Notes, Questions, and Hints to Accompany a Careful Reading of The Prince by Nicolo Machiavelli

by Salvatore G. Rotella
Riverside Community College

August 1999

Machiavelli organizes The Prince in the following order:

Dedicatory Letter

  1. Kinds of Principalities
  2. Hereditary Principalities
  3. Mixed Principalities
  4. Why the Kingdom of Dariug Which Alexander eized Did Not Rebel from His Successors after Alexander’s Death
  5. How the Cities or Principalities Which Lived under Their Own Laws before They Were Occupied Should Be Administered
  6. Of New Principalities That Are Acquired through One’s Own Arms and Virtue
  7. Of New Principalities That Are Acquired by Others’ Arms and Fortune
  8. Of Those Who Have Attained a Principality through Crimes
  9. Of the Civil Principality
  10. In What Mode the Forces of All Principalities Should Be Measured
  11. Of Ecclesiastical Principalities
  12. How Many Kinds of Military There Are and Concerning Mercenary Soldiers
  13. Of Auxiliary, Mixed, and One’s Own Soldiers
  14. What a Prince Should Do Regarding the Military
  15. Of Those Things for Which Men And Especially Princes are Praised or Blamed
  16. Of Liberality and Parsimony
  17. Of Cruelty and Mercy, and Whether It Is Better to Be Loved Than Feared, or the Contrary
  18. In What Mode Faith Should Be Kept by Princes
  19. Of Avoiding Contempt and Hatred
  20. Whether Fortresses and Many Other Things Which Are Made and Done by Princess Every Day Are Useful or Useless
  21. What a Prince Should Do to Be Held in Esteem
  22. Of Those Whom Princes Have as Secretaries
  23. In What Mode Flatterers Are to Be Avoided
  24. Why the princes of Italy Have Lost Their States
  25. How Much Fortune Can Do in Human Affars, and in What Mode it May Be Opposed
  26. Exhortation to Seize Italy and to Free Her from the Barbarians

A contemporary Machiavelli scholar, professor Harvey Mansfield of Harvard, opens his introduction to The Prince with these words, “Anyone who picks up Machiavelli’s The Prince holds in his hands the most famous book on politics ever written.” While this is probably true, The Prince should be approached with the same disposition owed any classic work: l) an open mind, 2) a determined effort to follow closely and carefully the topics and arguments set forth by the author, and 3) an understanding of the context that the author is writing about. A proper reading of a classic work, especially the first time one comes across it, requires that the reader set aside any preconceived notions he or she has about the author or the work itself. This is especially important, and especially difficult, in the case of Machiavelli. Everyone has heard about Machiavelli, and rare is the person who has not formed a judgement on his contribution to our culture. Of course, much rarer is finding anyone who has read Machiavelli. You are the exception. Consider, for instance, that in current language the word Machiavellian has come to mean, “characterized by unscrupulous cunning, deception, or expediency.”(Webster’s College Dictionary.)

In very simple terms, The Prince is an essay that deals with the nature of political power, how to get it, how to maintain it, and how to use it. It is dedicated to Lorenzo dei Medici, a grandson of Lorenzo il Magnifico. It is based on a unique understanding of human nature, is interspersed with statements about human behavior, and is backed by historical examples drawn from Machiavelli’s time, the Renaissance, and from antiquity, Roman and Greek history.

The Historical Setting

A word about the historical setting may be of value in navigating through the text of The Prince. Lorenzo dei Medici and Machiavelli are Florentines. Machiavelli had served in the diplomatic service of Florence and thus had quite an understanding of the general political situation not only in Florence and Italy, but also in Europe. Florence was not just another city of the Italian peninsula, as it is today, but a city state among the various states present in Italy at the time. Note that every reference made to the Italy of Machiavelli’s time, differently, for instance, from France or Spain, implies a reference to a geographic and not to a political reality. In addition to Florence, the other major political players in Italy at the time were Milan, Genova, and Venice to the north. Rome, the state of the pope, was a political power in its own right around and to the south of Florence. Below Rome, was the kingdom of Naples. Each of the city-states had control of its own hinterland and extended its power further through the domination of, or alliance with, other cities. The various states of the peninsula kept each other in check and constituted a unique balance of power. Domination of the entire peninsula by one state was difficult for political and geographic reasons.

To round up the historical picture, outside Italy to the north there were Switzerland and Germany not as unified as they are today, but in somewhat of a unified state. In comparison, France, to the northwest, was unified under a monarchy and Spain, to the west, was at the beginning of a process of unification started by King Ferdinand and Queen Isabella, who had taken on the mantle of Catholic Kings. To the east of Italy was the Ottoman Empire, generally referred to by Machiavelli as the Turk.

The parallelogram of forces inside the Italian peninsula could be broken, and was broken, by inviting outside powers. The presence in Italy of France and Spain, directly or indirectly, lasted until 1860-1870 when Italy emerged as the unified state of today. As Machiavelli puts it in chapter II of The Prince, “King Louis (France) was brought into Italy by the ambition of the Venetians, who had wanted to gain half the state of Lombardy for themselves by his coming.”

Structure of The Prince

The Prince is comprised of an introduction, or dedicatory preface, and twenty-six chapters. There is an open debate among scholars about the actual structure of the work. Some suggest that it is part of a larger work that includes the much longer Discourses on Livy; for our purpose we shall limit ourselves to The Prince itself and seek a structure in it. The most obvious one, based on the flow of the material, is to divide it into six parts. 1) The Introduction; 2) Chapters One through Eleven, devoted to definitions and discussion of principalities; 3) Chapters Twelve though Fourteen, devoted to a discussion of the military and armies; 4) Chapter Fifteen through Nineteen, devoted to the qualities and character of the prince; 5) Chapters Twenty through Twenty-three, devoted to a discussion of what the prince should do to stay in power; 6) Chapters Twenty-four though Twenty-six discuss what a prince can do if he uses power properly, i.e. according to Machiavelli’s advice. The structure suggested here is based on some breakpoints which should come in handy if one wants to read The Prince in more than one sitting.

l. The Introduction

The introduction sets the tone of the work in a number of ways.

What is it that Machiavelli has reduced into “one small volume?”

The Prince wants to be a guide-book for those who want to succeed in politics. Consider carefully the statement, “. . . to give you the capacity to be able to understand in a very short time (emphasis mine) all that I have learned and understood in so many years.”

In addressing the difference in status between the prince and the common man, Machiavelli states quite openly the relativity of truth about things political. It is all a matter of perspective. “To know well the nature of the people one needs to be a prince, and to know well the nature of princes one needs to be of the people.” It is like in drawing, to get a good perspective of the mountain, one goes to the valley; to get a good perspective of the valley, one goes up the mountain.

Another important principle of Machiavelli’s teachings is to be found here. To know or to discourse about power, one must stay with an analysis of power itself and of power relationships. Understanding should not be sought outside the context of the very subject matter being studied. Religion and ethics which are usually imposed in the discussion of political life are not critical in the study of power. Attention and study must be restricted to those who exercise or have exercised power, and are or have become famous, or infamous, because of it; either in our own time or in the past. Hence, the need to study history.

Finally, at the end of the introduction there is a first reference to fortune, in Italian fortuna. This, and virtue, in Italian virt├╣, are two important concepts in Machiavelli’s discussion of politics. As you run into these terms, pause and consider carefully how the author is using them.

One final note, a note of curiosity perhaps, but with Machiavelli nothing should be taken for granted, The Prince is written in Italian; however, the title of each chapter, including the dedicatory, is in Latin.

Part II. Chapters I – XI. Definition of, and Types of Principalities. [back to top]

There are two types of states, principalities and republics, which one does Machiavelli deal with in The Prince?

Give examples of hereditary vs. new type of principalities.

At the end of Chapter I, fortune is juxtaposed to virtue. Consider carefully the statement: “…and are acquired either with the arms of others or with one’s own, either by fortune or virtue.”

Why is it easier to govern hereditary states and not new ones?

Consider carefully: “For the natural prince has less cause and less necessity to offend. Given time, people get used to change, …for one change always leaves a dentation for the building of another?” What does it mean?

At the opening of Chapter III, note the relationship between human nature and the holding of power. New principalities are difficult to hold on to. “Men willingly change their master,” but eventually they realize that they are worse off. Another prescript based on human nature: “One must always offend those over whom he becomes a new prince…”

Armies are necessary to take over a territory, but what is absolutely necessary to hold on to it? Consider the examples of Louis XII of France and Ludovico il Moro and their rule over Milan.

What should a prince do when he occupies a state that is dissimilar in nature? The Romans were very good at this. How did they succeed?

How did Louis XII of France fail to hold on to Italy? What six errors did he make?

Chapter IV continues the discussion of how to hold on to states newly acquired. What is the difference between power held by one prince and his servants and power held by a prince and his vassals who do not owe their power to the prince? Consider the example of the kingdom of Darius. The case of the French vs. the Turk.

In Chapter V, what are the three ways to hold on to states “accustomed to live by their laws and in liberty?” What did the Spartans do to Athens and Thebes. Instead, what did the Romans do to Capua, Carthage and Numantia?

In Chapter VI, Machiavelli discusses the principalities that are acquired through one’s own army or virtue. Here we encounter his four great heroes: Moses, Cyrus, Romolus, and Theseus. What do you know about each one of them? Why is the situation of Moses different from that of the other three? In each case, what is the interplay between fortune (opportunity), and virtue?

Why is change difficult?

Armed prophets conquered, unarmed ones went to ruin? Why? Can you think of examples of both. Who was Girolamo Savonarola? How did he end up?

To the four heroes mentioned above, at the end of the chapter, Machiavelli adds Hyero of Syracuse. Why?

In Chapter VI, there is a discussion of principalities acquired with others’ arms and fortune. Contrast Francesco Sforza to Cesare Borgia. The first did it all by himself, the second acquired his state through the fortune of his father and lost it through the same.

But, as it turns out, there is something quite admirable about Cesare Borgia. What is it?

How did Borgia behave with the French? How did he manage to get control of Rome? What were the ultimate reasons for his failure? Why should he have favored a Spaniard for pope? Or prefer Rouen to San Piero in Vincula?

Chapter VII is devoted to the discussion of those who have attained a principality through crime. Agathocles of Syracuse and Oliverotto da Fermo. Why did Agathocles live a long time and Oliverotto did not? What are cruelties badly used or well used? Why should injuries be done all at once and benefits little by little?

Chapter IX is devoted to civil principalities, i.e. when a prince ascends to power with the support of the people, or of the prominent citizens (the great). Why is it better to get power with the support of the people and not of the great?

Chapter X is devoted to the discussion of how all principalities should be measured. On the one hand, there is the prince that can keep control by himself and defend his state without the help of others. On the other, the prince who needs others, who cannot mount a defense, and needs walls to defend his city. Why should the latter type of prince supply his town? Who is less likely to be attacked? What is his relationship with the people? What happens in the relationship between prince and people when the people see their possessions outside the wall done away by the attacking powers? What is meant by “the nature of men is to be obligated as much by benefits they give as by benefits they receive?”

Chapter XI discusses ecclesiastical principalities. Technically since this type of principality is ordained by God, it should be perfect, and there should be no need to discuss it. Remember the case of Moses vis-a-vis the other three heroes of Machiavelli?

How did Pope Alexander VI end up consolidating his power in Rome? Duke Valentino and the French were the instrument and opportunity for his success. Explain. How did Pope Julius II continue the work of making Rome great started by Alexander VI?

What was the role of God in making Rome great? Ultimately, in Machiavelli’s mind, is there a difference between ecclesiastical states and other types of states?

Part III. On the Offense and Defense Benefitting All the States Named. [back to top]

For Machiavelli, what is the principal foundation of all states?

A prince can defend himself through his own arms, mercenary or auxiliary arms. Why are mercenary and auxiliary arms useless? What are some examples? Why were Rome and Sparta for many centuries armed and free? As far as the defense of the state is concerned, for Machiavelli, what are the respective roles of the prince and of the people?

Chapter XIII, What did Cesare Borgia do with auxiliary and mercenary arms? Ultimately, what was the secret of his success? How did David meet Goliath according to the Bible?

In Chapter XIV Machiavelli speaks of what a prince should do regarding the military. As commander, the prince should have only one art? Which? Who was Francesco Sforza? How did he ascend to power? How can a prince cultivate the art of war at all times? What is he to do in times of peace? A prince should read history. Why? Great men imitate other great men. Who did Alexander the Great imitate? Who did Caesar and Scipio imitate?

Part IV. How Should a Prince Behave Towards His Subjects and His Friends. [back to top]

Chapter XV is devoted to the discussion of those things for which men and especially princes are praised or blamed. The chapter opens with a paragraph that deserves careful reading. Here Machiavelli states that his approach is different from that of others, “departs from the order of others.” He wants to write something “useful to whomever understands it.” Hence, he goes “to the truth of the thing and not the imagination of it.” Good or not good are relative concepts. A prince must “learn to be able not to be good, and to use this or not use it according to necessity.”

List of qualities considered: liberality – meanness; giving – rapacity; cruelty – mercy; breaking faith – faithfulness; lasciviousness – chastity; honesty – cleverness; hard – agreeable; grave – light; religious – unbelieving; effeminate – fierce; pusillanimous – spirited; humane – proud. If you are not acquainted with the proper meaning of some of these terms, look them up in the dictionary.

Something that appears to be virtuous can lead to one’s ruin. Something that appears to be vice, can result in one’s security and well-being. How did Pope Julius II, the King of France and Caesar behave with regard to liberality? Cyrus, Alexander and Caesar did not hesitate to spend and give away resources. Under what circumstances?

In Chapter XVII, Machiavelli discusses cruelty and mercy and whether it is better to be loved than feared. Cruelty can be useful. How did it serve Cesare Borgia? The Florentines wanted to avoid cruelty towards the city of Pistoia. What happened to Pistoia? What makes cruelty on the part of the prince useful? Why is it safer to be feared than loved?

Consider carefully this statement “men forget the death of a father sooner than the loss of patrimony.” Why? How did Hannibal keep his large army united and faithful to him?

Consider carefully the last paragraph in chapter XVII, “Men love at their convenience and fear at the convenience of the prince, a wise prince should found himself on what is his, not on what is someone else’s; he should only contrive to avoid hatred.”

Should the prince keep the faith? (Chapter XVIII) The real question for the prince is whether or not he wants to accomplish great things. There are two kinds of combat: with laws (i.e. rules) and with force. Both are useful. When necessary, rules should be broken. Beast and man. Both are useful. Tradition has it that Achilles and other ancient princes were raised by Chiron (half man, half beast). Why?

The prince should know how to be a fox and a lion. Why? How does all this relate to the nature of man? Even Alexander VI, a pope, did nothing but deceive men. How did he get away with it?

The prince must make sure that he is identified with mercy, faith, honesty, humanity, and religion. But if he can get away with it, he must do anything that is useful to maintain his power and the state.

At this point Machiavelli sets forth the principle for which he has become famous, or infamous, through the centuries: the end justifies the means. “…and in the actions of all men, and especially princes, where there is no court to appeal to, one looks at the end. So let the prince win and maintain his state: the means will always be judged honorable, and will be praised by everyone.” In fact, says Machiavelli, a certain prince of Europe, “…never preaches anything but peace and faith and is hostile to both.” That prince is Ferdinand the Catholic.

In Chapter XIX, Machiavelli discusses whether the prince should avoid contempt and hatred. What actually makes a prince most hateful to his citizens? And most contemptible? How can a prince avoid conspiracies and deception?

What does the story of Annibale Bentivoglio teach?

France, claims Machiavelli, is a well-ordered and governed kingdom. How is it ordered and governed? How are the institutions arranged? In what way does it make possible that “blameable” actions are taken by others, and favors by the king?

In the rest of this chapter, Machiavelli discusses the role of several Roman emperors in maintaining themselves in power, their relationship to the people, and the military. How did they balance various forces? How did Severus, in particular, who is referred to as both a fox and a lion, manage to stay in power? Today’s rulers except the Sultan, concludes Machiavelli, have no soldiers to satisfy, hence their concentration should be on what?

Part V. How Can a Prince Stay in Power. [back to top]

Should the prince build fortresses and what should he do (Chapter XX). All depends on specific circumstances. But some general principles can be learned from experience. What are they?

A new prince who has found his subjects unarmed, should arm them. Why?

“But when a prince acquires a new state that is added as a member of his old one, he should disarm that state except those who were partisans in acquiring the state.” Why?

“The prince who has more fear of the people than of foreigners ought to make fortresses.” Why? What ultimately is a prince’s best fortress?

A prince can keep himself in esteem by doing great things. (Chapter XXI) What did Ferdinand of Aragon, in Spain, do? What was his act of “pious cruelty?” What did Messer Bernab├│ da Milano do to keep himself in esteem?

Should a prince be a true friend, a true enemy, or stay neutral?

Ministers and secretaries (Chapter XXII). What should be the relationship between the prince and his ministers? Consider the role of each vis-a-vis the other.

The prince should avoid flatterers. Why? What kind of advice should the prince seek, when should he seek it, and from whom? Consider carefully the conclusion of this discussion, “…good counsel, from wherever it comes, must arise from the prudence of the prince, and not the prudence of the prince from good counsel.”

Part VII. What Machiavelli’s Teachings Can Lead a Prince To! [back to top]

Why have the princes of Italy lost their states? (Chapter XXIV) Machiavelli’s teachings can make a new prince appear ancient, hereditary, hence more serene. “A new prince is observed more in his actions,” as men are “much more taken by present things than by past ones.” This is what leads them to “take up every defense on behalf of a new prince.”

A prince needs good arms, good friends, good examples. Which is more important?

The King of Naples and the Duke of Milan (Ludovico Sforza) lost their state because of “defect as to arms” and because of hostility from the people. It was not fortune but indolence. What are the best defenses for a prince?

What ultimately is the role of fortune? (Chapter XXV)

First give some thought to the meaning of fortune, i.e. something that happens over which man has absolutely no control. Then, consider how Machiavelli intends to deal with it.

Also, note that fortune and God are mentioned by Machiavelli in the same breath. Are we to think of them as one and the same? This is the third time that God and the divine are brought up. The first time is in the context of the founders, e.g., Moses leader of the Jews against the Egyptians; the second refers to the context of religious principalities, i.e., are they ordained by God? In both instances, however, the divine is dismissed quickly from consideration.

Should man be governed by chance? Machiavelli notes that events in Italy at his time, would lead one to think so. They are “beyond every human conjecture.” He is willing to make some concession, but not all the way. “…In order that our free will not be eliminated, I judge that it might be true that fortune is arbiter of half of our actions, but also that she leaves the other half, or close to it, for us to govern.”

Fortune like a violent river cannot be controlled when it becomes enraged. But there is a way to control rivers: build dikes and dams. Compared with Germany, Spain and France, Italy is a country that has not been “diked by suitable virtue.”

The prince must “adapt his mode of proceeding to the qualities of the time.” Why? It is up to the prince to assess what is best to do, given the circumstances. Pope Julius II managed to defeat Bologna, the Venetians, the King of Spain, and the King of France. How?

If fortune is like a woman, how should one deal with her? With caution or impetuosity?

Finally, there is the exhortation to seize Italy and free her from the barbarians (Chapter XXVI). Moses emerged because of the enslavement of the Jews; Cyrus because the Persians were oppressed by the Medes; Theseus because the Athenians were dispersed. Italy presents the same opportunity for leadership to emerge. Pray, but God alone will not do it, “so as not to take free will from us…” (sounds like the reference to fortune in the previous chapter.)

Italians need to form an army to be trained by a new prince. The strengths and defects of other armies, the Swiss, the Spanish, the French are known. What are they? What is needed is “regeneration of arms and change in orders.” What does it mean?

“The ancient valor in the Italian hearts is not yet dead.” How can this connect with the discussion of the relation between the prince and the people?

6 responses to “Notes, Questions, and Hints to Accompany a Careful Reading of The Prince by Nicolo Machiavelli

  1. There is a lot of work done by Machiavelli to prepare for this book. He studied history and other great leaders from the past and saw that there was a common thread to them all. He outlined these different points within his point. I can see why his text has been able to stand the text of time and is still applicable to this day

  2. This directed me throughmy reading, and gave me ideas for my research paper. There are so many ideas in ThePrince to focus on, and this pinpoints the important.

  3. I really enjoyed this book because it is very intersting. It has a lot of great principles that should be applied to everyday living. At first I had a hard time comprehending the book but then I realized it was not so bad after all. I really enjoyed reading this book. I cannot belive I had not read it before.

  4. great book with alot of history. Has many different applications which can be applied to modern day living. Im tring to use machiavelli advice you should pick a side to stand on and not always remain nuetral.

  5. Before reading the book i honestly thought that it would be really complicated to read. I imagined that the wording would be really complicated. in the end it was pretty easy to read. I guess i will never learn to stop judging a book by its cover.

  6. This book is an interesting read. Why did I not hear of this book before this class?