This study conducts an detailed examination of James S. Gale’s translation methodology applied to 104 titles from Yi Kyoo-bo (1168~1241)’s Dongguk Yi Sangguk Jip (Collection of Works by Yi Kyoo-bo, the Minister of the Eastern Country, 東國李相國集). Despite the non-realization of Gale’s publication aspirations, this marks early and pivotal efforts to acquaint English-speaking readers with Yi Kyoo-bo’s prose and poetry, thus promoting the global recognition of Korean literary heritage. A comparative analysis of the original Chinese titles against their English renditions allows this paper to categorize the translations into five distinct methodologies: omission, condensation, literal translation, creative translation, and expansion. The findings reveal Gale’s inclination towards crafting succinct titles, frequently at the expense of excluding details that might elucidate the original texts’ contexts. This approach remains consistent across his translations of works by another eminent Korean author, Choi Chi-won. Contrarily, Kevin O’Rourke, a contemporary translator of Yi Kyoo-bo’s compositions, adopts a notably divergent strategy, favoring titles that adhere more closely to literal translation. Gale’s translation philosophy not only sought to transmit the essential messages encapsulated within the original texts but also endeavored to situate them within the ambit of Western literary conventions. This aspect underscores Gale’s instrumental role in the transcultural dissemination of Korean literature.