Machiavelli's most famous political work, The Prince, was a masterful act of political deception. I argue that Machiavelli's intention was a republican one: to undo Lorenzo de Medici by giving him advice that would jeopardize his power, hasten his overthrow, and allow for the resurgence of the Florentine republic. This interpretation returns The Prince to its specific historical context. It considers Machiavelli's advice to Lorenzo on where to reside, how to behave, and whom to arm in light of the political reality of sixteenth-century Florence. Evidence external to The Prince, including Machiavelli's other writings and his own political biography, confirms his anti-Medicean sentiments, his republican convictions, and his proclivity for deception. Understanding The Prince as an act of political deception continues a tradition of reading Machiavelli as a radical republican. Moreover, it overcomes the difficulties of previous republican interpretations, and provides new insight into the strategic perspective and Renaissance artistry Machiavelli employed as a theoretician.