The Machiavellian Maze

Power, politics, and painful tradeoffs

“Machiavelli’s doctrine was a sword thrust in the body politic of Western humanity, causing it to cry out and struggle against itself.”

—Friedrich Meinecke (1862-1954)

This is an overview of Niccolò Machiavelli—his backstory, his personal views, a summary of Machiavellian thought, and an explanation for why his ideas have been so despised throughout history.

Throughout his books, Machiavelli seems to take delight in demonstrating—much to his reader’s discomfort—the distance between our lofty intentions and the actual consequences of our deeds.

Writing in the sixteenth century, Machiavelli anticipated Nietzsche’s conception of master and slave morality by some three hundred years.

In Ch. 15 of The Prince he wrote:

“Since it is my intent to write something useful to whoever understands it, it has appeared to me more fitting to go directly to the effectual truth of things than to the imagination of it…many have imagined republics and principalities that have never been seen or known to exist in truth…he who lets go of what is done for what should be done learns his ruin rather than his preservation.”

This passage is often viewed as the essence of Machiavellianism. He had no intentions of disguising unpleasant realities. He wanted to describe the world as it is, and not as people wish it to be.

A very brief bit of background: Niccolò Machiavelli was born in 1469. He descended from minor nobility. Serving as a diplomat, Machiavelli had direct experience in Florentine politics. Later, he organized a Florentine militia against the Medici family who had risen to power. He failed, and was subsequently imprisoned, tortured, and exiled. He spent his remaining days reading and writing. He’d seen the best and worst of human nature.

In the David vs. Goliath biblical story, God was on David’s side because God had chosen him to be king. Recall that in the story, David was armed with only a sling.

In Machiavelli’s own retelling of the story in chapter 13 of The Prince, he includes a subtle addition. He says that David went into battle against Goliath with “a sling and a knife.” Machiavelli gives him a knife. Where did this come from? Perhaps it was Machiavelli’s mischievous way of saying, “Trust in God’s promises, yes. But bring a knife just in case.”

Machiavelli’s preface in Discourses on Livy:

“Although the envious nature of men has always made it no less dangerous to find new modes and orders than to seek unknown waters and lands, because men are more ready to blame than to praise the actions of others, nonetheless, driven by that natural desire that has always been in me to work, without any respect, for those things I believe will bring common benefit to everyone, I have decided to take a path as yet untrodden by anyone, and if it brings me trouble and difficulty, it could also bring me reward through those who consider humanely the end of these labors of mine.”

He goes on:

“If poor talent, little experience of present things, and weak knowledge of ancient things make this attempt of mine defective and not of much utility, it will at least show the path to someone with more virtue, more discourse and judgment, will be able to fulfill this intention of mine, which, if it will not bring me praise, ought not to incur blame.”

Machiavelli says he aims to do for politics what Columbus did for geography.

He has a new world in mind, “new modes and orders.” And he argues that it requires a displacement of the previous one.

Machiavelli rejected the dominant utopian ideas of his day, including Platonic or Augustinian cities of God and the concept of Christian universalism (or its modern variant of Humanism).

Machiavelli warns rulers to be on guard against those who do not see men as they are, and see them through spectacles colored by their hopes and wishes, their loves and hatreds, in terms of an idealized image that they want men to be, and not as they are.

Some pieces of advice Machiavelli offers to rulers:

• Employ brutality or kindness, as the case requires. Brutality is usually more effective, but kindness, in some situations, bears more fruit

• It’s better to be feared than loved. Love is fickle, but fear is predictable. The worst is to be hated. Hatred will lead your subjects to destroy you

• It's a good idea to keep your people in a state of poverty and always prepared for war. This helps to reduce both ambition and boredom—two qualities that can undermine obedience

• Fierce competition in a society is desirable, for it generates energy and ambition

• Religion must be promoted regardless of how truthful it is, because it supplies social solidarity

• When you confer benefits to the people, make sure to do so yourself. But let minions do the dirty work of inflicting punishments because then they, not you, will be blamed, and you can then gain the people’s favor by cutting off your minions’ heads

• Men prefer vengeance and security to liberty

• If you have to commit a crime, don’t advertise it beforehand. Otherwise your enemies may destroy you before you destroy them

• Punishment should be delivered in a swift and brutal manner, while rewards should be dispersed in small amounts over time

• Be wary of powerful advisors and servants—victorious generals should be purged after they have served their purpose, otherwise they may attempt to usurp you

• You can be violent and use your power to command obedience, but if you break your own laws you will undermine societal stability

• Men should either be caressed or annihilated; appeasement and neutralism always lead to ruin. Your adversaries can recover from minor injuries and setbacks to seek revenge. But if you crush them totally, you neutralize any threat.

• Rulers must live in the constant expectation of war

• Success inspires more devotion than friendliness and affability

• Men will lie to you unless you compel them to be truthful by creating circumstances in which deception will not pay

This list could continue but I’ll stop here.

In Ch. 25 of The Prince, Machiavelli uses two metaphors to describe the idea of “fortune,” or luck.

One metaphor is that fortune is like a violent river that can, to a limited extent, be managed and contained and navigated.

The other metaphor from The Prince, more objectionable in our modern times, is that fortune is like a woman:

“It is better to be impetuous than cautious, because fortune is a woman; and it is necessary, if one wants to hold her down, to beat her and strike her down. And one sees that she lets herself be won more by the impetuous than by those who proceed coldly. And so always, like a woman, she is the friend of the young, because they are less cautious, more ferocious, and command her with more audacity.”

Commenting on this passage, the Harvard political philosopher Harvey Mansfield has remarked, “The young men who master Lady Fortune come with audacity and leave exhausted, but she remains ageless.”

Here Machiavelli describes his reading routine in a letter to Francesco Vettori:

“When evening has come, I return to my house and go into my study. At the door I take off my clothes of the day, covered in mud and mire, and I put on my regal and courtly garments; and decently reclothed, I enter the ancient courts of ancient men, where, received by them lovingly, I feed on the food that alone is mine and that I was born for. There I am not ashamed to speak with them and to ask them the reason for their actions; and they in their humanity reply to me. And for the space of four hours I feel no boredom, I forget every pain, I do not fear poverty, death does not frighten me. I deliver myself entirely to them.”

Elsewhere in the letter, Machiavelli states that he loves his native city of Florence more than his own soul. Keep this in mind.

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When asked about Machiavelli’s reputation, people use terms like “amoral,” “cynical,” “unethical,” or “unprincipled.” But this is incorrect. Machiavelli did believe in moral virtues, just not Christian or Humanistic ones.

What did he actually believe? 

In 1953, the British philosopher Isaiah Berlin delivered a lecture titled “The Originality of Machiavelli”.

Berlin began by posing a simple question: Why has Machiavelli unsettled so many people over the years?

Machiavelli believed that the Italy of his day was both materially and morally weak. He saw vice, corruption, weakness, and, as Berlin says, “lives unworthy of human beings.” It’s worth noting here that around the time that Machiavelli died in 1527, the Age of Exploration was just kicking off, and adventurers from Italy and elsewhere in Europe were in the process of transforming the world. Even the shrewdest individuals aren’t always the best judges of their own time.

So what did Machiavelli want? He wanted a strong and glorious society. Something akin to Athens at its height, or Sparta, or the kingdoms of David and Solomon. But really, Machiavelli’s ideal was the Roman Republic.

To build a good state, a well-governed state, men require “inner moral strength, magnanimity, vigour, vitality, generosity, loyalty, above all public spirit, civic sense, dedication to security, power, glory.”

According to Machiavelli, these are the Roman virtues.

In contrast, the ideals of Christianity are “charity, mercy, sacrifice, love of God, forgiveness of enemies, contempt for the goods of this world, faith in the hereafter.”

Machiavelli wrote that one must choose between Roman and Christian virtues. If you choose Christianity, you are selecting a moral framework that is not favorable to building and preserving a strong state.

Machiavelli does not say that humility, compassion, and kindness are bad or unimportant. He actually agrees that they are, in fact, good and righteous virtues. He simply says that if you adhere to them, then you will be overrun by more unscrupulous men.

In some instances, Machiavelli would say, rulers may have to commit war crimes in order to ensure the survival of their state. As one Machiavelli translator has put it: “Men cannot afford justice in any sense that transcends their own preservation.”

From Berlin’s lecture:

"If you object to the political methods recommended because they seem to you morally detestable…Machiavelli has no answer, no argument…But you must not make yourself responsible for the lives of others or expect good fortune; you must expect to be ignored or destroyed."

In a famous passage, Machiavelli writes that Christianity has made men “weak,” easy prey to “wicked men,” since they “think more about enduring their injuries than about avenging them.” He compares Christianity (or Humanism) unfavorably with Paganism, which made men more “ferocious.”

“One can save one’s soul,” writes Berlin, “or one can found or maintain or service a great and glorious state; but not always both at once.”

Again, Machiavelli’s tone is descriptive. He is not making claims about how things should be, but rather how things are. Although it is clear what his preference is.

He writes that Christian virtues are “praiseworthy.” And that it is right to praise them. But he says they are dead ends when it comes to statecraft.

Machiavelli wrote:

“Any man who under all conditions insists on making it his business to be good, will surely be destroyed among so many who are not good. Hence a prince…must acquire the power to be not good, and understand when to use it and when not to use it, in accord with necessity.”

To create a strong state, one cannot hold delusions about human nature:

“Everything that occurs in the world, in every epoch, has something that corresponds to it in the ancient times. The reason is that these things were done by men, who have and have always had the same passions.”

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In The Prince, Machiavelli wrote that men are “ungrateful, wanton, false,” and “cowardly, greedy, arrogant and mean, and their natural impulse is to be insolent when their affairs are prospering and abjectly servile when adversity hits them.”

Actual, empirical, flesh-and-blood human beings are not as they are described by those who idealize them nor by those who want them to be wildly different from what in fact they are and always have been and cannot help being.

Machiavelli believed ruthlessness was sometimes necessary for a ruler—fraud, force, treachery, and even slaying the innocent may be used in the service of building and preserving a strong and stable state.

In the Discourses on Livy, Machiavelli argued that Romulus's murder of his brother Remus was necessary to gain the power he needed to found Rome.

The political philosopher Leo Strauss later applied this logic to the United States, writing that Machiavelli, "would not hesitate to suggest a mischievous interpretation of the Louisiana Purchase and of the fate of the Red Indians. He would conclude that facts like these are an additional proof for his contention that there cannot be a great and glorious society without the equivalent of the murder of Remus by his brother Romulus."

Again, Machiavelli contrasted Roman vs. Christian ideals. One can save one’s soul by adhering to the Christian ideals of mercy, charity, forgiveness of one’s enemies, and contempt for the goods of this world. But to create and preserve a strong state, Machiavelli asserted, one must adhere to the Roman ideal: Power, magnificence, pride, austerity, discipline, pursuit of glory.

His great transgression, according to Berlin, was to say aloud what everyone knows but no one will admit: multiple ideals cannot be simultaneously attained. We can’t have everything good all at once.

Not only did Machiavelli admit this, but he showed, “no trace of agony” about it. He was interested in achieving “security, independence, success, glory, strength, vigour, felicity on earth, not in heaven.”

There is no way to comfortably reconcile the virtues of Christian meekness with the virtues of Roman strength.

“Consequently,” suggests Isaiah Berlin, “a man must choose. To choose to lead a Christian life is to condemn oneself to political impotence: to being used and crushed by powerful, ambitious, unscrupulous men; if one wishes to build a glorious community like those of Athens or Rome at their best, then one must abandon Christian education and substitute one better suited to the purpose.”

Elaborating on Machiavelli’s contributions, Berlin stated:

“One of the deepest assumptions of western political thought is the doctrine, scarcely questioned during its long ascendancy, that there exists some single principle which not only regulates the course of the sun and the stars, but prescribes their behaviour to all animate creatures.”

“Machiavelli’s cardinal achievement is… his de facto recognition that ends equally ultimate, equally sacred, may contradict each other, that entire systems of value may come into collision without the possibility of rational arbitration, and not merely in exceptional circumstances, as a result of abnormality or accident or error…but as part of the normal human situation.”

“If what Machiavelli believed is true, this undermines one major assumption of western thought: namely that somewhere in the past or the future, in this world or the next, in the church or the laboratory, in the speculations of the metaphysician or the findings of the social scientist, or in the uncorrupted heart of the simple good man, there is to be found a final solution of the question of how men should live. If this is false (and if more than one equally valid answer to the question can be returned, then it is false) the idea of the sole, true, objective, universal human ideal crumbles. The very search for it becomes not merely Utopian in practice, but conceptually incoherent.”

Machiavelli’s detractors say what disturbs them is Machiavelli’s comfort with unscrupulous (Roman) methods to establish and maintain a powerful and well-governed state.

Berlin, though, says what unsettles them is that Machiavelli had inadvertently revealed that there are multiple equally desirable ideals, and that it is impossible to achieve one without sacrificing others. He implicitly recognized that equally sacred ends can collide with no possibility of reconciliation.

Machiavelli contrasts the Christian (or Humanistic) and Roman moral universes. You can choose the first and save your soul, or you can choose the second and save your state. Machiavelli loved Florence more than his own soul. He wanted to save it and restore it to glory. Through is writing, he made clear which morality he preferred.

Machiavelli unintentionally revealed that people must make choices between virtues that are incompatible with one another. He demonstrated that there are no final solutions that harmonize all equally valid moral ends. There are only tradeoffs and compromises. This, Berlin suggests, is why the infamous Florentine has been so hated and maligned throughout history. The character assassination of Machiavelli is due to his having uncovered an uncomfortable truth that most people do not want to confront: you can’t have all good things at the same time.