After being rescued by the latest Nightingale, Jackson repaid him by teaching him a few tricks on the art of thievery. In his downtime he found himself around the Nightingale and Prodigal's family. In that time he taught Annie the truth, that older people are the REAL ones to go after in terms of love. Unfortunately, it backfired as she now claims to love him.
Annie was never interested in love with real, non-anime people until she met Jackson. He opened her eyes, showing her that it wasn't that she was uninterested, it was just that she wasn't looking in the right area! And it was proven when she felt her heart do flips for Jackson.
Being brainwashed by an all-powerful being put a damper on Jackson's aging process, so by the time he was back to normal he found that the entire world had moved forward a good few decades. He remembered Jey's grandkids when they were babies, and now their kids were grown up! Lock's energy reminded him a lot of himself, and he got the idea to pass down the Master Thief's title to him.
Lock had heard about Jackson from his father and grandfather, but this was the first time he actually met him. The guy was fun and talented! It was easy for Lock to look up to him. And when offered the chance to follow in his footsteps he could only eagerly accept.
One of the first people Jackson ran across after his time jump was Kestrel and her son. He met her when Cher showed him where she worked. He liked the atmosphere, and he DEFINITELY liked the looks. However, he found himself more attached to Dabbie, reminded of his own youth, and tried to be a good role model for him.
Despite the odd introduction, Kestrel finds a very good friend in Jackson, especially after seeing how good he is for Dabbie. She appreciate all that he's done for her son, and as far as she's concerned, he's as much a part of their family as her or Dabbie.
[Lovers] Having come out of a near 30 year nightmare, Jackson found himself in an entirely new world completely alone until he ran into an old friend. It was there that he met Commandant, and no matter how much the man yelled and spat at him, the thief never got tired of being around him. Maybe, just maybe, everything that happened in his life was for this very moment.
Dabbie reminds Jackson a lot of himself at that age, well, mainly having bad fathers. He tries his best to fill that roll and help Dabbie grow up with a normal, healthy life. It's because of that desire to let him grow up well that Jackson chose to not make him the next Master Thief.
Dabbie looks up to Jackson like no one else in his life, thinking that's he's one of the dopest people he knows! He's a big role model for what a good father figure should be like, and one day, Dabbie wants to be that for other kids like him.
[Related] Though not by blood, Jackson is Gil's uncle. He's still bewildered every time they meet, having been so used to seeing Gil as just a toddler at the time. Now look at him, arguably older than him, and taking up his grandfather's job. Jackson only roots for him in the sidelines, and he's proud of how his uncle raised him and Ellie.
[Related] With Jackson being his step-dad, Cecil's nephew, the two are somewhat a bonded family. Gil finds him fascinating, especially considering this is the same thief his grandfather chased years and years ago. How Jackson hasn't aged is completely beyond him, though he likes to take moments to talk with him and hear about what Jey was like.
[Related] Jackson is like an uncle to Ellie, though not by blood. When he came out of his coma-like state, he was surprised to find his uncle had married, and to the family of the detective that once hunted him down! It seems, though, that Ellie more grew up with Cecil's influence, so Jackson gets quite the nostalgia trip whenever he talks to her.
[Related] Although not blood related, Ellie considers Jackson an uncle, especially with his relation to her step-dad. She'd always heard stories about him, meeting him in person gave her some form of shellshock. He doesn't seem to be a bigtime thief anymore, much to her relief, because she's not sure if she could handle trying to catch him. Or if she even COULD.
It makes sense for human resources to want to keep an eye on Jackson and question him plenty of times since he broke the laws of physics with his age and being mind controlled, and typically he'd enjoy this situation. A beautiful, wonderful beauty visiting him often to talk? It was almost like a dream come true!
Almost.
She's... Holly honestly freaks Jackson out a bit. There's just... something WILD in her eyes when she badgers him about how he was mind controlled.
An agent who by all means has broken all known natural laws and hasn't aged a day past his twenties in over 30 years? How could Holly NOT want to run experiments on him; what kind of good scientist would she be if she just left that alone? Even when she asks sweetly for him to allow her to run some tests, Rivers always seems so jittery when she's around. Wonder why that is?
[Rivals] Jackson isn't sure if Ad's aware that he's dating Teddy, but you know what? He doesn't care anymore! That... That TWERP is always trying to be around Teddy and kiss his ass! Only one person gets to kiss his ass and that's HIM.
[Rivals] Addy feels like he deserves to be an Agent, and to do that he needs to suck up to the boss of agents: The Commandant. Only problem is that someone's beat him to it! Jackson is ALWAYS there hovering around the boss! What the hell!