The reputation of the Florentine politician, political thinker, and writer Niccolò Machiavelli (1469–1527) has been largely shaped by his controversial political treatises, The Prince and Discourses on Livy. However, Machiavelli left us a broader and diverse corpus of writings. This dissertation focuses on what is perhaps the least-known portion of this corpus: Machiavelli’s poetry. Traditionally, scholars of Machiavelli have considered his engagement with poetry as a narrow and marginal component of his intellectual biography. Conversely, this project showcases how Machiavelli’s poetic activity, which he pursued throughout the vast majority of his adult life, intersected a broad spectrum of human and intellectual concerns, cultural practices, and social interactions. In light of this, poetry provides a unique opportunity to reassess the figure of Machiavelli across its full range of dimensions. Concurrently, Machiavelli’s poetic writings offer valuable insight into the manifold roles that poetry could play in the cultural and social world of Renaissance Florence. To illustrate the scope of Machiavelli’s poetic activity, this dissertation analyzes selections of Machiavelli’s political, amorous, and comic poems. In Chapter 1, devoted to Machiavelli’s political poetry, I address the three poems On Fortune, On Ingratitude, and On Ambition (also known as the Capitoli on account of their meter). I begin by assessing how Florence’s tradition of civic and poetic rhetoric influenced Machiavelli’s three poems, which allows me to then elucidate how the poems fit into Machiavelli’s anthropological-political laboratory. Indeed, my analysis shows how a rhetorically-informed approach facilitates the task of interpreting Machiavelli’s political thought across prose and poetry. In Chapter 2, I look at Machiavelli’s love poetry in relation to notions of desire, gender, and sexuality. Specifically, I focus on two poems that appear to voice homoerotic desire as well as on the two poems that Machiavelli addressed to the Florentine courtesan, virtuosa, and poet Barbera (b. 1500). My analysis highlights two complementary functions that the practice of love poetry had for Machiavelli and his contemporaries. On the one hand, love poetry was a vehicle for articulating reflections on love, gender, and sexuality. On the other, the practice of love poetry facilitated an array of homosocial and mixed-gender interactions. In Chapter 3, I move on to consider Machiavelli’s comic poetry. In particular, I analyze Machiavelli’s three sonnets to Giuliano de’ Medici and his two political epigrams. In so doing, I foreground how Machiavelli’s comic poetry intertwined humor and gravity by leveraging four ingredients: wordplay, parody, satire, and gallows humor. As part of my analysis, I also call attention to the role that those ingredients played in some literary and social practices of the Italian Renaissance.