Sweepy was a pirate who joined Captain Jack Sparrow's crew on the quest for the Dead Man's Chest. He had been hired in Tortuga along with several other new crew members, none of whom knew that their new Captain intended to trade them to Davy Jones in exchange for his freedom.
Sweepy lived in Tortuga. In the Twelve Daggers bar, he met Joshamee Gibbs, who was signing up crew mates for the Motley crew of the Black Pearl under famed Captain Jack Sparrow. Sweepy signed up, along with several others. When a drunken former Commodore James Norrington tried to shoot Sparrow with a Flintlock, the new crew mates demonstrated their loyalty by restraining the crazed Navy officer turner pirate, causing him to shoot up towards the ceiling, inadvertently starting a bar fight. In the ensuing chaos, the crew escaped, and left aboard the Pearl. When the ship sailed to the isle of Isla Cruces where the fabled Dead Man's Chest belonging to Jack's enemy Davy Jones, Sparrow and several trusted crewmates rowed ashore, while the old man stayed under the command of Gibbs. Sweepy stood with many other recruits on the main deck as the Flying Dutchman surfaced from the depths of the ocean, and watched as his captain made a fool of himself trying to bargain with Jones.
The Dutchman opened fire on the Black Pearl, damaging her greatly. The ship managed to outrun the ghostly Dutchman, but would soon suffer a worse fate. The whole ship shook, and fellow crewman Lejon yelled that they must have hit a reef. This was not the case; crewman William Turner Jr. knew of what was happening, and the crew was ordered to get to their stations as the Kraken was about to attack. Sweepy served as a cannoneer, stationed at a cannon along with another pirate. They were terrified as they saw the Kraken's tentacles climbing up the side of the ship, and immediately opened fire on command along with all of the other cannons. However, the longboats were destroyed by the Kraken, so they had to fight again. Sweepy prepared for the coming fight, readying the gunpowder. When they ran out of gunpowder, Will Turner suggested they use rum instead, and the whole crew went silent waiting for Gibbs' approval. Gibbs reluctantly agreed to this, and Sweepy cried in despair as he and the crew relayed the order. The second Kraken attack would come suddenly and swiftly as the entire ship shook again, and its tentacles came crashing through into the ship. A tentacle grabbed Sweepy and pulled him right through a cannon hole. Pintel and Ragetti witnessed his death, cringing at the sound of his ribs cracking as he was squeezed through the cannon hole to be devoured by the Kraken.
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