The Prince

Based on Wikipedia: The Prince

In 1513, a frustrated Italian diplomat sat down to write the most infamous instruction manual in Western history. Niccolò Machiavelli had just been kicked out of government, tortured on the rack for allegedly plotting against the Medici family, and exiled to his small farm outside Florence. And there, bitter and broke, he wrote The Prince—a book that would make his name synonymous with ruthless cunning for the next five centuries.

What makes this slim treatise so shocking? Machiavelli told rulers what everyone already knew but no one dared say out loud: that holding onto power sometimes requires doing terrible things. That being good will get you killed. That morality is a luxury princes cannot always afford.

A Book Born in Exile

Machiavelli originally titled his work De Principatibus, meaning "Of Principalities," writing it in Latin for an audience of the learned. But the version that circulated—and scandalized Europe—was in vernacular Italian. This was still relatively novel in 1513. Dante had published his Divine Comedy in Italian less than two centuries earlier, breaking with the tradition that serious works belonged in Latin.

The book wasn't published until 1532, five years after Machiavelli's death. Even then, it required permission from Pope Clement the Seventh, himself a member of the Medici family to whom Machiavelli had dedicated the work. But manuscript copies had been circulating for years, and controversy had been swirling since the moment people first read it.

Why? Because The Prince reads like a handbook for tyrants.

What Makes It Different

At first glance, The Prince looks like it belongs to an old genre called "mirrors for princes"—advice books telling rulers how to govern well. Medieval Europe was full of these earnest treatises about kingly virtue and Christian duty.

But Machiavelli's approach was radically different. Where other writers told princes to be good, Machiavelli told them to be effective. Where others preached Christian virtue, Machiavelli studied what actually worked. He filled his pages with examples from history—Roman generals, biblical figures, medieval kings—but also from his own lifetime. Most notoriously, he held up Cesare Borgia as a model to imitate.

Cesare Borgia. A man who murdered his way across central Italy, executed his own lieutenants when they became inconvenient, and had his enforcer cut in half in the town square as a public relations stunt.

This is who Machiavelli told princes to emulate.

Politics Without God

The Prince is sometimes called one of the first works of modern political philosophy. What makes it modern is that it treats practical results as more important than abstract ideals. It asks not "what should a good ruler do?" but "what does a ruler need to do to stay in power?"

This worldview crashed headlong into Catholic and scholastic doctrine. The medieval church taught that rulers derived their authority from God and must govern according to Christian principles. Machiavelli swept all that aside. In his analysis, power comes from force and cunning, and it must be held by whatever means necessary.

The book's influence extended beyond political theory. It helped shape the modern negative connotations of the words "politics" and "politician" in Western languages. When we say someone is "Machiavellian," we mean they're manipulative and amoral. When we say "it's just politics," we mean ruthless self-interest dressed up as principle. We have this one short book to thank for that.

How to Read The Prince

Machiavelli begins with a letter to Lorenzo de' Medici, Duke of Urbino. This is a remarkable piece of sycophancy from a man who had been tortured by Lorenzo's family. But Machiavelli desperately wanted back into political life, and he was willing to flatter his way there.

The opening sentence introduces a key term: "state." In Italian, stato could mean either "state" or "status," and Machiavelli uses it to describe "all forms of organization of supreme political power, whether republican or princely." Scholars have spent centuries debating how the word "state" acquired its modern meaning, and this sentence sits at the center of that debate.

Types of Princedoms

Machiavelli announces that he's writing about princedoms, not republics. He's already written about republics elsewhere—a reference to his longer work, the Discourses on Livy. But even as he makes this distinction, he blurs it. Throughout The Prince, he discusses republics alongside principalities, effectively treating republics as a type of princedom with certain advantages.

More importantly, he distinguishes between hereditary princedoms and new ones. Hereditary princedoms are easy. If you inherit a kingdom your family has ruled for generations, your subjects are "naturally well disposed towards you" unless you're spectacularly awful. The real challenge comes with new princedoms—territories you've just conquered, positions you've just seized.

This focus on new princes was itself an innovation. Traditional advice books addressed hereditary rulers. But Machiavelli writes for the upstart, the ambitious man who needs to establish himself "in defiance of custom." This may reflect his own experience in Florentine politics, where he watched new men rise and fall with bewildering speed.

His categorization of regime types also breaks with tradition. Aristotle, in his Politics, had divided governments into rule by one person, by a few people, or by many people—and then further divided these into good and corrupt forms. So you had monarchy versus tyranny, aristocracy versus oligarchy, democracy versus mob rule.

Machiavelli ignores all of that. He doesn't care whether a regime is "good" or "corrupt." He only cares whether it's stable and effective.

How to Hold a Conquest

New princedoms, Machiavelli explains, are either completely new or "mixed"—meaning you've added new territory to an existing state. He looks to Rome for lessons on how to hold a newly acquired province:

• Install yourself there personally, or send colonies of your own people
• Keep smaller local powers happy without making them stronger
• Crush anyone powerful enough to threaten you
• Don't let foreign powers gain influence

More broadly, don't just solve present problems—anticipate future ones. Time brings evil as well as good, so you can't simply wait and hope things work out.

Machiavelli notes that acquiring territory stems from a "natural and ordinary desire." People who act on this desire can be "praised or blamed" depending on whether they succeed. He then analyzes how the King of France failed to conquer Italy, explaining exactly what went wrong and how it could have succeeded.

One chilling line stands out: "If an injury is to be done to a man, it should be so severe that the prince is not in fear of revenge." In other words, if you're going to hurt someone, hurt them so badly they can never strike back.

Two Kinds of Kingdoms

Some kingdoms depend on powerful nobles who have their own power bases. Sixteenth-century France was like this—the king ruled, but great nobles controlled vast territories and could cause trouble. These kingdoms are easy to invade because you can ally with discontented nobles. But they're hard to hold because those same nobles will turn against you.

Other kingdoms revolve entirely around the monarch, with everyone else merely a servant. These are hard to invade because there's no faction to ally with. But once you conquer them, they're easy to hold. Just eliminate the old royal bloodline.

Machiavelli uses the Persian Empire as an example. When Alexander the Great conquered Persia, he faced fierce resistance. But once he defeated King Darius the Third, Persia stayed conquered. Why? Because the entire government structure depended on the king. Remove the king and his family, and there's no one left to lead a rebellion.

He then compares this to the Ottoman Empire of his own time—suggesting it would be easier to hold than France if anyone could conquer it.

The Problem of Free Republics

This chapter is unusual. Previous advice books for princes rarely discussed conquering republics, perhaps because most of Europe was already ruled by monarchies. But Italy had several free republics—Florence, Venice, Genoa—and Machiavelli's dream was to see Italy united.

The problem? Republics are incredibly difficult to hold. People who have tasted freedom never forget it. Machiavelli gives three options:

• Destroy the republic completely, as Rome destroyed Carthage
• Move there and rule it personally
• Keep the republic's structure intact but install a loyal oligarchy

He recommends the first option. "If a prince does not destroy a city, he can expect to be destroyed by it."

Virtue Versus Fortune

Now we reach the heart of Machiavelli's analysis. Some princes rise through their own ability and cunning—what he calls virtù, a term that means something closer to "effectiveness" or "prowess" than our modern "virtue." Others rise through luck or circumstance—fortuna.

Princes who rise by their own virtù have a hard time gaining power. They face fierce opposition. They must fight for every inch of ground. But once they reach the top, they're secure. They've crushed their enemies and earned everyone's respect. They depend on no one but themselves.

The Challenge of Reform

Reforming an existing order is one of the most dangerous things a prince can attempt. People resist change instinctively. Those who benefited from the old system will fight you tooth and nail. Those who might benefit from the new system will offer only lukewarm support, because they're not sure the new order will deliver on its promises.

Moreover, a prince cannot possibly satisfy everyone's expectations. He will inevitably disappoint some of his followers. Therefore, he must have the power to force his supporters to keep supporting him even when they start having second thoughts.

Only armed prophets succeed in bringing lasting change. Machiavelli points to Moses, who killed "uncountable numbers" of his own people to enforce his will.

This insight wasn't entirely original. Aristotle had noted the danger in new laws. But Machiavelli emphasized it far more strongly, perhaps because he'd seen the extraordinary level of corruption in Italian politics.

Princes Who Rise by Luck

When a prince gains power through luck or powerful patrons, he has an easy time rising but a hard time staying on top. His power depends on his benefactors' goodwill. He doesn't command personal loyalty from armies and officials. These can be withdrawn at a whim. And having risen the easy way, he may not have the skill to stand on his own.

But there are exceptions. Cesare Borgia is Machiavelli's favorite example.

Borgia was made commander of the papal armies by his father, Pope Alexander the Sixth. He depended heavily on mercenaries loyal to the Orsini brothers and on support from the French king. But through cunning maneuvers, he secured his own power base.

He won over the Orsini followers with better pay and prestigious positions. He sent his enforcer, Remirro de Orco, to pacify the Romagna region through brutal violence. When Remirro became hated, Borgia had him cut in two and displayed in the town square—showing the people that the cruelty hadn't come from Borgia himself, though of course it had. When mercenary captains plotted against him, he captured and executed them. When the French king seemed ready to abandon him, Borgia sought new alliances.

Machiavelli also makes a darker observation: bringing new benefits to conquered people will never erase the memory of old injuries. The original inhabitants will always resent you.

Criminal Virtue

Some princes secure power through outright criminal acts—eliminating political rivals through murder and treachery. Machiavelli offers two examples to study and imitate.

First, Agathocles of Syracuse. After becoming Praetor, he called a meeting of the city's elite. At his signal, soldiers killed all the senators and wealthiest citizens, completely destroying the old oligarchy. He then declared himself ruler with no opposition. His power was so secure that he could leave the city to campaign in Africa without fear.

But Machiavelli hesitates to call this virtù. "Yet one cannot call it virtue to kill one's citizens, betray one's friends, to be without faith, without mercy, without religion. These modes can enable one to acquire empire, but not glory." Agathocles gained power but not honor.

Second, Oliverotto de Fermo, a condottiero who killed his uncle and all his enemies at a banquet. He terrorized the city into submission and set himself up as absolute ruler. But in an ironic twist, Cesare Borgia later invited Oliverotto to a friendly meeting—and had him strangled.

Machiavelli's advice? Calculate all the cruel deeds you need to do, then execute them all at once. This way, people will slowly forget. If you commit atrocities gradually, you'll have to "keep a knife by your side" forever, because your subjects will never trust you.

This directly contradicts Aristotle, who advised the opposite—spread out your harsh measures so people don't feel overwhelmed. Machiavelli says rip off the bandage all at once.

The Civil Principality

A "civil principality" is one where a citizen rises to power with the support of his fellow citizens—not through crime or violence, but through what Machiavelli calls "fortunate astuteness."

In every city, two groups exist with opposite desires: the "great" and the "people." The great want to oppress and rule. The people want not to be ruled or oppressed. These conflicting appetites can lead to three outcomes: a principality, liberty, or license (chaos).

A principality emerges when either the great or the people see an opportunity to take power but face resistance from the other side. They install a leader—someone popular with the people but beneficial to the great, or someone strong enough to protect the people from the great.

This sets up one of the key questions in The Prince: Should a ruler align with the great or with the people? Machiavelli will return to this question repeatedly, and his answer is more subtle than you might expect.

Why This Book Still Matters

The Prince is only about twenty-five thousand words long. You can read it in an afternoon. Yet it has provoked more commentary, inspired more outrage, and influenced more political thought than books ten times its length.

Why? Because Machiavelli said what everyone knows but pretends not to know. That politics is about power, not principle. That leaders often must choose between being good and being effective. That the world rewards ruthlessness more often than it rewards virtue.

He wrote these truths down in clear, cold prose, illustrated with historical examples, and offered them as practical advice. In doing so, he created the template for modern political realism—the view that in politics, outcomes matter more than intentions, and power is its own justification.

We've been arguing with him ever since.