Monkey D. Luffy's personality shines during the Clockwork Island Adventure, beginning with a carefree moment on a beach where a washed-up toy windmill captures his attention. This distraction allows the Trump Pirates to steal the Going Merry and the crew's belongings. Faced with this loss, Luffy shifts focus, determined to recover his ship and protect his crewmates.
He wears his signature straw hat, red vest, and denim shorts. His problem-solving consistently relies on straightforward physical action. Pursuing the thieves, Luffy and his crew acquire a crude paddleboat and temporary clothing. They encounter the Thief Brothers—Akisu and Borodo—who trap them in a net. After resolving the conflict, Luffy forms a temporary alliance with the brothers to confront the Trump Pirates on Clockwork Island and rescue the captured Nami.
Luffy's fierce loyalty drives him when Nami is abducted by Trump Pirates lieutenants Honey Queen and Boo Jack. He leads the assault, navigating Clockwork Island's hazardous spiral staircase as it transforms into deadly traps, including flooding waters and falling boulders. Using his rubber abilities, he physically supports crewmates through these obstacles, demonstrating resilience and protective instincts. His combat employs signature stretching attacks like Gum-Gum Pistol and Gum-Gum Whip against the Trump Pirates' foot soldiers.
He interacts with Clockwork Island's oppressed engineers, learning about the mechanical island's structure and the threat of Bear King's superweapon, the King Cannon. Urged to abandon the mission for safety, Luffy rejects the idea, stating that staking one's life is necessary to create a future, reflecting his willingness to confront overwhelming odds for what he deems just.
During the parasail assault on Trump Castle, Luffy confronts Honey Queen's Toro Toro no Mi fluid logia powers and Boo Jack's spiked weapons. Despite setbacks, including crew captures and Borodo's betrayal, Luffy remains fixed on the rescue. His resolve hardens upon seeing his crucified crewmates and recalling the Thief Brothers' bond. He breaks free from a crushing ceiling trap, confronts Bear King, and shields Nami from the King Cannon. His final victory involves redirecting the cannon fire to destroy the weapon and defeat Bear King, consistent with his approach of defeating antagonists without killing them.
Luffy's captaincy is evident through his crisis leadership and prioritization of crew safety. He departs the island only after ensuring the Thief Brothers' future on their reclaimed homeland.