My jumper tried to redeem/recruit her because he liked her, but him being a 13 year old upgraded me, at his core he still had no idea about anything related to girls, much less Azula, making girls on a whole appear completely rational

But between his lack of experience, Vaatu's constant influence, him being aware of being manipulated by both, and Azula "killing" Aang, that was completely derailed. Maybe for my next chains I can focus on alternate paths he could've chosen, like Marvel's What If, although it kind of is already a bit like that.

As for companioned villains, there's Victoria Von Doom from Marvel Magic, but I don't think she's be a villain, not voluntarily and definitely not by the time they met. Most Villains I redeem aren't really companioned, just left to improve their worlds in my stead.