The prince of the title is both subject and reader. Machiavelli wrote this book as advice to any man with political aspirations who wishes to be the ideal prince. He also had a specific prince in mind, though that prince’s identity may have changed during the writing. He told a friend, while still working on it, that it was for Giuliano de Medici but ultimately presented it to Lorenzo de Medici.

Machiavelli’s ideal prince is one who successfully holds onto power without a reason for wielding it, much like the perfect murder is committed at random. He idealizes stability than morality. The book provides advice on how to stay in power once power has been attained. This was something that seemed to elude the leaders of the various Italian states of his era. Given the amount of suffering eternal strife caused the people of the Italian states, Machiavelli’s ennobling of the ability to stay in power is understandable.

Some of his advice is pretty simple, yet still the sort of thing people think won’t happen to them. Such as, if you bring someone else to power, you’re the first person they’ll turn on if they have any ambition whatsoever.

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.

Of course sometimes that just means betraying them before they betray you. Promise much, provide little. It’s always easy to find someone who will believe your promises.

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.

This inability to trust anyone doesn’t mean you shouldn’t take sides, as he advises in this somewhat Solomonic advice:

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. And irresolute princes, to avoid present dangers, generally follow the neutral path, and are generally ruined.

Machiavelli’s The Prince is easily quoted out of context to prove any point. That may even have been its purpose. It was written in the hope of regaining favor and contains much contradictory advice usable to justify any tactic, from mass murder to avoiding excessive patronage.

He asks simple questions—is it better to be liked than to be feared?—and provides long-winded answers.

One cannot by fair dealing, and without injury to others, satisfy the nobles, but you can satisfy the people, for their object is more righteous than that of the nobles, the latter wishing to oppress, while the former only desire not to be oppressed. It is to be added also that a prince can never secure himself against a hostile people, because of their being too many, whilst from the nobles he can secure himself, as they are few in number.

What he’s saying here is, if you’re going to have to betray someone, and you are going to have to betray someone, screw the nobles before you screw the people. They’re more predictable, and more easily forget.

Here’s interesting advice on the dangers of being liberal; his use (or more specifically his translator’s use circa 1908) of liberal almost matches modern use of the term.

There is nothing wastes so rapidly as liberality, for even whilst you exercise it you lose the power to do so, and so become either poor or despised, or else, in avoiding poverty, rapacious and hated.

He’s talking liberal in the sense of giving lots of free shit to a select group of people, not liberal in the sense of supporting civil rights and free markets. That is, liberal (giving stuff away) vs. mean (saving money).

Liberality exercised in a way that does not bring you the reputation for it, injures you; for if one exercises it honestly and as it should be exercised, it may not become known, and you will not avoid the reproach of its opposite. Therefore, any one wishing to maintain among men the name of liberal is obliged to avoid no attribute of magnificence; so that a prince thus inclined will consume in such acts all his property, and will be compelled in the end, if he wish to maintain the name of liberal, to unduly weigh down his people, and tax them, and do everything he can to get money… If he is wise he ought not to fear the reputation of being mean, for in time he will come to be more considered than if liberal, seeing that with his economy his revenues are enough, that he can defend himself against all attacks, and is able to engage in enterprises without burdening his people; thus it comes to pass that he exercises liberality towards all from whom he does not take, who are numberless, and meanness towards those to whom he does not give, who are few.

Above all things he must keep his hands off the property of others, because men more quickly forget the death of their father than the loss of their patrimony. Besides, pretexts for taking away the property are never wanting; for he who has once begun to live by robbery will always find pretexts for seizing what belongs to others.

He advises appearances more than reality, because only a few people know what you really are, and everyone else goes only by appearances.

Men judge generally more by the eye than by the hand, because it belongs to everybody to see you, to few to come in touch with you. Every one sees what you appear to be, few really know what you are, and those few dare not oppose themselves to the opinion of the many.

He appears to recognize that obstructing economic development through excessive regulation and taxation is a bad idea, I think because it hurts the mass of people more than it helps the few who do benefit and who try to encourage growth-limiting regulation for short-term personal advantage.

He should encourage his citizens to practise their callings peaceably, both in commerce and agriculture, and in every other following, so that the one should not be deterred from improving his possessions for fear lest they be taken away from him or another from opening up trade for fear of taxes.

Machiavelli recognized that even following good advice to the letter would still mean failure if fortune was against the unfortunate prince. He compared fortune to a raging river and to a woman. He recommends being prepared to withstand bad fortune and to take advantage of good.

Fortune is the arbiter of one-half of our actions, but she still leaves us to direct the other half, or perhaps a little less. I compare her to one of those raging rivers, which when in flood overflows the plains, sweeping away trees and buildings, bearing away the soil from place to place; everything flies before it, all yield to its violence, without being able in any way to withstand it; and yet, though its nature be such, it does not follow therefore that men, when the weather becomes fair, shall not make provision, both with defences and barriers, in such a manner that, rising again, the waters may pass away by canal, and their force neither be so unrestrained nor so dangerous.

Preparation isn’t the end of mastering fortune. The potential prince must be bold.

For my part I consider it better to be adventurous than cautious, because fortune is a woman, and if you wish to keep her under it is necessary to beat and ill-use her.

Contrasting with the abusive analogy to beating women, there is an odd beauty in his final advice to the prince. “God helps those who help themselves” becomes a 66-word hosanna:

How extraordinarily the ways of God have been manifested beyond example: the sea is divided, a cloud has led the way, the rock has poured forth water, it has rained manna, everything has contributed to your greatness; you ought to do the rest. God is not willing to do everything, and thus take away our free will and that share of glory which belongs to us.

The Prince is not the must-read it may have been in the past. His examples are archaic and his methods only moderately less so. His advice on rulership probably appeals to the fifties-era management style that is killing so many old-wave companies today. It is still an interesting read and if you take it in the spirit it was probably meant, you can cherry-pick the inspiration you feel most useful to you.

I read it as a libertarian and see a call to treat the populace fairly and to let them mostly alone. A Chicago-style politician would read it and see the advice to destroy your enemies and neuter your more powerful and ambitious supporters. A law-and-order hawk will read it and it obviously shows the need for a strong defense and a tough criminal justice system. I expect The Prince is more of a mirror than a model. What you get out of it is what you are. Which, I guess, makes this a very Machiavellian work.