Wenches Scarlett (Lauren Maher) and Giselle (Vanessa Branch) fix each other up for their wedding, in which they would each marry their groom. Upon realizing that both their grooms were the same man, Jack Sparrow, the two wenches found themselves in an auction led by the Auctioneer. The short film serves as a prequel to The Curse of the Black Pearl, explaining just why Jack Sparrow's boat the Jolly Mon was seen sinking at the beginning of the whole story, and explaining why wenches Scarlett and Giselle were so upset with him and implies how Cotton lost his tongue.

Paul "Wrecking" Crewe was a revered football superstar back in his day, but that time has since faded. But when a messy drunk driving incident lands him in jail, Paul finds he was specifically requested by Warden Hazen (James Cromwell), a duplicitous prison official well aware of Paul's athletic skills. Paul has been assigned the task of assembling a team of convicts, to square off in a big football game against the sadistic guards. With the help of fellow convict Caretaker, and an old legend named Nate Scarborough to coach, Crewe is ready for what promises to be a very interesting game. It's only the warden and the guards who have no idea who or what they're up against, with Paul the driving force behind the new team. Written by mystic80