Rensberry.com
This classic is a book I have intended to read for quite some time. When I read it, it was nothing like I expected. Now I understand the meaning behind Machiavelli as an adjective. I also see how his thought processes, while ruthless, work. I found myself thinking of many current world events as I read this - I thought of the US, President Trump, North Korea, China, Russia, Cuba, and more.
I think this book would be a fascinating in depth study. It would be fun to rewrite with modern examples.
Anyways, here are some quotes that stood out to me:
He who has annexed them, if he wishes to hold them, has only to bear in mind two considerations: the one, that the family of their former lord is extinguished; the other, with the old principality.
[With annexation] if one is on the spot, disorders are seen as they spring up, and one can quickly remedy them; but if one is not at hand, they are heard of only when they are great, and then one can no longer remedy them.
...men ought either to be well treated or crushed, because they can avenge themselves of lighter injuries, of more serious ones they cannot; therefore the injury that is to be done to a man ought to be of such a kind that one does not stand in fear of revenge.
He who is the cause of another becoming powerful is ruined; because that predominancy has been brought about either by astuteness or else by force, and both are distrusted by him who has been raised to power.
For injuries ought to be done all at one time, so that, being tasted less, they offend less; benefits ought to be given little by little, so that the flavor of them may last longer.
If everything is well considered, it will not be difficult for a wise prince to keep the minds of his citizens steadfast from first to last, when he does not fail to support and defend them.
The chief foundations of all states, new as well as old or composite, are good laws and good arms; and as there cannot be good laws where the state is not well armed, it follows that where they are, I say, therefore, that the arms with which a prince defends his state are either his own, or they are mercenaries, auxiliaries, or mixed. Mercenaries and auxiliaries are useless and dangerous; and if one holds his state based on these arms, he will stand neither firm nor safe...
Auxiliaries...are employed when a prince is called in with his forces to aid and defend. ... These arms may be useful and good in themselves, but for him who calls them in they are always disadvantageous; for losing, one is undone, and winning, one is their captive.
The arms of others either fall from your back, or they weigh you down, or they bind you fast.
He ought to be slow to believe and to act, nor should he himself show fear, but proceed in a temperate manner with prudence and humanity.
A wise prince should establish himself on that which is in his own control and not in that of others; he must endeavor only to avoid hatred.
It is necessary to be a fox to discover the snares and a lion to terrify the wolves.
Never lets anything slip from his lips that is not replete with the above-named five qualities, that he may appear to him who sees and hears him altogether merciful, faithful, humane, upright, and religious.
A prince ought to reckon conspiracies of little account when his people hold him in esteem; but when it is hostile to him, and bears hatred towards him, he ought to fear everything and everybody.
The best possible fortress is not to be hated by the people.
Nothing makes a prince so much esteemed as great enterprises and setting a fine example.
A prince is also 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; which course will always be more advantageous than standing neutral.
It will always happen that he who is not your friend will demand your neutrality, whilst he who is your friend will entreat you to declare yourself with arms.
I consider it is better to be adventurous than cautious.