I think, like his mother, he has in the past had just cause for worry and real concern.
I also think that, like his mother, he lacks the maturity and intellect and wisdom to see beyond that. He’ll probably feel paranoid and gaslit, just like his mother. And the more people tell him not to worry, the deeper the paranoia will run. Just like his mother.
And, like his mother, left with nowhere to turn and not knowing who to trust, and being surrounded by people who will kowtow to him and/or seek to exploit him at every turn, he’s made rash and poor choices. He wants to be in charge of himself, flex his muscles, and throw in some machismo there too.
I cannot imagine, as a parent myself, ever thinking that a woman I’ve known for a few years and who’s known (surely he’s heard all this gossip) to be grasping and grifting would have his best interests at heart more than his own remaining parent and brother. I can’t believe he really thinks his choices in the past 5 years have been the best ones - more so, the more he says they have been. I think he was just desperate to get out, and now he’s desperate to get back but on his own terms and saving face. Ain’t gonna happen, not for as long as he’s married to Meghan. It’s all terribly sad.