The Prince

*These assignments draw on material from the author’s introductory letter and chapters XV-XXVI (pages 3-4 and 50-84).

Informal Prompts

Much of Machiavelli’s discussion of The Prince is dedicated to teaching politicians how to gain and retain power. What is power? Give your own, 1-sentence definition of the term. Who or what has power over your life? Who or what do you have power over?

One of the most famous quotations from the text is the question, “whether it is better to be loved than feared, or the reverse” (pg. 54)?

  • Before reading Machiavelli’s answer, make your own argument for whether it is better to be loved or feared? Is it better to be loved in some cases and feared in others?
  • After reading the text summarize Machiavelli’s answer to this question.

Machiavelli’s opinion of mankind as a whole could be summarized by his quip, “men will always do badly by you unless they are forced to be virtuous” (77). Do you agree with Machiavelli? Is he being realistic or pessimistic in his evaluation of humans? Explain your reasoning.

When describing princes who lost their kingdoms, Machiavelli explains, “Their own indolence was to blame, because, having never imagined when times were quiet that they could change (and this is a common failing of mankind, never to anticipate a storm when the sea is calm), when adversity came their first thoughts were of flight and not of resistance” (78).

  • Paraphrase Machiavelli’s idea in your own words,
  • Then describe a time when you either followed his advice and were prepared for an unexpected storm, or did not and had to deal with the consequences.

In chapter XXV Machiavelli gives his opinions on how much of human fate is governed by fortune (or divine favor) and how much is under human control.

  • Before reading the chapter, state your opinion on whether the fate of a individual is governed by an outer force, or whether each person is self-determining. How does your opinion affect the way you act? How does it affect the way you feel when good or bad things happen to you?
  • After reading the chapter, give a 2-3 sentence summary of how Machiavelli believes “fortune” functions. Have his opinions on fortune influenced the way you think about the subject?

Short-Answer/Critical Response Prompts

Re-read Machiavelli’s extended metaphor of the fox and lion (pgs. 55-58, 63-65). Describe in your own words the behaviors of a “fox” and those of a “lion.” Why does Machiavelli believe that a good leader needs to embody the characteristics of both these animals?

Machiavelli’s advice is primarily aimed at political leaders, but does he show any interest in promoting the common good (i.e. is he interested in helping common people as well as their “Princes” or does his advice only further the interests of the ruling class)? Choose a position and then select two passages from the text that defend your decision.

In chapter XXI Machiavelli addresses how princes can “win honor.” He advises: “nothing brings a prince more prestige than great campaigns and striking demonstrations of his personal abilities” (71). As an example, Machiavelli cites Ferdinand of Spain saying that the prince’s actions, “have always kept his subjects in a state of suspense and wonder” (72). Modern political leaders, celebrities, or popular figures often follow Machiavelli’s advice of making “striking demonstrations of his personal abilities.” Find an example in of a modern public figure who you feel makes “striking demonstrations.” Cite a specific example of the individual’s “demonstrations” as recounted by the media, then explain how you feel the individual’s actions align with Machiavelli’s thinking. How do these public actions build the individual’s reputation? What is the importance of “reputation” today and in the time of Machiavelli?

Machiavelli states, “Prudence consists in being able to assess the nature of a particular threat and in accepting the lesser evil” (73). What does he mean by this statement? You may want to follow the steps below as you analyze Machiavelli’s meaning:

  • Define “prudence” (you can look up the definition if you do not already know it).
  • Paraphrase the quotation (restate the meaning in your own words).
  • Briefly describe the context of this quotation–what is Machiavelli’s larger argument in the chapter?

Summarize Machiavelli’s viewpoints on friendship as stated on pages 72-73. Is what Machiavelli describes “true” friendship, or opportunism? Defend your reasoning.

In chapters XXII and XXIII Machiavelli discusses the types of people with whom a prince should surround himself. Using the text of these two chapters, write a “help wanted” add from a prince seeking an advisor. Include the qualities the advisor should have, and those which he/she must not. Include a sentence or two about how the prince will treat his new counselor according to the recommendations given by Machiavelli.

Essay Prompts

Re-read the introductory letter to “The Prince” and the last chapter. What do you think was Machiavelli’s primary purpose in writing this text? What did he hope to accomplish or prove? Does he accomplish his goal? Use specific quotations from the introduction, conclusion, or selected chapters to support your thesis.

Imagine that after writing his text, Machiavelli was given the opportunity of selecting the next “prince” of all of Italy, and that you were interviewing for the position. Write a letter of interest to Machiavelli explaining why you would make a good Prince, citing specific qualities Machiavelli outlines in his text.

Machiavelli lists many qualities of a good political leader. Select 3-5 of the qualities outlined by Machiavelli in the sections we read. Explain each quality as described by Machiavelli, citing references from the book. Why are these qualities essential to good leadership?

On page 74 Machiavelli addresses how a prince should treat average citizens. Many of the suggestions he gives are the subject of contemporary debate: Does the United States tax too much and discourage business? Do governmental leaders do enough to support the arts?, etc. Choose one of Machiavelli’s admonitions and then explain whether you think the United States does a good job of pleasing its citizens in the way Machiavelli describes. Research the issue in online news sites (NY Times, Washington Post, LA Times, etc.) and use citations from these news outlets to support your argument.

Machiavelli’s understanding of the role of rulers vs. the role of the public is very different from what the framers of the American Constitution understood the role of rulers vs. the role of the public to be. Write an essay in which you compare and contrast how either rulers OR the public is treated in Machiavelli’s text and in the American Revolutionary documents. Use citations from the texts to analyze the responsibilities, dangers, habits, and/or attitudes of the group you chose. How do the authors compare in their evaluations of the group you chose: is one more skeptical, trusting, disdaining, etc.?

Both Wollstonecraft and the writers of the American Revolutionary documents directed their texts towards a general audience of educated citizens. This is much different than the anticipated readership of Machiavelli, whose writing is directed at “princes” and other members of the aristocracy. How does the difference in expected audience change the way the author writes? Choose 2-3 pairs of passages that demonstrate the differences between the authors writing to common citizens and Machiavelli, who writes for the nobility. How do the tone, vocabulary, and subject matters of the authors differ as a result of the difference in their readership?


Paraphrase the following quotations and then give a 2-3 sentence description of how the quotations fit into the larger argument of the chapter from which each is drawn.

XV: “The fact is that a man who wants to act virtuously in every way necessarily comes to grief among so many who are not virtuous.” (50)

XVI: “You hurt yourself only when you give away what is your own.” (53)

XVII: “Men sooner forget the death of their fathers than the loss of their patrimony.” (55)

XVIII: “Those who simply act like lions are stupid.” (57)

XIV: “One of the most powerful safeguards a prince can have against conspiracies is to avoid being hated by the populace.” (59)

XX: “When he has the chance an able prince should cunningly foster some opposition to himself so that by overcoming it he can enhance his own stature.” (69)

XXI: “He has always planned and completed great projects, which have always kept his subjects in a state of suspense and wonder.” (72)

XXII: “The first opinion that is formed of a ruler’s intelligence is based on the quality of the men he has around him.” (74)

XXIII: “All the same, he should be a constant questioner, and he must listen patiently to the truth regarding what he has inquired about.” (76)

XXIV: “The only sound, sure, and enduring methods of defense are those based on your own actions and prowess.” (78)

XXV: “She shows her potency where there is no well-regulated power to resist her, and her impetus is felt where she knows there are no embankments and dykes built to restrain her.” (79)

XXVI: “I believe that so many things conspire to favor a new prince, that I cannot imagine there ever was a more suitable time than the present.” (82)