>>42923610Delia, the professors, Gary, Brock, Misty, May, Dawn, Iris, Clemont, Bonnie, Serena, and the Alola crew don't betray him under any circumstances--not maliciously. If you worked under the old fan theory (debunked by BW2) that the Striaton Gym Leaders were working for Team Plasma as the Shadow Triad, you could have Cilan betray him--but it'd have to be written in the context of that theory. Being young and dumb, Max could be manipulated into unintentionally betraying Ash; I don't include Bonnie in this because Clemont is a better check on her than May is on Max in this scenario--otherwise, you could maybe try it with her, too. As
>>42923718 says, you'd have to corrupt Ash in order to get any of the former to actually "betray" him, and that would only be as a response, basically, to him betraying them, and thus them "betraying" him in order to overall save him from himself or the corrupting influence in question. And even then, it's extremely hard to see Brock, Misty, or Serena giving up on him even in such a state.