This paper examines Machiavelli’s theorization of the Florentine vernacular, particularly in writing (Discorso o dialogo intorno alla nostra lingua, 1525), and how it is applied as both a propagandizing weapon and as an eloquent gift. Instances of this dual function are especially evident in both Il principe and the Madragola. The paper argues that Machiavelli’s contribution to the Questione della lingua in Italy is singular, but at the same time his negotiation with and deployment of vernacularity are equally pivotal to the enrichment and problematization of the Italian language.