The Prince

In Chapter 16, Machiavelli’s use of the word liberality is synonymous with generosity. He further admits that a prince’s subjects should consider him generous. However, he cautions that if generosity is exercised in the way it truly should be, it will go unnoticed and be harmful to the prince. Therefore, a prince wishing to have the reputation of generosity must be brazen about it to let it be known. As a matter of practice, however, Machiavelli warns strongly against generosity. The primary reason is because it is not sustainable and will eventually lead to an exhaustion of resources and excessive taxes, which will cause the prince to be hated. If the prince is generous at first but then pulls back from that, he will be seen as being miserly, which will also lead him to being hated. As previously stated, Machiavelli argues that a prince, above all things, should guard against being hated. Therefore, as long as the prince does not rob his subjects and can defend himself, he should not be concerned about a reputation for meanness because “it is one of those vices which will enable him to govern” (62).

Machiavelli compares the benefits of a prince having a reputation for cruelty to one having the reputation for clemency. While he acknowledges that every prince ought to desire to be considered clement, one should be cautious not to misuse clemency. He argues that a prince, “so long as he keeps his subjects united and loyal, ought not to mind the reproach of cruelty” (65). This is because too much mercy results in disorder. Too much disorder, in turn, results in injuries to the people as a whole. Targeted cruelties, such as executions, on the other hand, result in offending only the individual. Therefore, in the long run, the cruel ruler is more merciful by keeping order. Machiavelli offers Cesare Borgia as an example of this, pointing out that Borgia reconciled the Romagna, unifying and restoring it to peace and loyalty precisely because of his reputation for cruelty. While it is impossible for rulers of new principalities to avoid the reputation of cruelty, they should be prudent in judgement because too much confidence makes them incautious and too much distrust makes them seem intolerable.

This discussion brings up the question of whether it is better for a prince to be loved or feared. Machiavelli argues that “one should wish to be both, but, because it is difficult to unite them in one person, it is much safer to be feared than loved, when, of the two, either must be dispensed with” (66). According to Machiavelli, men are generally ungrateful, fickle, and cowardly, and princes should not rely on their promises. Friendships obtained by payments might be earned, but they are not secured. Men are less concerned with offending someone who is loved than someone who is feared because love is preserved by the link of obligation while fear is preserved “by a dread of punishment which never fails” (66). Once again using a historical example to prove his point, Machiavelli explains that Hannibal led an army composed of different races of men to fight in foreign lands but had no dissensions because of his reputation for inhuman cruelty. Scipio, on the other hand, saw his army rebel in Spain because of his reputation for clemency. 

In what is perhaps the most controversial chapter of The Prince, Machiavelli examines the truthfulness and integrity of princes. Although it is praiseworthy for a prince to keep his word and live with integrity, history shows that the most successful rulers have not held that characteristic. They simply knew “how to circumvent the intellect of men by craft” (69). Machiavelli uses the metaphor of the fox and the lion to explain that princes must use both cunning and power in order to be successful. Whereas men contest things by law, animals do so by force, and when the former does not work, a prince should practice the latter. Knowing that he should transform into the ways of the animal, a prince should choose both the fox and the lion. The fox uses cunning to avoid traps but does not have the power to avoid wolves; the lion has the power to avoid wolves, but not the cunning to avoid traps.

However, Machiavelli also argues that “it is necessary to know well how to disguise this characteristic [...] and men are so simple, and so subject to present necessities, that he who seeks to deceive will always find someone who will allow himself to be deceived” (70). In other words, the prince need not be virtuous, but he must appear to be virtuous and truthful. This is possible, according to the author, because men are simple and willing to be deceived. A prince should avoid deception if possible, but he must be able and ready to deceive because it is a necessary vice. While it is unnecessary for a prince to be merciful, faithful, humane, religious, and upright, it is extremely important that he appear to be. To have these qualities and to always observe them, according to Machiavelli, is injurious to the prince, but to appear to have them is useful. 

In Chapter 19, Machiavelli returns to the familiar theme concerning how and why a prince should avoid being hated and contemptible. A prince will be hated if he becomes “a violator of the property and women of his subjects;” he will be contemptible if he is considered “fickle, frivolous, effeminate, mean-spirited, or irresolute” (73). It is important for the prince to be highly esteemed because “he who is highly esteemed is not easily conspired against” (73). Machiavelli warns that a prince should have two fears: “one from within, on account of his subjects, the other from without, on account of external powers” (73). The prince can guard against the latter threat by being well armed and having good allies, but he must guard against the former by avoiding hatred and contempt. A potential conspirator against the prince from within has the fear of punishment and also the fear that his actions against a popular prince will anger the people.

To prove his point, Machiavelli uses the example of Messer Annibale Bentivogli, the former prince of Bologna. Annibale was murdered by the Canneschi family but was held in such esteem by the people that they rose up and in turn killed all of the Canneschi family. The prince must protect himself from internal conspirators by avoiding hatred while keeping the nobles contented. Machiavelli uses the kingdom of France as an example of the balance that a prince must strike between avoiding hatred from the people and keeping the nobles contented. In the case of France, this is possible because the parliament keeps both in check and allows the prince to avoid the appearance of favoritism for either the people or the nobles

Machiavelli discusses how princes can secure and hold their states. He writes that some princes have disarmed their subjects. Others have created factions among the subjects, while still others have purposely created hostility with neighboring states. Some build fortresses while others have destroyed their fortresses. Machiavelli does not pass on judgment on the right path to follow because each case is different, but he addresses each one in terms of how a prince should behave. He argues that a new prince would never disarm his subjects, but instead he should arm them if they are unarmed. This is because the arms of the subjects also become the arms of the prince. Similarly, this also tends to sway the disloyal to loyal and the already loyal to extremely loyal. In turn, disarming the subjects leads to the prince being hated due to his reputation of suspicion and distrust. Just as importantly, disarming the subjects means that a prince will be forced to rely on mercenaries, which will lead to ruin.

When a prince annexes a new state to add to his principality, however, he should disarm those subjects, except those who helped the prince in acquiring it. Although it was at one time useful to a prince, Machiavelli strongly warns against now creating factions within his state because no good can come from dissension. Regarding the practice of purposely creating hostility with neighbors, Machiavelli argues that this deceptive policy is useful because “princes become great when they overcome the difficulties and obstacles by which they are confronted” (84). This is especially true for new princes needing to build a reputation. Finally, concerning the building of fortresses, Machiavelli admits that this policy has been useful since ancient times, but plenty of examples prove otherwise. The best fortress, according to Machiavelli, is not to be hated by the people, but he also adds that “the prince who has more to fear from the people than from foreigners ought to build fortresses, but he who has more to fear from foreigners than from the people ought to leave them alone” (86). 

In Chapter 21, Machiavelli focuses even more closely on the reputation of princes, and specifically on how they should gain prestige and win honor. He states that “nothing makes a prince so much esteemed as great enterprises and setting a fine example” (87). Ferdinand of Aragon, the King of Spain at the time, is cited by Machiavelli as a ruler who precisely attained such renown. Ferdinand drove the Moors out of Spain and attacked Granada, Africa, Italy, and France. In doing so he kept his people occupied and amazed with his great enterprises. Regarding internal affairs, Machiavelli suggests that princes should “always endeavor in every action to gain for himself the reputation of being a great and remarkable man” (88). He can do this by elaborately rewarding or punishing his subjects for extraordinary actions.

Machiavelli also argues that a prince is respected “when he is either a true friend or a downright enemy, that is to say, when, without any reservation, he declares himself in favor of one party against the other” (88). What this refers to is that a prince should always choose sides and never remain neutral in the conflicts of neighboring states. Not doing so will result in being at the mercy of the winner while drawing the disdain of the loser. However, Machiavelli suggests that a prince should not ally with a more powerful neighbor because doing so will leave him at the ally’s mercy if he is victorious. Moving back to domestic policy, Machiavelli states that a prince should “show himself a patron of ability,” meaning that he should reward talent and encourage his subjects to “prosper in their occupations” (89). Similarly, a prince can gain renown by entertaining his people with festivals and spectacles and by associating with the guilds and societies of his cities

Machiavelli examines the servants and advisors of a prince in Chapter 22. The choice of servants for a prince is of “no little importance” because the first opinion one forms of a prince comes from “observing the men he has around him” (91). When those around the prince are capable and faithful, the prince appears to be wise, but the opposite is true when they are not. Machiavelli writes that the one test that a prince should apply to servants is whether they think of their own interests or only of the prince’s interests. On the other hand, the prince should work to keep his servant honest and trustworthy by honoring and enriching him. In doing this, the servant will desire more honors and more riches. 

Chapter 23 relates to the counsel and advice that a prince obtains. Machiavelli warns that the courts are full of flatterers and that men can easily fall victim to flattery because so many are self-absorbed in their own affairs. The author argues that “there is no other way of guarding oneself from flatterers except letting men understand that to tell you the truth does not offend you; but when everyone may tell you the truth, respect for you abates” (93). In other words, a prince must be open to the truth, but with such honesty from anyone the prince runs the risk of losing respect. One remedy for this is that a prince should choose able advisors and allow only them to speak the truth freely, and only upon the prince’s request. When given advice and truthfulness upon request, the prince should be an attentive and patient listener and a thorough inquirer before reaching any decision, which should be made by the prince alone.