Machiavelli uses the quality of liberality to illustrate the point he made in the previous chapter about a prince's reputation. In the case of liberality, it is obvious that a prince who is generous is considered virtuous. But in practice, it is impossible for a prince to have a reputation for generosity and also be prudent. The only way for a prince to sustain generosity is to burden his people with taxes, which causes resentment. As soon as he ceases to be generous, he will be labeled a miser.
Therefore, it is better for a prince to be parsimonious. Only men with reputations for parsimony have been able to rule effectively. Machiavelli answers the charge that some rulers were reputed to be generous by stating that they were generous only on their way to power, such as Julius Caesar. Others who were reputed to be generous did so by plundering the resources of their conquests. A prince's liberality breeds contempt from his subjects either through burdensome taxation or the malicious reputation of plundering. Guarding against the people's hatred is more important than building up a reputation for generosity. A wise prince should be willing to be reputed a miser than be hated for trying to be too generous.
