Machiavelli is the most misunderstood thinker of all time – Ada Palmer

Summary

• The Prince is a frequently mislabeled document: not a get-ahead manual but a stabilization memo and job application, kept “secret and proprietary, the secret sauce of how to maintain power” and shared only with Florence’s rulers and intimate friends. Palmer’s core irony: “Machiavellian” means self-serving, yet Machiavelli was “possibly one of the most patriotic patriots in Earth’s history” — rotting in exile, begging to serve the regime that ordered his torture.
• Instability compounds once legitimacy is cut: one regime change begets five, and by 1513 dozens of Italian city-states had lost their thread of continuity while the papacy turned over roughly every ten years to “a coalition of all the people who hate the current pope.” Machiavelli’s ask of the Medici was not to unify Italy but to stabilize it — get big enough that the papacy “fears them and must negotiate.”
• Fortune is half of all outcomes, so judge strategies by the most probable pre-fortune result: Cesare Borgia “did everything right” and lost only to simultaneous food poisoning with his father — Machiavelli’s verdict is “we should imitate them,” not “don’t do what the Borgias did.”
• Means determine durability, not morality: lying works if backed by fear (Borgia betraying allies made the survivors more loyal) and fails when your power rests on credibility (Savonarola’s flip-flopping prophecies). Feared beats loved because “people will act as badly as they are allowed to” — and Machiavelli is the first European thinker to propose two political parties coexisting rather than one salting the other’s earth.
• Patronage was the operating system: Rome rioted for more nepotism, 99 of 100 capital trials ended in fines because a patron intervened, and Giordano Bruno burned only after losing his. A route to modern nation-state stability was disintermediating patrons — impartial justice, welfare, fast communications. That same logic explains why Borgia’s neutral justice made a murdering tyrant beloved.
• Culture was Florence’s cheapest defense budget: “dollar for dollar, diplomacy is cheaper than war” — a city that could never out-arm France played “the culture victory game” instead, in an era when imitating antiquity was cutting-edge technology and original ideas were “out of vogue.”
• Every new information technology triggers a censorship wave — and copyright was literally born from the Inquisition’s license-plus-monopoly system. The Prince itself surged only when each era’s questions found it: first as “the daddy monster” behind Hobbes, then as the 19th century’s toolkit for separation of church and state.

Deep dive

1. Italy’s perfect storm: cut legitimacy threads plus papal roulette

• Palmer’s two-part answer to why The Prince’s final chapter cries ruin: when long-continuous government cracks, “boom, boom, boom” — you get chaos — one overthrow guarantees more (the French Republic’s cycles, England’s Wars of the Roses). Six or seven city-states had been uprooted at Machiavelli’s birth; by the writing of The Prince it’s dozens — “almost every government is ripe for yet another replacement.”
• The other half is the papacy: assume a ~10-year average reign; very frequently, the next pope was elected by a coalition of people who hated the current pope, inheriting a precedent that let each new pope feel authorized to knock down “every pawn upon the chessboard” — including to install illegitimate sons. “Even a fairly nice pope still inherits the idea that the pope is going to overthrow and replace governments” — an instability “no other part of Europe is subject to.”
• Hence the actual ask of the Medici — Dwarkesh’s gloss, confirmed: stabilize, not unify — conquer enough of a chunk that the papacy “fears them and must negotiate with them,” the play Cesare Borgia attempted. And with a Medici pope sitting at that moment, it was plausible.
• The texture of that world: Florence’s standing tactic was an annual bribing-a-king budget — “Okay, who do we need to bribe this year to not invade us?” — and Machiavelli’s diplomatic career was largely being sent to courts like Maximilian’s to judge, “Hey, is this a serious person?”

2. In the room with Valentino

• The Prince strains to stay balanced across examples until the veil breaks at Borgia’s fall: “He told me” — first person — that he’d planned for everything at his father’s death “except the possibility that he himself would also be incapacitated.” Palmer: Machiavelli was in the room with a man contemporaries described as either the most charismatic leader alive or “literally the Antichrist or an incarnation of the angel of death.”
• His job was to stand beside the scariest man in Europe: Tuscany is the puzzle-piece notch Borgia must conquer, so the only play is abject loyalty — break the 300-year Bologna alliance, hand over money and forces, and whisper “Florence is loyal” to win “the boon of Polyphemus… I like you, my guest. I’ll eat you last.”
• Dwarkesh’s catch — doesn’t this violate The Prince’s own warning against rising via great powers? Palmer’s answer: this isn’t rising. Florence knows it will lose; had Alexander lived another year, Valentino takes Florence. “But popes are mortal. Buying time is sometimes the survival mechanism.”
• Senigallia is the case study: Borgia forgives plotters with sacred cathedral vows, then massacres them at the banquet — a hospitality violation so heinous Dante says a devil inhabits your still-living body. “And yet, it works” — the surviving men become more loyal than ever. Machiavelli’s wife and children waited months to learn he hadn’t been slaughtered too.

3. Fortune is half the game — judge the pre-fortune odds

• Machiavelli’s constant reminder: “We have power over, at maximum, half of what causes outcomes. The other half is always going to be fortune.” Dwarkesh frames him as the origin of utilitarian thought: he doesn’t just judge deeds by outcome — he judges by “the most probable outcome before fortune intervened.”
• The Borgia coats of arms chiseled off every Roman surface — “you sit down at a pizzeria and there’s a weird scar on the wall” — read to most as “don’t do what the Borgias did.” Machiavelli’s reading: they fell to food poisoning, Pius III dying too fast, and Julius’s outmaneuvering — “everything they did was right,” therefore imitate them.

4. The means matter far more than the caricature

• Dwarkesh’s confessed misconception: he’d assumed Machiavelli says “the means don’t matter, the end matters” — in fact he’s obsessed with means, because how you gain power determines its stability: rise via mercenaries or great powers and you’ve empowered someone stronger than you.
• Lying is conditional, not licensed: Savonarola’s power rested on being believed divinely inspired, so flip-flopping prophecies destroyed him — despite charisma so great that Michelangelo, asked decades later, said “I still hear his voice.” Borgia could betray his top general and his other allies just stepped “even further into line” — “lying is sometimes okay if you check these other boxes, and it’s not if you don’t.”
• Feared-over-loved is pure cynicism about human nature: promises evaporate the moment your rule tatters; expected punishment is stable. Dwarkesh links this to the American founders’ checks and balances; Palmer says “he basically thinks people will act as badly as they are allowed to.”
• Palmer’s historical flag: Machiavelli is the first person in the European tradition to suggest two political parties could coexist and “vent the society’s tension through competition” (his example: Siena) — against the standard that one party must die, as when Florence massacred its Ghibellines and “rubbed salt into the earth where the houses used to be. Nothing still grows there.”

5. Up close, the pope is “that guy” — and the corruption ratchet turns

• Distance manufactures papal majesty: in Denmark or Iceland the pope is pomp and abstraction; in Italy “the pope is that asshole who went to college with your brother and beat him up… He’s a specific dude.” Hence the paradox of hereditarily papal-loyal cities warring against the pope — Guelph vs. Ghibelline theory having long decayed into “those jerks murdered Uncle Tybalt, and we will never forgive them.”
• Palmer’s best specimen — “the most passive-aggressive letter ever written in the entire history of time”: after Pope Sixtus organized the Pazzi conspiracy and killed Lorenzo de’ Medici’s brother, Lorenzo sent his son to the next pope’s obedience ceremony with the message: “the last time this duty fell upon me, I had a brother upon whom I could leave the burden of the state… Since now I have no brother, I cannot come in person.”
• The ratchet: pious donations compound Church wealth, wealth is power, so every ambitious family bids for offices — Machiavelli’s own letters haggle over the correct-sized bribe for brother Totto’s priesthood, a top-5%-but-not-top-1% family treating it as routine. It becomes a prisoner’s dilemma: “If I don’t manipulate the Church, my enemies may manipulate the Church.”
• Every generation for a century says popes are worse than before — Dante in 1300, Machiavelli in 1500 — peaking in the Reformation, which Machiavelli anticipates: “All institutions are gradually corrupted and need to be reformed and returned to their foundations, or they will collapse” — St. Francis’s reform, on his read, bought Christianity 200 extra years.

6. Patronage was the operating system — all the way down

• Not one glue among several but “the fundamental glue of the society.” When Paul III appointed a competent general instead of his incompetent illegitimate son, Rome rioted: “Your Holiness, the people demand more nepotism” — the son rises and falls with you, and in a world where a soldier’s oath runs to his commander rather than a constitution, nepotism was the trust technology.
• Trial records decode it: law codes say death for everything, yet maybe 1 in 100 convictions ends in execution — the 99 had a patron put in a good word; the one had fallen out of the network. And the theology endorsed this: the trial was designed as an earthly preview of divine judgment — terror, begging, then mercy — aimed at “the spiritual improvement of the sinner,” versus the Enlightenment’s proportional justice.
• Giordano Bruno burned not for being uniquely radical but because his patron turned him in (“He’s a charlatan… Throw the book at him”). Pico — “candidly substantially more radical” — was rescued by Lorenzo via the Orsini; Ficino, who wrote “this young man is the reincarnation of St. Thomas Aquinas, so you should give him a job” as a recommendation letter, got the Inquisition waved off the same way. “You can’t even stay in a hotel or buy an apple — I’m not kidding — without a patron.”
• The Inquisition itself ran on patronage: no jails, funding, or arrest powers of its own — Palmer’s comparison: it operated “kind of like Doctors Without Borders,” only as strong as local government collaboration. Spain’s infamy came from Ferdinand and Isabella’s funding; a Medici duke’s “No, that guy works for me” created bubbles of privileged access where radical magic, philosophy, and homosexuality were untouchable — Machiavelli (in Palmer’s reading “very definitely solidly bisexual”) and his gay friends traded notes on racing to work for cardinals, with one holdout hiring courtesans as cover.

7. Neutral justice, liberty, and why falling to the Medici is gentlest

• The shock of Borgia’s conquests: he massacres a city’s ruling family, imposes authoritarian rule — and is beloved. Why? Outsiders with no local factions implement neutral justice, ending generations of “justice for some and injustice for others.” Feared but not hated works: the conquered manned his fortresses.
• Dwarkesh’s synthesis, with Palmer’s Borgia example as a response: the instability obsessing The Prince and the Discourses dissolves once you have impartial criminal justice, an impartial welfare state, and fast communications — the things that disintermediate patrons and distant generals (Rome’s frontier commanders, Caesar’s decades-loyal legions) so loyalty can attach to the regime itself. That’s the recipe for modern nation-states.
• But Machiavelli’s definition of liberty survives any fairness calculus: if a man can point at you in the street and say “Him, kill him,” “you are a slave” — while even a biased system (the very one that tortured and exiled him) is liberty, because there is a process. Florentines rioted under the LIBERTAS banner to defend a Signoria drawn from a “1% super mega elite” — “rioting to defend their boss’s boss’s right to be in the republic.”
• Falling to the Medici is “gentlest” because insiders want Florence to stay Florence — they’d never threaten to raze the cathedral. “You preserve some important rights when you’re conquered from inside that you don’t when you’re conquered from outside.”

8. The culture victory: art as defense budget, antiquity as cutting-edge tech

• How does a war-zone fund a $30 million library for Lorenzo’s grandsons? Half the answer is that finance and “Big Wool” were staggeringly profitable. The other half is Dwarkesh’s Fulbright analogy, which Palmer extends: “dollar for dollar, diplomacy is cheaper than war” — “If we fought [the King of France], we would lose. But if we play the culture victory game, that’s cheaper, and we can try to win.”
• “Backwards is forwards”: the period’s cutting-edge technology is imitating Rome — whether moderns can ever equal the Romans is a live debate, not a given. Florence’s buildings read to contemporaries like impossible skyscrapers, not heritage sites.
• They curated Roman history as deliberately as we do: what stood out wasn’t orgies and massacres — “their present has plenty” — but the successes and stability of the good emperors, including 70 years of peace, so alien and precious that medieval canon held Pope Gregory baptized Trajan’s ghost so a beloved pagan persecutor could reach heaven.
• To Dwarkesh’s “surely they believed oath-breakers go to hell”: everyone sinned constantly, and pre-Calvinist Christianity had no purity culture — sin, repent, repeat. Dante’s hell full of Florentines (“Congratulations, Florence, a city famous in hell”) was the stern outlier; a popular counterexample is St. Julian the Hospitaller, “patron saint of murderers,” whose icons dot Florence — each one “commissioned by somebody who committed a homicide and is trying to live with it.” Palmer’s verdict: “a complicated, sophisticated hypocrisy.”

9. Exile, and The Prince as classified technology

• Florentine exile was provisional loyalty-testing — go to Bruges or London, run diplomatic errands, earn recall. Machiavelli’s was harsher: a middle-of-nowhere Tuscan hamlet, “go rot.” Everyone expected him to defect to one of a dozen courts that would pay triple; instead he stayed and wrote The Prince as “my job application” begging the new regime to bring him back.
• The Prince circulated only to Florence’s rulers and his intimate scholarly circle — “secret and proprietary, the secret sauce of how to maintain power,” like “a nuclear scientist with diplomatic secrets who is faithful to his country.” Hence the irony Palmer keeps returning to: “Machiavellian” means self-serving, yet “Machiavelli himself is one of the most selfless men I’ve ever read about in the history of the Earth.”
• Audience-of-one books were normal: Alfonso of Naples commissioned bespoke handbooks of rule for each child — and “prince” was gender-neutral (“even Queen Elizabeth is Prince Elizabeth”). Dwarkesh’s AI parallel — bespoke masterpieces may return — draws Palmer’s correction: it never left; half the words anyone reads each day are bespoke — letters and email, and her historian friends at the Department of Defense Intelligence still write book-length reports for “an audience of five.”
• Why spend two decades on Discourses on Livy? “Nobody wants original ideas. Original ideas are out of vogue” — the Renaissance style guide demanded originality disguised as commentary, “the ancients as the trellis up which the rose climbs”: Ficino sincerely (and wrongly) believing his cosmology was coded in Plato, Annius of Viterbo burying forged artifacts to dig up theatrically. Hence the 19th-century slur Palmer quotes to demolish: “The Renaissance is 200 years of people being wrong about Plato.”

10. From typo panic to Old Nick: copyright, Hobbes, and the double image

• Machiavelli is among the first authors ever to suffer printing without copyright — a local printer’s typo-riddled unauthorized edition: “everyone’s going to think I’m a bad scholar… There’s nothing I can do.” Palmer’s mini-thesis: every new information technology triggers a censorship wave, and copyright and censorship were born together from the Inquisition — post-1515, all books “effectively born pre-banned” until licensed, with the license doubling as a monopoly you could sue on; England’s proto-copyright was explicitly an imitation.
• Reception ran on demand, not merit: published in 1532 by relatives wanting family fame, censored 27 years later in a general wave — though not in all-caps arch-heretic status, to Palmer’s mock outrage (“He should be in all caps”; that honor went to Luther and Calvin). Like Lucretius surging with germ theory, books wait “until the new questions being asked in that decade are answered by something in that text.”
• The Prince’s first surge came after Leviathan hit European thought “like a truck full of bricks” — 40 years of philosophy devoted to refuting Hobbes meant reading “the daddy monster that spawned the baby monster.” The 19th century then made him a global staple: post-Enlightenment states needed politics thought “in a box without plugging into religion,” and Italy bid him as “the first modern man” against England’s Bacon and France’s Descartes.
• Dwarkesh’s counter-thesis — the Discourses insist religion is vital to republics (Numa—or whoever the prophet was— mattering more than Romulus; Scipio’s sword-point oath after a battle in which Hannibal destroyed the Roman armies) — Palmer accepts via the Thomas Paine parallel: religion valued for its psychological utility, not its truth. Roman ghost-religion, where a forgotten name means “an empty, mindless, wandering shade,” beat Christianity for patriotism — “but Christianity has the advantage of being true,” period, end of chapter. And the final split: Old Nick — literally a nickname for the devil — Shakespeare’s “murderous Machiavel,” Spain’s “prince of the Jews,” a useful character with a separate life. Palmer’s close: read The Prince remembering “it was written by somebody who was willing to give up anything to serve his country.”