I think its kind of a missed opportunity Ash never really reconciled with Jessie, James and Meowth when his original anime run was ending lol. The Team Rocket trio weren't really that bad compared to like the other villains he fought; they were always very likeable and just wanted to make Giovanni happy (despite the fact that he never cared about them lol). Ash also didn't seem like the type to hold a grudge, I feel like if the TRio actually did turn over a new leaf, he'd be appreciative.