Popes Reshuffled the Deck Every Decade — Machiavelli Wrote 'The Prince' in the Wreckage

Source: Dwarkesh Patel | Published: 2026-06-16T17:54:40Z

Exiled and broken, Machiavelli refused to serve any foreign power. Instead, he wrote The Prince from a desolate village as a job application — begging the very regime that tortured him to let him serve Florence again.

The Unique Instability Created by the Papacy

Italy's chaos had a catalyst found nowhere else: the Vatican. In the pontificates preceding Machiavelli's lifetime, each successive pope expanded his administrative power, especially over military matters. One pope had an illegitimate son and wanted him installed as ruler of a city, so he overthrew that city's government and planted his son there. The next pope did this to three cities. The one after that, five. Before long, "every new pope gets to overturn every piece on the board" became standard practice.

The critical factor: the papacy isn't hereditary. You can't predict who the next pope will be. And the logic of electoral politics dictates that his successor is typically chosen by a coalition of "everyone who hates the current guy." If the average papal tenure during this period was ten years, then every decade you got a completely unpredictable new sovereign who was almost guaranteed to be his predecessor's enemy, ready to rip out everything the last pope had built. This kind of instability didn't exist elsewhere in Europe—because nowhere else had an unpredictable, non-hereditary superpower center that turned over every ten years.

What Machiavelli Actually Wanted Wasn't Unification—It Was Stability

The logic of The Prince's final chapter is actually quite clear: nearly every regime on the peninsula had just been overthrown and lacked legitimacy; the Vatican reshuffled the deck every ten years, and nobody could stop it. The only way out: a secular power strong enough—with territory, sons, and inheritance rights—to establish a lasting presence near the Vatican, forcing it to negotiate rather than casually manipulating the surrounding small states.

He wasn't calling on the Medici to unify Italy. He was saying: you need to conquer enough territory to make the pope afraid of you. And the pope at the time happened to be a Medici, which made this plan look especially feasible.

Standing Next to the Most Terrifying Man Alive, Whispering "Florence Is Loyal"

Before writing The Prince, Machiavelli was a diplomatic bureaucrat for Florence. His career brought him into close contact with the era's most feared figure: Cesare Borgia, the "Valentino" who appears throughout the text.

The strategic situation was obvious at a glance: Borgia was conquering the papal territories of central Italy, and on the map, Florence looked like a missing puzzle piece on the edge of the Papal States—anyone could see you couldn't build a complete kingdom while skipping over it. Machiavelli's advice was: we can't stop him, and we can't buy him off permanently, but we can buy time. Grovel completely. Swear to do everything he demands—give him troops, give him money, betray our allies. Florence had a 300-year defensive alliance with Bologna. Machiavelli said: tear it up. The whole world has shattered, and we must break every promise and every hereditary alliance along with it.

His job was to stand next to the most terrifying man Europe had seen since Emperor Barbarossa, whispering ceaselessly: "Florence is loyal." What he bought was the conqueror's Polyphemus-style promise—"I like you, my guest. I'll eat you last."

The "He Told Me" Moment

There's a passage in The Prince that Palmer describes as a "magic moment." Throughout the book, Machiavelli works hard to maintain balance—this example, that example, Valentino, another example. But when describing Borgia's downfall, his composure breaks.

Borgia had conquered nearly everything. Then suddenly, he and his father—Pope Alexander VI—fell ill at the same time. Machiavelli should have written "Valentino had prepared for everything that might follow his father's death, except he never anticipated that he himself would be gravely ill at that very moment." But what he actually wrote was: "He told me he had prepared for everything that might follow his father's death..."

First person, bursting in uninvited. The historian's veil can no longer hold. In that instant, the reader realizes: those other figures, Machiavelli observed from a distance. But he had been right there beside Valentino, living through everything firsthand—including the Sinigaglia massacre, where Borgia pretended to forgive the conspirators, renewed oaths of friendship with them in the cathedral, then slaughtered them all at dinner.

Months after the massacre, Machiavelli's family finally received word that he was still alive. The postal system had completely collapsed in the chaos. They didn't know whether he'd been caught up in the conspiracy, whether he'd already been executed. His wife and children waited months before learning he had survived.

"Everything He Did Was Right"

Borgia's end tempts many to extract a moral lesson: see, the Borgias were feared, hated, and ultimately destroyed. To this day, if you walk the streets of Rome and sit down in a pizza shop, those strange scars on the walls are where the Borgia family's bull crests were chiseled away.

But Machiavelli refuses this narrative. He says: Borgia didn't fail because of his choices. Half of everything that happens in the world is forever beyond our control. You can do everything right, and then fortune intervenes. So what we should evaluate isn't the outcome, but what the most likely outcome would have been before fortune intervened. By that standard, everything Borgia did was right.

If Alexander VI had lived one more year, Borgia would have completed his conquest, and Florence would have fallen. His puppet pope Pius III died too quickly, and then he was defeated by Julius II—a streak of bad luck, not bad decisions.

Means Matter Far More Than You Think

A common misreading is that Machiavelli believed "the ends justify the means." Palmer points out that he actually cared intensely about means—because how you acquire power determines how stable that power will be.

Did you gain power through mercenaries or a stronger patron's help? Extremely dangerous, because whoever helped you is more powerful than you, and you're at their mercy. Did you gain power through deception and broken oaths? That depends on who you are. Borgia could betray allies because he was so terrifying—other allies didn't rebel but instead thought, "I'd better be even more loyal, so I'm not the next one betrayed." But Savonarola couldn't. Savonarola's power base was people believing he was divinely inspired and infallible. The moment his prophecies went wrong and he contradicted himself, the foundation crumbled.

Decades later, someone asked Michelangelo what Savonarola had been like—by then Savonarola had been dead for decades—and Michelangelo answered: "I can still hear his voice."

That kind of extraordinary charisma wasn't enough. Borgia's capacity to inspire terror was. Lying is sometimes fine, but only if you've checked several other boxes first. What Machiavelli cared about was the subtle combination of those conditions.

What "Better to Be Feared Than Loved" Actually Means

Behind this famous line lies a profound pessimism about human nature. Machiavelli believed that if your power base depends on people's promises and loyalty, the moment cracks appear in your rule, they'll break their word. But if your power base rests on the expectation that "breaking an oath will be punished," it's far more durable. He essentially believed that whether tyrants, nobles, or commoners, people will do as much evil as they can get away with.

This connects directly to his argument for checks and balances in the Discourses on Livy—strikingly similar to the reasoning the American Founders used when designing their own system of checks and balances.

The Inventor of Multi-Party Competition

Palmer raises a rarely mentioned fact: in the European tradition, Machiavelli was the first person to propose that "a state can have multiple parties coexisting, releasing social tension through competition."

Before him, the standard position was: if a country has two parties, it won't be stable until one is completely annihilated—heads chopped off, houses burned, salt sown on the ruins. That's exactly what Florence did: first it massacred the Ghibellines and salted the ground where their houses had stood so nothing would grow; later, when the Guelphs split into Black and White factions, they immediately began slaughtering each other.

Machiavelli studied a handful of cases like Siena and discovered that if competition between parties was stable enough, it could actually release internal tensions and allow for internal adjustments of power. This was a revolutionary idea at the time.

Why Valentino Was Loved by the People

When Cesare Borgia conquered cities in central Italy, he would slaughter the ruling families and then implement impartial justice. This caught everyone off guard—a brutal conqueror who was deeply popular with ordinary people.

The reason was simple: before he arrived, justice depended entirely on which faction you belonged to. If you were a carpenter for the ruling family and your son beat someone to death while drunk, he'd get a small fine; if you worked for the losing side, your son would get the death penalty. But Borgia and his men had no local allegiances, no stake in any family's feuds. When they adjudicated cases, they were neutral—for the first time in generations, ordinary people experienced fair justice. The populace was willing to join his army and defend his fortresses as a result.

Why Florentines Would Rather Die Than Lose Their "Freedom"

Machiavelli had a clear definition of freedom: if you live in a place where someone can walk down the street, point at you, and say "kill him" and have you killed, you are a slave. If there must be a trial, due process, and public scrutiny, you have freedom. The system might be unjust—it might even be the very system that tortured and exiled him—but having a system at all makes the difference.

Florentines were repeatedly willing to take to the streets, risking their lives under banners reading "LIBERTAS." The irony is that the banner represented a senate composed of the top 1% ultra-elite. Ordinary citizens weren't defending their own right to participate in politics—they were defending the right of their boss's boss to participate. But they believed this was fundamentally different from dictatorship and were willing to die for it.

Patronage: The Fundamental Glue Holding Society Together

Palmer emphasizes that patronage wasn't merely "more common than today"—it was the fundamental glue of the entire society.

A famous example: Pope Paul III passed over his incompetent illegitimate son and instead named an experienced general to command the papal army. The result? Riots broke out in Rome. The public demanded more nepotism. Because the pope's son would never betray the pope, while an outsider might. If a rift opened between the pope and the papal army, the whole system became unsafe.

This logic extended all the way to the justice system. Medieval legal codes prescribed death for nearly every crime, but in practice only 1 out of every 100 convictions actually resulted in execution. The other 99 saw a patron intervene, plead the case, and secure a lighter sentence. This wasn't judicial corruption—this was how justice was supposed to work. Being tried, fearing death, appealing to your patron, and then receiving mercy—the process was designed as an earthly rehearsal for what the soul would experience at divine judgment.

The one person who was actually executed didn't die because their crime was especially severe. They died because they'd lost their patronage network.

The Real Reason Giordano Bruno Died

Bruno is famous as a "martyr for science," but few people know he'd been investigated by the Inquisition several times before. Each time followed the standard procedure: he had a patron, the patron intervened, the Inquisition told him to "behave," and life went on.

The final time was different because he'd alienated his patron. The patron himself handed Bruno over to the Inquisition, calling him a fraud unworthy of protection. Without a patron, the trial went all the way to execution. Meanwhile, Pico della Mirandola, far more radical than Bruno, had Lorenzo de' Medici's full protection and merely received a comfortable "house arrest" at Lorenzo's estate. Ficino—who translated Plato and wrote books about astral projection and summoning angels—was even more outrageous. When the Inquisition came knocking, a single word from Lorenzo made it go away.

The Inquisition Operated Like Doctors Without Borders

The Inquisition was far less centralized and powerful than its own propaganda suggested. Palmer uses a striking analogy: it operated more like Doctors Without Borders—an international organization trying to achieve specific goals in different locations, but only effective when local governments were willing to cooperate.

Inquisitors were typically Dominican friars with no substantial funds of their own, no prisons of their own, no power of arrest. Everything depended on what local governments provided. If the local duke was an enlightened intellectual radical—like the early Medici dukes—and the inquisitor asked, "Can I arrest this person?" and the duke said, "No, he works for me," then nothing could be done. The Spanish Inquisition became notorious because Ferdinand and Isabella wanted Jews and Muslims as scapegoats and poured money into the institution. The pressure came from the crown, not from Rome.

This created a bubble of privilege: under the protection of the powerful, you could practice radical magic, radical philosophy, and radical sexual behavior, and the Inquisition couldn't touch you. Machiavelli himself was an example—he corresponded with gay friends about a Roman magistrate who was cracking down on homosexuality, and their friends were all scrambling to work for cardinals to gain protection. One friend who couldn't find such a position hired two female prostitutes to accompany him at all times so he'd look straight.

Copyright Was Born from the Inquisition

Machiavelli belonged to one of the first generations in human history to need copyright protection. In a letter, he wrote in a panic: a local printer had published his book without permission, riddled with typos. Everyone would think those errors were his—but there was no legal recourse, no remedy whatsoever. His friends' advice: write to every important person you know and tell them the typos aren't yours. That was it.

The birth of copyright is perversely intertwined with censorship. After 1515, the Inquisition required all books to receive censorship approval before printing. In exchange, approved printers received a monopoly license—only they could print that book. The censorship record itself became the legal document proving exclusive printing rights. History's first copyright system was the Inquisition's censorship system. England later copied this model, and when censorship was eventually abolished, the copyright component was retained—this is the origin of Anglo-American copyright law.

The Prince: A Job Application Addressed Only to His Country

When Machiavelli was exiled, everyone expected him to go work for a foreign power—a man versed in the classics, with military and diplomatic experience and political connections in Rome and France could have found a lucrative position at any court in Europe. But he didn't. He went to a desolate Tuscan village designated by the authorities and rotted there, writing The Prince.

The book was his job application—begging the new regime that had tortured and exiled him to let him come back and work for them.

He wouldn't let any other power get hold of the book. He shared it only with Florence's rulers and a tight circle of scholar friends he'd known for decades. Palmer compares it to a nuclear scientist's classified research—he knew he'd grasped the embryo of a new political science, but he would only hand it over to his own country.

This is the ultimate irony of the word "Machiavellian": it means "selfish and scheming," but Machiavelli himself may have been one of the most selfless patriots in human history. He would rather do nothing at all than contribute even a single hour to any cause other than Florence.

Why Original Ideas Had to Masquerade as Classical Commentary

The Renaissance had a peculiar stylistic rule: nobody wanted original ideas. If your book was a commentary on a classical work, it would be more widely read and more highly regarded than any original treatise. Scholars went to extraordinary lengths to pretend their new ideas were actually what Plato or Livy had meant all along. Giordano Bruno, while commenting on Aristotle, claimed Aristotle had said things Aristotle absolutely never said—because attributing it to Aristotle made people take it more seriously.

An extreme case was Annius of Viterbo, who forged ancient texts and faked archaeological excavations—secretly burying artifacts and then dramatically digging them up—because claims of ancient provenance were more convincing than original work.

This is why Machiavelli wrote the Discourses on Livy—a commentary on Livy was the proper work of a serious scholar. Something like The Prince, which presented itself as original, was considered an odd, secondary side project. Throughout the 1600s, enormous amounts of radical political thought were smuggled into annotated editions of Seneca and Livy—a small block of original text in the center of the page, surrounded by vast expanses of commentary, with the real intellectual innovation happening in those margins.

Nineteenth-century historians of philosophy looked back at the Renaissance and concluded "those 200 years produced almost no original thought." Palmer quotes a philosophy department colleague: "The Renaissance was 200 years of people getting Plato wrong." But if you understand the stylistic convention—that original ideas had to be presented as classical commentary—then it was actually 200 years of original thought blooming on the trellis of the classics.

"Old Nick" and the Real Machiavelli

Machiavelli ultimately split into two figures. One is the real Machiavelli—a patriot who sacrificed everything for his country and wrote a manual on how to maintain regime stability and protect people's lives. The other is "Old Nick"—the "murderous Machiavel" that Shakespeare's Richard III claims to outdo, an atheistic, self-serving political schemer. The nickname "Old Nick" for the devil became popular precisely because of Niccolò Machiavelli.

Palmer notes that similar splitting happened to many thinkers—Hobbes became "the Beast of Malmesbury," Spinoza became "the chief heretic" (though if you actually read Spinoza, he's warm, devout, and believes the entire universe is the body of God). Society has a tendency to take real, complex thinkers, reduce them to a caricature, and then let that caricature take on an independent life in public discourse.

If you have The Prince on your bookshelf, Palmer suggests reading it with this understanding: the man who wrote those words was willing to give up wealth, fame, social life, even the chance to visit his wife, rotting away in the countryside just for the possibility of one day serving his country again. A very different Machiavelli emerges from the pages.