This article examines the self-fashioning of a sixteenth-century convert who became a Catholic and Muslim various times throughout his life. Giorgio del Giglio Pannilini addressed his multiple loyalities in innovative ways in his writings. Starting with a thorough analysis of his autobiography and the way Giorgio described the Battle of Lepanto, the article then addresses the letters which Giorgio sent to Florence, Genoa, Savoy, and the Ottoman Empire. The synopsis of this outstanding and yet partially unknown sources reveals that Giorgio narrated his life with a double audience in mind. As he wrote for Muslims and Catholics, Giorgio likewise consciously adapted a cross-cultural ornamental language and aesthetic signs for his strategic self-positioning within a plurireligious Mediterranean. In that sense, Giorgio’s enslavement not only opened up a story of constraint and subjugation but similarly entailed new and creative ways of self-fashioning. Through such acts, Giorgio claimed interpretative authority over his life; and he thereby also shaped the ways how he was able to behave as a former Muslim in Catholic Rome.