Ash: I like this guy but he is unfortunately pretty dumb, and his lack of knowledge or fact of being incredibly dense can be highly irritating at times. Even for most obvious things like TR setting up trap through his friends could see through with no problem(special mention to Misty who was more skilled in that than any other companion).
Everyone seemed more apt against Team Rocket early on because the writers put way more effort and charm into their face-offs, even in some points of AG, Ash was savvy to some of their traps, seeing a TR pit coming a mile away (and even a backup one after) and scanning Meowth with a Pokedex when becoming suspicious of a disguise. It's only later on where, like I said earlier, the face-offs became completely automated, with the twerps falling for the dumbest of schemes to chain off the plot and TR always being curb stomped in some form with practically no developed effort or character input from the twerps whatsoever. Only a few odd characters like Clemont or Pikachu have had good cerebral face-offs with antagonists like the villain teams in modern episodes, and even then only in rare individual moments, otherwise it's just 'hero smash bad guy'. If Misty came back she would likely be exactly the same as Ash is right now.
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