- Though others try to gain the approval of princes by means of expensive material gifts and riches, Machiavelli asserts that the most valuable possession he can give is his political knowledge "acquired in the course of a long experience of modern affairs and a continual study of antiquity."
- Machiavelli criticizes Louis for conquering lands that couldn't be kept.The teacher explains, "The wish to acquire is in truth very natural and common, and men always do so when they can.but when they cannot do so, yet wish to do so by any means, then there is folly and blame."
- Using the Spartans and Romans as examples, Machiavelli proves that letting the people live in freedom is the worst option because it encourages them to rebel against the prince. He explains, "he who becomes master of a city accustomed to freedom and does not destroy it, may expect to be destroyed by it.."
- Machiavelli stresses, "A wise man ought always to follow the paths beaten by great men, and to imitate those who have been supreme, so that if his ability does not equal theirs, at least it will savor of it." Though new princes must have either fortune or ability in order to reach the pinnacle of authority, Machiavelli asserts that ability is the better quality because it is more dependable in time of struggle.
- Indeed being prince is no easy task. It requires constant manipulation of others and continual calculation of future actions. As Machiavelli puts it, "he who considers it necessary to secure himself in his new principality, to win friends, to overcome either by force or fraud, to make himself beloved and feared by the people, to be followed and revered by the soldiers, to exterminate those who have power or reason to hurt him, to change the old order of things for new, to be severe and gracious, magnanimous and liberal, to destroy a disloyal soldiery and to create new, to maintain friendship with kings and princes in such a way that they must help him with zeal and offend with caution, cannot find a more lively example than the actions of [Borgia]." Yet even these favorable conditions were not enough to keep Borgia from being dethroned. Here, Machiavelli outlines the prerequisites for being prince as well as showing how hard it is to hold power.
- A prince chosen by the noble class yet favored by the people after proving to them that he is kind, is the best prince of all, for "men, when they receive good from him of whom they were expecting evil, are bound more closely to their benefactor; thus the people quickly become more devoted to him than if he had been raised to the principality by their favors." Thus, keeping the peoples' good will is shown to be a matter of utmost importance to Machiavelli.
- Machiavelli sees an inherent connection between laws and arms: "as there cannot be good laws where the state is not well armed, it follows that where they are well armed they have good laws."
- Machiavelli stresses the value of knowing one's kingdom, saying, "the prince that lacks this skill lacks the essential which it is desirable that a captain should possess, for it teaches him to surprise his enemy, to select quarters, to lead armies, to array the battle, to besiege towns to advantage."
- Some of the first few lines in this chapter underline the entire theme behind Machiavelli's work: "for many have pictured republics and principalities which in fact have never been known or seen, because how one lives is so far distant from how one ought to live, that he who neglects what is done for what ought to be done, sooner effects his ruin than his preservation; for a man who wishes to act entirely up to his professions of virtue soon meets with what destroys him among so much that is evil."
- Next, Machiavelli asserts that it's "safer" for a prince to be feared than loved because men who merely love a prince but don't fear him will abandon him when the going gets rough. The teacher explains, "love is preserved by the link of obligation which, owing to the baseness of men, is broken at every opportunity for their advantage; but fear preserves you by a dread of punishment which never fails." Yet again, the prince must not go so far that he becomes hated, for hatred is to be avoided at all costs.