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Gordon is fiercely protective of Jail Island, especially after it came under attack by pirates. He confronted Luffy when the pirate came into town, and purchased a rifle after deeming it necessary. He is supportive, as he encouraged Jeanne's desire to grow as a leader.
When Monkey D. Luffy came into Sapphire Town, Gordon stopped and confronted him, but before they could fight, Jeanne came in and told him that Luffy was a friend of Chopper's. Gordon went to the church to meet with Chopper, but was confronted by two Marine soldiers, who had captured Chopper and interrogated Gordon about the other Straw Hat Pirates' whereabouts. Luffy then arrived and knocked out the Marines, and Gordon told him that Chopper was being held in the Marine base to the north.