This chapter discusses how Machiavelli’s The Prince prescribes deception as a matter of necessity in leadership and political life. The author shows how Machiavelli’s ideas present a radical break from the classical and Christian notions of morality and human soul. The classical conception of virtue is made new by Machiavelli’s idea of virtù (virtue) supported by a modern understanding of human nature, which is at once unlimited in its acquisitive desires and bound by necessity. By stripping people down to their true nature, Machiavelli unburdens leaders from their conscience and moral obligations. Through a reversal of conventional moral pieties, Machiavelli endorses the practice of deception in political life. The prince reaches the apex of leadership when he finally understands Machiavelli’s teaching of the beast and man. Represented by the famous image of the fox, the prince learns the art of deception by creating and managing the perceptions of followers.