A reputation for generosity is thought to be desirable, but developing it can be dangerous. Generosity exercised in truly virtuous ways is never seen by others, so if you want to be thought of as a generous ruler, you must keep up a lavish public display. To support this habit, a prince must raise taxes and squeeze money from his subjects. Generosity of this sort benefits few and harms many. The prince's subjects will hate him, and no one will respect him because he is poor. Therefore, a wise prince will not mind being called a miser, because stinginess is a vice that allows him to reign. If a prince is giving away other people's property, he can afford to be generous, but if he is giving away his own resources, he will become grasping and hated or poor and despised.
After teasing the reader with shocking revelations in Chapter 15, Machiavelli comes away sounding thoroughly conservative in this chapter, discussing the supposed virtue of generosity. His focus is on the appearance of generosity and what one must do to develop one's public image. True generosity, he notes, would not get a prince a reputation for being generous, because no one would see it. This is an important distinction. Machiavelli does not say that true generosity is bad. What concerns him is the kind of forced display that a prince must put on to develop a public image as a generous man. Supporting lavish displays eventually makes a prince poor, forcing him to exploit his subjects' resources. This does real harm to everyone, including the prince. Thus the supposed virtue is no virtue at all.
He does qualify this observation by saying that new princes who are trying to gain power must be seen to be generous, but after they have power, they should immediately curtail their spending. He offers good examples: Both Louis XII of France and Ferdinand of Spain were noted for their thrifty habits, and both were energetic conquerors. On the subject of conquerors, Machiavelli makes the interesting observation that because armies live off looting and extortion, a leader of armies had better be generous or his soldiers may decide to leave. According to Machiavelli, this is desirable, because the property involved is not the prince's or his subjects', and therefore the integrity of the state is not harmed.
Caesar Julius Caesar had a reputation for generosity that contributed to his popularity. He was assassinated in 44 B.C., only a year after his triumphal return to Rome from a series of military victories.