Quotes from Machiavelli

These are the quotations taken from Machiavelli’s works, used in this book. I used the public domain versions of his books for most of my sources, however some of the wording and punctuation may be updated or altered for clarity and modernity. See the Bibliography for details on sources.

In the book, quotations from The Prince are shown entirely in bold.

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“When a prince acquires a new state, it is necessary to disarm the men of that state, except those who have been his supporters in acquiring it. These, with time and opportunity, should be rendered soft and weak; things should be organized so that all the armed men in the state shall be your own soldiers who, in your old state, were at your side.” — Niccolo Machiavelli, The Prince, Ch. XX

“I do not believe that factions can ever be useful. When the enemy sees your city divided by factions, you are quickly lost, because the weakest group among
those factions will always assist the outside forces, and the rest will not be able to resist.”
— Niccolo Machiavelli, The Prince, Ch. XX

“Without doubt, princes become great when they overcome the hurdles that are placed in their path…” — Niccolo Machiavelli, The Prince, Ch. XX

“A wise prince, when he has the opportunity, ought to cunningly foster some opposition to himself, so that, by crushing it, his reputation may rise higher.” — Niccolo Machiavelli, The Prince, Ch. XX

“Princes, especially new ones, have found more loyalty and assistance from those men who they distrusted in the beginning of their rule than among those were trusted friends. If men who were initially opponents need assistance to maintain their position, they can always be easily won over. They will be forced to serve the prince with loyalty, because they know it is necessary for them to cancel by their deeds the bad impression the prince had formed of them. Thus the prince always extracts more use from former enemies than from those who, serving him with too much confidence to feel fear, may neglect his affairs.” — Niccolo Machiavelli, The Prince, Ch. XX

“Consider the reasons which convinced those to favour the prince; and if it be not a natural affection towards him, but only discontent with their former government, then he will only keep them friendly with great effort and difficulty, for it will be impossible to satisfy them.” — Niccolo Machiavelli, The Prince, Ch. XX

“It is easier for the prince to make friends of those who were contented under the former government, and were therefore his enemies, than of those who, being discontented with it, were instant friends with him and encouraged him to seize control.” — Niccolo Machiavelli, The Prince, Ch. XX

“Fortresses… can be useful or not, according to circumstances; if they do you good in one way they are harmful in another…” — Niccolo Machiavelli, The Prince, Ch. XX

“Fortresses provide a safe refuge from sudden attack.” — Niccolo Machiavelli, The Prince, Ch. XX

A 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.” — Niccolo Machiavelli, The Prince, Ch. XX

“The best fortress in the world is simply to be loved by the people, because no fortress will save you if the people hate you. Once the people take up arms against you, there will be no shortage of outsiders eager to come to their aid.” — Niccolo Machiavelli, The Prince, Ch. XX

“I shall praise both the prince who builds fortresses as well as he who does not. I shall blame the prince who relies on fortresses, but cares nothing about being hated by the people.” — Niccolo Machiavelli, The Prince, Ch. XX

“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 in those they at first confided in.” — Niccolo Machiavelli, The Prince, Ch. XX

“Nothing makes a prince so well esteemed as undertaking great enterprises and setting a fine example.” — Niccolo Machiavelli, The Prince, Ch. XXI

“…using religion as a plea, so as to undertake greater schemes, he devoted himself with a pious cruelty to driving out and clearing his kingdom of the Moors… Under this same guise he assailed Africa, he campaigned in Italy, and attacked France. His has always planned and achieved great undertakings, which have captured the imagination and admiration of his people, and kept everyone in suspense about their outcome. He has undertaken his actions in such a way and so quickly that men have never have the opportunity to conspire against him. ” — Niccolo Machiavelli, The Prince, Ch. XXI

“It is very profitable for a prince to give outstanding examples of his abilities in his government’s affairs… when anyone in civic life does something extraordinary, either good or bad, they should be rewarded or punished in a way that will arouse considerable comment…” — Niccolo Machiavelli, The Prince, Ch. XXI

“Above all, in every action a prince should strive to gain for himself the reputation of being a great and remarkable man…” — Niccolo Machiavelli, The Prince, Ch. XXI

“A prince is also respected when he is either a true friend or a true enemy …When he declares himself in favour of one party against the other, without any reservation, this action will always be more advantageous than remaining neutral.” — Niccolo Machiavelli, The Prince, Ch. XXI

“It will always be more advantageous for you to declare yourself and to wage a vigorous war. If you do not declare yourself, you will invariably fall prey to the winner, which will be to the pleasure and satisfaction of the loser, and you will have nothing nor anyone to protect or to shelter you.” — Niccolo Machiavelli, The Prince, Ch. XXI

“The winner does not want doubtful friends who would not aid him when he was in difficulty; and the loser will not harbour you because you did not willingly come to his aid with your sword in hand.” — Niccolo Machiavelli, The Prince, Ch. XXI

“The one who is not your friend will demand your neutrality, while your friend will ask for your armed support…Irresolute princes, to avoid immediate dangers, follow the path of neutrality, and are generally ruined. But when a bold prince declares himself in favour of one side, if his allies win, although the victor is powerful and may have the prince at his mercy, the winner is indebted to the prince, and a bond of allegiance is established. Men are never so unprincipled as to show such monumental ingratitude by oppressing you after you aided them.” — Niccolo Machiavelli, The Prince, Ch. XXI

“Victories are never so complete that the victor must not show you some regard, especially to justice. Even if your ally loses, you may be sheltered by him, and he will help you while he is able, and you become companions whose joint fortune may rise again.” — Niccolo Machiavelli, The Prince, Ch. XXI

“When you are not worried about who will win, it shows greater prudence to be allied with one side, because you instigate the destruction of the other ruler by the aid of your ally who, if he had been wise, should have saved the other. It is impossible that your ally should not win with your assistance, so he remains your debt.” — Niccolo Machiavelli, The Prince, Ch. XXI

“A prince should never make an alliance with a more powerful ruler than himself simply for the purpose of attacking another, unless necessity compels him… If your ally conquers, you are in his debt, and princes should avoid as much as possible being in debt to anyone.” — Niccolo Machiavelli, The Prince, Ch. XXI

“When it cannot be avoided… the prince should enter an alliance with one of the parties.” — Niccolo Machiavelli, The Prince, Ch. XXI

“Never let any government imagine it can always choose perfectly safe courses; rather let it regard all choices as risky, because in everyday affairs, when one tries to avoid one trouble, you always run into another. Wisdom consists of knowing how to distinguish the nature of trouble, and in choosing the lesser evil.” — Niccolo Machiavelli, The Prince, Ch. XXI

“A prince ought to show himself a patron of talent, and to encourage proficiency in every art… He should encourage his citizens to practice their business unhampered and peacefully, in trade and agriculture and in every other profession. No one should be afraid of accumulating possessions for fear these will be taken away from him; nor deterred from opening a business for fear of taxes. The prince should offer rewards to whomever wishes to do these things that improve or honour his city.” — Niccolo Machiavelli, The Prince, Ch. XXI

“Further, he should entertain the citizen with festivals and spectacles at suitable times of the year. Since every city is divided into guilds and organizations, he should respect such bodies in esteem, and meet with them regularly. He should show himself the prime example of courtesy and generosity; while always maintaining the majesty of his rank, which he must never abate.” — Niccolo Machiavelli, The Prince, Ch. XXI

“The choice of servants is very important to a prince… the first opinion which one forms of a prince, and of his wisdom, is by observing the men he has around him. If they are capable and loyal he will be considered wise, because he knows how to recognize their ability and to keep them faithful. But when they are lacking in those qualities, one forms a bad opinion of the prince, for his first error was in choosing them.” — Niccolo Machiavelli, The Prince, Ch. XXII

“There are three classes of intellects… one which understands things by itself; the second which appreciates what others can understand; and a third which neither understands for
itself nor through others; the first kind is excellent, the second is good enough, the third is useless.”
— Niccolo Machiavelli, The Prince, Ch. XXII

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