A Florentine bureaucrat of the late 15th and early 16th century has continued to fascinate politicians, scholars, and the public alike. Although he witnessed at close hand the deeds of both hapless and ruthless European rulers of the Renaissance that resulted in devastating wars for the Italian peninsula, it is not the life but rather the words of Niccolò Machiavelli that have earned him fame—and infamy. Both types of notoriety derive from his most well-known work, his small treatise The Prince.

In this online seminar, led by scholar Vickie Sullivan, fellows will carefully study this classic text to understand Machiavelli’s account of virtue and the low, but solid ground on which he recommends we construct our political regimes. The chronology in The Prince (pp. xxix–xxxi) and the indexes and glossaries in both works can assist in elucidating the particular characters, incidents, and key terms one finds in his writings. In particular, fellows explore the following themes and terms: founding, corruption, renewal, fortune vs. virtue, ordinary vs. extraordinary, appearance vs. truth, nature, necessity, acquisition, glory, and prudence.

Image: Statue of Niccolo Machiavelli, Circa 1500

Vickie Sullivan on Machiavelli & Religion


Vickie Sullivan

Vickie Sullivan is the Cornelia M. Jackson Professor of Political Science and teaches and studies political thought and philosophy.  She also maintains teaching and research interests in politics and literature. She has published extensively on Montesquieu and Machiavelli and is the co-editor of  Shakespeare’s Political Pageant.

Preview the Syllabus by Week/Session


  • The Prince, Dedicatory Letter
  • The Prince, Chs. 1–5

Discussion Questions:

  1. What light does the dedicatory letter of The Prince cast on the addressee and purposes of the work?
  2. What might be the significance of Machiavelli’s claim that his political knowledge derives both from modern experience and reading ancient works?
  3. What light does the analogy to those who sketch landscapes in the dedicatory letter of The Prince cast on the distinction between the natures of princes and peoples and on Machiavelli’s own status?
  4. What is the underlying basis of the typology of states in The Prince, Chapter 1?
  5. Does Machiavelli stick to his announcement in The Prince, Chapter 2 that he will leave out reasoning on republics? (Note the example he offers for wise princes to imitate in The Prince, Chapter 3).
  6. What are the implications and the moral and political consequences of Machiavelli’s assertion in The Prince, Chapter 3 that the desire to acquire is “a very natural and ordinary thing”?
  7. What mistakes did King Louis of France make when he invaded Italy? Consider what his errors have in common.
  8. What are the critical distinctions between the two forms of princely rule that he introduces in Chapter 4?
  9. What are the implications of the treatment of republics in The Prince, Chapter 5?


  • The Prince, Chs. 6–10

Discussion Questions:

  1. Why are founders the most important examples for Machiavelli? What can we learn from their examples that we might not learn otherwise?
  2. How should we understand the treatment of Moses in The Prince, Chapter 6?
  3. What is the point of the story of Remirro de Orco in The Prince, Chapter 7?
  4. Is Cesare Borgia Machiavelli’s model prince? What mistakes did he make? What does he have in common with Machiavelli?
  5. Do the distinctions between acquiring by one’s own arms and virtue, and acquiring by the arms of others and fortune, hold up?
  6. Is crime compatible with virtue and glory?
  7. Should a would-be prince in a republic seek to come to power with the support of the people or that of the great?
  8. What is the ultimate distinction between the people and the great? Is it a difference of natures?
  9. What does Machiavelli teach about the nature of obligation in Chapter 10?


  • The Prince, Ch. 11–18

Discussion Questions:

  1. Why does Machiavelli tell the story of Pope Alexander and his son Cesare Borgia differently in Chapters 6 and 11?
  2. What are the differences between mercenary and auxiliary arms? Why might Italy have become disarmed?
  3. How does the point of Machiavelli’s story of David and Goliath differ from its point in the Bible?
  4. What is the role of writers according to The Prince, Chapter 14? How does this square with his discussion of previous writers in The Prince, Chapter 15?
  5. What does Machiavelli mean when he declares his “intent” “to write something useful to whoever understands it”? What are the implications of this statement for his apparent addressee, Lorenzo de Medici?
  6. What is Machiavelli’s teaching on “imaginary republics”? Who might he be implicitly attacking, and what are the revolutionary implications of this teaching?
  7. What harm comes from liberality, according to Machiavelli?
  8. What harm comes from mercy, according to Machiavelli?
  9. What is Machiavelli’s teaching about morality?
  10. Does Machiavelli’s teaching about morality serve only the prince or his subjects as well?
  11. What are the similarities and differences, if any, between the teaching Machiavelli ascribes to the ancient writers in The Prince, Chapter 18, and his own teaching in that chapter?
  12. Does it matter what qualities a prince really has, or is appearance all that matters?


  • The Prince, 19–26
  • Letter to Vettori, pp. 107–11

Discussion Questions:

  1. What is the point of the discussion of conspiracies in The Prince, Chapter 19?
  2. What is the point of the discussion of the Roman emperors in The Prince, Chapter 19?
  3. Do princes have to avoid being hated by the people?
  4. What are the implications of the advice in The Prince, Chapter 20 to arm one’s subjects and not to build fortresses for princely rule?
  5. Does the end of Chapter 21 make Machiavelli a forerunner of modern liberalism?
  6. How is it possible for a minister “never to think of himself but always of the prince,” given Machiavelli’s view of human nature?
  7. Compare the threefold typology of brains in The Prince, Chapter 22 to the distinctions between princes and peoples in the dedicatory letter and between the great and the people in Chapter 9.
  8. What does Machiavelli’s discussion of advisers imply for his own role as a teacher or adviser of princes?
  9. What is Machiavelli’s teaching about virtue and fortune?
  10. How should we understand the treatment of Moses in The Prince, Chapter 26?
  11. Is the plea to liberate Italy in Chapter 26 the culmination or a contradiction of the overall argument of The Prince?
  12. How can Machiavelli be said to be an Italian patriot? In what ways does he appear to be disloyal to Italy?
  13. Do the sentiments that Machiavelli expresses in his letter to Vettori make him a philosopher?

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