Bootstrap is eventually reunited with his son on "Flying Dutchman", where Bootstrap is given the task of whipping Will. Despite the flogging, Bootstrap and Will bond, albeit rather uneasily, and Bootstrap eventually aids Will in stealing the key to the Dead Man's Chest from a sleeping Jones. This comes at the cost of surrendering his soul to Jones for eternity during a game of Liar's Dice. Despite Bootstrap admitting that he had abandoned him at an early age and does not deserve salvation, Will promises to free his father from Jones. However, Jones discovers this and punishes Bootstrap by forcing him to watch the Kraken destroy "Edinburgh Trader", the ship which is harbouring Will. Following the devastation, Jones orders Bootstrap to be locked in the brig. Bootstrap believes that Will perished on the ship. While in the brig, due to grief and the effects of the "Flying Dutchman"s curse, Bootstrap begins to lose his humanity and to be absorbed into the ship's hull. He becomes delusional. In "At World's End", Elizabeth Swann is locked in the same brig as Bootstrap. She tells him that Will survived and that he will come to save him. He says Will cannot save both Elizabeth and himself—he will only choose her. Bootstrap forgets their conversation completely immediately. Later, when Admiral James Norrington helps Elizabeth and the other prisoners escape, Bootstrap alerts the other crewmen. In his delusion, Bootstrap kills Norrington. This apparently wins him Jones's trust, as Jones does not order him to be imprisoned again.