Regardless of whether Law is actually meant to be the real Crimson Jack, or it’s a name he stole off the actual red bearded pirate we know from the comics, or it’s a reimagining of the pirate master, the reveal does setup some interesting possibilities for the character’s story. After all, in the comics, Crimson Jack was one of the first rivals Han Solo and Chewbacca encountered after the Battle of Yavin. Jack and his band of pirate scum even stole the reward the duo received for saving the Rebellion’s skin in A New Hope, a prize Han and Chewie had intended to use to pay off Jabba the Hutt.
Later, in Star Wars #11-15 by Archie Goodwin and Carmine Infantino, Crimson Jack also kidnapped Princess Leia and Han and Chewie went on a mission to rescue her. It was during this second encounter that Han managed to kill Crimson Jack in a duel in space.
Crimson Jack’s death is no longer canon, of course. Interestingly enough, a red bearded Crimson Jack that looks a lot closer to the original Legends character has already made it into current Star Wars canon, but in a completely different era. Marvel’s Star Wars: Halcyon Legacy miniseries by Ethan Sacks and Will Sliney, which was created as tie-in story for Disney’s shuttered Star Wars hotel, brought Crimson Jack to the Sequel Trilogy era. Once again a villain, he shows up on the Halcyon to collect a bounty from the First Order.
It doesn’t currently seem like that Crimson Jack is the same one Law is playing in Skeleton Crew. Law isn’t a redhead and isn’t dressed in ridiculous armor like his comic book counterpart. And how canon can one really consider a thinly-veiled comic book commercial for a hotel anyway? Either way, Law’s Crimson Jack exists a lot closer to when the character originally appeared in those old comics. Skeleton Crew takes place almost a decade after A New Hope, meaning it’s possible Law’s Crimson Jack has had a few of his own run-ins with Han and Chewie along the way. Perhaps we’ll hear about one or two of those times on Skeleton Crew? Or maybe it’s all just a lie…