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1. “… you find enemies in all those whom you have injured by occupying that dominion, and you cannot maintain the friendship of those who have helped you to obtain this possession, as you will not be able to fulfil their expectations, nor can you use strong measures with them, being under an obligation to them; for which reason, however strong your armies may be, you will always need the favour of the inhabitants to take possession of a province”. (Machiavelli, 8)

What Machiavelli means by the above quotation is that no matter how strong your armies or defenses are, you cannot rule without consent of the people. Machiavelli thought that, in order to attain this loyalty, you can’t be friends with the people because they won’t respect you enough. However you can’t be cruel to them because without their help you wouldn’t have been able to take control of the city. To support his logic, Machiavelli exemplified what happened with the French acquisition of Milan. France originally gained control of Milan through a political alliance. However, they lost control to an inferior military force because the people did not respect the King properly and felt no need to remain loyal. When France gained control of Milan a second time, the king did not try to be friends with the people of Milan. He was just, but not cruel. This caused the people to give him respect and remain obedient, and allowed the king to rule Milan.

2. “…one of the best and most certain means of doing so [maintaining control of a conquered area] would be for the new ruler to take up his residence there. This would render the possession more secure and durable…” (10)

By the quotation above, Machiavelli means to say that best way to keep control of a newly acquired territory is for the new ruler to live there. Machiavelli advised this because he thought that by living in the city, the ruler could deal with problems as they arose and not have to waste time. He also thought that by living in the city, the recently conquered people would have better access to their new prince. This would give them greater opportunity to grow to love, or fear, him, in which case they are more likely to remain loyal and obedient. Further more, Machiavelli believed that by living inside a newly acquired territory, political rivals would be more afraid to attack and have a harder time taking the area.

3. “…consider not only the present but also future discords and diligently guard against them…” (12)

By this Machiavelli means that you should deal the present, but plan for the future. Machiavelli thought that if one waited for the problem to occur before coming up with a plan deal with it, the problem would grow while options were discussed. Eventually, a solution would arise, but by then the damage would have been done.

4. “…one ought never to allow a disorder to take place in order to avoid war, for war is not thereby avoided, but only deferred to your disadvantage” (Machiavelli, 16).

By the above, Machiavelli means that you cannot allow issues to arise and proceed to ignore them in the hope of averting a war. He thought that war could not be avoided; that it could only be delayed and cause the pacifist, who originally tried to avert the war, further harm.

5. “…whoever becomes the ruler of a free city and does not destroy it, can expect to be destroyed by it…” (22)

This quotation is fairly straightforward. Machiavelli means to say that if a prince comes to rule a city whose citizens have been allotted more freedom than usual, he

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must quickly solidify his rule before it can destroy him. Machiavelli reasoned that this was sound advice because of the difference in how the Spartans and the Romans controlled Greece. The Spartans tried to hold Greece by politics; they created a small group of leaders to control the area. In the end, the leaders failed and Greece was lost because the Spartans were not strict enough. Rome went to Greece and tried to do the same thing the Spartans had done, and because of this they nearly lost Greece for the same reasons as the Spartans. In the end, the Romans devastated multiple cities in Greece, but maintained control.

6. “…always follow in the path trodden by great men and imitate those who are most excellent, so that if he does not attain to their greatness, at any rate he will get some tinge of it” (23).

In other words, imitate and learn from the best and soon you will gain some level prestige. Machiavelli advised this because he thought that you had to aim higher than you wished to go in order to reach your desired destination. This can be seen in his metaphor about archers. Machiavelli compared his idea of following great leaders to archers, who aim higher at a very distant target in order to have better chance of hitting their desired mark.

7. “And whoever thinks that in high personages new benefits cause old offences to be forgotten makes a great mistake” (34).

By this Machiavelli means that just because someone has risen in rank, that doesn’t mean that they have forgotten the wrongs committed against them, or who committed those wrongs. Machiavelli advised this because of what happened to Cesare Borgia. Cesare had offended several cardinals who were popular candidates for pope. He had had the influence to stop the men he had offended from becoming cardinals, but he let them rise in rank anyway. Then, when the time for electing the new Pope came, Cesare had the power to prevent one of his enemies from becoming pope, but was unable to hinder any of the others’ chances. The papal election was really all that stood in the way of his attaining his goals. By allowing his enemies to rise in power instead of heading them off when they were insignificant, he sealed his own fate. Machiavelli thought that if Cesare had followed the above advice, he would have been much better off.

8. “…injuries should be done all together, so that being less tasted, they will give less offence. Benefits should be granted little by little, so that they may be better enjoyed” (39).

In this quotation, Machiavelli is saying that you should do all the bad things at once so that people are upset for a shorter period of time, and you should spread the good things out so that people are happier for a longer period of time. Machiavelli’s reasoning behind this is that if you spread the cruelties out people will always hate and fear you; to Machiavelli, fear is acceptable, hatred is not. Machiavelli also reasoned that when the people hate their prince, the prince cannot rely upon them. However, by spreading the good things out, the people will come to think well of and trust their prince.

9. “It must also be added that the prince can never insure himself against a hostile populace on account of their number but he can against the hostility of the great as they are but few” (41).

In this piece of advice, Machiavelli is saying that a prince can’t protect himself

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from his people; there are too many of them. A prince can, however, protect himself from the nobility and the powerful because they are a much smaller group. Machiavelli thought this was good advice on the account that he believed the people to be more honest than the nobility. He thought that a prince’s people just wanted to avoid oppression, whereas the nobility wanted to keep the people oppressed. Also, Machiavelli reasoned that although a prince’s people may abandon him if he does not perform to their standards, the nobility still pose a greater threat. The nobility have the option not only of abandoning their prince, they have the power to divert, or even destroy his plans.

10. “…a wise prince will seek means by which his subjects will always and in every possible condition of things have need of his government, and then they will always be faithful to him” (43).

Machiavelli here advises that a prince should make his people utterly dependant upon him, that way they will always remain loyal and serve him. Machiavelli reasoned that you cannot be sure of who is faithful or not in peaceful times because their faith has not been tested. He thought that when a threat actually came, very few people would honor their promises of fidelity and aid. In order to increase the number of people who would stand by his side in times of adversity, Machiavelli advised that a prince make his people as dependant upon him as possible.

11. “…armies are to be used either by a prince or by a republic, the prince must go in person to take the position of captain, and the republic must send its own citizens” (51).

By this Machiavelli means that armies should not be possessed by mercenaries, that the prince himself should command his armies, and that a republic’s own people should be its military defense. Machiavelli thought that mercenaries had no loyalty. As such, a talented mercenary would always do what benefitted himself the most, regardless of his employer, and an untalented mercenary would cause more harm than good because he didn’t know what he was doing. Thus Machiavelli advises that a prince command his own armies in order to ensure they’re effective, and a republic use its own manpower in order to be sure that a mercenary force does not leave it defenseless if a better offer comes along.

12. “A prince, therefore, must not mind incurring the charge of cruelty for the purpose of keeping his subjects united and faithful…” (Machiavelli, 68)

By this Machiavelli means that you cannot be afraid to be seen as cruel in your quest to do the right thing for your people. As an example, Machiavelli compares Cesare Borgia to the Florentines. Cesare was not afraid of being considered cruel, and was able to organize and unify the Romagna. The Florentines on the other hand were afraid of being considered cruel, and because of this Pistoia was eradicated. Machiavelli thought that had the Florentines ignored their fear, Pistoia would have been spared.

13. “…it is much safer to be feared than loved, if one of the two has to be wanting” (69).

In this Machiavelli means that if you can only be feared or loved, and that you cannot be both, it is better to be feared. Machiavelli thought that it was human nature to be greedy, and that a people who loved their prince would be more likely to betray him for their own personal gain; since he loved them, he would hate to punish them.

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A feared prince however, would not be betrayed because his people would be afraid of how they would be punished for their betrayal.

14. “It is therefore necessary for a prince to know well how to use both the beast and the man” (72).

The “beast” Machiavelli is referring to is a nation’s armed forces; the “man” is the general populace. Although Machiavelli used many examples to rationalize his advice, the best example he provides is that of Severus, a roman emperor. Severus was a military leader before he acceded to the throne. He had the respect and loyalty of his troops because he was willing to give them work to do instead of sitting idle, and was willing to do that work with them. Although Severus was ruthless, that made him feared by the people so they were complacent beneath him. Severus succeeded because he correctly used the beast and the man by giving the beast work and scaring the man into submission.

15. “generally a conspirator has to fear before the execution of his plot, in this case, having the people as an enemy, he must also fear after his crime is accomplished, and thus he is not able to hope for any refuge” (78).

This quote means that conspirators are usually afraid of being discovered before they can follow through with their plan. However, if their plan is against the people, the conspirators need to be wary after they have completed their goal as well. Machiavelli thought this was good advice to give because of what happened to the Canneschi family, who assassinated Annibale Bentivogli, Prince of Bologna. The Bentivogli family had been popular during their rule, and the people were so outraged that the family had been harmed, they killed all the Canneschi. Machiavelli reasoned that if the Canneshi had been as wary after their plans had been carried out as they had been before hand, they would have been able to gain control.

16. “…princes should let the carrying out of unpopular duties devolve on others, and bestow favours themselves” (79).

The above means that a prince should let someone else be seen as the executioner, so that he may be seen as more merciful or benevolent. Machiavelli advised this because of France’s successful use of the Parliament. The king established the parliament so that he could not be seen as favoring either the people or the nobility; the king was seen as fair. And because the king was not directly in charge of the parliament, it was parliament, not the king, which incurred the wrath of a displeased noble or populace. In the end, the king was seen only to be giving “favours”, and parliament was carrying out the “unpopular duties”.

17. “…hatred is gained as much by good works as by evil, and therefore, as I said before, a prince who wished to maintain the state is often forced to do evil…” (81)

In this, Machiavelli says that good deeds and bad deeds can both incur hatred. Thus, sometimes you have to do a little evil in order to do more good. To exemplify this idea, Machiavelli used former ruler Alexander. According to Machiavelli, “no one was put to death by him [Alexander] without a fair trial”. This caused Alexander to seem weak in the eyes of his soldiers, and so they rose up against him and killed him. Machiavelli thought that if Alexander had done a little evil, say convicted someone he knew to be guilty but without a trial, his soldiers would not have seen him as weak, he would gone on to have a longer and more glorious career.

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18. “Princes, and especially new ones, have found more faith and more usefulness in those men, whom at the beginning of their power they regarded with suspicion, than those they at first confided in” (89)

By this Machiavelli means that Princes often eventually come to trust those who were originally thought to be untrustworthy, more than their original circle of trusted acquaintances. Machiavelli considered this logical advice because of what happened to Pandolfo Petrucci. Petrucci was Prince of Sienna and successfully ruled his country with the aid of people whom he originally distrusted, rather than those he did trust. Machiavelli also supports this statement with the logic that the people a prince distrusts will do more to earn his trust than those who are already esteemed will do to keep their position (89).

19. “…the best fortress is to be found in the love of the people…” (91).Machiavelli means to say that the best protection a prince can have from losing

his state is the people’s affection. Machiavelli thought as such because if the people were discontented, there would be a multitude of foreigners who would assist the rebelling people rather than the Prince they were rebelling against. Thus the best way to protect one’s self is to make yourself loved by the people so that they have no reason to be discontented in the first place.

20. “Nothing causes a prince to be so much esteemed as great enterprise and giving proof of prowess” (92).

In other words: doing the unlikely or impossible is the fastest way to gain respect. In support of this Machiavelli uses King Ferdinand as an example. At first Ferdinand was thought of as, in Machiavelli’s own words, “weak”. His initial feat of conquering Granada caused people to become wary of him. His succeeding attacks of Africa, France, and Italy, in Machiavelli’s opinion, constantly surprised people, kept his enemies at arms length, and caused them to reevaluate their original impression.

21. “A prince is further esteemed when he is a true friend or a true enemy, when, that is, he declares himself without reserve in favour of some one or against another” (93).

In this Machiavelli means that it’s better to dedicate yourself to one side or the other than to remain neutral. Machiavelli was of the opinion that if you remain neutral, the victor will take advantage of you and the loser will ignore you. Both will act as such for the same reason: they don’t want friends who don’t stand beside them. To further support his idea, Machiavelli provides the words of a Roman ambassador, who lived during a time when the Romans were at war with the Ætolians, for support.

The Ætolians sent an ambassador to the Achæns, a country that was friendly with Rome, to convince them to stay neutral. Rome also sent an ambassador to the Achæns, to convince them to ally with Rome. In his effort to convince them, the Roman ambassador said: “as to what is said that it is best and most useful for your state not to meddle in our war, nothing is further from the truth; for if you do not meddle in it you will become the prize of the victor”. This tactic worked well for Rome, arguably one of the greatest civilizations of all time, thus Machiavelli believed his idea to be a good one.

22. “…a prince ought never to make a common cause with one more powerful than himself to injure another, unless necessity forces him to it…” (95).

In other words, if at all possible, don’t ally with a country more powerful than

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yourself just to hurt a third party. Machiavelli reasoned that if you and your party won, you would be indebted to your more powerful ally. He used the Venetians as an example. The Venetians allied with France, a more powerful nation, in order to defeat the Duke of Milan. The alliance was unnecessary, and resulted in the eventual defeat of the Venetians.

23. “The choice of a prince’s ministers is of no little importance; they are either good or not according to the prudence of the prince” (97).

By the above quotation, Machiavelli means that a prince’s ministers reflect his competence as a ruler. Machiavelli uses Pandolfo Petrucci as an example. Pandolfo employed Antonio da Venafro as a minister, and “there was nobody…who did not consider Pandolfo to be a very prudent man, having him [Antonio da Venafro] for his minister”. Machiavelli thought that Pandolfo, because he employed Antonio, a well educated and successful man, as a minister, was respected and seen as an intelligent ruler.

24. “Because there is no other way of guarding one’s self against flattery than by letting men understand that they will not offend you by speaking the truth; but when every one can tell you the truth, you lose their respect. A prudent prince must therefore take a third course, by choosing for his council wise men, and giving these alone full liberty to speak the truth to him…” (99).

In this quotation, Machiavelli is advising that a prince choose a select group of people who are encouraged to speak frankly with him. In Machiavelli’s opinion, doing so allows the prince to receive other viewpoints, yet retain respect and make his own decisions.

25. “A prince, therefore, ought always to take counsel, but only when he wishes, not when others wish, […] but he ought to be a great asker, and a patient hearer of the truth about those things of which he has inquired…” (100)

The above quotation means that a prince should always have people to advise him, but they should only advise him when he chooses. Also, he should ask a lot of questions and listen and consider the answers he receives. Machiavelli reasoned this was good advice based on what happened to emperor Pre’ Luca. Pre’ Luca never asked for advice and was never able to do what he wanted. This, in Machiavelli’s opinion, occurred because once Pre’ Luca put his plans in motion, people could guess what he had planned and stop him. And, because he never accomplished his desires, Pre’ Luca was not respected. If Pre’ Luca had followed Machiavelli’s advice and asked a lot of questions of his advisors and listened to the answers, his plans would not have been guessed so easily, he would have accomplished more, and he would have been respected.