Source of book: I own this
As regular readers of this blog know, I was homeschooled from 2nd grade on - one of the first, before it became popular. The main reason for this was that I was a sickly child, and missed so much school that the principal recommended my parents homeschool me.
Back in the day, the curriculum you could buy was extremely limited. Most publishers refused to sell to individuals, so even what we were able to get when we first started was “grey market” - a middleman would pose as a “private school” and pass it along to parents.
By the time I graduated high school, this had completely changed. The profit motive finally kicked in. Fast forward to when we homeschooled our own kids (mostly through 8th grade), and a true explosion of options had occurred, and every mainstream (and a lot of fringe) stuff was easily available for ordering, and fairly affordable.
But back when I was a kid, the available curriculum broke down into: (1) right wing (2) really right wing, and (3) lunatic fringe fucking racist nazi right wing.
Or, in other words, A Beka, most other curriculum, and Bob Jones, respectively. We went mostly with (1).
Which is to say, academically rigorous for math and English, biased as fuck for history, and utter propaganda for science. Fortunately, my parents supplemented it with other sources. For example, their anti-racist beliefs (which unfortunately they later abandoned) meant we read books like Roll of Thunder Hear My Cry.
I mention this because as part of the high school curriculum for World History, the Renaissance was a topic covered. Let’s just say that Fundies are not down with the Renaissance in many, many ways. (Which is ironic because Fundamentalism is rooted in both the Renaissance and the Enlightenment in ways that Fundies do not understand or even see.)
Machiavelli was particularly contemned: he was blamed for “moral relativism” as if what he wrote about was somehow something new; that before him, realpolitik and unscrupulous power plays never plagued “christian” governments.
Allow me to die laughing over here.
Over the course of my informal self-education, one of the things I have tried to do is go back and actually read these classic writings myself, and see if they actually hold up.
And, of course, if they actually say what people claim they do. (Case in point: most of what Fundies claim the Bible says isn’t actually in there, but was made up relatively recently.)
Now, having read The Prince for myself, I was struck by how, well, mild it is. I mean, the basic ideas aren’t even controversial, and I doubt they were back then to most people living in the real world. True, he challenged the official Catholic doctrines of the time, but for centuries, popes had been living his ideas in practice. Just saying.
The book is addressed to a particular prince, and assumes that the political system in play is one of “principalities.” That is, one where a single ruler has the power, perhaps tempered by other nobles. In other words, not a “republic,” which definitely existed, and which Machiavelli refers to throughout the work. (He also wrote Discourses on Livy, which looks at various forms of government, and he refers to that as well.)
Given the specifics of his target audience and specific political situations addressed, Machiavelli comes across as perceptive, in my view.
Actual governance - and staying in power - has always been about pragmatism rather than abstract morality. Whether you think this is a good thing likely depends on your perspective, of course.
For me, having endured far too much of governance by ideology myself, I find Machiavelli’s ideas to be compelling at times. And also dated and questionable at others.
At a fundamental level, I believe in democracy and representative government, derived from the consent of the governed. In other words, I am a post-Enlightenment thinker. Monarchy, particularly hereditary monarchy, is not something I approve of, and I think history supports me in this.
Modern readers will also take issue with the idea of murdering political opponents. That said, in a system where the Rule of Law is non-existent, and political change can only occur by removal of politicians, political violence becomes the norm - inevitable even. (Again, history is on my side here - which is why autocracy isn’t stable, but leads to assassination after assassination…)
Despite the differences in the political assumptions, there are actually a lot of things that hold up really well in this book. For example, the grave risks of trying to change traditional laws, rights, and tax structures that affect the common people. And the advice to “avoid being hated by the common people.”
I was also struck by the fact that even though Trump and the Theofascists and Technofascists supporting him have adopted the unscrupulousness and “win at all costs” commonly termed “Machiavellian,” the actual book reveals them to have failed to learn any of the lessons. They are fundamentally incompetent and self-defeating.
Will this self-destruction occur quickly? I’m not sure. And in the meantime, the damage they are doing is incredible and will probably not be reversed during my lifetime. But what they are not doing is actual governance, but throwing tantrums and breaking stuff because they can. This is not the way to build a stable government with the public support needed. This is how you find yourself bleeding out in the plaza after a violent coup. (Gotta love Italian Renaissance politics…)
My particular edition (I have two, actually, with different material added) contains two additional works. One is the story of how Duke Valentino murdered his political opponents. It’s every bit as violent and lurid as you would expect. The other is a semi-fictionalized account of Medieval politician Castruccio Castracani, written late in his life. This one is commonly paired with The Prince because it demonstrates many of the dilemmas and political maneuvers necessary to maintain power in turbulent times.
Anyway, I found the book fascinating. It does contain a lot of Italian history, with footnotes to explain who everyone is. Which is helpful. These parts can drag a bit, but are interesting to demonstrate who Machiavelli is thinking of for his ideas.
I would compare this book in a number of ways to The Art of War, in that both look at human politics and violence in a philosophical light, and both advocate for many of the same realpolitik pragmatism in action, while noting that pragmatism tends to support doing right by your people in the end.
I should mention that The Prince was avant garde in its time for being written not in scholarly Latin, but in the vernacular of the Italian at the time. It was readable by anyone literate, not merely the educated elite. My translation is by W. K. Marriott.
I wrote down quite a few lines, of course. The book is definitely quotable, not least for “it is better to be feared than loved” - although that one is often quoted out of context. Machiavelli noted that it is best to be both feared (by one’s enemies) and loved (by one’s people and allies), but if you have to pick, fear is more effective when the chips are down.
Let’s start with the dedication. It is helpful to remember that Machiavelli wasn’t just a writer and philosopher - he was a working diplomat.
Those who strive to obtain the good graces of a prince are accustomed to come before him with such things as they hold most precious, or in which they seem him take the most delight: whence one often sees horses, arms, cloth of gold, precious stones, and similar ornaments presented to princes, worthy of greatness.
Desiring therefore to present myself to your Magnificence with some testimony of my devotion towards you, I have not found among my possessions anything which I hold more dear than, or value so much as, the knowledge of the actions of great men, acquired by long experience in contemporary affairs, and a continual study of antiquity; which, having reflected upon it with great and prolonged diligence, I now send, digested into a little volume, to your Magnificence.
That’s a pretty epic humblebrag. “I may not have gold and stuff, but my own wisdom is more precious anyway.” He’s not wrong, but damn, that's hella cheeky.
Early in the book, Machiavelli looks at what a prince needs to do to maintain power when he has annexed a new territory. There are two parts to this:
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 the their former lord is extinguished; the other, that neither their laws nor their taxes are altered, so that in a very short time they will become entirely one body with the old principality.
In other words, whack the old guy and his heirs, so nobody can claim your throne, but leave the basic government and tax burden in place, so the people will say “meet the new boss, same as the old boss” and not rebel.
This is a lesson most authoritarians fail to learn, to their own disaster. (And yes, they also forget that the usual cure for unpopular tyrants is the extermination of their entire families. Fail to learn from history…)
Later, Machiavelli expands on this. If you acquire a state which is used to its own laws and freedoms, there are a limited number of approaches you can use. One is to utterly destroy it. Which causes its own problems, not least of which is destroying much of the value of what you gain. You can also personally live in and govern a state - this gives personal control and a feel of the pulse of the place. Or, you can leave the laws and freedoms in place. Failure to do that leads to disaster.
And he who becomes master of a city accustomed to freedom and does not destroy it, may expect to be destroyed by it, for in rebellion it has always been the watchword of liberty and its ancient privileges as a rallying point, which neither time nor benefits will ever cause it to forget.
This is a reality that the Trump Regime is already running up against with the increasing ineffectiveness of ICE in the face of popular displeasure and resistance.
Also related to this is that the most effective and long-lasting changes are evolutionary, rather than revolutionary. Machiavelli puts his finger on why.
And it ought to be remembered that there is nothing more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new.
After all, the new hasn’t yet been proven. This cuts across political lines, of course. Which is one reason progress is difficult, and often comes as the result of the clear failure of the old ways. (Great example: the New Deal arising out of the Depression.)
Another insight of the book is that success is often due, not to merit, but to good fortune and the aid of others. And neither of these is to be counted on to last forever - particularly for those who lack the personal merit to maintain what they have inherited.
Such stand simply on the goodwill and the fortune of him who has elevated them - the two most inconstant and unstable things. Neither have they the knowledge requisite for the position; because, unless they are men of great worth and ability, it is not reasonable to expect that they should know now to command, having always lived in a private condition; besides they cannot hold it because they have not forces which they can keep friendly and faithful.
This is, in my view, the future of MAGA. Here is another relevant passage, on whether one should try to please the oligarchs or the people. In Machiavelli’s view, the oligarchs will always consider themselves equal to the prince, and thus perfectly willing to overthrow him if he fails to suit their purposes. Whereas the people….
Besides this, 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, whilst 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.
War is a significant topic of the book, and Machiavelli challenges the common practice of relying on mercenaries. In his view, a prince needs soldiers who are loyal to him personally, not just to their paycheck. (After all, if the other guy offers more…) But also interesting is that he sees the soldiers of republics to be the most formidable of all - they are the ones loyal to their country, not to a person or a paycheck.
And experience has shown princes and republics, single-handed, making the greatest progress, and mercenaries doing nothing except damage; and it is more difficult to bring a republic, armed with its own arms, under the sway of one of its citizens than it is to being one armed with foreign arms.
A pair of world wars gave strong evidence of the truth of this.
It is chapter 15 that contains the statement of the core values of Machiavellianism. I think it is more nuanced than the stereotype, but it does contain the amoral pragmatism as its core.
But, it being my intention to write a thing which shall be useful to him who apprehends it, it appears to me more appropriate to follow up the real truth of a matter than the imagination of it; 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.
Hence it is necessary for a prince wishing to hold his own to know how to do wrong, and to make use of it according to necessity.
That really is the core idea of that particular chapter, but in context of the entire work, it is a lot more nuanced than it has often been made out to be. Likewise, the idea of “fear or love” isn’t a simple dichotomy.
Upon this a question arises: whether it be better to be loved than feared or feared than loved? It may be answered that one should wish to be both, but, because it is difficult to unite them in one person, it is much safer to be feared than loved, when, of the two, either must be dispensed with. Because this is to be asserted in general of men, that they are ungrateful, fickle, false, cowardly, covetous, and as long as you succeed, they are yours entirely; they will offer you their blood, property, life, and children, as is said above, when the need is far distant; but when it approaches they turn against you.
He also clarifies another distinction:
Nevertheless a prince ought to inspire fear in such a way that, if he does not win love, he avoids hatred; because he can endure very well being feared whilst he is not hated, which will always be as long as he abstains from the property of his citizens and subjects and from their women.
For Machiavelli, this is a line you don’t cross. If you have to be harsh, be harsh in a defensible way, for a defensible reason, but not because of greed or selfishness.
I would update this idea a bit for our own time and situations. For a manager (like my wife), it is more important that she be respected than loved. For the same reasons Machiavelli notes here. But on the other hand, hate often comes from favoritism and arbitrary decisions, while scrupulous fairness and rational decision making earn respect in the long run.
I suspect that another “controversial” assertion of the book is that appearance is more important than reality; hypocrisy is a virtue and a tool in its own way. Unfortunately the truth of this is all too apparent in practice. Here are a few highlights:
But it is necessary to know well how to disguise this characteristic, and to be a great pretender and dissembler; and 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.
Sigh.
Therefore it is unnecessary for a prince to have all the good qualities I have enumerated, but it is very necessary to appear to have them. And I shall dare to say this also, that to have them and always to observe them is injurious, and that to appear to have them is useful; to appear merciful, faithful, humane, religious, upright, and to be so, but with a mind so framed that should you require not to be so, you may be able and know how to change to the opposite.
…
For this reason a prince ought to take care that he 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.
I might note again that this is an area where Trump and MAGA seem to have skipped the assignment. If the goal was to win over a majority of the population, this is the way, not flaunting one’s horribleness. Sure, that works for the racist base, but being hated by more than a majority seems….risky. See above…and this next one in the longer chapter on how and why to avoid being hated.
But concerning his subjects, when affairs outside are disturbed he has only to fear that they will conspire secretly, from which a prince can easily secure himself by avoiding being hated and despised, and by keeping the people satisfied with him, which it is most necessary for him to accomplish, as I said above at length. And one of the most efficacious remedies that a prince can have against conspiracies is not to be hated and despised by the people, for he who conspires against a prince always expects to please them by his removal; but when the conspirator can only look forward to offending them, he will not have the courage to take such a course, for the difficulties that confront a conspirator are infinite.
Uneasy is the head that wears the crown indeed.
In contrast, Machiavelli argues that a prince should inspire the love and admiration of his people through his deeds.
Nothing makes a prince so much esteemed as great enterprises and setting a fine example.
While Machiavelli sees “renown” primarily in a military context, I think that it should be expanded beyond that - and indeed “renown” in a national context in our world (and the past too, actually) goes beyond whose military is the best. Commerce, education, opportunity, infrastructure - all of these can and do inspire pride in a people and attract others to join them.
Machiavelli expands this into the question of meddling in foreign wars, and choosing a side in an inevitable conflict. For him, it is better to pick the losing side - at least in that case you have a future ally when fortunes turn - than to try to straddle the fence. Only “irresolute princes” fear present dangers and try to play both sides, thus being ruined no matter who wins. Show some backbone.
In the same chapter, Machiavelli expands his ideas beyond war to advise a prince to encourage those of ability and skill, and thus enrich his nation.
A prince ought also to show himself a patron of ability, and to honor the proficient in every art. At the same time he should encourage his citizens to practice 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; but the prince ought to offer rewards to whoever wishes to do these things and designs in any way to honour his city or state.
Um, again, the Trump Regime hasn’t done its homework. The smart, skilled, competent people are the ones you should encourage, not the ignorant, stupid, and often drunk grifters. And slapping tariffs on commerce…well, not recommended.
Does Machiavelli also have opinions about who to hire for one’s cabinet? Of course he does!
The choice of servants is of no little importance to a prince, and they are good or not according to the discrimination of the prince. And the first opinion one forms of a prince, and of his understanding, is by observing the men he has around him; and when they are capable and faithful he may always be considered wise, because he has known how to recognize the capable and to keep them faithful. But when they are otherwise one cannot form a good opinion of him, for the prime error which he made was in choosing them.
I’ll end with an interesting passage about the effect of fortune in human affairs. I think that Machiavelli is pretty accurate here - and his advice is sound. Understand that fortune plays a significant role, but make provision to take the tide in the affairs of men. (Although maybe Brutus isn’t the one to consult for when the tide is favorable…) This seems like fitting for our own turbulent times.
It is not unknown to me how many men have had, and still have, the opinion that the affairs of the world are in such wise governed by Fortune and by God that men with their wisdom cannot direct them and that no one can even help them; and because of this they would have us believe that it is not necessary to labour much in affairs, but to let chance govern them. This opinion has been more credited in our times because of the great changes in affairs which have been seen, and may still be seen, every day, beyond all human conjecture. Sometimes pondering over this, I am in some degree inclined to their opinion. Nevertheless, not to extinguish our free will, I hold it to be true that Fortune is the arbiter of one-half of our actions, but that she still leaves us to direct the other half, or perhaps a little less.
So yes, fate, fortune, god, whatever - it all does have an effect. But not the whole effect. We are left with choices.
I think as a whole, what Machiavelli is attempting to do with this book is to give advice as to how to act wisely, within his framework of what that means. It is not a moral absolute, but a practical and pragmatic approach to governance, power, and stability. Sure, be unscrupulous at times, and earn respect before love. But also, win the hearts of your people, reward competence, build alliances with discretion, and do what you can within the bounds of the fortune you have.
The Prince is neither the “godless, immoral poison” that I was taught it was, nor an infallible guide to politics; but it is interesting, with some good insights, and pragmatic lessons for governance. It is both of its time and timeless, in varying measure.
So, read it like one would govern: pragmatically, and practically, and with an open and flexible mind.

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