This article explores an alternative logic of imprudence at work in Machiavelli's The Prince, a text seemingly defined by its prudence. Arguing that crucial engagements with The Prince by Eugene Garver and Robert Hariman operate as “prudent” readings, I note that the text offers durable resources for radical political and rhetorical imagination. Such resources are recoverable, however, only in and through an alternative, imprudent, reading strategy. Following the work of Maurice Merleau-Ponty, I read The Prince—particularly in its aesthetic and rhetorical articulation of “the people”—neither as a manual for princes or realpolitik but as both irreducible plurality and differential network, reflecting a political imagination at work in the text beyond modern calculation. Reading The Prince imprudently, I explore the necessary interconnection between rhetorical reading and political thinking—and the subsequent importance of understanding political theory as an aesthetic and textual practice.