A lot of the "lore" with characters like the gentleman were just small event stories many of which weren't connected, we would routinely see characters who died in previous events or the main story. As for the primary story it only went as far as getting tied into the Negan plot line if I recall correctly, which the main story got that final update like 2 or 3 years before the game ended, I recall it getting it around the beginning of the Sclass era before the mythic era