The Prince

Chapter 1 — How many kinds of Principalities there are, and by what means they are acquired

Every political system that rules people—every state, every government, every power structure—ultimately falls into one of two buckets:

• Republics
• Principalities (states ruled by a single prince)

Since this book focuses on principalities, we need a clean map of the different kinds—and how people end up holding them.

Two Main Types of Principalities

A principality is either:

• Hereditary: the same ruling family has held power for a long time.
• New: the ruler hasn’t “always” been the ruler—power has recently changed hands.

What “New” Can Mean

A “new” principality comes in two forms:

• Completely new: a ruler builds a state that didn’t belong to him at all before. (Machiavelli’s example: Milan becoming Francesco Sforza’s.)
• Attached to an old one: a ruler adds a new territory onto a state he already had—like bolting on an extra piece. (Example: Naples added to the King of Spain’s realm.)

What Makes a New Territory Hard—or Easy—to Hold

When you take over a territory, it usually has one of two political habits:

• It’s used to living under a prince.
• It’s used to living free (governing itself).

And there are only a few ways anyone acquires a state in the first place:

• By your own force (your own troops and power)
• By someone else’s force (you ride in on an ally’s army)
• By luck (fortune: timing, accidents, circumstances)
• By skill (ability: planning, strategy, competence)

That’s the basic toolkit. The rest of the book is about what happens after you get the prize—and whether you can keep it.

The king moved fast. Once he took Lombardy, he instantly recovered the influence Charles had squandered. City after city leaned his way: Genoa gave in; Florence switched to friendly; and a long line of local rulers and city-states—from Mantua and Ferrara to Forlì, Faenza, Pesaro, Rimini, Camerino, Piombino, Lucca, Pisa, Siena—hurried to be seen as his allies.

Only then did Venice fully grasp how badly it had misplayed things. To lock down two towns in Lombardy, it had helped make the French king master of roughly two-thirds of Italy.

Now, picture how easily he could’ve held Italy if he’d followed the basic rules already laid out—especially one: keep your allies safe and invested. He had plenty of friends, and most of them were both weak and nervous. Some feared the Church. Others feared Venice. In other words, they had every incentive to cling to him for protection, and through them he could’ve boxed in the remaining powerful players.

Instead, the moment he reached Milan, he did the opposite. He helped Pope Alexander seize the Romagna.

He didn’t seem to notice what he was doing to himself:

• He was shrinking his own position.
• He was pushing away allies who had practically thrown themselves at him.
• And he was inflating the Church’s power—not just spiritually, but with real territory and soldiers—giving it far more authority than it had before.

That first mistake forced a chain of follow-up mistakes. To contain Alexander’s ambition and keep him from becoming dominant in Tuscany, the king then had to return to Italy himself.

And as if strengthening the Church and losing his allies weren’t enough, he decided he also wanted Naples. So he split it with the King of Spain. Where he had been the clear referee of Italy, he voluntarily brought in a powerful partner-rival—giving Italy’s ambitious factions and his own dissatisfied subjects somewhere to run for shelter. Worse, he drove out the king he could’ve kept as a dependent and installed someone strong enough to push him out in return.

Wanting to acquire more is natural; it’s practically universal. When people can expand, they try—and they’re usually praised for it, not blamed. The problem is when they can’t do it, yet still insist on doing it anyway, by any means necessary. That’s where the foolishness starts.

So if France could’ve taken Naples with its own strength, it should’ve done so. If it couldn’t, it shouldn’t have tried to take it by sharing it.

Yes, France’s earlier deal with Venice over Lombardy had at least a plausible excuse: it bought France a foothold in Italy. But this later partition of Naples deserved blame, because it didn’t even have that necessity behind it.

So Louis made five major errors:

• He wiped out the smaller powers.
• He strengthened one of the major powers already in Italy (the Church).
• He invited in a foreign power (Spain).
• He didn’t settle in the country himself.
• He didn’t plant colonies to anchor his control.

And those five, by themselves, might not have ruined him during his lifetime—if he hadn’t made a sixth: he stripped territory from Venice.

Because here’s the irony: if he hadn’t swollen the Church and hadn’t brought Spain into Italy, then humbling Venice would’ve been sensible, even necessary. But after taking those earlier steps, he should never have agreed to Venice’s destruction. A strong Venice would always have deterred others from making grabs at Lombardy—and Venice would never have tolerated anyone else trying to take Lombardy unless Venice expected to take it for itself. And the other powers wouldn’t have had the nerve to fight both France and Venice at once.

If someone says, “Louis gave the Romagna to Alexander and Naples to Spain to avoid war,” the answer is simple: you don’t commit a blunder to dodge a war. You don’t avoid it. You just postpone it—and you postpone it on worse terms.

And if someone argues that Louis had promised the Pope help in exchange for personal political favors, I’ll address later what promises between princes are worth, and when they should be kept.

In the end, Louis lost Lombardy because he ignored every condition that experienced conquerors follow when they want to take a country and hold it. Nothing mysterious happened. It was all painfully logical.

I once discussed this in Nantes with Cardinal Rouen, around the time Cesare Borgia (often called “Valentino”) was occupying the Romagna. The cardinal remarked that Italians didn’t understand war. I told him the French didn’t understand politics—because if they did, they never would’ve let the Church grow so powerful.

And the evidence backs it up: the rise of both the Church and Spain in Italy was driven by France, and France’s collapse there can be traced back to those same choices.

From this comes a rule that almost never fails:

If you make someone else powerful, you ruin yourself.
Because the power you helped create was built either through skill or force—and either way, the person you raised will distrust you.

---

Chapter 4: Why Darius’s kingdom didn’t rebel after Alexander died

When people struggle to hold newly acquired states, it’s fair to wonder about Alexander the Great. He conquered Asia quickly, then died before his rule was fully settled. By ordinary logic, you’d expect the whole empire to revolt the moment he was gone. Yet his successors kept control, and their biggest troubles came from their own rivalries—not from the empire rising up.

The key is that states tend to be governed in one of two basic ways:

1. A single prince with officials: the ruler governs through ministers who hold power only because the prince allows it.
2. A prince with hereditary barons: powerful nobles rule their own territories by longstanding blood right, with subjects who recognize and even feel loyalty toward them.

These two models look similar from a distance, but they behave very differently under conquest.

In our time, you can see them clearly in the Turk and the King of France.

• Under the Turk, one lord stands above everyone; the rest are his servants. He divides the realm into districts and sends administrators, moving and replacing them whenever he chooses.
• In France, the king sits among an old class of lords who are rooted in their own lands, recognized by their own people, and protected by their own privileges—privileges the king cannot strip away without putting himself in danger.

From this, a conqueror learns something counterintuitive:

• It’s harder to conquer a state like the Turk’s, but easier to hold once you’ve conquered it.
• It’s easier to enter a state like France’s, but much harder to keep afterward.

Why is the Turk’s realm hard to seize? Because the attacker can’t expect help from insiders. The ruler’s ministers are dependent and isolated; they can’t easily be turned, and even if bribed they can’t carry the population with them. So anyone who attacks must assume they’ll meet a unified resistance and will have to rely mainly on their own force.

But once that ruler is beaten decisively—once his army is crushed so he can’t quickly replace it—there’s usually only one serious danger left: the prince’s family line. Remove that, and there’s no one else with enough authority or affection from the people to become a rallying point. The conqueror didn’t depend on those officials before victory, and he doesn’t need to fear them after.

France is the reverse. You can often enter it by winning over a baron, because you’ll always find the discontented—people eager for change. That makes the first victory easier. But holding the country later is a nightmare. You face resistance both from those who helped you (now negotiating for advantage) and from those you harmed. And even if you eliminate the king’s family, the surviving nobles can spark new movements. Since you can’t fully satisfy them and can’t easily eliminate them, you lose the state the moment circumstances give them an opening.

Now apply this to Darius. His government was closer to the Turk’s model. So Alexander needed only to defeat him in open battle and then take possession of the country. After that, Darius was killed, and the state stayed secure for the reasons above. If Alexander’s successors had remained united, they would’ve ruled it calmly and easily; the only unrest that arose was the unrest they created through their own conflicts.

States organized like France can’t be held with that kind of quiet. That’s why Rome faced repeated rebellions in Spain, France, and Greece: those places contained many principalities and many long memories. As long as people remembered their former rulers, Roman control stayed shaky. Over time, the empire’s length and strength erased those memories, and only then did Rome become secure.

Later, when Romans fought each other, each leader could attach portions of the territory to himself based on the authority he had built there. And with the former ruling families eliminated, no one remained who could claim legitimate leadership except the Romans themselves.

Remember all this, and Alexander’s story stops looking miraculous. His successors’ hold over Asia wasn’t a fluke. And when other conquerors struggle to keep new acquisitions, it’s not always about the conqueror’s brilliance or incompetence—it’s often about whether the conquered state is uniform in its structure or fragmented among competing centers of power.

---

Chapter 5: How to govern cities that used to live under their own laws

When you take a state that has long lived free, under its own laws, you have three options if you want to keep it:

1. Destroy it.
2. Move there yourself.
3. Let it keep its laws, impose tribute, and install a small oligarchy that depends on you.

That third option works because a government you create knows it can’t survive without you. Its leaders will work hard to keep your friendship, because their own power hangs on it. In that sense, you can sometimes hold a freedom-loving city more easily through its own citizens than through direct occupation.

History gives sharp examples.

The Spartans tried to control Athens and Thebes by setting up oligarchies. They still lost them. The Romans, by contrast, kept Capua, Carthage, and Numantia by dismantling them—and they didn’t lose them. When Rome tried the Spartan approach in Greece—leaving cities “free” and preserving their laws—it failed. In the end, Rome had to dismantle many cities there too.

The hard truth is this: there is no safe way to hold a city accustomed to freedom except by ruining it. If you don’t destroy it, expect it to destroy you. In rebellion, it always rallies around the word liberty and its old privileges—things neither time nor benefits will erase from memory. No matter what precautions you take, those ideas remain ready to ignite. Unless the city is divided or dispersed, it snaps back to that identity the moment it sees a chance—just as Pisa did, even after a century under Florentine control.

But when a people are used to living under a prince, and that prince’s family is eliminated, they behave differently. They’re accustomed to obedience, and they no longer have an established house to reunite around. They can’t easily agree on a new ruler from among themselves, and they don’t know how to govern themselves. As a result, they’re slow to take up arms—and a new prince can win them over and secure the territory far more easily.

Republics are another matter. They have more energy, more resentment, and a deeper hunger for revenge. They don’t let the memory of former liberty go quiet. So again, the safest paths are the harsh ones: destroy them or live among them.

---

Chapter 6: New principalities won by your own arms and ability

Don’t be surprised if, when discussing entirely new principalities, I use the highest-profile examples of rulers and states. People usually walk along paths others have already cleared; they imitate what worked before. But imitation has limits: you can’t perfectly copy another person’s methods, and you rarely reach their full power.

A wise person studies great leaders and aims to follow their strongest patterns. Even if you can’t match them, you can at least catch something of their caliber.

Think of an archer shooting at a distant target. Knowing the bow’s limits, the archer aims above the bullseye—not because they expect the arrow to reach the sky, but because that higher aim helps the arrow land where it needs to. That’s how you should treat great examples: aim high so your real shot lands closer to your mark.

In entirely new principalities—where there is a new prince—holding the state is harder or easier depending on the ability of the person who took it. Rising from private citizen to prince usually happens through ability or luck, and either one can soften some of the difficulties. Still, the ruler who relies least on luck tends to be the most secure.

It also helps when the new prince has no other state and is therefore compelled to live in the new territory himself.

Now, for those who rise by their own ability rather than fortune, the best examples are Moses, Cyrus, Romulus, Theseus, and others like them. We needn’t analyze Moses in the same way, since he acted as the executor of divine will, but he is still admirable for the favor that made him worthy of such a role.

As for Cyrus and the others who founded or seized kingdoms, their deeds and choices are consistently impressive. And if you look closely, you’ll see that fortune gave them little more than opportunity—raw material. Their ability shaped that material into the form they wanted. Without opportunity, their talents might have stayed buried. Without talent, opportunity would have come and gone without producing anything lasting.

Each of these founders needed a particular opening:

• Moses needed the Israelites oppressed in Egypt so they would be ready to follow someone who promised deliverance.
• Romulus needed to be cut off from Alba and abandoned at birth so he could become king and founder of a new homeland.
• Cyrus needed Persians dissatisfied with Median rule, and Medes softened by long peace.
• Theseus needed Athens scattered and disorganized so he could prove his strength by unifying it.

Opportunity made them “fortunate,” but their ability let them recognize the moment and use it to elevate their country and make it famous.

When people become princes by bold, capable action like this, they acquire power with difficulty—but they hold it with relative ease. The difficulty lies largely in what they must introduce: new rules and new methods to stabilize their government and secure it.

And keep this in mind: nothing is harder to begin, more dangerous to lead, or more uncertain to succeed than launching a new order of things. The reformer immediately makes enemies of everyone who benefited under the old system, and gains only half-hearted support from those who might benefit under the new.

People don’t usually embrace a new order of things right away. Part of that hesitation comes from fear: the people who benefit from the old system have the law, the institutions, and the habits of the public on their side. And part of it comes from plain human skepticism. Most of us don’t fully trust “the new way” until we’ve lived with it long enough to see it work.

That creates an imbalance that’s dangerous for any reformer. When opponents get an opening, they attack like a disciplined faction fighting for its life. Meanwhile, supporters often defend halfheartedly—so the innovator, and everyone tied to them, ends up exposed.

So if we want to understand how new regimes actually succeed, we have to ask a blunt question: can the innovator stand on their own, or do they need someone else to hold them up?

In other words:

• Do they have to rely on pleading and persuasion?
• Or can they back their project with force?

If they can only beg and bargain, they almost always fail. They can’t finish what they started. But if they can rely on themselves—especially if they can use force when persuasion runs out—then they’re rarely in real danger.

That’s why, as harsh as it sounds, armed prophets win and unarmed prophets get crushed.

There’s another reason. People are inconsistent. It’s often easy to persuade a crowd in the moment, but it’s hard to keep them committed when enthusiasm fades or costs appear. So a reformer has to arrange things so that when belief evaporates, they can still compel obedience—so that the “maybe” turns back into “yes.”

Think of the legendary founders: Moses, Cyrus, Theseus, Romulus. If they’d had no way to enforce what they built, their laws wouldn’t have lasted. You can see the same pattern in a smaller, more recent case: Fra Girolamo Savonarola. His “new order” collapsed the minute the crowd stopped believing. He had no way to steady the faithful, and no leverage to bring skeptics back into line.

So innovators face their worst danger on the climb. Every step upward triggers resistance, envy, and counterattacks. But if they have the skill to push through that phase—and if they remove the people who are most invested in their failure—then the situation flips. They gain legitimacy. They start to look inevitable. And from there they can become powerful, secure, respected, and—by the standards of politics—happy.

A Smaller Example: Hiero of Syracuse

To make the point without relying only on mythic founders, take a lesser example that still fits the pattern: Hiero of Syracuse.

Hiero began as a private citizen. He didn’t become ruler because luck handed him a crown; he became ruler because circumstances created an opening. Syracuse was under pressure and in trouble, and the people chose him as their military commander. Later, they rewarded him by making him prince.

What mattered most was ability. Even before he held office, he had the kind of competence that made observers say, in effect, “Give this man a kingdom and you’d instantly have a king.”

Once in power, he didn’t try to govern with someone else’s tools. He rebuilt the system:

• He disbanded the old army and built a new one.
• He dropped old alliances and formed new ones.
• He made sure his soldiers and partners were his, not borrowed.

With his own forces and his own relationships, he could build whatever political structure he wanted. The climb cost him plenty. But once he had power, keeping it was comparatively easy.

Chapter 7: New Principalities Won by Luck or by Other People’s Arms

Now consider the opposite route: people who become princes mainly through good fortune—sudden elevation from private life to the top.

They often have little trouble rising. The ascent feels effortless, like being lifted by an elevator instead of climbing stairs. The problem shows up afterward. Staying on top is hard.

This kind of prince usually gets a state in one of two ways:

• Someone hands it to them (as a favor, or in return for money).
• Someone else’s power installs them for that other person’s security and prestige.

History is full of these arrangements: rulers set up “princes” in distant cities to secure control, and emperors have been made by troops who were bought rather than loyal.

But the foundation here is shaky, because it rests on two things that almost never sit still:

• the benefactor’s goodwill
• the benefactor’s luck

And there’s a second weakness: the new ruler often doesn’t know how to rule. If they haven’t had to command before—if they’ve lived as a private person—it’s not reasonable to expect them to suddenly have the instincts and skills of leadership. Worse, they usually can’t hold their position because they lack forces that are reliably theirs—troops and supporters who stay friendly and faithful under pressure.

In nature, things that shoot up too fast usually have fragile roots. Political power is the same. A state that appears overnight rarely has time to build the relationships, habits, and institutional supports that let it survive its first real storm. The only exception is the rare person with so much talent that they immediately understand what’s missing—and rush to build, after the fact, the foundations that others lay before they take power.

Two Modern Examples: Francesco Sforza and Cesare Borgia

To compare these two paths—rising by skill versus rising by fortune—consider two examples from recent memory: Francesco Sforza and Cesare Borgia.

Sforza rose from private life to become Duke of Milan through competent, deliberate action. It cost him years of anxiety and struggle to acquire the duchy. But once he had it, he maintained it with relatively little trouble.

Borgia—known publicly as Duke Valentino—followed the other route. He gained territory during his father’s rise to power, and he lost it when his father’s power fell. And that happened even though he did everything a sharp, capable ruler could do to put down roots in territories that had been granted to him by someone else’s arms and luck.

Still, if you look closely at what Borgia actually did, you see a masterclass in building foundations quickly under impossible conditions. And if there’s any better instruction for a new prince than a good example, it’s hard to find one clearer than this. If Borgia ultimately failed, it wasn’t because he misunderstood the problem; it was because fortune turned unusually and brutally against him.

The Problem Alexander VI Faced

Alexander VI wanted to expand his son’s power, but the obstacles were immediate.

First, there was the map: Alexander couldn’t easily give Borgia land that wasn’t connected to the Church’s sphere of control. And if he tried to seize territory too openly, powerful players—like Milan and Venice—would block him. Some key cities were already under Venetian protection.

Second, there was the military reality: much of Italy’s fighting strength sat in the hands of families and factions that didn’t want the Pope growing stronger—especially the Orsini and the Colonna and their networks.

So Alexander had to change the board itself. He needed to disrupt alliances and stir up conflicts so he could take pieces while everyone else was distracted.

He found an opening because Venice, for its own reasons, was willing to invite French power back into Italy. Alexander didn’t resist; he helped make it happen—one move was dissolving the previous marriage of King Louis, clearing political space for a French campaign.

Once the French king entered Italy and took Milan, the Pope gained soldiers for the next step: the push into Romagna. The region surrendered largely on the king’s reputation—power is contagious, and fear travels fast.

Why Borgia Stopped Relying on Borrowed Power

With Romagna taken and the Colonna knocked back, Borgia wanted to hold what he had and expand further. Two threats stopped him:

1. His troops might not be loyal—especially those connected to the Orsini.
2. France’s support might vanish—or worse, turn predatory.

He saw the risk with his own eyes. When he attacked Bologna after taking Faenza, the Orsini went along reluctantly, like people who were already deciding how to betray him later. And he learned France’s limits when, after seizing Urbino and moving toward Tuscany, the French king forced him to back off.

At that point, Borgia made a clear decision: no more dependence on other people’s weapons or other people’s luck.

Step One: Break the Factions

He began by weakening the Orsini and Colonna in Rome. He didn’t do it by open war at first. He did it by recruitment and absorption—pulling their gentlemen into his own orbit with:

• good pay
• honors and offices
• commands matched to status

Within months, loyalty to the old factions dissolved and shifted toward him.

Then he waited for the right moment to crush the Orsini leadership.

That moment came quickly, and he used it.

The Orsini finally realized that Borgia’s rise—along with the Church’s expanding reach—would ruin them. They met at Magione, and that meeting triggered rebellion in Urbino and unrest across Romagna. The danger was real and immediate. Borgia survived it with French help, but he didn’t intend to stay exposed like that again.

So he switched tactics. Rather than trust the French—or any outsider—he relied on deception, and he executed it with extraordinary control. Through mediation by Paolo Orsini (whom he courted with money, clothing, and horses), he reconciled with the Orsini, projecting friendliness while preparing a trap. Their confidence and simplicity led them straight into his hands at Sinigaglia. He killed the leaders and converted their followers into allies.

At that point he had built a solid base:

• all of Romagna
• the Duchy of Urbino

And as the population began to feel the benefits of stability, they started to support him—not because they loved him, but because life improved.

Step Two: Fix Romagna’s Governance—and Take the Blame Off Himself

When Borgia first occupied Romagna, he found a mess. The local rulers were weak, predatory, and chaotic. They treated the population like something to loot rather than govern. The result was exactly what you’d expect:

• robbery
• feuds
• constant violence
• social fragmentation

To restore order, he appointed a governor with absolute power: Ramiro d’Orco, a fast, ruthless operator. Ramiro did what ruthless operators do—he crushed disorder quickly and restored unity.

But Borgia understood the next problem: excessive authority makes a man hated, and the hatred often splashes onto whoever appointed him. So Borgia rebalanced the system. He established a court of judgment led by a respected president, with representation for the cities.

Then he staged a piece of political theater with a very specific purpose. Knowing that the earlier severity had created resentment, he wanted the people to see that “the cruelty” hadn’t come from him, but from his minister’s nature. Under that pretext, he executed Ramiro publicly and left the body displayed in the main square of Cesena, with the block and a bloody knife beside it.

It was horrifying—and it worked. The spectacle both satisfied and terrified the public: the old fear was redirected away from Borgia, and a new fear warned everyone what happens when power is crossed.

Step Three: Prepare for a World Without France

Now Borgia had armed himself in his own way and neutralized nearby threats. Next he had to deal with France, because he knew the French king—realizing too late that he’d helped create a dangerous figure—wouldn’t support him forever.

So Borgia began looking for new alliances, playing for time, and negotiating carefully while France moved against Spain in the fight over Naples. His goal was simple: protect himself from being swallowed by either side.

If Alexander had lived, Borgia likely would have secured himself quickly.

Step Four: Plan for the Succession Crisis

Borgia also had to think beyond the present. The most obvious future danger was this: a new pope might not be friendly, and might try to strip away what Alexander had given.

So Borgia prepared four defenses:

1. Eliminate the families of the lords he had dispossessed, removing a ready-made excuse for retaliation.
2. Win over the gentlemen of Rome so he could pressure the pope through their influence.
3. Secure strong support within the college of cardinals.
4. Accumulate enough power before the pope died that he could absorb the first удар—the first shock—on his own.

By the time Alexander died, Borgia had completed three of these. He had killed as many dispossessed lords as he could reach (only a few escaped). He had the Roman gentlemen. He had the largest bloc in the college.

For further expansion, he aimed at Tuscany. He already held Perugia and Piombino, and Pisa was under his protection. And because France had been pushed out of Naples by Spain, neither France nor Spain could ignore him; both needed his cooperation.

So he moved. He struck at Pisa. Lucca and Siena quickly yielded—partly out of hatred, partly out of fear of Florence. And Florence, had Borgia’s momentum continued, would have struggled to respond. By the year Alexander died, Borgia’s reputation and power had grown so much that he was on the verge of standing entirely on his own—no longer depending on other people’s luck or other people’s armies.

Why It Still Collapsed

Alexander died five years after Borgia first took up arms. He left Borgia with Romagna truly consolidated—but everything else still unsettled, suspended between two powerful hostile armies. And Borgia himself was dangerously ill.

Even so, his foundations were strong enough to show their quality. Romagna waited for him for more than a month. In Rome, though barely alive, he remained secure. Even if rival families came to the city, they couldn’t immediately strike him down.

If Borgia had been healthy when his father died, many of the remaining obstacles would have been manageable. In fact, the new pope, Julius II, later told the narrator that Borgia had prepared for every scenario—except one: he never imagined that at the moment of his father’s death, he himself would be close to dying.

Looking back on Borgia’s actions, it’s hard to blame him for his strategy. If anything, he’s an example worth studying by anyone who rises to power through the fortune or the arms of others. His goals were expansive, his mind was long-range, and given what he faced, he could hardly have acted differently. Only two things broke his plan: Alexander’s short life and Borgia’s sickness.

And from his case you can draw a practical checklist for any new ruler who wants to survive:

• secure yourself in your new state
• make friends and neutralize enemies
• overcome obstacles by force or deception
• win the people’s support—or at least their acceptance
• earn loyalty from soldiers and keep them disciplined
• remove those with the power and motive to hurt you
• replace unreliable troops with new, dependable ones
• maintain relationships with other rulers so they help you eagerly and hesitate to harm you

The One Mistake That Mattered

There is one decision Borgia can be blamed for: he supported the election of Julius II.

He couldn’t guarantee a pope of his own choosing, but he could have blocked certain candidates. He should never have accepted the rise of any cardinal he had personally injured—or who had reason to fear him—because people don’t forget old wounds just because you offer new favors. When men strike back, they do it out of fear or out of hate.

By backing a pope who had every reason to turn against him, Borgia made a fatal choice. That single error became the cause of his ultimate ruin.

Chapter 8: Those Who Gain Power Through Wickedness

A person can rise from private life to ruling a state in a couple of ways that don’t neatly fit under either luck or ability. I can’t ignore them—even though they’d make more sense in a longer discussion about republics.

These two routes are:

• Taking power through crimes and betrayal
• Being elevated by fellow citizens (we’ll get to that in the next chapter)

Let’s focus on the first path. Two examples—one from antiquity and one from more recent history—are enough to show how it works.

Agathocles of Syracuse: From Nobody to Ruler

Agathocles, a Sicilian, became ruler of Syracuse despite starting from a humiliating position. He wasn’t born into status; he was the son of a potter. His reputation was ugly, and he lived in ways most people would call disgraceful. And yet, he had the kind of raw competence—physical toughness, nerve, and strategic intelligence—that can carry someone far in military life.

He rose step by step through the army until he reached the top ranks and became a leading official in Syracuse. Once there, he decided he didn’t want influence. He wanted the whole state.

To pull that off, he made a working arrangement with Hamilcar of Carthage, whose forces were fighting in Sicily. Then, one morning, Agathocles summoned the senate and the people as if he needed to discuss routine affairs of government. At a prearranged signal, his soldiers slaughtered the senators and the wealthiest citizens. With the leadership wiped out, he seized control—and, remarkably, the city didn’t explode into immediate civil chaos.

Carthage fought back hard. Agathocles was defeated twice and eventually trapped under siege. But he managed to hold Syracuse anyway. He left part of his force to defend the city, took the rest across the sea, and attacked Carthage’s own territory in Africa. That move forced Carthage to loosen its grip. In short order, the siege of Syracuse collapsed, and Carthage—desperate—made terms. Agathocles kept Sicily; Carthage settled for holding Africa.

If you look at his career closely, you’ll find very little that can be credited to luck. No one handed him power out of kindness. He earned position through danger, hardship, and relentless climbing—and then he held what he seized with the same stubborn courage.

But here’s the moral problem: none of that makes his actions admirable.

It isn’t “talent” to murder your fellow citizens, betray friends, break faith, and throw away mercy and religion. Those methods can win you power, but they don’t earn you honor. Still, if we judge only the military side—his boldness in entering danger and his steadiness in escaping it, his endurance under pressure and his capacity to overcome setbacks—it’s hard to deny that he had the qualities of a formidable commander.

And yet his cruelty and brutality block him from being celebrated among great men. What he achieved doesn’t belong in the category of noble achievement, even if it can’t be dismissed as mere chance.

Oliverotto da Fermo: A Fast Rise—and a Faster End

Now for a modern example from the time of Pope Alexander VI.

Oliverotto da Fermo was orphaned young and raised by his maternal uncle, Giovanni Fogliani. As a teenager he was sent to serve under a respected military leader so he could learn the craft of war and make a name for himself. After that commander died, Oliverotto served under his brother and quickly rose to the top of his profession—sharp mind, strong body, and an aggressive drive to stand out.

Soon, serving under others felt too small for him. He decided he wanted Fermo for himself.

He enlisted help from two groups:

• Certain citizens of Fermo who preferred submission to liberty
• Powerful military allies who could supply force when needed

Then he set the trap with a letter to his uncle. He wrote that he’d been away for years, wanted to visit home, and wanted to check on his inheritance. He insisted he’d pursued only honor—but also asked to return with a grand entourage: one hundred horsemen, friends and retainers. He urged Giovanni to arrange a public, honorable reception—not only for Oliverotto’s sake, but for Giovanni’s reputation as the man who had raised him.

Giovanni did exactly that. He welcomed his nephew warmly and hosted him in his own house. After a few days—once Oliverotto had put his plan in place—he held a formal banquet and invited Giovanni and the leading men of Fermo.

When the meal ended, Oliverotto steered the conversation toward big political talk: the power of the Pope, the Pope’s son Cesare, and their campaigns. Everyone engaged. Then Oliverotto suddenly said this kind of discussion belonged somewhere more private. He led them into an inner room.

The moment they sat down, soldiers poured out from hiding places and butchered Giovanni and the rest.

After the killings, Oliverotto rode through the town, rallied force, and pressured the chief magistrate inside the palace. The citizens, terrified, obeyed. A new government was assembled, and Oliverotto made himself its head. He eliminated anyone likely to resist him and quickly rewired the city’s civil and military order to make his control durable.

For the year he ruled, he wasn’t just safe inside Fermo—he became threatening to neighboring powers. If he had stayed alert, removing him might have been as difficult as removing Agathocles.

But he made one fatal mistake: he let himself be outplayed by Cesare Borgia. Borgia captured him along with other major figures at Sinigaglia. Within a year of murdering his uncle, Oliverotto was strangled—alongside the same military leader whose courage and wickedness he had relied on.

Why Some Cruel Rulers Stay Secure

People often ask how someone like Agathocles—after endless betrayals and violence—can rule for years, defend against foreign enemies, and avoid being overthrown by his own citizens. After all, many others who used cruelty couldn’t hold power even in peace, let alone in war.

The difference is how cruelty is used: well or badly.

If we can speak of “well-used” cruelty at all, it means this:

• It’s done all at once, in a single decisive strike
• It’s done only as much as necessary for security
• It’s not repeated, unless later actions can genuinely be turned toward the subjects’ benefit

“Badly used” cruelty looks different:

• It may start small
• But it keeps growing over time instead of shrinking

A ruler who uses the first pattern can sometimes stabilize the regime and soften it later, as Agathocles did. A ruler who uses the second pattern can’t maintain power for long, because the state becomes a machine that must keep hurting people to keep moving.

So if you seize a state, you should take a cold, realistic inventory of the harms you believe you must do—and then do them in one stroke, so you don’t have to repeat them day after day. When you don’t keep reopening wounds, you give people space to settle down. Then you can win them over with benefits.

If you don’t do this—whether from timidity or bad advice—you end up living with the knife in your hand. Your people won’t trust you, and they won’t attach themselves to you, because the injuries keep arriving.

The principle is simple:

• Injuries should be delivered all at once, so they’re felt less repeatedly and sting less over time.
• Benefits should be handed out gradually, so their effect lasts.

Above all, a ruler should live among his people in a way that doesn’t force him to abruptly change character when circumstances change. If trouble hits and you suddenly try to become harsh, it’s too late to be effective. If you suddenly try to become gentle, it won’t help either—people will see it as forced, and they won’t feel grateful for it.

---

Chapter 9: The Civil Principality

Now let’s turn to the other route: when a prominent citizen becomes ruler not by obvious crimes or unbearable violence, but because fellow citizens raise him up. This is a civil principality.

You don’t need extraordinary genius or wild good fortune to reach this position. What you need is good political judgment and timing.

The Two Forces Inside Every City

In every city you’ll find two groups with opposing desires:

• The people want to avoid being ruled and squeezed by the powerful.
• The nobles want to rule and squeeze the people.

Out of that tension, a city tends to end up in one of three conditions:

• A principality (one person rules)
• Self-government
• Chaos

A principality forms when either the people or the nobles get an opening—and use it.

• When nobles can’t withstand popular pressure, they elevate one of their own as prince so they can pursue their ambitions under his protection.
• When the people can’t resist noble pressure, they elevate someone as prince so he can shield them with his authority.

Why “Chosen by the People” Is Easier Than “Chosen by the Nobles”

A prince raised by nobles holds power with more difficulty than one raised by the people.

The noble-backed prince is surrounded by peers—many who see themselves as his equal. That makes them hard to command and harder to manage. They resist being led like subordinates.

The people-backed prince, by contrast, typically stands alone at the top. Few around him expect equality, and most are ready to obey.

There’s also a basic asymmetry in what the two groups want.

You can’t satisfy the nobles without harming others, because their aim is domination. But you can satisfy the people much more easily, because their aim is simply not to be oppressed.

And there’s a practical security issue too:

• A prince can’t truly protect himself against a hostile people—they’re too numerous.
• But he can protect himself against hostile nobles—there are fewer of them.

The worst a hostile people can do is abandon you. Hostile nobles can do that and actively move against you. They’re quicker to see which way things are going, and they’re skilled at switching sides early to save themselves and win favors from whoever they think will prevail.

Also, you can’t replace “the people.” You must live among them. But you can do without the same nobles. You can raise and lower them, grant and revoke status, and reshape who matters from one day to the next.

How to Handle the Nobles

You should look at nobles in two broad categories:

1. Those who tie their fortunes to yours
   If they aren’t predatory, reward them and keep them close.

2. Those who refuse to tie themselves to you
   Treat them differently depending on why they hold back:

   • If they hold back from timidity or lack of courage, they can still be useful—especially if they give good advice. Use them. In good times they reflect well on you; in bad times they’re not a serious threat.
   • But if they hold back because they’re ambitious and self-protective, that’s a warning sign. They’re thinking about themselves more than you. In hard times, they’ll help bring you down. Treat them like open enemies.

Keeping the People on Your Side

If you become prince through the favor of the people, your main task is simple: keep them friendly. That’s usually easy, because they mainly want you not to mistreat them.

If you become prince through the nobles against the people, your first priority is to win the people over. The fastest way is to take them under your protection. People bond strongly to someone who does them good when they expected harm. Done right, they can become even more devoted to you than if they had originally raised you.

There are many tactics for winning affection, and the best ones depend on circumstances, so there’s no fixed formula. But the core point doesn’t change: without the people, you have no security when adversity hits.

“Building on the People” Isn’t Always “Building on Mud”

Consider Nabis of Sparta, who faced attack from all Greece and from a victorious Roman army—and still managed to defend both his state and his rule. In that situation, it was enough for him to secure himself against a few powerful opponents.

This fact matters because people love to quote the proverb: “Whoever builds on the people builds on mud.” That warning can be true when a private citizen tries to lean on popular support and imagines the crowd will rescue him from enemies or officials. In that case he’ll often be disappointed.

But a prince is not in the same position. If he is established in power, can command, has courage, stays steady under pressure, and keeps the public’s spirit up through his own resolve and energy, he won’t find the people slipping away when he needs them most. In that case, he has built on solid ground.

The Danger in Sliding from “Civil” to “Absolute”

Civil principalities become especially risky when they transition from shared, law-bound authority to more absolute rule.

A prince governs either:

• Personally, or
• Through magistrates

Governing through magistrates is weaker and less secure, because it depends on the goodwill of citizens placed into office. In turbulent times, those officials can wreck the regime easily—through quiet maneuvering or open defiance.

Worse, in moments of unrest the prince can’t suddenly exercise absolute authority, because the people are used to taking orders from magistrates, not from him directly. In confusion and fear, loyalty becomes scarce, and trustworthy supporters are hard to find.

In peaceful times, everyone seems committed: they promise everything, and when death feels far away they talk as if they’d die for you. But when crisis comes and the state truly needs its citizens, the crowd thins fast.

And because this test can only be run once, it’s especially dangerous.

So a wise prince should organize things so that, in every kind of circumstance, citizens feel they need the state—and need him. When they do, they remain faithful.

---

Chapter 10: Measuring the Strength of a Principality

There’s another key question when you evaluate any principality: can the prince, when necessary, stand on his own, or does he always need outside help?

Here’s the dividing line.

A prince can support himself if he can, through ample men or money, raise an army strong enough to meet any attacker in open battle.

A prince needs others if he can’t face an enemy in the field and must survive by hiding behind city walls.

We’ve already touched on the first case, and we’ll return to it if it comes up again. For the second case, the practical advice is straightforward: such princes should stockpile supplies and fortify their towns—and they should not try to defend the countryside at all costs.

If you fortify your city properly—and you handle your people’s everyday concerns the way I’ve described (and will keep coming back to)—you’re unlikely to be attacked except with extreme caution. People avoid projects where the obstacles are obvious. And when a city is well defended and its ruler isn’t hated, the obstacles are obvious.

A good example is the free cities of Germany. They control only a small amount of surrounding territory. They obey the emperor when it suits them, and they don’t panic about nearby powers—because taking them by force looks like a miserable, grinding job.

Here’s what makes them so hard to crack:

• Serious defenses: deep ditches, strong walls, and enough artillery to make an assault expensive.
• Stockpiles for endurance: public stores of food, drink, and ammunition sufficient for a full year.
• A stable civilian economy: steady work for the population in the industries that keep the city alive, so people stay calm without draining the public treasury.
• A culture of readiness: regular military exercises, supported by rules and institutions that keep them going.

So a prince with a strong city who hasn’t made himself detestable is rarely attacked. And even if someone tries, the attacker is likely to be driven off in disgrace. The world changes fast; it’s nearly impossible to keep an army in the field for an entire year without something interfering.

Someone will object: “What if the citizens own property outside the walls and watch it burn? Won’t they lose patience? Won’t a long siege and self-interest make them forget their prince?” A strong, bold ruler can manage that. He alternates tactics: sometimes he gives hope that the suffering won’t last long; other times he highlights the enemy’s cruelty; and he stays alert to anyone inside the city who becomes too reckless or too influential.

In fact, an invading army usually burns and wrecks the countryside immediately—right when people’s emotions are hottest and their will to defend is strongest. That’s exactly why a prince shouldn’t hesitate at the start. Later, when tempers cool, the damage is already done. There’s no easy fix. And once people have paid that price, they often cling more tightly to their ruler—because he now seems to “owe” them for what they lost while standing by him.

That may sound backward, but it’s human nature: people feel bound not only by favors they receive, but also by the sacrifices they’ve made and the benefits they believe they’ve given. So if a prince thinks clearly and keeps supporting and protecting his citizens, he can hold their loyalty from the first day of a crisis to the last.

Chapter 11: Ecclesiastical Principalities

Now we come to ecclesiastical principalities. All the hard work happens before you get them, because you usually acquire them through personal ability or sheer luck. But once you have them, you can keep them without either. They’re propped up by religious institutions—forces so powerful that these states remain secure regardless of how their rulers behave.

These rulers are unusual:

• They possess states but don’t have to defend them.
• They have subjects but don’t really govern them.
• Their states can look unguarded, yet no one takes them.
• Their subjects can look ungoverned, yet they don’t rebel or separate.

Such principalities are uniquely safe and, in their way, fortunate. And since they’re sustained by powers beyond ordinary human calculation, I won’t say more about their inner foundations. Arguing too boldly about them would be reckless.

Still, someone might ask a practical question: how did the Church become so strong as a temporal power? For a long time—especially before Alexander—the Italian powers treated the pope’s political strength as minor. Yet later even the king of France trembled before it; the Church pushed the French out of Italy and broke Venetian power. The explanation is widely known, but it’s worth reviewing.

Before King Charles of France entered Italy, the peninsula was dominated by five powers: the pope, the Venetians, the King of Naples, the Duke of Milan, and the Florentines. They worried about two things above all:

• No foreign army should enter Italy.
• No Italian power should swallow up too much territory.

The greatest anxiety centered on the pope and the Venetians. To restrain Venice, the others had to unite—just as they did when defending Ferrara. To restrain the pope, they relied on the barons of Rome, divided into two rival factions, Orsini and Colonna. Their constant feuding gave them endless excuses for disorder, and by standing armed under the pope’s nose, they kept the papacy politically weak.

Even if a courageous pope appeared—like Sixtus—neither luck nor skill could fully eliminate these headaches. Another built-in weakness was the short lifespan of popes: in roughly a decade, it’s hard to crush even one faction completely. And if one pope nearly destroyed the Colonna, the next might arrive hostile to the Orsini and revive the struggle. This is why the pope’s temporal power was long held in low regard.

Then Alexander VI rose—more clearly than any other pontiff demonstrating what a pope can do with money and arms. Using the Duke Valentino as his instrument, and taking advantage of the French entry into Italy, he accomplished the very moves I’ve already discussed in the duke’s story. Alexander’s goal wasn’t to enlarge the Church for its own sake; he aimed to build up the duke. Even so, his actions strengthened the Church, which—after his death and the duke’s fall—inherited the results.

After him came Pope Julius, who found the Church already strong: it held all of Romagna, the Roman barons were reduced to impotence, and the old factions had been beaten down. Julius also found a clear path to accumulate money on a scale not previously practiced. He didn’t just maintain these advantages; he expanded them. He set out to gain Bologna, crush Venetian power, and drive the French out of Italy—and he succeeded. His success is even more impressive because he worked to strengthen the Church, not to enrich a private individual.

He also kept the Orsini and Colonna within the limits he inherited. Even when they were tempted to stir trouble, he held two levers firmly:

• The sheer power of the Church, which frightened them into caution.
• A ban on “their own” cardinals, who would otherwise fuel factional conflict.

When these factions have cardinals, they don’t stay quiet for long. Cardinals nourish the rivalries inside Rome and beyond it, and the barons are dragged into the fight. From the ambitions of high clergy come disorder and turmoil among the nobility.

Because of this, Pope Leo inherited an exceptionally powerful papacy. And if earlier popes made it great through force, one can hope he will make it even more respected through character and other virtues.

Chapter 12: The Types of Armies—and Mercenaries

Having described the main types of principalities I set out to discuss—why some are stable and others fail, and how people try to acquire and hold them—I now need to talk about something every state depends on: how it fights and how it defends itself.

We’ve already seen that a ruler must lay solid foundations or he’ll collapse. The core foundations of any state—new or old, simple or mixed—are good laws and good arms. And because you won’t get good laws without being well armed, where arms are strong, laws tend to be strong too. I’ll set laws aside here and focus on arms.

A prince’s military forces fall into four categories:

• His own troops
• Mercenaries
• Auxiliaries (troops lent by another power)
• Mixed forces

Mercenaries and auxiliaries are both useless and dangerous. If you rely on them, you won’t be secure. They’re fragmented, ambitious, undisciplined, and unfaithful. They look brave around friends and melt away before enemies. They fear neither God nor human obligation. Your destruction is only delayed until someone attacks—because in peacetime they rob you, and in wartime your enemies do.

They stay in the field for one reason: a small paycheck. And that’s never enough to make them willing to die for you. They’ll serve as long as there’s no war; when war arrives, they vanish or run.

Italy’s ruin came from this single mistake: for years it bet everything on mercenaries. They looked impressive when fighting each other, but when foreign armies appeared, they revealed what they really were. People blamed “sins,” and in a sense they were right—but the real sins were political: princes choosing the wrong foundation, and then paying the price.

There’s another problem. Mercenary captains fall into two types: competent or incompetent.

• If they’re competent, you can’t trust them. They inevitably chase their own greatness—either by pressuring you, their employer, or by pursuing goals that clash with yours.
• If they’re incompetent, you’re ruined in the obvious way.

Someone might say, “But anyone with weapons behaves the same way—mercenary or not.” The difference is structure and control. When a state must depend on arms, then:

• A prince should personally take the field and act as captain.
• A republic should send citizens, recall commanders who fail, and restrain worthy ones with law so they can’t turn their command into private power.

Experience shows princes and republics that fight with their own forces can make real progress. Mercenaries mostly bring trouble. It’s harder for a republic armed with its own citizens to be dominated by one of them than it is for a republic armed with foreigners to be captured from within.

Think of Rome and Sparta: they stayed armed and free for centuries. The Swiss are armed and free as well.

History is full of warnings. Carthage, after its first war with Rome, was nearly crushed by its own mercenary troops—even though Carthaginian citizens served as captains. After Epaminondas died, the Thebans appointed Philip of Macedon to command their forces; after victory, he took their liberty. After Duke Filippo died, Milan hired Francesco Sforza against Venice; after he defeated the Venetians, he allied with them and turned on Milan, his employer. Sforza’s father, hired by Queen Johanna of Naples, abandoned her, leaving her so exposed that she had to lean on the King of Aragon to save her kingdom.

If someone replies, “But Venice and Florence expanded with mercenaries, and their captains didn’t seize power,” the answer is: Florence was helped by luck and by the particular dynamics among commanders. Some capable captains never won the decisive victory that would have made them dangerous. Others were checked by rivals. Others aimed their ambition elsewhere.

But look at the risk. Florence once raised Paolo Vitelli—a highly prudent man—from private status to great renown and gave him command. If he had taken Pisa, Florence would have been trapped: if he joined their enemies, they had no way to resist; if they kept him, they’d have to obey him.

As for Venice, it acted boldly and safely when it went to war with its own people—armed nobles and commoners fighting side by side. That was before it began land campaigns. Once it started fighting on land, it abandoned that strength and adopted Italy’s mercenary habit. Early on, with little territory and a huge reputation, Venice had less to fear from commanders. But once it expanded—especially in the time of Carmignola—it learned the danger. Carmignola was extremely capable: under him Venice defeated Milan. Yet his half-hearted conduct in war made Venice fear it would stop winning. Venice couldn’t safely keep him, but also couldn’t safely let him go—so to protect itself, it killed him.

Later Venice relied on other commanders, under whom it had to fear loss more than hope for gain. Eventually, in a single battle, it lost what it had built up over many centuries. That’s the pattern with mercenary arms: conquests arrive slowly, delayed, and small; losses come suddenly and are devastating.

Since these examples lead directly to Italy’s recent history, we need to face the mercenary system head-on—how it rose, how it developed, and how to counter it.

The background matters. In recent times, the authority of the empire was rejected in Italy; the pope gained more temporal power; and Italy fractured into more states. Many great cities took up arms against their nobles—nobles once protected by the emperor, but now oppressive. The Church supported these revolts to build political authority. Elsewhere, citizens turned themselves into princes.

As a result, Italy fell partly into the hands of the Church and partly into republics. But the Church was run by clergy and the republics by civilians—neither trained for war. Both began hiring foreign troops.

The first figure to give this new military class real prestige was Alberigo da Conio of Romagna. From his “school” emerged commanders like Braccio and Sforza, who became—effectively—the power brokers of Italy. After them came the long parade of captains who directed Italy’s arms. And the final result of all their supposed “valor” was humiliating: Italy was overrun, robbed, ravaged, and treated with contempt.

Their guiding strategy was straightforward: downgrade infantry so they could inflate their own importance. Living on pay with no land of their own, they couldn’t maintain large armies. A small body of foot soldiers didn’t give them political weight. So they emphasized cavalry, and with relatively modest mounted forces they kept their status and their income.

The imbalance became absurd: in an army of twenty thousand, you might not find even two thousand infantry.

They also used every trick to reduce danger and fatigue—for themselves and their men. They avoided killing in battle, preferring to take prisoners and release them without ransom. They avoided night attacks on towns, and garrisons avoided night raids on camps. They didn’t fortify camps with palisades or ditches. They avoided winter campaigning.

All of this was baked into their “rules of war,” designed to dodge hardship and risk—and in doing so, they brought Italy to slavery and contempt.

The French marched the length of Italy almost unopposed. As Pope Alexander liked to joke, they showed up carrying chalk to mark which houses they’d sleep in, not swords to fight.

Chapter 13 — Auxiliaries, Mixed Troops, and Your Own

Let’s talk about auxiliaries—the other kind of “useless” military help. You use auxiliaries when you call in a foreign ruler and ask for their troops to “help” you defend your territory. Pope Julius II did this in recent memory: after being disappointed by his mercenaries in the campaign against Ferrara, he struck a deal with Ferdinand, King of Spain, to send men and weapons.

Here’s the catch: auxiliary troops can be excellent soldiers. That’s not the problem. The problem is what they do to you.

• If they lose, you’re finished—because your defense just collapsed.
• If they win, you’re still in trouble—because now you’re in their hands.

With auxiliaries, disaster is built in. They arrive already unified, and they take orders from someone else. You don’t truly command them.

Julius II is the clearest warning. Wanting Ferrara, he handed the whole project to a foreign power. He escaped the consequences only because luck threw in a third event: his auxiliaries were beaten at Ravenna, then the Swiss unexpectedly rose up and drove out the conquerors. So Julius didn’t end up captive—neither to enemies (who fled) nor to his auxiliaries (because the final success came through forces other than theirs).

History offers plenty of similar lessons:

• The Florentines, lacking troops of their own, sent for ten thousand French soldiers to seize Pisa—and they put themselves in more danger than at almost any other moment in their crisis.
• The Emperor of Constantinople, trying to check his neighbors, brought ten thousand Turks into Greece. When the war ended, the Turks refused to leave. That invitation became the opening act of Greece’s servitude to “infidels.”

So if you don’t want to conquer, then yes—use auxiliaries, because they are even more hazardous than mercenaries. With mercenaries, harm takes longer to ripen. Mercenaries aren’t automatically unified, you hire and pay them yourself, and the leader you appoint can’t instantly gain enough authority to crush you in one stroke. But auxiliaries? Their unity and obedience to someone else means your ruin can arrive all at once.

The difference comes down to this:

• With mercenaries, the biggest danger is their cowardice.
• With auxiliaries, the biggest danger is their competence.

A wise ruler avoids both and relies on his own forces. He’d rather lose with troops he commands than win with troops that belong to someone else—because a victory borrowed from another power is not a “real” victory.

Cesare Borgia is the cleanest illustration. He entered Romagna using auxiliaries—French soldiers—and with them he took Imola and Forlì. But he decided those forces weren’t reliable enough, so he shifted to mercenaries, judging them the lesser risk. He hired the Orsini and Vitelli. Then he tested them, found them uncertain and dangerous, destroyed them, and finally built up his own troops.

Watch what happened to his reputation through each phase:

• With French forces, he looked dependent.
• With Orsini and Vitelli, he looked exposed.
• With his own soldiers, he looked like a true master—because his strength rested on loyalty he could count on.

I don’t want to stay only with recent Italian examples. Consider Hiero of Syracuse. After being made head of the army, he quickly realized that mercenaries—structured like our Italian condottieri—were useless. And because he couldn’t safely keep them or safely dismiss them, he had them massacred and then fought with his own forces rather than with outsiders.

Even Scripture makes the same point. When David offered to fight Goliath, Saul tried to outfit him with Saul’s own armor. David put it on, immediately took it off, and said he couldn’t use it; he would meet the enemy with his sling and knife. That’s what borrowed arms do: they either slip off your back, weigh you down, or tie you up.

France provides a larger, state-level example. Charles VII—father of Louis XI—freed France from the English through good fortune and courage, and then recognized the core necessity: a kingdom must have its own military strength. He created ordinances organizing men-at-arms and infantry.

Louis XI later made a fateful mistake: he abolished the infantry and began hiring Swiss troops. That single choice, followed by others like it, planted a long-term danger. By boosting the Swiss reputation, he hollowed out confidence in France’s own arms. French men-at-arms grew accustomed to fighting beside Swiss soldiers and eventually seemed unable to win without them. The result was predictable:

• The French struggled against the Swiss.
• And without the Swiss, they struggled against everyone else.

Their armies became mixed—part national, part mercenary. That’s better than relying on mercenaries alone, and better than relying on auxiliaries alone, but it’s still far inferior to relying on your own troops. France would be nearly unconquerable if Charles’s ordinances had been expanded or even just preserved.

The deeper lesson is about human judgment. When something looks attractive at first glance, we often can’t see the poison hidden inside it—like a fever that seems mild until it has already taken hold. Most rulers don’t recognize an evil until it’s already on them. And only a few are granted the kind of insight that spots danger early.

Look at Rome. If you study the Roman Empire’s first major slide, you’ll find it began when Rome started enlisting the Goths. From that point, Rome’s vigor declined, and the valor that built the empire slowly migrated to others.

So the conclusion is blunt: no principality is secure without its own forces. Without them, it lives on luck—because it lacks the internal strength that can hold when adversity arrives. Wise people have always judged that nothing is more unstable than fame or power not grounded in one’s own strength.

When I say “one’s own forces,” I mean troops drawn from:

• subjects,
• citizens,
• or dependents.

Everything else is mercenaries or auxiliaries. And how to prepare your own forces will be clear if you reflect on the rules I’ve laid out—and if you study how Philip (Alexander the Great’s father), along with many republics and princes, armed and organized themselves. To those examples, I refer you.

Chapter 14 — What a Prince Must Know About War

A ruler should have one central focus: war—its rules, its discipline, and the habits that make it possible to fight well. It’s the one “art” that truly belongs to someone who governs. It doesn’t just protect princes who inherit power; it’s also what lets ordinary people climb into power. And the reverse is just as common: when princes care more about comfort than arms, they lose their states.

Neglecting military skill is the first step toward losing what you have. Mastering it is a major route to gaining what you want. Francesco Sforza became Duke of Milan through his military ability; his sons, avoiding the hardship of arms, fell from dukes back into private life.

Being unarmed brings many harms, but one stands out: it makes you despised. And a prince must protect himself against contempt. There’s no stable relationship between armed and unarmed people. It isn’t reasonable to expect armed men to obey an unarmed leader willingly, or for an unarmed leader to feel secure among armed servants. One side feels disdain; the other feels suspicion. That combination doesn’t cooperate well.

So if a prince doesn’t understand war:

• his soldiers won’t respect him,
• and he can’t truly rely on them.

He should never let war leave his thoughts. In peacetime, he should practice it even more than in wartime. There are two routes: action and study.

By action, he should keep his troops organized and drilled, and he should constantly train his body for hardship. Machiavelli’s favored method here is hunting—not for sport, but for what it teaches. It forces a ruler to move through real terrain and learn:

• how mountains rise,
• how valleys open,
• how plains spread,
• and how rivers and marshes behave.

That knowledge pays off twice. First, he learns his own country and can defend it better. Second, by understanding one landscape deeply, he can read other landscapes faster, because many features repeat across regions. Without this skill, a captain lacks something essential. Terrain knowledge helps you surprise enemies, choose camp locations, move armies, set battle lines, and conduct sieges effectively.

Philopoemen, Prince of the Achaeans, was praised for this habit: in peacetime he thought about war constantly. Walking through the countryside with friends, he would stop and pose practical scenarios—enemy on that hill, our army here—who has the advantage? How do we advance while keeping formation? If we retreat, what’s the method? If they retreat, how do we pursue? He’d listen to others, argue his own view, and back it with reasons. Because he rehearsed possibilities endlessly, war rarely surprised him with a situation he couldn’t handle.

By study, a prince should read histories and examine what great commanders did—how they conducted wars, why they won, and why they lost. The point isn’t admiration; it’s pattern recognition: avoid the causes of defeat, copy the causes of victory.

Better still, choose a great figure as a deliberate model, keep that person’s deeds in mind, and measure yourself against them. Tradition says Alexander the Great imitated Achilles; Caesar imitated Alexander; Scipio imitated Cyrus. If you read Xenophon’s Life of Cyrus, and then look at Scipio’s life, you can see the imitation in action: Scipio’s chastity, warmth, humanity, and generosity align with the virtues Xenophon attributes to Cyrus.

A wise prince follows this kind of discipline. He doesn’t waste peacetime. He builds strength through steady effort so that when fortune turns—and it will—he’s ready to take the blow and stay standing.

Chapter 15 — Why Princes Get Praised or Blamed

Now we have to ask: what rules should guide a prince’s behavior toward his subjects and friends?

Many writers have addressed this, and I know I’ll look presumptuous for doing it again—especially because I won’t follow their methods. But my goal is usefulness, not decoration. That means I’m going to chase the truth of how things actually work, not the fantasy of how we wish they worked.

Plenty of people have imagined republics and principalities that never existed outside the mind. The distance between how people live and how they ought to live is enormous. And if a ruler ignores what people do in favor of what people “should” do, he invites ruin. A man determined to act virtuously in every situation will get destroyed in a world full of those who don’t.

So a prince who wants to keep his state must learn how to do wrong—and to use that capacity or not, depending on necessity. Setting aside imaginary ideals, let’s talk about real reputations.

When people discuss men—and especially princes, because their rank puts them under a brighter spotlight—they quickly label them by qualities that earn praise or blame. One is called generous, another stingy; one is seen as giving, another as grasping; one cruel, another compassionate; one breaks faith, another keeps it; one is cowardly, another brave; one approachable, another arrogant; one lustful, another chaste; one sincere, another cunning; one hard, another easygoing; one serious, another frivolous; one religious, another skeptical—and so on.

Everyone will admit it would be best for a prince to possess all the “good” qualities. But human life doesn’t allow perfect consistency. You can’t fully have them all, and you can’t always practice them. So a prince must be prudent enough to do two things:

1. Avoid the vices that would cost him his state.
2. And, if possible, avoid the vices that merely stain his reputation—but don’t be paralyzed if avoiding them isn’t possible.

He shouldn’t torment himself over blame for actions without which the state can’t be saved. If you look closely, you’ll find that some things that look like virtue can lead straight to ruin if pursued rigidly, while some things that look like vice can, in practice, produce security and prosperity.

Chapter 16 — On Generosity and Stinginess

Start with generosity. It’s good to be thought generous.

But there’s a trap: generosity that doesn’t earn you the reputation of generosity hurts you, because it spends your resources without buying you the political benefit people assume generosity brings. If you give in a truly “proper” and honest way, it may not even be noticed—so you still get accused of stinginess.

That’s why anyone who wants to maintain the public name of “generous” feels pressured to avoid nothing that looks magnificent. A prince inclined that way will burn through his wealth on grand gestures, and sooner or later—if he insists on keeping the label—he’ll be forced to squeeze his people with taxes and burdens, doing whatever he can to raise money.

Spending Money: Why “Generosity” Can Backfire

Here’s the trap: if a ruler tries to look generous by constantly handing out money, he has to fund that image somehow. And the easiest source is usually his own people.

Over time, that “generosity” produces a predictable chain reaction:

• He spends heavily to impress.
• His finances thin out.
• He starts squeezing his subjects—through taxes, fees, confiscations, or other pressure—to keep spending.
• People feel used, not cared for.
• He ends up hated for taking and disrespected for being broke.

At that point, the first real crisis—an invasion, a revolt, a bad harvest, a budget shock—hits harder than it should. He’s offended many, truly helped only a few, and now he has less money and less goodwill than he thought.

So if a prince is thinking clearly, he shouldn’t panic about being called “cheap.” In fact, being seen as careful with money is often safer than chasing a reputation for generosity.

Why? Because a ruler who lives within his means can:

• keep revenue steady without draining the public,
• defend himself without begging or extorting,
• fund big projects without turning the population against him.

In other words, he can be “generous” in the only way that scales: by not taking from people unnecessarily. That kind of generosity reaches everyone. Meanwhile, he’ll disappoint only the smaller group who hoped to receive gifts.

Look around, Machiavelli says: the leaders who actually accomplished lasting things were often labeled “stingy.” The ones who tried to buy admiration tended to collapse.

He points to examples:

• Pope Julius II benefited from a reputation for liberality when he was climbing. But once in power, he didn’t keep spending to maintain the image. He went to war repeatedly, yet avoided extraordinary taxes because earlier thrift left him reserves.
• The King of Spain (in Machiavelli’s time) could attempt and win major campaigns precisely because he wasn’t known as a free spender. If people expected lavish giveaways, the funding would have broken him.

So the practical rule is simple: if a prince can avoid robbing his subjects, can defend the state, and doesn’t let himself become poor and contemptible, then he should treat the label “miserly” as a minor insult. It’s one of those “vices” that can actually make stable government possible.

“But Caesar Won by Generosity…”

Someone might object: didn’t Julius Caesar rise by spending freely? Didn’t other leaders reach the top by being famously generous?

Machiavelli’s answer: it depends on where you are in the power cycle.

• If you’re already ruling, flashy generosity is dangerous.
• If you’re trying to become the ruler, it can be useful—because reputations help you climb.

Caesar was aiming to become dominant in Rome. Spending helped him get there. But if he’d lived long enough to rule securely and kept spending at that rate, he would’ve hollowed out his own government.

Another objection: plenty of princes have led armies and achieved great things while being considered extremely generous.

Again, Machiavelli splits the situation in two: whose money are you spending?

1. If you’re spending your own money or your subjects’ money, you should be careful.
2. If you’re spending someone else’s money, be generous all you want.

A commander marching with an army, living off plunder, forced contributions, and whatever he can seize from others is, in a sense, spending other people’s resources. In that situation, “generosity” is practically required—because soldiers follow leaders who reward them.

And there’s a cynical bonus: giving away what isn’t yours can boost your reputation without costing you the thing that matters—your own base of support. Cyrus, Caesar, and Alexander could look magnificent because the bill was paid by conquered people. The kind of generosity that ruins you is the kind funded by your own treasury.

Finally, Machiavelli puts a hard point on it: nothing burns through power faster than constant giving. The more you give, the more you need to give, and the less able you are to keep it up. Then you’re pushed into one of two ugly outcomes:

• you become poor and therefore despised, or
• you start taking aggressively to avoid poverty, and become hated.

And since a prince’s top priority is to avoid being despised and hated, chasing a reputation for generosity is a high-risk strategy. Better to accept the criticism of being “tight” (which people grumble about) than to be driven into predation (which people remember and resent).

---

Cruelty and Mercy: The Point Isn’t “Nice,” It’s “Stable”

A prince should want to be seen as merciful, not cruel. But he also has to be careful with mercy—because mercy used badly can create a larger, messier cruelty later.

Machiavelli’s example is Cesare Borgia. People called him cruel, but his harsh measures brought a turbulent region under control, unified it, and restored order. In practical terms, that “cruelty” produced peace and loyalty.

And that leads to the uncomfortable claim: a ruler who uses a small number of decisive punishments can be more truly merciful than a ruler who avoids punishment entirely and allows disorder to spread. When chaos takes over, you don’t just get a few targeted victims—you get murders, robberies, vendettas, and whole communities living in fear. That harms everyone. A prince’s punishments hit individuals; unchecked disorder hits the public.

New rulers, especially, can’t avoid being accused of cruelty. New states are fragile and full of danger. Still, a prince shouldn’t be jumpy or impulsive. He should move carefully: slow to believe rumors, steady in action, calm in tone, and guided by prudence and basic humanity. Too much trust makes him reckless; too much suspicion makes him unbearable.

Loved or Feared?

So which is better: to be loved or feared?

Ideally, both. In reality, you usually have to choose—and Machiavelli says it’s safer to be feared than loved.

His reasoning is blunt: people often behave well while things are going smoothly, but many are unreliable under pressure. When danger feels distant, they’ll promise anything—money, effort, even their lives. When danger is close, many vanish or flip.

If a prince builds his security on affection alone, he’s betting his survival on other people’s moods. That’s a bad bet.

Love depends on a feeling of obligation—and when self-interest shows up, that obligation breaks easily. Fear depends on the expectation of punishment, and that expectation doesn’t get tired, distracted, or tempted.

But fear has a boundary: a prince should aim to be feared without being hated. That’s achievable if he follows two core rules:

• Don’t touch people’s property.
• Don’t touch their families—especially their women.

When a prince must take someone’s life, he should do it with clear public justification and an obvious cause. But above all, he should keep his hands off other people’s assets. People will often forgive—or at least move on from—many things faster than they forgive the loss of what they consider their inheritance.

And once a ruler starts living by confiscation, he’ll always find excuses to keep doing it. Taking property is easy to rationalize and hard to stop. Taking lives is harder to justify and tends to create larger, more immediate consequences.

There’s one major exception: the prince with an army in the field. A commander controlling large numbers of soldiers may need a reputation for harshness to keep discipline. Without it, the army fractures.

Machiavelli points to Hannibal: he led a massive, diverse army in foreign territory, and it didn’t splinter—whether he was winning or losing. Why? Because his severe discipline, paired with his courage, made him both respected and terrifying. Without that severity, bravery alone wouldn’t have held the army together.

He contrasts this with Scipio, an exceptional leader whose troops rebelled in Spain. The cause wasn’t incompetence—it was excessive leniency, which gave soldiers more freedom than discipline can tolerate. Even when Scipio’s officials harmed allies, he didn’t correct them sharply, and that “easygoing” reputation became a liability. Under the Senate’s oversight, this weakness was contained and even polished into glory—but left unchecked, it would eventually have damaged him.

So Machiavelli’s conclusion stays the same: since people love based on their own choice but fear based on the prince’s decisions, a wise prince should anchor his safety in what he can control. He should build fear carefully and, above all, avoid hatred.

---

Keeping Faith: Why Power Can’t Run on Promises Alone

Everyone agrees it’s admirable for a ruler to keep his word and live with integrity rather than trickery. But Machiavelli says the track record of successful rulers tells a different story: the ones who achieved big results often treated promises as flexible tools, not sacred restraints.

He argues there are two ways to compete:

• by law (the human way),
• by force (the animal way).

Law is better when it works. But it often doesn’t. So a prince must know how to use both—the human and the beast.

Ancient writers, he says, hinted at this with myths: heroes trained by beings that were half human, half animal. The point wasn’t biology. It was training in dual strategy.

If a prince must act like a beast, Machiavelli recommends two animals:

• the fox, to recognize traps,
• the lion, to scare off wolves.

A lion is strong but can’t spot snares. A fox sees snares but can’t fight wolves. The effective ruler combines both.

From there, Machiavelli pushes the controversial claim: a wise ruler can’t—and sometimes shouldn’t—keep faith when keeping it will harm him, or when the original reasons for the promise no longer apply. If people were good, this advice wouldn’t be necessary. But since many people won’t keep faith with you when it costs them, you shouldn’t treat yourself as uniquely bound when the deal becomes one-sided.

He adds that rulers never lack “respectable” excuses for breaking promises, and history is full of treaties that dissolved the moment it was convenient.

Still, deception has to be done intelligently. The prince must be able to mask the move. He must be a convincing actor—because people are often simple, focused on immediate needs, and eager to believe what helps them in the moment. A deceiver will almost always find someone ready to be deceived.

He offers an example from his own era: Pope Alexander VI, who constantly promised, swore, and reassured—and then did what benefited him. His deceptions worked, Machiavelli says, because he understood human psychology: people want certainty, and they prefer comforting stories to uncomfortable truth.

The Reality: You Don’t Need Every Virtue—You Need the Appearance

Machiavelli then draws a sharp line between being and seeming.

A prince doesn’t need to possess every celebrated virtue in full. But he absolutely needs to look like he does.

In fact, always practicing the virtues can be harmful, because ruling sometimes requires actions that contradict them. Appearing virtuous is often useful; being rigidly virtuous can be dangerous.

So a prince should aim to appear:

• merciful,
• faithful,
• humane,
• upright,
• religious.

He can even be those things—until necessity forces a change. The crucial skill is flexibility: a mind prepared to shift with circumstances, staying with the good when possible, but knowing how to move against it when survival requires.

That’s especially true for a new prince, who inherits instability and threats. Maintaining the state may force him to act against promises, friendship, compassion, or religious scruples.

Even so, Machiavelli warns: the prince should never sound like anything other than virtue. His public words should be saturated with those five qualities. Because most people judge leaders the way they judge products: by the packaging, not the internal engineering.

Almost everyone can see what you project. Very few can touch the reality. And the few who know better often won’t challenge the majority, because the state’s authority shields the ruler and isolates dissenters.

In politics, outcomes dominate moral accounting. When a prince succeeds—when he conquers and holds power—most people will call the methods “necessary” and praise the result. The crowd is captivated by what something looks like and what it produces. The few who see through the performance matter less when the many feel secure.

Machiavelli even notes a contemporary ruler—he won’t name him—who endlessly preaches peace and good faith while privately opposing both. And Machiavelli’s implication is chillingly practical: if that ruler had actually lived by his preaching, he would have lost power more than once.

---

Avoid Being Despised and Hated: The One Rule That Keeps Coming Back

Bringing these traits together, Machiavelli says the prince should focus on one overarching goal: avoid the behaviors that make people hate you or look down on you. If you achieve that, you can survive a lot of criticism.

And the fastest way to become hated is the one he keeps repeating: be rapacious—especially by violating people’s property and their families. Those are the lines a prince must not cross.

When People Feel Safe, They Stay Calm

Most people are perfectly fine living under a ruler as long as two things stay intact: their property and their sense of dignity. If you don’t mess with those, the majority will stay content, and your real problem shrinks to a small circle of ambitious rivals—people you can usually rein in without too much trouble.

That said, a ruler can still destroy his own position by projecting the wrong image. Nothing makes a prince look weaker than being seen as:

• fickle (changing his mind constantly)
• frivolous (treating serious matters lightly)
• effeminate (in the sense of seeming soft or easily pushed around)
• small-minded or mean-spirited
• indecisive

A prince should avoid those traits like a ship avoids rocks. Instead, he should make his public actions communicate scale and steadiness—greatness, courage, seriousness, and strength. And in everyday dealings with his subjects, he should give off one unmistakable message: his judgments stand. If people believe you can be talked out of decisions, manipulated, or “worked,” they’ll try. If they believe you can’t, they won’t.

That reputation matters for one big reason: a prince who is highly esteemed is hard to conspire against. If everyone knows he’s capable and the people genuinely respect him, attackers face a steep climb.

---

Two Kinds of Danger: Inside and Outside

A prince has two sources of fear:

1. From within: his own subjects
2. From without: foreign powers

Against foreign threats, the formula is straightforward: be well armed and have strong allies. If you’re well armed, you tend to attract good partners; and when things are calm abroad, things usually stay calm at home—unless a conspiracy is already in motion.

Even when trouble erupts outside the borders, a prince who prepared early and lived with the steadiness described above can hold the line, so long as he doesn’t panic. Think of it like a siege: if you stocked supplies and built strong walls before the attack, you can outlast the storm.

---

Why Popular Support Is the Best Anti-Conspiracy System

When foreign affairs are chaotic, the prince’s main internal risk is secret plotting. But there’s a reliable way to reduce that risk: don’t become hated or despised, and keep the people broadly satisfied.

Here’s why this works. A conspirator usually tells himself, “If I remove the prince, the public will thank me.” But if the prince is liked, the plot flips: removing him would anger the people. And when a would-be assassin imagines that the outcome is not applause but outrage, he hesitates—because the odds are terrible.

Conspiracies fail so often for practical reasons, not just moral ones:

• A conspirator can’t safely act alone.
• If he recruits a partner, it’s almost always someone he believes is unhappy with the regime.
• But the moment you confide in a “malcontent,” you hand them leverage: they can gain far more by betraying you than by risking everything with you.

If turning you in comes with certain rewards—and the plot comes with uncertainty, danger, and punishment—then only an unusually loyal friend, or an exceptionally stubborn enemy of the prince, will keep faith with you.

In short, the conspirator’s side is stacked with fear, jealousy, and the expectation of punishment. The prince’s side has the weight of office, the law, the state’s defenders, and the protection of allies. Add public goodwill, and conspiring becomes an act of pure recklessness. And there’s an extra twist: most criminals fear getting caught before the act; in this case they also have to fear what comes after, because the people—if they loved the prince—become their enemy, and escape routes vanish.

---

A Concrete Example: Bologna’s Backlash

One example is enough. In Bologna, a prince named Annibale Bentivoglio was murdered by a family who plotted against him. Afterward, the city didn’t reward the conspirators. It erupted—and the people killed them all.

That reaction didn’t happen by accident. It came from the deep goodwill Bologna felt toward the Bentivoglio household at the time. In fact, the loyalty ran so strong that even when no obvious Bentivoglio remained who could govern, the Bolognese sought out a surviving family member in Florence—someone who had previously been treated as insignificant—and brought him back to rule the city until the rightful heir was old enough to govern.

The lesson is blunt: if the people esteem you, conspiracies are a manageable nuisance. If the people hate you, you should fear everything and everyone.

---

What Smart States Do: Keep Nobles Stable, Keep People Content

Well-run states and wise princes take great care not to push the nobility into desperation and to keep the public satisfied. That balance isn’t cosmetic. It’s one of the most important goals a ruler can pursue.

Consider France, one of the best-governed kingdoms of the time. It has institutions that support the king’s freedom of action and the kingdom’s stability. A key one is the parliament and its authority. The founders understood two realities at once:

• The nobles are ambitious and bold; they need a “bit in the mouth”—a restraint.
• The people tend to distrust the nobles and fear their power; they need protection.

But the founder didn’t want the king personally blamed for constantly siding with one group against the other. So an arbiter was set up—an authority that could restrain the great and protect the lesser without dragging the king into daily resentment. It’s hard to design something more prudent, or more stabilizing, for both king and country.

From this you can draw another principle: princes should push unpopular, blameworthy actions onto others, and keep acts of grace in their own hands. And a prince should value the nobles—just not in a way that makes the people hate him.

---

A Major Objection: “What About the Roman Emperors?”

Someone might object: “But look at the Roman emperors. Some lived honorably, showed real greatness, and still lost their thrones or were murdered by conspiracies.”

To answer that, it’s enough to examine the emperors from Marcus Aurelius down to Maximinus: Marcus and his son Commodus, Pertinax, Julian, Severus and his son Antoninus Caracalla, Macrinus, Heliogabalus, Alexander, and Maximinus.

The Roman emperors faced a problem many other princes don’t face in the same way. In most states, you mainly manage two forces:

• the ambition of the nobles
• the mood of the people

Rome added a third—and it was often decisive: the cruelty and greed of the soldiers.

This created an almost impossible balancing act. The people loved peace, so they preferred a prince who wasn’t constantly chasing glory or war. The soldiers preferred a warlike prince—bold, harsh, willing to loot—because they wanted higher pay and more opportunities to satisfy their appetites. Often, they were happy for those appetites to be satisfied at the public’s expense.

So emperors with weak natural authority—especially new men without deep legitimacy—were frequently toppled. Many of them tried to survive by pleasing the soldiers and worrying less about harming the people. Sometimes that bought time; sometimes it accelerated collapse. The result depended on whether the prince knew how to keep command over the soldiers rather than become their hostage.

A prince can’t avoid being hated by someone. The first priority, then, is not “be loved by all,” but don’t be hated by everyone. When that’s impossible, avoid the hatred of the most powerful group.

---

Why the “Good” Emperors Still Fell

Three emperors—Marcus Aurelius, Pertinax, and Alexander—lived modestly, loved justice, rejected cruelty, and acted humanely. Yet two of them ended badly.

Marcus is the exception: he lived and died honored. Why? He inherited the throne, owed his position to no faction, and possessed virtues that kept him respected. He held both the people and the soldiers in their proper places without becoming hated or despised.

Pertinax, however, became emperor against the soldiers’ wishes. Under Commodus, the troops had grown used to a loose, indulgent lifestyle. Pertinax tried to restore discipline and an “honest” standard of behavior. The soldiers couldn’t stand it. He earned their hatred, and because he was also elderly, they despised him as well. He was overthrown almost immediately.

This reveals an uncomfortable truth: you can earn hatred not only through bad deeds, but through good ones. If the group you need to keep you in power is corrupt—whether that’s soldiers, nobles, or even the people—you may be forced to cater to their appetites. In that situation, doing the “right” thing can become politically fatal.

Alexander illustrates a different route to ruin. He was so mild that in the fourteen years he ruled, no one was executed without due judgment. Yet he was judged soft, and worse, someone governed by his mother. That image made him contemptible in the army’s eyes, and they eventually conspired and murdered him.

---

The “Bad” Emperors—and Why One of Them Succeeded

Now look at the opposite type: Commodus, Severus, Antoninus Caracalla, and Maximinus. They were harsh and predatory, and to satisfy their soldiers they didn’t hesitate to commit injustices against the people. All of them ended badly—except Severus.

Severus had one thing in abundance: valor. He kept the soldiers on his side, and even though the people suffered under him, he ruled successfully. His reputation made him admired by the troops, and it left the public stunned and intimidated—awed enough to endure.

Severus also understood something every new prince needs: how to be both fox and lion—clever in deception and strong in force.

He exploited the laziness of Emperor Julian by persuading the army he commanded in Sclavonia that they should march on Rome to avenge Pertinax, who had been killed by the praetorian soldiers. Under that pretext—without openly declaring himself a contender—he moved fast and reached Italy before people even understood what he was doing. When he arrived, the Senate, frightened, elected him emperor and killed Julian.

After that, Severus faced two rivals:

• Niger in Asia, backed by the eastern army
• Albinus in the West, also aiming for the throne

He judged it dangerous to fight both at once. So he attacked Niger and tricked Albinus. He wrote to Albinus saying he was willing to share honor, gave him the title of Caesar, and presented him as a partner endorsed by the Senate. Albinus accepted.

Once Severus defeated and killed Niger and stabilized the East, he returned to Rome and reframed Albinus as a traitor who had plotted against him. He claimed he was forced to punish ingratitude. Then he went after Albinus in France, stripped him of power, and killed him.

Study Severus closely and you see both animals: a fearless lion and a calculating fox. He made himself feared and respected without becoming hated by the army. And as a new ruler, his towering reputation shielded him from the hatred the people might have developed because of his violence.

---

Caracalla: Loved by Soldiers, Hated by Everyone Else

Severus’s son, Antoninus Caracalla, had striking qualities. He was tough, built for hardship, and scorned luxury—traits that made him popular with the armies.

But his savagery was extreme. After countless murders of individuals, he ordered mass killings in Rome and slaughtered many in Alexandria. He became hated across the empire and feared even by those closest to him. He was eventually killed in his own camp by a centurion.

There’s another lesson here: some threats can’t be fully prevented. A determined killer who doesn’t fear death can strike even a powerful ruler. But these attacks are rare, and a prince can reduce the risk by following one rule: don’t grievously injure the people you rely on and keep close. Caracalla ignored that. He had insulted and killed a close relative of the centurion—then kept the centurion in his guard while threatening him daily. That was reckless, and it cost him his life.

---

Commodus: Inherited Power, Threw It Away

Commodus should have found ruling easy. As Marcus’s son, he inherited the empire and could have stayed secure simply by following his father’s example, keeping both soldiers and people satisfied.

Instead, his nature was cruel and brutish. He focused on entertaining and corrupting the troops so he could prey on the public. He also failed to maintain the dignity of his office—publicly debasing himself, even appearing in the arena with gladiators and doing other things unworthy of imperial majesty. The result was predictable: the soldiers despised him, the people hated him, and he was conspired against and killed.

---

Maximinus: Ferocious, Low-Status, and Politically Clumsy

Maximinus was a born fighter. The armies, disgusted by Alexander’s softness, murdered Alexander and elevated Maximinus.

He didn’t last long, because he managed to become both hated and despised.

• He was scorned because he had once been a shepherd in Thrace—an origin everyone knew and many found degrading for an emperor.
• He worsened matters by delaying his trip to Rome to take the imperial seat, reinforcing the sense that he didn’t belong.
• He also gained a reputation for brutal cruelty, carried out through officials across Rome and the provinces, which made the world fear him.

First Africa rebelled. Then the Senate, the people of Rome, and much of Italy turned against him. Finally, even his own army turned—especially during the siege of Aquileia, where delays and hardship made the troops resentful. Seeing so many forces aligned against him, they feared him less and murdered him.

---

What This Means for Princes “Now”

I won’t linger on Heliogabalus, Macrinus, or Julian, who were so contemptible that they were quickly wiped out. The larger point is this: modern princes face the problem of overindulging soldiers far less than the Roman emperors did. Even when you must grant the military some allowances, it’s usually manageable.

Roman armies were different. They were effectively veterans not only of war, but of governing provinces—deeply entangled in administration and political power. In that world, it often mattered more to satisfy the soldiers than the people. In most states now, the balance shifts the other way: it’s more important—except in certain special cases—to keep the people satisfied, because they are the more powerful force.

---

Exceptions: The Turk and the Soldan

One exception is the Turk, who keeps close at hand a fixed core of troops—twelve thousand infantry and fifteen thousand cavalry—and the kingdom’s safety depends on them. In that situation, the ruler has to set aside the people’s favor and keep those forces loyal.

The kingdom of the Soldan is similar: because it rests entirely in the hands of soldiers, he too must keep them his friends, without regard to the people.

Because this is an old, established arrangement, it doesn’t really count as a new principality. The ruler might be new, but the state itself is not. Its institutions are already built to accept a prince as if he’d always belonged there—almost like a system designed to “adopt” him as a hereditary lord.

Now, back to the point. If you look closely at the emperors I mentioned, a pattern jumps out: what destroys rulers is usually either hatred or contempt. And you can also see why, even though different emperors tried very different approaches, only a rare few ended well.

Here’s the key: a new ruler can’t copy just anyone.

• It would have been reckless—and basically impossible—for Pertinax or Alexander, both new princes, to imitate Marcus, who inherited power and benefited from the stability that comes with succession.
• And it would have been suicidal for Caracalla, Commodus, or Maximinus to imitate Severus, because they didn’t have the force of character and courage needed to carry Severus’s hard-edged methods without falling apart or getting overthrown.

So what should a new prince do? Not cosplay as Marcus. Not blindly follow Severus either. Instead, he should borrow selectively:

• From Severus, take what you need to build and secure a new state.
• From Marcus, take what is admirable and honorable for maintaining a state that has already become stable and firmly rooted.

Chapter 20 — Are Fortresses (and Similar Tactics) Helpful or Harmful?

Princes use all kinds of tricks to hold on to power. Some disarm their subjects. Others keep towns divided into factions. Some deliberately make people hate them. Others work hard to win over the people they initially mistrusted. Some build fortresses; others tear them down.

You can’t give one universal verdict without knowing the specific situation of each state. Still, we can talk about what generally holds true.

Disarming vs. Arming the People

A striking fact: a truly new prince almost never disarms his subjects. More often, he does the opposite—especially if he finds them already disarmed.

Why? Because arming them makes them yours.

• The weapons become tied to your rule.
• People you didn’t trust at first often become loyal, because you’ve shown confidence in them and given them a stake in your survival.
• People who were already loyal tend to stay that way.
• Over time, armed subjects start acting like supporters, not merely people who endure you.

Of course, you can’t arm everyone. But that limitation can actually work in your favor. If you arm some and not others, the ones you arm feel rewarded—and the others usually understand the logic: the people who take the biggest risks and carry the biggest burdens get the biggest benefits. That makes it easier to manage the rest.

Disarm them, though, and you instantly insult them. You’re announcing, “I don’t trust you.” Whether they interpret that as you thinking they’re cowards or traitors, either way it breeds hatred.

And once you’ve disarmed your own people, you’re forced to lean on mercenaries. Even if those mercenaries are decent, they’re rarely enough to protect you from both powerful enemies and resentful subjects at the same time.

So yes: in a new principality, a new prince typically distributes arms. History is full of examples.

There’s one major exception. If you annex a new state and turn it into a province attached to your old state, then you generally must disarm the new province—except for those who actively helped you take it. Even then, over time you should make sure that the only serious armed force in that province is your own, ideally soldiers rooted in your original territory and close to you.

Factions as a Tool of Control

Old political “wisdom” used to say things like: hold one city by keeping it divided into factions, and hold another by building fortresses. In some earlier Italian conditions—when power was more evenly balanced—this may have seemed workable.

But as a rule for today? It’s a trap.

A divided city is a city that collapses fast when pressure hits. When an outside enemy arrives:

• the weaker faction will almost always invite or assist the outsider,
• and the stronger faction won’t be able to hold the city alone.

The Venetians tried this method in their subject cities, keeping old rival parties alive (carefully, without letting them turn into open violence) so citizens would stay busy fighting each other instead of uniting against Venice. It didn’t work the way they hoped. After their defeat at Vaila, one faction immediately seized the opportunity and took control.

So if a prince relies on factions, it’s usually a sign of weakness. A vigorous, well-run principality doesn’t need that kind of internal sabotage. It may look useful in peacetime, but the moment war arrives, the strategy reveals itself as wishful thinking.

Should a Prince “Cultivate” Enemies?

Princes become great by overcoming obstacles. And fortune, when she wants to elevate a new prince—someone who must earn fame rather than inherit it—often supplies those obstacles in the form of enemies and plots.

That’s why some people argue a wise prince should, when the opportunity arises, allow a manageable hostility to form, so he can crush it and climb higher—like using your enemies as the rungs of a ladder they accidentally built for you.

Winning Over the People You Initially Distrusted

New princes often discover something counterintuitive: they get more reliable support from people they distrusted at first than from those they initially trusted.

Why? Because people who begin on the “outside” and later get pulled in often work harder to prove themselves. If they were once hostile but are the kind who need your protection to steady their own position, they can be won over very easily—and once won, they cling tightly, because they know they must erase their earlier hostility through real service.

Meanwhile, people who serve you with too much comfort and certainty can grow careless.

One warning, though. If you took a new state with the help of secret supporters, you must ask: Why did they help me? If it wasn’t genuine loyalty to you, but simply hatred for the previous government, then keeping them satisfied will be difficult—sometimes impossible—because you can’t fulfill the hopes of people whose main desire was “anything but the old regime.”

In practice, it’s often easier to reconcile with those who were content under the previous ruler (and therefore resisted you) than to manage those who supported you mainly out of frustration and expectation.

Fortresses: Safety Net or Liability?

Princes often build fortresses for two reasons:

• as a bit and bridle to restrain subjects who might rebel, and
• as a refuge against the first shock of an attack.

This has a long history, and it can be sensible. But we’ve also seen capable rulers do the opposite—tear fortresses down—because in their circumstances, fortresses would have made them less secure.

So what’s the real rule?

A fortress helps or hurts depending on what you fear most.

• If you fear your own people more than foreign powers, fortresses can help.
• If you fear foreign powers more than your people, fortresses can become a distraction—or worse, a liability.

In fact, the most reliable “fortress” is not stone and mortar. It’s this: don’t be hated by the people. Because if the population turns against you, fortresses won’t save you. Foreign allies will always be found to support an armed people who want you gone.

In recent times, fortresses have rarely saved a prince—except in one notable case, when a ruler was able to hold out long enough for outside help to arrive and retake control. But even there, the larger lesson still stands: later, when circumstances changed and foreign forces joined with internal enemies, fortresses offered little protection.

So I’ll praise a prince who builds fortresses and a prince who doesn’t—because both can be right, depending on the situation. But I’ll blame any prince who relies on fortresses and, because of that false confidence, stops caring whether the people hate him.

Chapter 21 — How a Prince Gains Renown

Nothing boosts a prince’s reputation like big, visible achievements—and the kind of leadership that feels like a public example.

A vivid case from our own time is Ferdinand of Aragon, the current King of Spain. In many ways he’s almost a “new prince”: he rose from being a relatively minor figure to becoming one of the most powerful rulers in Christendom, largely through fame and strategic success.

Look at his actions and you’ll notice two things: they’re consistently bold, and they often border on extraordinary.

Early in his reign, he attacked Granada, and that campaign became the foundation of his expanding power. He began carefully and quietly, without giving anyone an obvious reason to obstruct him. Meanwhile, he kept the nobles of Castile mentally occupied with the war so they wouldn’t anticipate how this long campaign would increase his authority over them.

He also sustained his armies with money drawn from the Church and from the people, and the length of the war helped him build the military skill that later defined his reign. And he repeatedly used religion as a banner for ever-larger projects—most dramatically by pushing the Moors out of his kingdom with a ruthlessness he wrapped in piety. Under the same pretext, he moved into Africa, intervened in Italy, and eventually attacked France.

The result is a kind of political momentum: one major move flows into the next, and people never get a calm stretch of time to organize steady opposition against him. Their minds stay occupied—suspended between suspense and admiration.

Striking Examples at Home

A prince can also strengthen his reputation through unusual, widely discussed decisions in domestic affairs—especially when he rewards or punishes extraordinary behavior in a way people can’t stop talking about.

Above all, a prince should aim for a reputation as someone great and remarkable—not merely competent.

Why Neutrality Is Dangerous

A prince also earns respect when he’s either a true friend or an unmistakable enemy—that is, when he openly commits to one side rather than trying to hover in the middle.

Neutrality often looks “safe,” but it’s usually the opposite.

If two powerful neighbors go to war, you either have reason to fear the winner or you don’t. In either case, it’s generally better to declare yourself and act decisively than to stand aside.

Because if you stay neutral and one side wins:

• the victor will treat you as a prize, not a partner,
• the loser won’t protect you, because you didn’t share their risk,
• and you’ll have no credible excuse to offer.

Conquerors don’t value doubtful friends who refused to help in the moment of danger. And defeated powers don’t shelter those who wouldn’t commit when commitment mattered.

There’s a classic example: Antiochus entered Greece at the invitation of the Aetolians to push out the Romans. He urged the Achaeans—friends of Rome—to stay neutral, while Rome urged them to take up arms. When the issue was debated, the Roman representative cut through the illusion: neutrality, he said, doesn’t buy safety; it simply leaves you “the reward of the conqueror.”

That’s the usual outcome. Whoever is not your friend will demand your neutrality, while whoever is your friend will urge you to stand with them openly.

Indecisive princes choose neutrality to dodge immediate danger—and often get ruined because of it.

What You Gain by Choosing a Side

If you commit and your side wins, you may be dealing with a powerful victor, yes. But that victor is now indebted to you. A bond forms. And people rarely go out of their way to immortalize themselves as monsters of ingratitude by crushing those who helped them win. Even the most complete victories still leave room for obligations—especially those tied to justice and reputation.

If your side loses, you may still gain shelter, support, and future opportunity. You become a partner in a fortune that could rise again.

A Crucial Warning About Alliances

One more caution: never ally with someone more powerful than you in order to attack others—unless necessity forces you to.

If your stronger ally wins, you are at his discretion. Princes should avoid being at anyone’s discretion whenever they can.

The Venetians allied with France against the Duke of Milan, and that choice helped bring about their ruin. They could have avoided it. But sometimes alliances can’t be avoided—like when circumstances corner you and multiple powers are moving against you. In those cases, for the reasons above, you still should commit to one side rather than pretend you can float safely between them.

Choosing the Lesser Evil

No government should imagine it can always choose perfectly safe options. Politics doesn’t work that way. Most decisions trade one danger for another. Prudence is the art of comparing risks—and choosing the lesser one.

Building Talent, Prosperity, and Public Life

A prince should also make a point of being a patron of skill and excellence, honoring those who excel in any craft or art.

At the same time, he should make it easy for people to live and work without fear:

• encourage commerce, agriculture, and every legitimate occupation,
• make sure people aren’t afraid to improve their property because it might be seized,
• and don’t make them fear opening businesses because taxes will immediately punish success.

If people want to build, trade, improve, or honor the city, the prince should support that with rewards and recognition.

Finally, he should give the public festivals and spectacles at appropriate times of year. And because every city is divided into guilds and associations, he should treat these groups with respect—sometimes even appearing among them—showing courtesy and generosity while still maintaining the authority and dignity of his rank, which he must never weaken.

Guild-like organizations existed in plenty of European towns: entire trades could be organized into a single, city-recognized body. Florence’s guilds are a famous example, and historians have documented how thoroughly they shaped the city’s working life.

You can find something broadly similar in modern Russia in groups called artels: cooperative work associations where (for example) sons might spend the working season as members. In larger towns, artels can be more elaborate—permanent organizations with significant shared capital, and collective financial responsibility for what individual members do.

Despite how it looks on the page, “artel” isn’t related to Latin ars or “arte.” The word traces back to a root meaning to bind oneself by an oath, and it’s linked to a term that later came to mean something like a company within a regiment. The common idea is the same in both: a body of people united by a sworn bond.

Some groups referred to as tribu may have been kin-based communities—people connected by common descent, with additional ties formed through marriage. In modern English, “clans” or “septs” probably comes closest.

---

Chapter 22 — Concerning the Secretaries of Princes

A prince’s choice of assistants isn’t a small detail—it’s a major signal of how competent he is.

In fact, one of the fastest ways to judge a ruler is to look at the people closest to him. If they’re capable and loyal, that usually means the prince has good judgment: he recognized talent and found ways to keep it aligned with his interests. If the people around him are mediocre, corrupt, or unreliable, it’s hard to give the prince much credit—because the first, basic mistake was choosing them.

Consider Pandolfo Petrucci, the ruler of Siena, and his secretary Messer Antonio da Venafro. Anyone who knew Venafro as Petrucci’s servant took it as evidence that Petrucci was sharp, because it takes discernment to keep someone like that close.

To see why, it helps to separate intellect into three types:

• First-rate: understands things on its own.
• Second-rate: doesn’t originate the insight, but recognizes and values it when others present it.
• Third-rate: understands neither on its own nor with help.

The first is excellent, the second is solid, and the third is useless.

So even if Petrucci wasn’t in the top category, he was at least in the second. Here’s why that matters: a leader may not generate every idea himself, but if he can reliably tell good judgment from bad—by watching what people do and listening to what they say—then he can reward what’s right and correct what’s wrong. A servant who knows his master can see through him has a harder time running games. That pressure keeps him honest.

There’s also a simple test that almost never fails when you’re evaluating an advisor. Watch what he optimizes for.

• If he consistently puts his own advantage ahead of yours, he won’t be a good servant.
• If he hunts for personal profit in everything, you can’t trust him with what belongs to you.

Someone who holds another person’s state in his hands should never center himself. His attention should stay on the prince and on matters that actually affect the prince.

At the same time, a prince shouldn’t rely only on suspicion. If he wants his servants to stay loyal, he should make loyalty worth it—and make betrayal unnecessary.

That means:

• Honor them and let that honor be visible.
• Pay them well and raise them when they do well.
• Do them favors and bind them with real gratitude.
• Share both recognition and responsibility, so they feel invested.

But there’s a second half to the strategy: make sure they understand they don’t stand securely on their own. In other words, arrange things so that:

• honors don’t make them crave even more honors,
• wealth doesn’t make them hunger for still more wealth, and
• responsibilities make them wary of sudden upheavals.

When princes and servants relate to each other like this, they can trust each other. When they don’t, the ending is predictable—and ugly—for one side or the other.

---

Chapter 23 — How Flatterers Should Be Avoided

There’s a danger in every court that’s so common it almost becomes background noise: flattery.

Princes have a hard time defending themselves from it unless they’re alert and selective. Courts are full of people who will tell you what you want to hear, partly because human beings are naturally pleased with themselves, and partly because we’re surprisingly easy to fool about our own judgment. That combination makes flattery feel good—and makes it hard to treat as the threat it is.

But defending yourself has its own trap. If you respond by trying to shut people down, you can end up looking petty or insecure. And there’s another awkward fact: the only foolproof way to block flatterers is to let it be known that truth won’t offend you. Yet if everyone can tell you the truth whenever they want, people start to lose some of their restraint around you, and your authority can erode.

So what’s the middle path?

A wise prince does something more controlled. He:

• selects a small group of wise people,
• gives them the freedom to speak honestly,
• but limits that freedom to the questions he asks, and to the topics he’s investigating—not everything under the sun.

Then he questions them broadly, listens closely, and finally decides for himself. And he manages these advisers—one-on-one and as a group—so that each person understands a clear rule: the more plainly you speak, the more you’re valued. Outside that circle, he doesn’t take counsel. Once he’s decided, he follows through and stays steady.

If you do the opposite—if you let flatterers steer you, or if you constantly revise yourself because every new voice pushes you a different direction—you’ll either be toppled or end up with a reputation for wobbling. Either way, people stop taking you seriously.

A real-world example makes the point. Fra Luca, an administrator close to the Emperor Maximilian, said something like this about him: He consulted no one, yet he never got his way.

That sounds paradoxical until you see the pattern. Maximilian kept his plans secret and didn’t invite opinions. But as soon as he began to act, the plan became visible. The people around him—who hadn’t been involved, who didn’t feel committed, and who had their own agendas—blocked him. And because he was pliable, he let himself be diverted. The result was whiplash: what he did one day he undid the next. No one could tell what he wanted, and no one could rely on his decisions.

So the rule is this: a prince should always take counsel—but only when he chooses, not whenever other people feel like offering it. He should discourage unsolicited advice, but he should also be a constant questioner. And once he asks, he should listen patiently. If he later discovers that someone knowingly hid the truth from him—whatever the motive—he should make his displeasure unmistakable.

Some people claim that when a prince seems wise, it’s not because he’s wise, but because he has brilliant advisers. That’s usually backwards. Here’s the principle that holds up in practice: a prince who isn’t wise will not consistently take good advice, unless he hands everything over to a single exceptionally prudent person. In that case he may be governed well for a time—but not for long, because the person doing the governing will soon have the power to take the state for himself.

And if an inexperienced prince tries to take advice from many people at once, things get worse, not better. Their recommendations won’t line up, and the prince won’t know how to combine them. Each counselor will pull toward his own interests, and the prince won’t have the skill to control them or see through their motives.

People don’t reliably stay loyal just because it’s “right.” If you want truth, you need structures that reward honesty and constrain self-serving behavior. So when good counsel appears—wherever it comes from—it ultimately reflects the prince’s own wisdom. It isn’t that advisers manufacture a prince’s wisdom; it’s that a wise prince knows how to produce good counsel by the way he chooses, frames, and uses advisers.

---

Chapter 24 — Why the Princes of Italy Lost Their States

If a new prince follows the guidance already laid out, he can look firmly established surprisingly fast—often more secure than someone who inherited power and has held it for years.

That’s because people watch a newcomer more closely. When his actions show capability, he earns support quickly, and he can bind followers more tightly than “ancient blood” ever could. Most people are pulled more by what’s happening now than by what happened long ago. If the present is good, they settle in, enjoy it, and stop searching for alternatives. And if the prince doesn’t fail them in other ways, they’ll defend him fiercely.

That creates a kind of double outcome:

• Double glory for the new prince who founds a state and then strengthens it—good laws, reliable military power, smart alliances, and a clear public example of competence.
• Double disgrace for the man born into rule who loses his state because he lacked the judgment to keep it.

Look at the lords who lost their states in Italy in recent times—the King of Naples, the Duke of Milan, and others. You’ll find a shared weakness, and it starts with arms—the military foundations discussed earlier. Beyond that, each case tends to show one of two failures:

• either the prince had the people against him,
• or, if the people were generally friendly, he failed to manage and secure the nobles.

Without those faults, a state that can put an army in the field doesn’t simply vanish.

A historical comparison helps. Philip of Macedon—not Alexander the Great’s father, but the later Philip who fought Titus Quintius—ruled a territory small compared with the power of Rome and the Greek forces aligned against him. Yet because he was a warlike leader who understood how to win popular support and keep the nobles onside, he sustained the conflict for years. Even when he lost control of certain cities, he still held on to his kingdom.

So princes shouldn’t blame “fortune” for losing principalities they held for many years. They should blame their own laziness. In peaceful times they never imagined circumstances could change. It’s a common human mistake: we don’t prepare for storms when the sky is clear. Then, when trouble arrives, they think first of fleeing rather than defending themselves. They tell themselves the people—once they’re sick of the conqueror’s arrogance—will call the old rulers back.

That might happen when all else fails, but it’s a terrible strategy to treat it as your plan. You’d never choose to fall just because you hope someone later will restore you. And even if restoration comes, it doesn’t make you safe, because rescue that depends on someone else is weak by nature. The only deliverance that lasts is the one rooted in your own strength and courage.

---

Chapter 25 — What Fortune Can Do in Human Affairs, and How to Resist It

Many people believe the world runs on fortune and God in such a way that human wisdom can’t steer events—and that no one can meaningfully help themselves. If that were true, there’d be no point in working hard or planning ahead; you’d just let chance drive.

That belief has gained traction in times of upheaval, because we’ve seen enormous changes that seem to arrive out of nowhere, beyond what anyone would predict. And honestly, when you sit with that for long enough, it can be tempting to agree.

Still, I don’t want to erase human choice. A more accurate view is this: fortune controls about half of what happens to us, but it leaves the other half—maybe a little less—to us.

Think of fortune like a violent river in flood. When it surges, it spills over the banks, sweeps away trees and buildings, tears up soil, and drags everything downstream. In that moment, nothing stands calmly in its way.

But the fact that floods happen doesn’t mean people can’t prepare. When weather is fair, they can build embankments and channels—structures that, when the river rises again, guide the water and reduce its damage. The river is still powerful, but it’s less free to destroy.

Fortune works the same way. It shows its power most where courage and preparation haven’t been built up to resist it. It rushes into the places that have no barriers.

If you look at Italy—the center of the upheavals being discussed—you can see the problem: it’s like an open plain with no defenses. If Italy had been defended with the kind of strength and organization seen in Germany, Spain, or France, either the invasions wouldn’t have caused such dramatic changes, or they wouldn’t have happened at all.

That’s enough about fortune in general. Now for the specific point: you can watch a prince go from successful today to ruined tomorrow without any obvious change in his personality. Why?

First, as already discussed, a prince who leans entirely on fortune collapses when fortune shifts. Second, success often belongs to the prince whose methods match the moment—who acts in harmony with the “spirit of the times.” When his habits don’t fit the era, he fails.

People chase the same ends—glory and wealth—by very different routes:

• one moves with caution, another with speed,
• one relies on force, another on skill,
• one works by patience, another by its opposite.

And different methods can reach the same goal. You even see two cautious people diverge—one succeeds, one doesn’t. Or two people with opposite styles succeed at the same time. The reason isn’t mystical. It’s whether their way of acting fits the times they’re living in.

This is also why changes in political “estate” happen. If someone governs with caution and patience, and circumstances line up with that approach, he thrives. But if circumstances change and he doesn’t change with them, he falls.

Yet most people aren’t flexible enough to adjust. They’re pulled by temperament—they can’t easily act against their nature. And if a person has prospered for years by doing things one way, he struggles to believe that changing course could be necessary. So the cautious man, when the moment demands boldness, often can’t do it. That’s how he gets ruined. If he could pivot with the times, fortune wouldn’t turn against him.

Pope Julius II is a vivid example. He acted impulsively and aggressively in nearly everything, and the times matched his temperament so well that he kept succeeding.

Take his first move against Bologna, when Messer Giovanni Bentivogli was still alive. The Venetians weren’t pleased. The King of Spain wasn’t pleased. Julius was still discussing the plan with the King of France. And yet he didn’t wait—he launched the campaign himself with his usual energy. That boldness froze Spain and the Venetians into hesitation: the Venetians out of fear, Spain out of hope of regaining Naples. Meanwhile, he pulled France along, because the French king—seeing the Pope moving and wanting his friendship in order to humble Venice—couldn’t refuse troops without openly insulting him.

Julius’s speed and forcefulness achieved what no other pope, relying on cautious “common wisdom,” would have managed. If he had stayed in Rome until every detail was settled and every ally fully committed, as cautious leaders tend to do, he would never have succeeded. France would have generated endless excuses, and the others would have raised endless alarms.

The rest of Julius’s actions followed the same pattern, and they succeeded for the same reason. His short life spared him the moment when his approach would have been the wrong one. But if circumstances had required careful, slow, cautious maneuvering, he would have been ruined—because he would never have stepped outside the methods his nature pushed him toward.

So the conclusion is blunt: fortune changes, and human beings tend to stay the same. When your habits match the world you’re in, you succeed. When they clash, you fail.

And for my part, I think it’s better to be bold than cautious. Fortune, like a person you’re trying to keep close, often yields more to those who press their advantage than to those who approach coldly.

Chapter 26 — A Call to Free Italy from the “Barbarians”

I’ve worked through everything I’ve argued in the chapters above, and I keep coming back to one question: are these times finally ripe for a new leader—someone with the judgment and grit to build a new political order that would earn lasting honor and, more importantly, actually improve life for the people?

The more I look at the moment we’re in, the more it seems that circumstances are lining up in a way that almost never happens. I don’t remember a time that looked more suited to the rise of a new prince than this one.

Think about how history usually sets the stage for its biggest figures. It’s not that greatness appears out of nowhere. It’s that the world gets pushed into a crisis that needs it.

• The Israelites had to be in captivity for Moses’s ability to become obvious.
• The Persians had to suffer under the Medes for Cyrus’s ambition and character to have room to show itself.
• The Athenians had to be scattered for Theseus to prove what he could do.

In the same way, if Italy is ever going to reveal what an Italian spirit can really do, then—painful as it is to say—Italy had to be brought to the condition she’s in now: more enslaved than the Hebrews, more squeezed than the Persians, more scattered than the Athenians. Look around and you see a country with no clear head, no plan, no order—beaten down, robbed, torn apart, invaded, and forced to endure every kind of humiliation.

Not long ago, one man seemed to flash like a spark—enough to make people believe he’d been chosen to rescue us. But at the peak of his run, fortune turned her back on him. And now Italy lies there like someone half-dead, waiting for the person who can finally do what no one has finished: close her wounds and end the steady bleeding.

That means stopping, once and for all:

• the ravaging and looting of Lombardy,
• the fraud and predatory taxation in the kingdom and in Tuscany,
• and the long-infected sores of corruption and disorder that have been festering for years.

You can see it in the air: Italy is begging heaven to send someone who will free her from these injuries and from the arrogance of foreign “barbarians.” And you can see something else, too: she’s ready. She’s willing to follow a banner—any banner—if only someone with real authority will raise it.

So who could she reasonably put her hope in right now?

I don’t see anyone more plausible than your illustrious house—strong in courage, favored by fortune, supported by God, and backed by the Church, which you now lead. If any family can stand at the head of this redemption, it’s yours.

And this won’t feel impossible if you keep the lives of those earlier liberators in mind. Yes, Moses, Cyrus, and Theseus were extraordinary. But they were still human. And each of them had no greater “opening” than what this moment offers you. Their missions weren’t more just than this one. They weren’t easier than this one. And God was not more on their side than He is on yours.

In fact, the moral case here is unusually straightforward. A war is just when it is necessary, and when there is no realistic hope except through arms, then arms take on a kind of legitimacy they don’t otherwise have. Here, the willingness of the people is immense—and when willingness is high, difficulty shrinks, if you follow the model of those leaders I’ve pointed to.

And notice something else. In these stories, the extraordinary doesn’t replace human effort; it supports it. Scripture describes seas dividing, clouds guiding the way, rocks pouring out water, manna falling from the sky—everything arranged to make the path possible. But the final step is always left to human hands. God doesn’t do everything, because if He did, He’d erase our freedom—and with it, the share of glory that belongs to us.

So don’t be surprised that none of the Italians we’ve seen recently have managed to do what your house is now being asked to do. With all Italy’s upheavals and all her campaigns, it’s looked as if military excellence has simply burned out. But the real reason is simpler: the old political order was rotten, and no one has known how to build a new one in its place.

And nothing brings a person more honor than this: creating new laws and new institutions at the moment he rises to power. When those reforms are solid and dignified, they make him respected—and even admired. And Italy, right now, has no shortage of places where that kind of rebuilding could take root.

Here’s the paradox of Italy: the strength is in the arms and legs, but the weakness is in the head. Watch Italians in duels and hand-to-hand fights. You’ll see it immediately: strength, agility, sharpness, finesse. But when they’re organized into armies, they don’t compare well with others. That failure comes almost entirely from leadership.

• The leaders who are capable aren’t obeyed.
• Everyone thinks he knows better.
• No single commander has stood out so clearly—through either skill or luck—that others willingly fall in line.

That’s why, for so long—especially across the fighting of the last twenty years—whenever an army has been purely Italian, it has performed badly. The record is there for anyone to read in the defeats and humiliations at places like Taro, Alessandria, Capua, Genoa, Vaila, Bologna, and Mestre.

So if your house truly wants to follow the path of those who redeemed their countries, you must start with the foundation that every serious project requires: your own forces. Nothing will ever be more loyal, more dependable, or ultimately better than soldiers who are your own.

Individually, Italians fight well. Collectively, they’ll fight far better when they are:

• commanded by their prince,
• honored by him,
• and supported at his expense.

Build that kind of force, and you can defend Italy against foreigners with Italian courage.

Now, people will tell you that Swiss and Spanish infantry are terrifying. And yes—they’re formidable. But both have weaknesses, and a third kind of infantry, designed with those flaws in mind, could not only stand up to them but even defeat them.

Here are the cracks:

• Spaniards don’t hold up against cavalry.
• Swiss fear infantry when the fight collapses into close, grinding contact.

We’ve seen this pattern before. Spanish foot soldiers struggle against French cavalry. Swiss formations get broken by infantry. And even if the Swiss point hasn’t been demonstrated in every possible way, there has been a strong hint: at Ravenna, Spanish infantry met German battalions trained in Swiss-style tactics. The Spaniards used speed and their shields to slip under the Germans’ pikes, keep themselves safe, and strike. The Germans, stuck and helpless, couldn’t respond—and if cavalry hadn’t arrived, the outcome would have been decisive.

So yes: if you understand the weaknesses of both styles, you can design an infantry that isn’t vulnerable to cavalry and isn’t intimidated by infantry. You don’t need to invent warfare from scratch. You need to improve the old system with smart variations.

And that—exactly that—is the kind of innovation that builds a new prince’s reputation and power.

So don’t let this moment pass. Let Italy finally see her liberator step into view.

It’s hard to put into words how deeply he would be loved in every province that has suffered under foreign invasions—how intense the hunger for payback would be, how stubborn the faith, how raw the devotion, how many tears would greet him. What gate would be shut to him? Who would refuse to obey? What jealousy could block him? What Italian would deny him loyalty? This foreign domination disgusts everyone.

So take up this cause with the courage and hope that belong to just undertakings. If you do, then under your banner Italy can regain her dignity—and under your protection Petrarch’s line can finally become true:

Virtue will take up arms against Fury, and the fight will be short—because the old valor has not yet died in Italian hearts.