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Based on their feats? Brendan and Lucas/Dawn had the most extreme, over the top legendary encounters and won. But ultimately, Red is the only one with a team we know would beat anyone else's team. Even if it's canon that anybody else caught the legendaries the player does, it hasn't been shown that they trained them to lvl80+. So based on training/battling, Red id the best trainer. Feats, the aforementioned, but it's difficult to judge.
Calem/Serena are eliminated because everything is handed to them and they're playing with a handicap.
