[I]t cannot be called virtue [virtù] to kill one’s fellow citizens, to betray one’s friends, to be without loyalty, without mercy, without religion; by such methods one can acquire power, but not glory.

The Italian word virtù has many meanings depending on its context, including skill, ability, vigor, and manliness. Here, this word also carries the English meaning of “virtue” with its evocation of goodness. Machiavelli, sometimes accused of having an amoral attitude towards power—whatever works, justifies the means—asserts that what makes a “good” prince does have limits: Using Agathocles the Sicilian as a teaching point, a man can have the skill to make himself a prince, but ruthless and immoral methods exclude him from consideration as one of the finest and most admired men.

[I]f everything is carefully considered, it will be found that something which seems a virtue [virtù] would, if practiced, become his ruin, and some other thing, which seems a vice, would, if practiced, result in his security and well-being.

Here, Machiavelli shows the flexibility towards definitions of virtue and vice that give him a reputation for amorality. He asserts that a prince cannot rely solely on the traditional understanding of virtues such as liberality, mercy, loyalty, kindness, honesty, and piety. If adhering to one of these virtues ruins him or his principality, the virtue becomes a vice. For example, if a prince shows too much mercy, he might let criminals run rampant, and the virtue will become a vice as his people are made miserable. If he hoards his assets, the vice of miserliness will become a virtue as he will have the money he needs to wage war.

The actions of a new prince are watched much more than those of an hereditary one, and when they are recognized as virtuous [virtuose], they attract men much more and bind them much more to him than ancient blood would do.

Machiavelli enumerates the many ways a prince must act to appear virtuous, as he defines the term. Here he points out the advantage a new prince has over rulers who take the throne by right of succession. People pay more attention to new princes, who garner good will built through public opinion and attract a following out of proportion to their level of virtuousness. Machiavelli makes the case to the dedicatee of The Prince, Lorenzo de Medici, that he should lead Italy in freeing itself from foreign invaders. He wants Lorenzo to believe that he would be successful if he took up the cause.