, Silver and Hop who have multiple potential wins) So...

I think this leads to a big point. Everyone has different experience with the various champions depending on what their team makeup is going into the match (levels, type coverage, stats)

I think it could go either way depending on the circumstances Dyna/G-max: Leon Mega: Cynthia Z-moves: either or, neither one of them are specialist on using z moves No gimmicks: also either or, both have a wide pool of Pokemon they use with different movesets, so it comes down to their team...

Leon, Cynthia, Red, and the Alolan Champion are consistently referred to the 4 strongest living champions, although in universe there are plenty of arguments of who is actually number 1. Galar and Unova have a somewhat tense relationship...making battles against Unovan Leaders/Elite 4/Champions...