To most contemporary readers, Niccolò Machiavelli is a name synonymous with deception, cunning, and manipulation, a reputation that derives almost entirely from his authorship of one of the central works of political philosophy modern: The prince. Given this image, it is incredibly ironic that the Italian word virtue and its derivatives appear no fewer than seventy-two times throughout the work. Although the translator goes to great lengths to adapt this versatile word to the context of the situation, it is nevertheless clear that virtue is closely related to its cognate English virtue. This, coupled with the political nature of Machiavelli's work, shapes the discussion on the nature of principalities into one in which the author explores the most fundamental questions of how a prince should act. Ultimately, virtue comes to mean not only virtue in the traditional ethical sense but also skill, virility, and strength of character, Roman virtues reorganized and shaped for modern statecraft and the challenges of Machiavelli's Italy. To better understand what the meaning of virtue is in The Prince, it is important to look at where and how he uses the word in the work to describe people and their actions. Although virtue appears first, chapter six provides the first clear treatment of the term, discussing kingdoms acquired through armies or skill. The title itself contains the word, which the translator first renders as “ability” (Machiavelli 18). Here the reader begins to get an idea of ​​what virtue is and what it is not. In the opening paragraph, Machiavelli provides the portrait of how a prudent man will imitate greater men, and his belief that, in doing so, “if [this man] is not as skilled [virtue] as they, at least . .. middle of the paper ...... nods to the difficulty the ruler faces in administering a state due to the uncertainty of the current circumstances. Both the former and the latter dedicate themselves to the subtle arts, one of translation, the other of statecraft, and only by closely examining the context in which they find themselves are they able to carry out their tasks more skillfully. The numerous historical examples contained in The Prince seek to demonstrate that there is no better guide to understanding the context of Italy's condition during Machiavelli's lifetime than knowing the past. The last chapter of The Prince is unequivocal in its message, as demonstrated by closing with Petrarca's words from Italia mia. For Machiavelli, his nation is the direct heir of the Roman legacy, and that legacy, in which virtue is paramount, is one that Italians, and especially the Medici, would do well to emulate..