Late in his life, Desiderius Erasmus recalled a dinner invitation that he once received from the mercenary captain Bartolomeo d’Alviano (1455–1515). At the time, Erasmus was in Venice working with Aldus Manutius on the 1508 edition of his Adages, and d’Alviano was captain general of Venice’s army. Although Erasmus dismissed d’Alviano as a man of war, this article proposes that the men shared a good deal in common, particularly an appreciation of Hellenistic studies in Venice. D’Alviano nurtured a literary circle and argued for the construction of what became the Biblioteca Marciana. The article also shows that each man (scholar and soldier by profession) at some point held the tools of the other’s craft. By investigating this exchange and their attempts to cross new linguistic divides, it argues for the importance of tracing connections between warcraft and literary production in the Renaissance.