Will Turner wants to take control of the Black Pearl near the climax ofDead Man’s Chest, but thePirates of the Caribbeansequel never explains why he requires the vessel in the sequel.ThePirates of the Caribbeansequelsall have their own unique problems, but 2006’sDead Man’s Chestis mostly bogged down by complexity. There is no denying that its 2007 follow-up,At World’s End, also features a complicated story, but that movie’s downbeat ending is its biggest issue. In contrast, a convoluted storyline is the primary problemDead Man’s Chestfaces.

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Where2003’s originalPirates of the Caribbeanwas admirable for its simplicity,Dead Man’s Chesthas a plot that includes over a dozen major characters and at least five warring factions. There is Jack Sparrow, who only ever looks out for himself, Will Turner and Elizabeth Swann, who are local to each other but few others, Elizabeth’s bitter former fiancée, Commander Norrington, Davy Jones and his undead crew, the East India Trading Company’s Chairman Lord Cutler Beckett, and eventually even Barbossa. Within this pileup, it is easy to miss out on Will’s specific motivations.

An image of Johnny Depp looking suspicious as Captain Jack Sparrow over images of Barbossa and Davy Jones from Pirates of the Caribbean

The Black Pearl Is The Only Ship Fast Enough To Take On The Flying Dutchman

The Black Pearl’s Speed Aided Will’s Plan

Midway throughDead Man’s Chest, Will is reunited with his father, Bootstrap Bill Turner. Played by an icy Stellan Skarsgård, Bootstrap Bill is an undead sailor who has escaped death by swearing his soul to Davy Jones and his cursed vessel, the Flying Dutchman. Will tries to negotiate his father’s release from this contract but, when this fails, he decides to take matters into his own hands. Although the sequel never makes this entirely clear,Will wants The Black Pearl as he intends to save Bootstrap Bill from The Flying Dutchman,and only Jack’s ship can outpace Jones’ vessel.

There is poetic justice to Will using the Black Pearl to help his father escape, although this doesn’t work out.

Stellan Skarsgård as Bootstrap Bill Turner in Pirates of the Caribbean Dead Man’s Chest (2006)

To make matters more complicated, Bootstrap Bill’s debt toPirates of the Caribbean’s best villain Davy Jonesoriginally came about because of the Black Pearl in the first place. Bill was a sailor on the Black Pearl when Barbossa staged a successful mutiny, and he was thrown overboard to drown when he refused to take part on either side. As such, the Black Pearl’s old crew was technically responsible for Bootstrap Bill saving his life by signing on to work for Jones. There is poetic justice to Will using the ship to help his father escape, although this doesn’t work out.

The Dutchman Couldn’t Catch Up To The Black Pearl

Things don’t go to plan for Will at the ending ofDead Man’s Chest, but he was right to use the Black Pearl in his attempt to outrun the Dutchman. The Black Pearl could have escaped the Flying Dutchman andPirates of the Caribbean’s underused Kraken, but Jones had more invested in the ship than Will realized. His father’s freedom was one matter, but Jack Sparrow also owed a debt to Jones, and the villain intended to have this repaid one way or another. This explains why the Kraken is only interested in killing Jack at the ending ofDead Man’s Chest.

This prompts a quick-thinking Elizabeth to trick Jack into sacrificing himself when she distracts him with a kiss and handcuffs him to the sinking ship. However, it is too late for Will’s plan to save his father. That said, it is hard to see how Bootstrap Bill was ever expected to make it off the Fling Dutchman in one piece regardless. Will seemed to misunderstand many elements of the curse that befell his father, from the conditions of his freedom to the Flying Dutchman’s practical function. Although this is never confirmed canonically, Will’s plan was most likely always doomed.

Pirates of the Caribbean Deadman’s Chest Poster

Why Will’s Plan To Free Bootstrap Bill Never Totally Made Sense

Bootstrap Bill Was Bound To The Ship

WhileElizabeth sacrificing Jack inDead Man’s Chestdoesn’t help Will’s cause, his plan was most likely already dead in the water. For one thing, it was contingent on having a crew to help him and Davy Jones had already slaughtered most of the Black Pearl’s crew by this point. The plan also ignored the fact that the Dutchman’s crew can’t die, meaning there was no way to stop them from pursuing the Black Pearl forever. Meanwhile, Will was likely unaware that Davy Jones had the Kraken and the Flying Dutchman at his disposal.

There is a chance that Bootstrap Bill wouldn’t have been able to board the Black Pear even if Will had saved him in the Pirates of the Caribbean sequel.

Will gives up on the plan to save Bootstrap Bill inAt World’s End, and it is easy to see why. Bootstrap Bill and the rest of Jones’ crew are seemingly bound to the Flying Dutchman itself, and their curse doesn’t seem to be something that can be lifted or altered. The vessel seems to be the problem as much as Jones’ will, so there is a chance thatDead Man’s Chest’s Bootstrap Bill wouldn’t have been able to board the Black Pearl even if Will had saved him in thePirates of the Caribbeansequel.

ThePirates of the Caribbeanmovies are available to stream on Disney+