Chapter 15 begins a series of chapters concerning the qualities and behavior of princes, which Machiavelli describes as “the rules of conduct for a prince towards subject and friends” (59). In this brief chapter, he stresses that his suggestions are realistic in nature rather than imaginary, because how one lives and how one ought to live are far apart. According to Machiavelli, a prince who is concerned with acting virtuously at all times will certainly come to ruin because he will be surrounded by others who are not virtuous. He argues further that “a prince wishing to hold his own to know how to do wrong, and to make use of it or not according to necessity” (59). Although it would be praiseworthy for a prince to exhibit all of the qualities that are considered good, it is not a realistic option because many things that look like virtue lead to ruin, while many things that look like vice will lead to security and prosperity. 

In Chapter 16, Machiavelli’s use of the word liberality is synonymous with generosity. He further admits that a prince’s subjects should consider him generous. However, he cautions that if generosity is exercised in the way it truly should be, it will go unnoticed and be harmful to the prince.