2/2 Perhaps after Thomas dies of old age, Flint goes to tavern to drown himself in rum (it would take some time) and mentions that he used to be Flint (not as bragging, but because he doesn’t give a fuck anymore). Or maybe someone who knows him happens to be there and recognises him. And the word goes out and his crew hears it and feels nostalgic (like they do in TI) and some of them go there.
It’s a point, Anon. It could very well be read that they escaped and that James simply came back to Savannah or that they stayed in Savannah all that time after they escaped, but I have a hard time imagining Thomas particularly being ok with that. He’s been enslaved for ten years, and I can’t imagine him actually feeling all that safe staying in one place considering that he was stolen from his own home at the start of that imprisonment. It just seems like the kind of experience that would make one want or even need to travel, and of course James would come with him.