Machiavelli, the Most Misunderstood Thinker of All Time — Ada Palmer

ELI5 / TLDR

We use “Machiavellian” to mean a scheming, self-serving snake. Historian Ada Palmer says the real Niccolò Machiavelli was almost the opposite — one of the most selfless patriots who ever lived, who chose to rot in a backwater rather than sell his talents to any country but Florence. The Prince wasn’t a how-to-get-ahead manual; it was a secret weapon he wanted only his own government to have, written in a world so chaotic that the average city had been violently overthrown a dozen times in his lifetime. Along the way Palmer rebuilds the whole strange machinery of Renaissance Italy — how the pope was a warlord, how justice was supposed to be unfair, how original thinkers had to disguise their ideas as footnotes on dead Romans, and how the villain “Machiavelli” and the real man split into two different people.

The Full Story

Why Machiavelli thought Italy was doomed

Picture a country where almost every government has been knocked over so many times that nobody believes in any of them anymore. That was Machiavelli’s Italy. His argument starts with a simple idea about stability: a government that has been around a long time has legitimacy — people are used to it, they believe in its institutions, even the complainers treat it as “the government.” Cut that thread of continuity once, and you usually don’t get one replacement, you get five in rapid fire. Think of how France cycled through republic, monarchy, republic, monarchy after its first break. England’s Wars of the Roses, same pattern.

“When a long thing cracks—boom, boom, boom, boom, boom—you get chaos.”

When Machiavelli was born, six or seven Italian city-states had recently had their governments uprooted. By the time he wrote The Prince (1513), it was dozens — the majority. Every polity was a knocked-over chess piece that had barely been stood back up, ready to fall again.

The second half of the problem was the papacy. The pope wasn’t just a spiritual leader; he was a temporal monarch who ran wars and could appoint rulers to the city-states he controlled. One pope overthrows a city to install his illegitimate son. The next does it to three cities, the next to five — and soon it’s simply expected that a new pope can knock over any government he likes. Worse, the office isn’t hereditary, so you can’t plan for succession. A pope is elected, usually by a coalition of everyone who hated the last pope. So roughly every decade an unpredictable new monarch appears, almost guaranteed to be an enemy of the previous one, who rips up everything his predecessor built.

That’s the “perfect storm” behind the famous last chapter of The Prince: Machiavelli wants the Medici not to unify Italy but merely to stabilize it — to conquer enough of a chunk that the papacy has to fear and negotiate with them, instead of being surrounded by weak powers that get overturned endlessly.

The man he couldn’t stop thinking about

Before writing the book, Machiavelli spent his career as a diplomat, standing in rooms with kings and warlords. The one who broke him was Cesare Borgia — “Valentino,” as the period called him. Palmer points to a moment where Machiavelli, normally a careful balanced writer, suddenly slips into the first person. He’s describing why Borgia’s empire collapsed, and instead of writing “he had planned for everything,” he writes: he told me that he had planned for everything except the chance that he too would be on death’s door when his father the pope died.

“It’s such a magical moment where the veil between the author and the reader breaks for just that moment.”

Machiavelli wasn’t observing Borgia from a distance like the other figures in the book. He was at his side. His actual job — and this is the terrifying part — was to stand next to the scariest man in Europe and whisper, over and over, that Florence was loyal. Florence couldn’t beat Borgia, couldn’t bribe him off permanently. The only survival strategy was total, abject submission: give him money, give him troops, betray Florence’s own 300-year alliance with Bologna, do anything — and buy time, because popes are mortal. Palmer calls it the boon of Polyphemus: the monster’s promise of “I like you, my guest — I’ll eat you last.”

Machiavelli was even there for the massacre at Senigallia, where Borgia summoned men he’d heard were plotting against him, forgave them warmly, renewed sacred vows of friendship in the cathedral, invited them to a banquet — and slaughtered them all. (By Dante’s rules, betraying a guest is so heinous that a devil yanks your soul out of your body and you’re already in Hell while still alive.) And it worked: Borgia’s surviving men became more loyal than ever, too scared to even whisper. The postal system was so broken that Machiavelli’s family waited months to learn he hadn’t been killed in the bloodbath.

”He did everything right” — the role of fortune

Here’s the misconception Palmer wants to kill. People assume Machiavelli says the ends justify the means and the means don’t matter. The truth is the reverse: he’s obsessed with means. The method by which you grab power determines how stable that power will be. Rise with the help of mercenaries or a greater power, and you’ve made someone stronger than yourself whose mercy you now depend on.

And he doesn’t judge deeds purely by outcome. He judges them by the most probable outcome before fortune intervened. Borgia did everything right and still fell — but only because he happened to eat the same food poisoning as his father at the worst possible moment, and the puppet pope he installed died too fast. So Machiavelli’s lesson isn’t “don’t do what the Borgias did.” It’s: imitate them, because their choices were correct, and we only ever control about half of what happens.

“We have power over, at maximum, half of what causes outcomes. The other half is always going to be fortune.”

This is why lying is sometimes fine and sometimes fatal. Borgia could betray his top general and seize his lands, and his other generals would only fall deeper into line — because he was so feared. Savonarola, the preacher, broke promises too, but his whole power base was the belief that he was divinely inspired and couldn’t err. The moment he flip-flopped, that base cracked. Same act, opposite result. “Better to be feared than loved” isn’t bloodlust — it’s the observation that love depends on people’s promises, which they’ll break the instant your rule wobbles, while fear depends on the expectation of punishment, which is stable. People, Machiavelli thinks, act as badly as you let them — tyrant, mob, or noble alike. (This is also, Palmer notes, the same cynicism that drove the US founders to design checks and balances. Machiavelli was also the first European to suggest multiple political parties could coexist and stabilize a state rather than one having to exterminate the other.)

The pope is “that asshole who went to college with your brother”

Why would Catholic cities go to war against the pope, the Vicar of Christ? Distance, says Palmer. If you’re in Iceland, the pope is an abstraction — pomp, edicts, judgments from afar, and one pope looks much like the next. If you’re in Italy, the pope is a specific guy whose dirty laundry you know, whose family is allied or at war with yours.

“If you’re in Italy, the pope is that asshole who went to college with your brother and beat him up… and you know this jerk.”

So Italy split into two ancient factions, Guelphs and Ghibellines — originally a real argument about whether pope or emperor was the rightful heir to Rome, but by Machiavelli’s day reduced to “those jerks murdered Uncle Tybalt and we’ll never forgive them.” It produced absurdities: a pope from a Ghibelline family promoting anti-papal allies, while the pro-papal faction united to make war on the pope himself.

And the papacy kept getting worse — not by accident but by compound interest. Every generation, pious widows left property to the Church; the Church grew richer; riches meant power; power meant every ambitious family sent a son in to grab a slice. (Machiavelli’s own letters haggle over the right-sized bribe to buy a priesthood for his little brother Totto — too big impoverishes the family, too small loses to a rival bidder.) It even became a prisoner’s dilemma: I must corrupt the Church, because if I don’t and my enemy does, I’m finished. For a hundred years every generation said “popes are worse now than when I was young” — Dante in 1300, Machiavelli in 1500 — until it peaked and triggered the Reformation. Machiavelli anticipated this: all institutions corrupt over time and must be periodically dragged back to their founding principles or collapse.

Patronage: the glue of everything

The deepest “you-are-not-in-Kansas” section. In this world, patronage wasn’t one social glue — it was the glue, fused with family loyalty. When a pope appointed a competent outside general instead of his own useless illegitimate son, there were riots demanding more nepotism:

“Your Holiness, the people demand more nepotism. You must appoint your illegitimate son… because your illegitimate son will never betray you.”

The logic: in an age when communication was too slow for daily orders, a soldier swore loyalty to his commander, not to the state. So an army was a weapon you handed to one man — and the only man you could trust with it was someone whose family rose and fell with yours. Nepotism was a trust technology.

It ran all the way down to justice — and this is the part that flips modern intuition completely. Medieval law codes prescribe death for almost everything, yet only about 1 in 100 convictions actually ended in execution. Why? Because justice was supposed to be unfair. The point of a trial wasn’t proportional punishment (that’s an Enlightenment idea from the 1700s) — it was the spiritual correction of the sinner’s soul. The ideal outcome: you stand before a terrifying judge representing God, you fear for your life, your patron intervenes, and you receive mercy — a dress rehearsal for divine judgment that should make you a better person. So when a carpenter’s son kills a man in a drunken brawl, the carpenter begs his patron (say, the Medici, whose furniture he makes), the patron leans on the judges, and the boy gets a fine. The rare person executed is usually the one who had fallen out of the patronage network. Giordano Bruno’s first Inquisition trials ended fine because he had a patron; the trial that burned him was the one where he’d angered the patron who then turned him in. The radical philosopher Pico della Mirandola — far more heretical than Bruno — walked free because Lorenzo de’ Medici pulled strings through his Orsini in-laws. You couldn’t even rent a hotel room or buy an apple as a stranger without a letter from your patron.

How the chaos finally ended

Dwarkesh threads it together: the modern stable nation-state required disintermediating all these personal loyalties. Replace the months-long communication gap so soldiers swear to a constitution, not a general. Replace patronage-justice with impartial deterministic courts so a murdered son’s family doesn’t need private vengeance. Replace patronage-welfare with a state welfare apparatus. Each one transfers loyalty from a person to the state itself — which is what finally bought legitimacy and stability.

Palmer adds a startling illustration: when Borgia conquered a city and exterminated its ruling families, the people often loved him. Why love a murdering tyrant? Because his cronies had no stake in the local feuds, so for the first time in generations they delivered neutral justice — the same verdict no matter whose carpenter you were. After lifetimes of “justice for some,” equity felt like a gift.

So why fear Medici rule, or Borgia rule, at all? Two reasons. First, liberty: Machiavelli’s definition is that if there exists any man who can point at you in the street and say “kill him” without trial, you are — in his vocabulary — a slave, even if the system that protects you is itself biased and cruel (it was the very system that tortured and exiled him). A process, however unfair, is freedom; arbitrary death is slavery. Florentines rioted under the banner LIBERTAS even though it defended the right of a tiny 1% elite to govern — they cared about the form that fiercely. Second, an inside conqueror is gentler than an outside one: the Medici wanted Florence to stay beautiful and Florentine because it was theirs, where an outsider would happily threaten to raze the cathedral.

Backwards is forwards

How did war-torn, broke city-states fund all that art? Partly because banking and wool were obscenely profitable. But mostly because art was diplomacy, and diplomacy is cheaper than war.

“We can’t afford enough armies to actually defend us against France… But we sure can spend it on… beautiful, expensive gifts for the King of France, so that when the King of France comes, he will feel like we are friends.”

It was a culture-victory strategy. And crucially, the art wasn’t seen as backward-looking nostalgia — it was high-tech. The Renaissance didn’t think of the future as the frontier of progress the way we do. The frontier was the past: recovering Rome. Backwards was forwards. A neoclassical building wasn’t an imitation; it was the cutting edge, like a record-breaking skyscraper. They genuinely debated whether they could ever match the Romans, let alone surpass them.

This even shaped how thinking worked. To be taken seriously, original ideas had to be disguised as commentary on the ancients. Nobody wanted original thought — they wanted “Discourses on Livy.” So scholars smuggled radical new ideas into footnotes on Seneca, or claimed Aristotle said the opposite of what he said, or (in one extreme case, Annius of Viterbo) forged ancient texts and faked archaeological digs to lend their visions authority. Which is why 19th-century historians, who demanded originality, dismissed the Renaissance as “200 years of people being wrong about Plato” — missing that it was 200 years of original thought using the ancients as the trellis up which the rose climbed. The Prince is a weird outlier precisely because it presents itself as original.

The patriot who became the devil

Now the reframe. Machiavelli was exiled — but Florentine exile was usually provisional: go to a useful city, run errands for the republic, behave, and get recalled. Machiavelli’s exile was crueler. They distrusted him so much they sent him to a nothing hamlet to “go rot.” Everyone expected him to defect — a skilled classicist-diplomat with contacts in Rome and France could have earned three times his Florentine salary at any of a dozen courts. He refused. He sat in the countryside and wrote The Prince as a job application, begging to serve the very regime that had arrested and tortured him.

“Machiavelli fundamentally is possibly one of the most patriotic patriots in Earth’s history.”

That’s why he kept The Prince secret. His other works circulated to build his fame; The Prince was proprietary — the secret sauce of how to keep power, shared only with Florence’s rulers and his closest scholar-friends. Like a nuclear scientist with state secrets he’d never sell. (Writing a book for an audience of one wasn’t strange then: scholars were paid handsomely to write bespoke, single-copy handbooks for individual princes — and “prince” was gender-neutral, so even Queen Elizabeth was “Prince Elizabeth.”)

So how did the secret manual become a global classic, and “Machiavellian” become a synonym for the devil? It drifted in obscurity until his heirs published it for family fame; the Medici allowed it because it flattered them. Books, Palmer notes, lie dormant until a century’s new questions wake them — Lucretius slept 2,000 years until germ theory and atomism made him urgent. Machiavelli surged first when philosophers needed to refute Hobbes (“let’s read the daddy-monster that spawned the baby-monster”), then exploded in the 19th century as the first thinker to analyze politics in a box, without plugging in God — perfect raw material for separation of church and state, and for Italian nationalists wanting their own “first modern man” to rival Bacon and Descartes.

(A nuance Dwarkesh raises: Machiavelli actually thought religion was vital to a stable state. But — like Thomas Paine, who wanted mandatory religion while not caring which one — he valued the psychological effect of religion on citizens, not its truth. He praised Roman religion for making men sacrifice themselves for the state, then ended the chapter: “Christianity has the advantage of being true,” period — the mandatory subscript everyone could hear.)

Meanwhile the character split off. Shakespeare’s Richard III models himself on “the murderous Machiavel”; “Old Nick,” a name for the devil, partly comes from Niccolò. The same thing happened to Hobbes (the Beast of Malmesbury) and to Spinoza, who turns out to be warm, sweet, and deeply pious when you actually read him, but became a byword for arch-heresy because his rare Jewish excommunication made him sound monstrous. Palmer’s closing thought is the most interesting: the fascinating thing isn’t the villain or the patriot but the double-imaging itself — our habit of taking something real and powerful and minting a useful fictional character beside it.

“If you have The Prince on your shelf, read it and remember it was written by somebody who was willing to give up anything to serve his country, and you’ll see a very different Machiavelli come through.”

Key Takeaways

Legitimacy is the load-bearing thing. Long-lived governments are stable because people believe in them; cut that continuity once and you typically get a cascade of overthrows, not one. Most of Italy had had that thread cut in Machiavelli’s lifetime.
The pope was a warlord with an unplannable succession. Non-hereditary, elected by enemies of the last pope, turning over roughly each decade — a structural instability no other part of Europe suffered.
The Prince judges deeds by their probable outcome before fortune intervened, not their actual outcome. Borgia “did everything right” and still fell to bad luck — so imitate him anyway.
Machiavelli was intensely focused on means, not dismissive of them. How you gain power determines whether it’s stable. Lying works if you’re feared (Borgia) and backfires if your power rests on perceived infallibility (Savonarola).
“Better to be feared than loved” is a stability argument, not a cruelty preference: love rests on promises people break; fear rests on expected punishment, which holds.
He was the first European to propose that rival political parties could coexist and stabilize a state rather than one needing to exterminate the other.
Renaissance justice was designed to be unfair. ~1 in 100 capital convictions ended in execution; the rest were saved by patrons. The goal was spiritual correction (fear, then mercy), a rehearsal for divine judgment — not proportional punishment, which is an Enlightenment idea.
Patronage was the society’s fundamental glue, fused with nepotism. Soldiers swore loyalty to commanders, not states, because communication was too slow — so nepotism functioned as a trust technology. People literally rioted demanding nepotism.
Borgia’s brutal regimes were often beloved because his outsiders delivered neutral justice for the first time in generations.
Machiavelli’s definition of liberty: if any man can have you killed without process, you are a “slave” — even under a biased system; a process, however unjust, is freedom.
Art was a cheaper substitute for war (a “culture victory”); the Renaissance treated reviving antiquity as the cutting edge — “backwards is forwards.”
Original ideas were disguised as commentary on ancient authors to be taken seriously; radical 1600s political theory often lived in the footnotes of Seneca and Livy. One forger (Annius of Viterbo) faked texts and digs.
Copyright was born from the Inquisition. Pre-publication censorship licenses doubled as monopoly print rights; England later kept the copyright half and reformed the censorship half. Machiavelli, furious at a printer publishing his typo-ridden book with no legal recourse, was among the first authors to need copyright.
The Inquisition was weak and decentralized, dependent on local rulers for jails, guards, and funding — so a liberal duke could shield his heretics (and his gay courtiers) entirely. “Bubbles of privileged access” worked like Doctors Without Borders, only as strong as the host government allowed.
Machiavelli was bisexual, with documented homoerotic and heterosexual poetry and a circle of gay scholar-friends who took jobs with cardinals for legal protection.
“Machiavellian” is nearly the opposite of the man. He chose poverty and obscurity over serving any country but Florence; The Prince was a secret weapon, not a self-help book — a manual for keeping power to protect a people, not gaining it.

Claude’s Take

This is a genuinely excellent two hours, and the rare history conversation where the host pushes hard enough to keep the guest honest rather than just nodding along. Palmer is the real thing — a working historian who has handled the manuscripts (she’s seen Machiavelli’s hand-copied Lucretius in the Vatican) and can turn dusty archival facts into vivid, load-bearing arguments. The recurring move that makes it sing: she keeps showing how a thing we treat as timeless (impartial justice, copyright, the lone original genius, even the word “Machiavellian”) was a contingent invention solving a specific problem of its moment.

The BS filter has little to flag, but a couple of calibrations. First, the “most selfless patriot in Earth’s history” framing is rhetorically loaded — Palmer is a Machiavelli partisan, and the patriot reading, while well-supported, is a reading; The Prince as cynical job application and The Prince as sincere political science aren’t mutually exclusive, and his patriotism doesn’t actually soften the brutality of the advice. Second, sweeping claims like “Machiavelli was the first European to suggest multiple parties could coexist” or “the first to think about government without God” are the kind of firsts historians love and rivals contest; treat them as strong-but-arguable, not settled. The justice-as-spiritual-theater and patronage-as-glue sections are the most valuable and the best evidenced — they genuinely rewire how you read the period. Docking nothing for the ad reads (cleanly skippable). A 9: dense, surprising, well-argued, and it actually changes how you’d read a book sitting on a lot of shelves.