Bootstrap was once an associate of Jack Sparrow's who remembers him fondly as a "good pirate and a good man" in the first film.
When Sparrow's first mate, Hector Barbossa, led a mutiny against Sparrow and left him stranded on a small island, Bootstrap was the only one who did not participate, and when the crew uncovered the cursed Aztec Gold, Bootstrap avenged Sparrow and atoned for not defending him by sending his coin to his young son, so that he and the crew would not be able to find it and thus remain cursed forever. This act enraged Barbossa greatly, and he punished Bootstrap by tying his bootstraps to a cannon and throwing him overboard. Due to the curse, Bootstrap could not die, and was forced to suffer constantly due to the lack of oxygen and crushing water on the seabed.
Ten years later, sometime before the curse was lifted and Barbossa defeated by Sparrow and William, Bootstrap is found by Davy Jones, captain of the Flying Dutchman, and offered to be rescued from his fate in exchange for one hundred years working on his ship. Bootstrap agrees, and is depicted as any other crew member on Jones' ship, with oceanic flora and fauna growing from his body.
Bootstrap Bill appears in the prequel novels, but before he was Bootstrap Bill, he was named Billy Turner.
Bootstrap is sent by Jones to remind Sparrow of his debt to him, since it was Jones who raised the Black Pearl from the bottom of the sea for Sparrow in the first place, and Bootstrap brands Sparrow with the Black Spot, a sign that the Kraken, Jones' leviathan, is hunting him.
Bootstrap is reunited with his son on the Dutchman following a confusion regarding their surnames, and Bootstrap is given the horrible task of whipping Will in the back (so that Jimmy Legs will not do Will any worse harm). Despite the flogging, Bootstrap and Will bond rather uneasily, and Bootstrap eventually aids Will in stealing the key to the Dead Man's Chest from a sleeping Jones, although at the cost of surrendering his soul to Jones for eternity during a game of Liar's Dice. Despite Bootstrap admitting that he abandoned him at an early age and does not deserve salvation, Will promises to free his father no matter what. However, Jones discovers this and punishes Bootstrap by forcing him watch the Kraken destroy the Edinburgh Trader, the ship which is harboring Will. Following the devastation, Jones orders Bootstrap locked in the brig. Bootstrap, however, remains unaware that Will survived, and is too devastated to resist his imprisonment.
While in the brig, Bootstrap begins to lose his humanity due to the grief of the loss of his son, and becomes slightly delusional, shown when Elizabeth Swann, Will's lover, is locked in the same brig as Bootstrap and briefly tells him that Will survived. Within a few minutes, Bootstrap forgets their conversation completely. Later, when Admiral James Norrington helps Elizabeth and the other prisoners escape, Bootstrap follows and corners Norrington on the edge of the ship, alerting the other crewmen. In his delusion, Bootstrap impales Norrington through the stomach, killing him. This apparently wins him Jones' trust, as Jones does not order him imprisoned again. In the final battle against Jones and Cutler Beckett, Bootstrap, still delusional, encounters and fights Will, not recognizing him. He is subdued by Will, and only recognizes his son after seeing Jones stab Will and catching a glimpse of Will's dagger. In a fit of rage, Bootstrap attacks Jones and is nearly killed before Sparrow uses Will to stab Jones' heart. With their captain gone, Bootstrap and the other crewmen cut out Will's heart and place it in the Dead Man's Chest, restoring him as the new captain of the Dutchman. Following the battle's end, Will offers the now-free Bootstrap to leave the Dutchman and live a normal life, but Bootstrap, desiring to make up for having abandoned Will when he was a boy, chooses to stay with his son aboard the Dutchman.
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