He appeared as one of the first Game Masters, in the fall of 2008. He appeared after the Curse of the Muertos Moon, on the docks of Port Royal where he told pirates of a certain Harkaway ship, and that a treasure fleet of ships were approaching. Later on, he made appearances in Brethren Feasts and the Feats of Strength Competition. He also crewed up with pirates during the battle of Padres, before the island was about to be thrown into a cauldron of flames by East India Trading Company's attack on pirates.