I think anime Jessie would find Team Skull appealing, don’t you? What with her growing up poor and becoming a criminal to ‘stick it to the man’ as it were, that’s some Team Skull motivation right there! Not sure if she and Guzma would get on, though… Maybe a frenemy relationship with Plumeria?
Well, I’ve seen exactly one and a half episodes of the Sun/Moon anime, and Team Skull did not feature, so grain of salt and all that, but yeah, I actually think all three of our Team Rocket trio would find a lot to like in Team Skull as they’re presented in the games. Jessie and Meowth would sympathise with their disadvantaged position in Alola’s society and respect their ambition, and I think James – despite his own privileged background – has enough of a rebellious streak to appreciate their desire for change. Also, given that a lot of individual members of Team Skull are actually not particularly malicious, I kinda think James and Jessie would fit right in, with their “only evil because I’m supposed to be” attitude. Jessie and Guzma would immediately battle to the death for control of the team though.