The subject matter: new princedoms (chapters 1 and 2)
The Prince starts by describing the subject matter it will handle. In the first sentence Machiavelli uses the word "state" (Italian stato which could also mean "status") in order to neutrally cover "all forms of organization of supreme political power, whether republican or princely". The way in which the word state came to acquire this modern type of meaning during the Renaissance has been the subject of many academic discussions, with this sentence and similar ones in the works of Machiavelli being considered particularly important.
Machiavelli said that The Prince would be about princedoms, mentioning that he has written about republics elsewhere (possibly referring to the Discourses on Livy although this is debated), but in fact he mixes discussion of republics into this in many places, effectively treating republics as a type of princedom also, and one with many strengths. More importantly, and less traditionally, he distinguishes new princedoms from hereditary established princedoms. He deals with hereditary princedoms quickly in Chapter 2, saying that they are much easier to rule. For such a prince, "unless extraordinary vices cause him to be hated, it is reasonable to expect that his subjects will be naturally well disposed towards him". Gilbert (1938:19–23), comparing to traditional presentations of advice for princes, stated that the novelty in chapters 1 and 2 is the "deliberate purpose of dealing with a new ruler who will need to establish himself in defiance of custom". Normally, these types of works were addressed only to hereditary princes. He thinks Machiavelli may have been influenced by Tacitus as well his own experience, but finds no clear predecessor for this.
This categorization of regime types is also "un-Aristotelian" and apparently simpler than the traditional one found for example in Aristotle's Politics, which divides regimes into those ruled by a single monarch, an oligarchy, or by the people, in a democracy. He also ignores the classical distinctions between the good and corrupt forms, for example between monarchy and tyranny.Strauss (1958:272) points out that Machiavelli frequently uses the words "prince" and "tyrant" as synonyms, "regardless of whether he speaks of criminal or non-criminal tyrants".
Xenophon, on the other hand, made exactly the same distinction between types of rulers in the opening of his Education of Cyrus where he says that, concerning the knowledge of how to rule human beings, Cyrus the Great, his exemplary prince, was very different "from all other kings, both those who have inherited their thrones from their fathers and those who have gained their crowns by their own efforts".
Machiavelli divides the subject of new states into two types, "mixed" cases and purely new states.
"Mixed" princedoms (chapters 3 to 5)
New princedoms are either totally new, or they are “mixed” meaning that they are new parts of an older state, already belonging to that prince.[28]
New conquests added to older states (chapter 3)
Machiavelli generalizes that there were several virtuous Roman ways to hold a newly acquired province, using a republic as an example of how new princes can act: * to install one's princedom in the new acquisition, or to install colonies of one's people there, which is better. * to indulge the lesser powers of the area without increasing their power. * to put down the powerful people. * not to allow a foreign power to gain reputation.
More generally, Machiavelli emphasizes that one should have regard not only for present problems but also for the future ones. One should not “enjoy the benefit of time” but rather the benefit of one's virtue and prudence, because time can bring evil as well as good.

Conquered kingdoms (chapter 4)

A 16th century Italian impression of the family of Darius III, emperor of Persia, before their conqueror, Alexander the Great. Machiavelli explained that in his time the Near East was again ruled by an empire, theOttoman empire, with similar characteristics to that of Darius - seen from the viewpoint of a potential conqueror.
In some cases the old king of the conquered kingdom depended on his lords. 16th century France, or in other words France as it was at the time of writing of the Prince, is given by Machiavelli as an example of such a kingdom. These are easy to enter but difficult to hold.
When the kingdom revolves around the king, then it is difficult to enter but easy to hold. The solution is to eliminate the old bloodline of the prince. Machiavelli used the Persian empire of Darius III, conquered by Alexander the Great, to illustrate this point and then noted that the Medici, if they think about it, will find this historical example similar to the "kingdom of the Turk" (Ottoman Empire) in their time - making this a potentially easier conquest to hold than France would be.
Conquered Free States, with their own laws and orders (Chapter 5)
Gilbert (1938:34) notes that this chapter is quite atypical of any previous books for princes. Gilbert supposed the need to discuss conquering free republics is linked to Machiavelli's project to unite Italy, which contained some free republics. As he also notes, the chapter in any case makes it clear that holding such a state is highly difficult for a prince. Machiavelli gives three options:- * Ruin them, like Rome destroyed Carthage, and also like Machiavelli says the Romans eventually had to do in Greece, even though they had wanted to avoid it. * Go to live there (or install colonies, if you are a prince of a republic). * Let them keep their own orders but install a puppet regime.

Totally New States (Chapters 6-9)
Conquests by virtue (Chapter 6)
Machiavelli described Moses as a conquering prince, who founded new modes and orders by force of arms, which he used willingly to kill many of his own people. The Bible describes the reasons behind his success differently.
Princes who rise to power through their own skill and resources (their "virtue") rather than luck tend to have a hard time rising to the top, but once they reach the top they are very secure in their position. This is because they effectively crush their opponents and earn great respect from everyone else. Because they are strong and more self-sufficient, they have to make fewer compromises with their allies.
Machiavelli writes that reforming an existing order is one of the most dangerous and difficult things a prince can do. Part of the reason is that people are naturally resistant to change and reform. Those who benefited from the old order will resist change very fiercely. By contrast, those who stand to benefit from the new order will be less fierce in their support, because the new order is unfamiliar and they are not certain it will live up to its promises. Moreover, it is impossible for the prince to satisfy everybody's expectations. Inevitably, he will disappoint some of his followers. Therefore, a prince must have the means to force his supporters to keep supporting him even when they start having second thoughts, otherwise he will lose his power. Only armed prophets, like Moses, succeed in bringing lasting change. Machiavelli claims that Moses killed uncountable numbers of his own people in order to enforce his will.
Machiavelli was not the first thinker to notice this pattern. Allan Gilbert wrote: "In wishing new laws and yet seeing danger in them Machiavelli was not himself an innovator," because this idea was traditional and could be found in Aristotle's writings. But Machiavelli went much further than any other author in his emphasis on this aim, and Gilbert associates Machiavelli's emphasis upon such drastic aims with the level of corruption to be found in Italy.
Conquest by fortune, meaning by someone else’s virtue (Chapter 7)
According to Machiavelli, when a prince comes to power through luck or the blessings of powerful figures within the regime, he typically has an easy time gaining power but a hard time keeping it thereafter, because his power is dependent on his benefactors' goodwill. He does not command the loyalty of the armies and officials that maintain his authority, and these can be withdrawn from him at a whim. Having risen the easy way, it is not even certain such a prince has the skill and strength to stand on his own feet.
This is not necessarily true in every case. Machiavelli cites Cesare Borgia as an example of a lucky prince who escaped this pattern. Through cunning political maneuvers, he managed to secure his power base. Cesare was made commander of the papal armies by his father, Pope Alexander VI, but was also heavily dependent on mercenary armies loyal to the Orsini brothers and the support of the French king. Borgia won over the allegiance of the Orsini's followers with better pay and prestigious government posts. When some of his mercenary captains started to plot against him, he had them imprisoned and executed. When it looked like the king of France would to abandon him, Borgia sought new alliances.
Finally, Machiavelli makes a point that bringing new benefits to a conquered people will not be enough to cancel the memory of old injuries, an idea Allan Gilbert said can be found in Tacitus andSeneca the Younger.
Conquests by “criminal virtue” (Chapter 8)
Conquests by "criminal virtue" are ones in which the new prince secures his power through cruel, immoral deeds, such as the execution of political rivals. Machiavelli advises that a prince should carefully calculate all the wicked deeds he needs to do to secure his power, and then execute them all in one stroke, such that he need not commit any more wickedness for the rest of his reign. In this way, his subjects will slowly forget his cruel deeds and his reputation can recover. Princes who fail to do this, who hesitate in their ruthlessness, find that their problems mushroom over time and they are forced to commit wicked deeds throughout their reign. Thus they continuously mar their reputations and alienate their people.
Machiavelli's case study is Agathocles of Syracuse. After Agathocles became Praetor of Syracuse, he called a meeting of the city's elite. At his signal, his soldiers killed all the senators and the wealthiest citizens, completely destroying the old oligarchy. He declared himself ruler with no opposition. So secure was his power that he could afford to absent himself to go off on military campaigns in Africa.
Gilbert (1938:51–55) remarks that this chapter is even less traditional than those it follows, not only in its treatment of criminal behavior, but also in the advice to take power from people at a stroke, noting that precisely the opposite had been advised by Aristotle in his Politics (5.11.1315a13). On the other hand Gilbert shows that another piece of advice in this chapter, to give benefits when it will not appear forced, was traditional.
Becoming a prince by the selection of one's fellow citizens (Chapter 9)
These "civic principalities" do not require real virtue, only “fortunate astuteness”. Machiavelli breaks this case into two basic types, depending upon which section of the populace supports the new prince.
Supported by the great (those who wish to command the people)
This, according to Machiavelli, is an unstable situation, which must be avoided after the initial coming to power. The great should be made and unmade every day at your convenience. There are two types of great people that might be encountered: 1. Those who are bound to the prince. Concerning these it is important to distinguish between two types of obligated great people, those who are rapacious and those who are not. It is the latter who can and should be honoured. 2. Those who are not bound to the new prince. Once again these need to be divided into two types: those with a weak spirit (a prince can make use of them if they are of good counsel) and those who shun being bound because of their own ambition (these should be watched and feared as enemies).
Supported by the people (those who wish not to be commanded by the great)
How to win over people depends on circumstances. Machiavelli advises: * Do not get frightened in adversity. * One should avoid ruling via magistrates, if one wishes to be able to “ascend” to absolute rule quickly and safely. * One should make sure that the people need the prince, especially if a time of need should come.

How to judge the strength of principalities (Chapter 10)
The way to judge the strength of a princedom is to see whether it can defend itself, or whether it needs to depend on allies. This does not just mean that the cities should be prepared and the people trained. A prince who is hated is also exposed.

Ecclesiastical principates (Chapter 11)
Leo X: a pope, but also a member of the Medici family. Machiavelli suggested they should treat the church as a princedom, like the Borgia family had, in order to conquer Italy, and found new modes and orders.
This type of "princedom" refers for example explicitly to the Catholic church, which is of course not traditionally thought of as a princedom. According to Machiavelli, these are relatively easy to maintain, once founded. They do not need to defend themselves militarily, nor to govern their subjects.
Machiavelli discusses the recent history of the Church as if it were a princedom that was in competition to conquer Italy against other princes. He points to factionalism as a historical weak point in the Church, and points to the recent example of the Borgia family as a better strategy which almost worked. He then explicitly proposes that the Medici are now in a position to try the same thing.

Defense and military (Chapter 12-14)
Having discussed the various types of principalities, Machiavelli turns to the ways a state can attack other territories or defend itself. The two most essential foundations for any state, whether old or new, are sound laws and strong military forces. A self-sufficient prince is one who can meet any enemy on the battlefield. He should be "armed" with his own arms. However, a prince that relies solely on fortifications or on the help of others and stands on the defensive is not self-sufficient. If he cannot raise a formidable army, but must rely on defense, he must fortify his city. A well-fortified city is unlikely to be attacked, and if it is, most armies cannot endure an extended siege. However, during a siege a virtuous prince will keep the morale of his subjects high while removing all dissenters. Thus, as long as the city is properly defended and has enough supplies, a wise prince can withstand any siege.
Machiavelli stands strongly against the use of mercenaries, and in this he was innovative, and he also had personal experience in Florence. He believes they are useless to a ruler because they are undisciplined, cowardly, and without any loyalty, being motivated only by money. Machiavelli attributes the Italian city states’ weakness to their reliance on mercenary armies.
Machiavelli also warns against using auxiliary forces, troops borrowed from an ally, because if they win, the employer is under their favor and if they lose, he is ruined. Auxiliary forces are more dangerous than mercenary forces because they are united and controlled by capable leaders who may turn against the employer.
The main concern for a prince should be war, or the preparation thereof, not books. Through war a hereditary prince maintains his power or a private citizen rises to power. Machiavelli advises that a prince must frequently hunt in order to keep his body fit and learn the landscape surrounding his kingdom. Through this, he can best learn how to protect his territory and advance upon others. For intellectual strength, he is advised to study great military men so he may imitate their successes and avoid their mistakes. A prince who is diligent in times of peace will be ready in times of adversity. Machiavelli writes, “thus, when fortune turns against him he will be prepared to resist it.”
The Qualities of a Prince (Chapters 14-19)
Each of the following chapters presents a discussion about a particular virtue or vice that a prince might have, and is therefore structured in a way which appears like traditional advice for a prince. However the advice is far from traditional.
A Prince's Duty Concerning Military Matters (Chapter 14)
Machiavelli believes that a prince's main focus should be on perfecting the art of war. He believes that by taking this profession a ruler will be able to protect his kingdom. He claims that "being disarmed makes you despised." He believes that the only way to ensure loyalty from one's soldiers is to understand military matters. The two activities Machiavelli recommends practicing to prepare for war are physical and mental. Physically, he believes rulers should learn the landscape of their territories. Mentally, he encouraged the study of past military events. He also warns against idleness.
Reputation of a prince (Chapter 15)
Because, says Machiavelli, he wants to write something useful to those who understand, he thought it more fitting "to go directly to the effectual truth ("verità effettuale") of the thing than to the imagination of it". This section is one where Machiavelli’s pragmatic ideal can be seen most clearly. The prince should, ideally, be virtuous, but he should be willing and able to abandon those virtues if it becomes necessary. Concerning the behavior of a prince toward his subjects, Machiavelli announces that he will depart from what other writers say, and writes:
Men have imagined republics and principalities that never really existed at all. Yet the way men live is so far removed from the way they ought to live that anyone who abandons what is for what should be pursues his downfall rather than his preservation; for a man who strives after goodness in all his acts is sure to come to ruin, since there are so many men who are not good.
Since there are many possible qualities that a prince can be said to possess, he must not be overly concerned about having all the good ones. Also, a prince may be perceived to be merciful, faithful, humane, frank, and religious, but most important is only to seem to have these qualities. A prince cannot truly have these qualities because at times it is necessary to act against them. In fact, he must sometimes deliberately choose evil. Although a bad reputation should be avoided, it is sometimes necessary to have one.
Generosity vs. parsimony (Chapter 16)
If a prince is overly generous to his subjects, Machiavelli asserts he will not be appreciated, and will only cause greed for more. Additionally, being overly generous is not economical, because eventually all resources will be exhausted. This results in higher taxes, and will bring grief upon the prince. Then, if he decides to discontinue or limit his generosity, he will be labeled as a miser. Thus, Machiavelli summarizes that guarding against the people’s hatred is more important than building up a reputation for generosity. A wise prince should be willing to be more reputed a miser than be hated for trying to be too generous.
On the other hand: "of what is not yours or your subjects' one can be a bigger giver, as were Cyrus, Caesar, and Alexander, because spending what is someone else's does not take reputation from you but adds it to you; only spending your own hurts you".

Cruelty vs. mercy (Chapter 17)

Hannibal meeting Scipio Africanus. Machiavelli describes Hannibal as having the "virtue" of "inhuman cruelty". But he lost to someone, Scipio Africanus, who showed the weakness of "excessive mercy" and who could therefore only have had power in a republic.
In addressing the question of whether it is better to be loved or feared, Machiavelli writes, “The answer is that one would like to be both the one and the other; but because it is difficult to combine them, it is far safer to be feared than loved if you cannot be both.” As Machiavelli asserts, commitments made in peace are not always kept in adversity; however, commitments made in fear are kept out of fear. Yet, a prince must ensure that he is not feared to the point of hatred, which is very possible.
This chapter is possibly the most well-known of the work, and it is important because of the reasoning behind Machiavelli’s famous idea that it is better to be feared than loved[32] – his justification is purely pragmatic; as he notes, “Men worry less about doing an injury to one who makes himself loved than to one who makes himself feared.” Fear is simply a means to an end, and that end is security for the prince. The fear instilled should never be excessive, for that could be dangerous to the prince. Above all, Machiavelli argues, a prince should not interfere with the property of their subjects, their women, or the life of somebody without proper justification.
Regarding the troops of the prince, fear is absolutely necessary to keep a large garrison united and a prince should not mind the thought of cruelty in that regard. For a prince who leads his own army, it is imperative for him to observe cruelty because that is the only way he can command his soldiers' absolute respect. Machiavelli compares two great military leaders: Hannibal and Scipio Africanus. Although Hannibal's army consisted of men of various races, they were never rebellious because they feared their leader. Machiavelli says this required "inhuman cruelty" which he refers to as a virtue. Scipio's men, on the other hand, were known for their mutiny and dissension, due to Scipio's "excessive mercy" - which was however a source of glory because he lived in a republic.
In what way princes should keep their word (Chapter 18)
Machiavelli notes that a prince is praised for keeping his word. However, he also notes that a prince is also praised for the illusion of being reliable in keeping his word. A prince, therefore, should only keep his word when it suits his purposes, but do his utmost to maintain the illusion that he does keep his word and that he is reliable in that regard. Therefore, a prince should not break his word unnecessarily.
As Machiavelli notes, “He should appear to be compassionate, faithful to his word, guileless, and devout. And indeed he should be so. But his disposition should be such that, if he needs to be the opposite, he knows how.” As noted in chapter 15, the prince must appear to be virtuous, and should be virtuous, but he should be able to be otherwise when the time calls for it; that includes being able to lie, though however much he lies he should always keep the appearance of being truthful.
Avoiding contempt and hatred (Chapter 19)
Machiavelli observes that most men are content as long as they are not deprived of their property and women. A prince should command respect through his conduct, because a prince that is highly respected by his people is unlikely to face internal struggles. Additionally, a prince who does not raise the contempt of the nobles and keeps the people satisfied, Machiavelli assures, should have no fear of conspirators. Machiavelli advises monarchs to have both internal and external fears. Internal fears exist inside his kingdom and focus on his subjects, Machiavelli warns to be suspicious of everyone when hostile attitudes emerge. External fears are of foreign powers.
The Prudence of the Prince (Chapters 20-25)
Whether ruling conquests with fortresses works (Chapter 20)
Machiavelli mentions that placing fortresses in conquered territories, although it sometimes works, often fails. Using fortresses can be a good plan, but Machiavelli says he shall "blame anyone who, trusting in fortresses, thinks little of being hated by the people".
Gaining honors (Chapter 21)
A prince truly earns honor by completing great feats. King Ferdinand of Spain is cited by Machiavelli as an example of a monarch who gained esteem by showing his ability through great feats and who, in the name of religion, conquered many territories and kept his subjects occupied so that they had no chance to rebel. Regarding two warring states, Machiavelli asserts it is always wiser to choose a side, rather than to be neutral. Machiavelli then provides the following reasons why: * If your allies win, you benefit whether or not you have more power than they have. * If you are more powerful, then your allies are under your command; if your allies are stronger, they will always feel a certain obligation to you for your help. * If your side loses, you still have an ally in the loser.
Machiavelli also notes that it is wise for a prince not to ally with a stronger force unless compelled to do so. In conclusion, the most important virtue is having the wisdom to discern what ventures will come with the most reward and then pursuing them courageously.
Nobles and staff (Chapter 22)
The selection of good servants is reflected directly upon the prince’s intelligence, so if they are loyal, the prince is considered wise; however, when they are otherwise, the prince is open to adverse criticism. Machiavelli asserts that there are three types of intelligence: * The kind that understands things for itself—which is excellent to have. * The kind that understands what others can understand—which is good to have. * The kind that does not understand for itself, nor through others—which is useless to have.
If the prince does not have the first type of intelligence, he should at the very least have the second type. For, as Machiavelli states, “A prince needs to have the discernment to recognize the good or bad in what another says or does even though he has no acumen himself".
Avoiding flatterers (Chapter 23)
This chapter shows a low opinion of flatterers; Machiavelli notes that “Men are so happily absorbed in their own affairs and indulge in such self-deception that it is difficult for them not to fall victim to this plague; and some efforts to protect oneself from flatterers involve the risk of becoming despised.” Flatterers were seen as a great danger to a prince, because their flattery could cause him to avoid wise counsel in favor of rash action, but avoiding all advice, flattery or otherwise, was equally bad; a middle road had to be taken. A prudent prince should have a select group of wise counselors to advise him truthfully on matters all the time. All their opinions should be taken into account. Ultimately, the decision should be made by the counselors and carried out absolutely. If a prince is given to changing his mind, his reputation will suffer. A prince must have the wisdom to recognize good advice from bad. Machiavelli gives a negative example in Emperor Maximilian I; Maximilian, who was secretive, never consulted others, but once he ordered his plans and met dissent, he immediately changed them.
Prudence and chance
Why the princes of Italy lost their states (Chapter 24)
After first mentioning that a new prince can quickly become as respected as a hereditary one, Machiavelli says princes in Italy who had long standing power and lost it can not blame bad luck, but should blame their own indolence. One "should never fall in the belief that you can find someone to pick you up". They all showed: * A defect of arms, already discussed. * Either had a hostile populace or else they did not know to secure themselves with the great.
Fortune (Chapter 25)
As pointed out by Gilbert (1938:206) it was traditional in the genre of Mirrors of Princes to mention fortune, but "Fortune pervades The Prince as she does no other similar work". Machiavelli argues that fortune is only the judge of half of our actions and that we have control over the other half with "sweat", prudence and virtue. Even more unusual, rather than simply suggesting caution as a prudent way to try to avoid the worst of bad luck, Machiavelli holds that the greatest princes in history tend to be ones who take more risks, and rise to power through their own labour, virtue, prudence, and particularly by their ability to adapt to changing circumstances.
Machiavelli even encourages risk taking as a reaction to risk. In a well-known metaphor, Machiavelli writes that "it is better to be impetuous than cautious, because fortune is a woman; and it is necessary, if one wants to hold her down, to beat her and strike her down."[33] Gilbert (p. 217) points out that Machiavelli's friend the historian and diplomat Francesco Guicciardini expressed similar ideas about fortune.
Machiavelli compares fortune to a torrential river that cannot be easily controlled during flooding season. In periods of calm, however, people can erect dams and levees in order to minimize its impact. Fortune, Machiavelli argues, seems to strike at the places where no resistance is offered, as had recently been the case in Italy. As de Alvarez (1999:125–130) points out that what Machiavelli actually says is that Italians in his time leave things not just to fortune, but to "fortune and God". Machiavelli is indicating in this passage, as in some others in his works, that Christianity itself was making Italians helpless and lazy concerning their own politics, as if they would leave dangerous rivers uncontrolled.[34]
Exhortation to Seize Italy and to Free Her from the Barbarians (Chapter 26)
Pope Leo X was pope at the time the book was written and a member of the de Medici family. This chapter directly appeals to the Medici to use what has been summarized in order to conquer Italy using Italian armies, following the advice in the book. Gilbert (1938:222–230) showed that including such exhortation was not unusual in the genre of books full of advice for princes. But it is unusual that the Medici family's position of Papal power is openly named as something that should be used as a personal power base, as a tool of secular politics. Indeed one example is the Borgia family's "recent" and controversial attempts to use church power in secular politics, often brutally executed. This continues a controversial theme throughout the book