Machiavelli's reputation rests above all on his political-historical writings, and secondarily on his notable contribution to the re-emergence of classicizing comic drama. Yet, as scholarship has increasingly shown, he was also profoundly engaged with poetry and poets, as reader and writer. This chapter focuses attention on four interrelated dimensions of Machiavelli's engagement with poetry: the “poetic” dimensions of the nonpoetic works (citations of and allusions to poetry, use of poetic devices and strategies); the poems he wrote; the poets he read (and more or less obliquely rewrote); and his “poetics,” that is, his concept(s) of what poetry is and what it does, and its relationship to other modes of discourse, particularly the political historical. What Machiavelli's “realism” consists of is a source of ongoing scholarly debate. The general perception that he had little patience for the world of imaginative fictions remains alive and well among readers of The Prince and the Discourses. For such readers, the fact that Machiavelli frequently names poets and allusively echoes poetry in these nonpoetic works has commonly been dismissed as attributable, on the one hand, to the fundamentally literary-rhetorical character of upper-class education in his time (which was immersed in classical Latin literature), and, on the other, to the increasing importance assigned by Florentine culture to its vernacular literary heritage, above all the newly canonized “three crowns” of the fourteenth century: Dante, Petrarch, and Boccaccio.