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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.
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