Crimson Jack’s flagship is a new vessel, so it is unknown if he commandeered a damaged Imperial vessel in the aftermath of the Battle of Scarif in the modern Star Wars canon.

Crimson Jack couldn’t be a man roughly Jude Law’s age during the New Republic, then pop back up as a still-in-his-prime pirate decades later.

Crimson Jack’s Star Wars history before Skeleton Crew explained. Crimson Jack is a pirate in Star Wars: Skeleton Crew. In episode 3, Jod manages to escape from the pirates along with the kids.