During Yucatán's Caste War, described in the nineteenth century as the Mayan rebel uprising against criollo (European-identified) hegemony, more than half the Yucatán Peninsula's population either perished or fled, fearing for their lives. As one of the most violent indigenous uprisings in the Americas, it was also one of the longest: the Caste Wars tormented the Mexican Southeast for over 50 years. While historical scholarship has examined the Caste War at length, the study of the peninsula's literary production has yet to be considered for the contribution it makes to fully understanding the sociohistorical context of the war. In this article, I examine the pirate novels of two of Yucatán's most prolific nineteenth-century letrados—Eligio Ancona and Justo Sierra O'Reilly—as they delve into the anxieties that the Caste War provoked in the elite population. Through analysis of the well-established genre of the pirate novel, I demonstrate the way literature served as a space to test new configurations of racial discourses that emerged from the criollo construction of a race war. When paired with historical monographs by the same authors, it becomes evident that the pirate took on new meaning in the context of the Caste War, allowing criollo intellectuals to substitute their increasingly threatened mastery of the land (under attack by rural uprisings) for an imagined mastery of the sea.