Diichiro Oda, born in 1975, is a Japanese manga artist most renowned for his work called One Piece which earned the title as the best-selling series of all time. The manga, or visual comic, primarily focuses on the adventures and liberty of pirates who defy the monarchical structures that control their world. A sub plot within this series features an antagonist known as Don Quixote Doflamingo, who bears striking similarities to the famous Don Quijote de la Mancha by Miguel de Cervantes. A critical focus in the paper analyzes the similarities between both versions of Don Quijote and how reinterpretation of the knight errant into an antagonist began in Japan. Specifically, this paper addresses how the changes in government from Imperial Japan to the Constitutional Monarchy following the events of World War II have led to an alternate representation in Don Quijote within Japanese culture. Furthermore it analyzes how manga, which relies on its visual representation of its characters, aides to the visualization of Don Quijote de la Mancha through a Japanese lens. The depiction of Don Quijote as an antagonist unravels the current sentiment by the Japanese people who either remember or try to understand Imperial Japan and how the acting monarchy of the time restricted the liberty of its people and others.