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Machiavelli, The Prince
For History Seminars – Reading Guide

Read Dedication, Chapters 1 – 7, 15 – 19, 24 - 26 carefully.

Read about half of this for the first seminar and the rest for the second seminar.

Skim the other chapters to get a sense of main point and types of evidence mentioned.
Background: Niccolo Machiavelli was a Florentine born in 1469 when the Medici were in power.
Under the Medici, Florence was a republic in name only since those who were not friends of the
Medici were excluded from political power. When the Medici were exiled in 1492, a more genuine
republic was restored and Machiavelli entered political service. When the Medici returned to power in
1513, Machiavelli lost his office and was imprisoned and tortured on their orders. He moved to his
country home outside of Florence where he wrote The Prince, dedicating it to Lorenzo de Medici,
grandson of Lorenzo the Magnificent. “Interpretations of The Prince vary: it has been viewed as
sincere advice, as a plea for political office, as a detached analysis of Italian politics, as evidence of
early Italian nationalism, and as a political satire on the Medici rule” (The Columbia Encyclopedia
1647). Please consider these interpretations as you read.
Some general questions to consider:
 Dedication: What is the tone of the dedication? Machiavelli has been called a sycophant (“a
servile self-seeker who attempts to win favor by flattering influential people”). Would you
agree? Explain.

What types of evidence does Machiavelli use throughout this work?

Chapter 7: Cesare Borgia (Duke Valentino) was the son of Pope Alexander VI—a very worldly
Renaissance pope. The two were trying to establish a powerful kingdom in central Italy tied
both to the papacy and the Borgia family. What are some the key accomplishments of Cesare
Borgia? What went wrong for Cesare Borgia?

What is Machiavelli’s purpose in chapters 1 – 7 (taken as a whole)?

Try making a list of the qualities that Machiavelli thinks an effective ruler must have.

In The Humanistic Tradition, Gloria K. Fiero gives the following description of the Renaissance
humanists: “The humanists of the Renaissance were the cultural archaeologists of their age. They
uncovered new evidence of the splendor of Greco-Roman antiquity and consumed the fruits of their
Western heritage. Unattached to any single school or university, this new breed of humanists pursued
what the ancient Romans had called studia humanitas, a program of study that embraced grammar,
rhetoric, history, poetry, and moral philosophy. These branches of learning fostered training in the
moral and aesthetic areas of human knowledge. . . While such an educational curriculum was assuredly
not antireligious—indeed, most Renaissance humanists were devout Catholics—its focus was secular
rather than religious. For these humanists, life on earth was not a vale of tears but, rather, an extended
occasion during which human beings might cultivate their unique talents and abilities.” (Fiero 23)

In your opinion, is Machiavelli a humanist? Why or why not?
Machiavelli, The Prince – Chapter Questions
For all chapters:
1. For each chapter, consider:
a. what is the thesis of the chapter?
b. what types of evidence does M. use: classical, contemporary, biblical, mythical?
Dedication:
2. What is the tone of the dedication? Machiavelli has been called a sycophant (“a servile selfseeker who attempts to win favor by flattering influential people”). Do you agree? Explain.
Chapter 1:
3. After you’ve analyzed Chapters 1–7, re-visit Chapter 1. What is the point of Chapter 1?
Chapter 2:
4. Machiavelli praises republics in his Discourses upon Livy. Why do you think he leaves
republics out entirely from The Prince?
Chapter 3:
5. Why is it so difficult to rule a Mixed Princedom?
6. What are some of the key recommendations Machiavelli makes in this chapter?
Chapter 7:
7. Cesare Borgia (Duke Valentino) and his father, Pope Alexander VI, were trying to establish a
powerful kingdom in central Italy tied both to the papacy and the Borgia family. What are
some accomplishments of Cesare Borgia? What went wrong for Cesare Borgia?
Chapter 15:
8. What are the important virtues and vices to acquire and to avoid? Why?
Chapter 16:
9. What does Machiavelli mean by “liberal”?
10. According to Machiavelli, in what circumstances is being “liberal” a good idea? Miserly?
Chapter 17:
11. Is it better to be feared or loved? Why? What are the two main examples he gives?
Chapter 18:
12. What is the gist of the lion and fox analogy?
13. What lesson does Machiavelli take from Pope Alexander VI (Cesare Borgia’s papa)?
Chapter 19:
14. What brought about Alexander’s downfall, according to Machiavelli? Do you see any problems
with the conclusion he draws from the lessons of Alexander?
Chapter 24:
15. This chapter turns to one of Machiavelli’s favorite topics: why Italy has so many weak rulers
and what can be done about them. What does the example of Philip of Macedon (as he says, not
the father of Alexander) let Machiavelli say about the Italian rulers?