>>54421788this, I rewatched the first season and some of the second to see the whole ash vs gary thing.
I sorta get what they were trying to do, but they didn't do it. Gary was basically just a boogeyman season 1 that had no interaction with Ash. And when he lost he just walked away showing barely any emotion or character. Like, yeah I get he's shocked or something that he's not the hot shit he thought he was but it was played off really poorly. Then the actual battle and payoff "Wow you beat me and it was a good fight." as some emotional moment, except we didn't actually see Gary enough for it to have any meaning. He was a 1 dimensional character with no characterization outside of Ash occasionally mentioning him and people saying it like he's hot shit, except they never showed him being hot shit. Hell, the first time we see him fight is what? Giovanni's gym where he gets the Worf treatment.
Gary was barely a character, and he didn't even do that right.