Machiavelli refused wealth and freedom to serve the regime that tortured him — "Machiavellian" self-interest is the exact opposite of who he actually was.
Dwarkesh Podcast
Machiavelli refused wealth and freedom to serve the regime that tortured him — "Machiavellian" self-interest is the exact opposite of who he actually was.
TL;DR
Historian Ada Palmer joins Dwarkesh Patel to reframe Machiavelli as perhaps the most misunderstood thinker in history. Far from a cynical schemer, Machiavelli was a patriot who refused lucrative foreign posts to rot in exile, writing The Prince as a job application to the very regime that tortured him [1] — Ada Palmer "In the Renaissance, original ideas were out of fashion. If you wanted people to take your thought seriously, you dressed it up as Livy or P…" 1:36:40 . Palmer illuminates Renaissance Florence's political fragility, the papacy's corrupting role, the patronage system's grip on justice and loyalty, and how Cesare Borgia's neutral justice made him beloved by the people he conquered [2] — Ada Palmer "Every foreign court in Europe would have paid to hire Machiavelli. He turned them all down and chose to rot in a countryside hamlet, writin…" 1:19:50 . The key takeaway: Machiavellian ruthlessness was always in service of protecting Florence, never personal advancement.
Ada Palmer joins Dwarkesh Patel for a deep-dive on Machiavelli — his diplomatic career, the historical context of Renaissance Italy, why The Prince was secret, and how the word 'Machiavellian' became the opposite of who Machiavelli actually was.
Ada Palmer describes Machiavelli's diplomatic strategy with Cesare Borgia — unconditional loyalty, betraying allies, whispering 'Florence is loyal' to buy time. The massacre at Senigallia and Borgia's terrifying charisma. [1] — Ada Palmer "Florence could not defeat Cesare Borgia — the math was simply impossible. Machiavelli's entire strategy was to pledge unconditional loyalty…" 11:20
The episode examines Machiavelli's core analytical innovations: how means determine power stability, fortune controlling half of all outcomes, when lying is acceptable, and his radical idea of coexisting political parties.
Ada Palmer explains how geographic proximity made Italians see popes as ordinary power-hungry men. Wealth accumulation, prisoner's dilemma dynamics, and generational corruption drove the papacy toward militarism. [1] — Ada Palmer "Every generation left wealth to the church. Wealthier church meant more political power. More power meant more incentive for ambitious fami…" 33:20
Patronage was the fundamental glue of Renaissance society — from papal army command to hotel stays. When Paul III chose competence over family, Romans rioted demanding more nepotism. [1] — Ada Palmer "99 of 100 death sentences commuted: In Renaissance Florence, perhaps 99 of 100 capital convictions ended in a fine rather than execution, b…" 45:00
The elder Lorenzo de' Medici spent ~$30M equivalent on education. Florence used art as cheaper diplomacy than armies — commissioning gifts for French kings was more cost-effective than fighting France. [1] — Ada Palmer "Florence couldn't afford armies to fight France. So it spent lavishly on art, architecture, and cultural gifts for French kings instead. Cu…" 59:20
The Renaissance believed potential lay in recapturing Rome, not advancing to the future. High-tech art was an attempt to match ancient achievement. Gibbon later called the Pax Romana humanity's peak.
Dante filled the Inferno with Florentines to condemn his city's hypocrisy. Ada Palmer contrasts Renaissance Catholic tolerance of universal sin with later Calvinist purity culture and the patron saint of murderers.
Machiavelli hand-copied Lucretius from memory. The Renaissance treated antiquity as the only credible source. Original ideas were disguised as Livy or Plato commentary — the Discourses were Machiavelli's prestige vehicle. [1] — Ada Palmer "In the Renaissance, original ideas were out of fashion. If you wanted people to take your thought seriously, you dressed it up as Livy or P…" 1:36:40
Pre-publication Inquisition censorship accidentally created the first publishing monopolies. England copied the mechanism. The entire modern copyright system descends from Inquisition licensing. Machiavelli was among the first authors to feel the need for it. [1] — Ada Palmer "The Inquisition required pre-publication approval for all books. In exchange, it granted printers a monopoly — the first copyright. England…" 1:48:10
The Inquisition depended entirely on local government for jails, funding, and arrest power. Liberal dukes could protect heretics and gay scholars. Machiavelli and bisexual artist friends used patronage as a shield.
'Old Nick' the villain character and Machiavelli the patriot are two separate things. Like Hobbes and Spinoza, the real person's ideas became a useful fictional monster. Reading The Prince knowing its author died in loyal poverty changes everything.
Chapter 1 · 00:00
Ada Palmer describes Machiavelli's diplomatic strategy with Cesare Borgia — unconditional loyalty, betraying allies, whispering 'Florence is loyal' to buy time. The massacre at Senigallia and Borgia's terrifying charisma. [1] — Ada Palmer "Florence could not defeat Cesare Borgia — the math was simply impossible. Machiavelli's entire strategy was to pledge unconditional loyalty…" 11:20
With an average papal reign of 10 years, Italy faced near-constant political upheaval since each new pope, often elected by enemies of the prior pope, reversed prior policies.
Florence could not defeat Cesare Borgia — the math was simply impossible. Machiavelli's entire strategy was to pledge unconditional loyalty, betray centuries-old alliances, and whisper 'Florence is loyal' into the most terrifying conqueror's ear in Europe, buying nothing more than the promise of being conquered last.
Machiavelli's diplomatic strategy with Cesare Borgia was to pledge total loyalty and buy time, knowing Florence could not militarily resist — just hoping to be conquered last.
The Borgias did everything right. Cesare built an empire through brilliant strategy. Then he got food poisoning at the exact wrong moment, and it all collapsed. Machiavelli's conclusion: that's not a reason not to imitate them. Fortune controls half of all outcomes. You evaluate deeds on their most probable result, not on how fortune intervened.
Machiavelli argues that no matter how skillful a ruler is, half of what determines outcomes is always fortune — entirely outside anyone's control.
Chapter 2 · 15:08
The episode examines Machiavelli's core analytical innovations: how means determine power stability, fortune controlling half of all outcomes, when lying is acceptable, and his radical idea of coexisting political parties.
Before Machiavelli, everyone agreed: two political parties in one state ends when one destroys the other. Florence literally salted the earth where its defeated faction's houses stood. Machiavelli looked at Siena and said — wait, maybe competition is better than massacre. That idea feels obvious now because we built entire democracies on it.
Machiavelli was the first European thinker to suggest that two political parties could coexist stably in a state, rather than one being exterminated by the other.
Chapter 3 · 23:58
Ada Palmer explains how geographic proximity made Italians see popes as ordinary power-hungry men. Wealth accumulation, prisoner's dilemma dynamics, and generational corruption drove the papacy toward militarism. [1] — Ada Palmer "Every generation left wealth to the church. Wealthier church meant more political power. More power meant more incentive for ambitious fami…" 33:20
Every generation left wealth to the church. Wealthier church meant more political power. More power meant more incentive for ambitious families to buy their sons into it — right down to Machiavelli's family debating the right-sized bribe for his brother's priesthood. The papacy wasn't corrupted by bad people; it was corrupted by a structural trap nobody could escape.
Chapter 4 · 36:13
Patronage was the fundamental glue of Renaissance society — from papal army command to hotel stays. When Paul III chose competence over family, Romans rioted demanding more nepotism. [1] — Ada Palmer "99 of 100 death sentences commuted: In Renaissance Florence, perhaps 99 of 100 capital convictions ended in a fine rather than execution, b…" 45:00
Death was the sentence on the books for almost everything. But in reality, your patron intervened, a word was put in, and you paid a fine. The one person who was actually executed was the one who had angered his patron. The entire justice system was a rehearsal for divine grace, with the patron standing in for the saint and the judge standing in for God.
In Renaissance Florence, perhaps 99 of 100 capital convictions ended in a fine rather than execution, because patronage networks intervened to win clemency for the accused.
Giordano Bruno survived multiple Inquisition trials through patronage, but when he angered his patron, that patron turned him in — leaving him without protection and leading to his execution.
Chapter 5 · 47:55
The elder Lorenzo de' Medici spent ~$30M equivalent on education. Florence used art as cheaper diplomacy than armies — commissioning gifts for French kings was more cost-effective than fighting France. [1] — Ada Palmer "Florence couldn't afford armies to fight France. So it spent lavishly on art, architecture, and cultural gifts for French kings instead. Cu…" 59:20
Borgia massacred the ruling families of the cities he conquered, then installed neutral justice — and became wildly popular. For the first time in generations, the carpenter whose son killed someone got the same verdict whether he worked for the faction in power or the faction out of power. Machiavelli was startled. The lesson: feared but not hated works.
Cesare Borgia became popular with common people after conquering cities because his neutral justice — unbeholden to local factions — was fairer than anything they had experienced before.
The elder Lorenzo de' Medici spent what would today be roughly $30 million building a library to educate his grandson, illustrating the scale of Renaissance humanist patronage.
Florence couldn't afford armies to fight France. So it spent lavishly on art, architecture, and cultural gifts for French kings instead. Culture wasn't a surplus from peace — it was a rational substitution for unaffordable military spending. Florence was playing the culture victory because the military victory wasn't available.
Florence could not afford armies sufficient to repel France, so it used spectacular art and cultural gifts as diplomatic tools — effectively buying peace for less than the cost of war.
Renaissance thinkers saw human potential as recapturing ancient Rome, not advancing into an unknown future — making imitation of antiquity the highest intellectual ambition.
Medieval Catholic tradition held that Pope Gregory the Great summoned and baptized the ghost of Emperor Trajan posthumously, because Europeans loved Trajan too much to accept that he was in hell.
Chapter 7 · 1:06:44
Dante filled the Inferno with Florentines to condemn his city's hypocrisy. Ada Palmer contrasts Renaissance Catholic tolerance of universal sin with later Calvinist purity culture and the patron saint of murderers.
Dante populated his Inferno with Florentines to condemn his city's hypocrisy, famously greeting a group of fellow citizens with the line 'Congratulations, Florence, a city famous in hell.'
Chapter 8 · 1:16:57
Machiavelli hand-copied Lucretius from memory. The Renaissance treated antiquity as the only credible source. Original ideas were disguised as Livy or Plato commentary — the Discourses were Machiavelli's prestige vehicle. [1] — Ada Palmer "In the Renaissance, original ideas were out of fashion. If you wanted people to take your thought seriously, you dressed it up as Livy or P…" 1:36:40
Every foreign court in Europe would have paid to hire Machiavelli. He turned them all down and chose to rot in a countryside hamlet, writing The Prince not for fame or publication but as a loyalty demonstration to the men who had tortured and exiled him. He wanted only one job: serving Florence.
Despite being tortured and exiled, Machiavelli refused lucrative positions at foreign courts and chose to remain in rural exile, writing The Prince as a loyalty demonstration to Florence.
Machiavelli did not circulate The Prince broadly; he treated it like classified state intelligence, sharing it only with Florence's rulers and his closest scholarly circle.
'Machiavellian' means calculating and self-serving. Machiavelli gave up wealth, social life, career, and freedom to serve the government that tortured him — refusing to let his political secrets benefit any other state. He is possibly the least Machiavellian person in history.
The Prince was first published in 1532, after Machiavelli's death, by relatives seeking family fame; it was placed on the Index of Forbidden Books by 1559.
The Prince drifted in obscurity until Hobbes's Leviathan hit European thought 'like a truck full of bricks.' Philosophers trying to refute Hobbes went back to Machiavelli as the ancestral monster. Then in the 19th century, newly republican governments needed a political framework without God — and Machiavelli was the only major theorist who didn't plug religion in.
Hobbes's Leviathan sparked a 40-year effort by European philosophers to refute it, which led scholars back to Machiavelli as the intellectual ancestor of Hobbesian thought.
Machiavelli hand-copied the entire text of Lucretius's De Rerum Natura, integrating corrections from a manuscript, even though printed copies existed — illustrating the intimacy of Renaissance scholarship.
In the Renaissance, original ideas were out of fashion. If you wanted people to take your thought seriously, you dressed it up as Livy or Plato — even if you were attributing things to Aristotle that Aristotle never said. The Discourses on Livy is where Machiavelli's most radical political innovations are hidden, precisely because it had a bigger audience than an original work.
Renaissance scholars routinely disguised original thought as commentary on classical authors like Livy or Plato, because originality was out of fashion and ancient authority commanded greater respect.
Chapter 10 · 1:41:39
The Inquisition depended entirely on local government for jails, funding, and arrest power. Liberal dukes could protect heretics and gay scholars. Machiavelli and bisexual artist friends used patronage as a shield.
The Inquisition had no jails, no arrest power, and no funding of its own. Everything depended on the local Duke. If the Duke liked heretics, the Inquisitor couldn't touch them. In Florence, a city of radical Platonists under radical Medici dukes, the Inquisition was nearly toothless.
Ada Palmer described Machiavelli as definitively bisexual, citing his homoerotic and heterosexual poetry and the documented fact that he had both boyfriends and girlfriends throughout his life.
The Inquisition required pre-publication approval for all books. In exchange, it granted printers a monopoly — the first copyright. England saw this, wanted the same mechanism, and copied it. The entire modern copyright system descends from Inquisition censorship licensing.
The first version of authorial copyright emerged from Inquisition censorship licensing: printers who cleared pre-publication review gained monopoly printing rights, which England later imitated.
No indexed bits in this chapter.
'Machiavellian' means calculating and self-serving. Machiavelli gave up wealth, social life, career, and freedom to serve the government that tortured him — refusing to let his political secrets benefit any other state. He is possibly the least Machiavellian person in history.
Death was the sentence on the books for almost everything. But in reality, your patron intervened, a word was put in, and you paid a fine. The one person who was actually executed was the one who had angered his patron. The entire justice system was a rehearsal for divine grace, with the patron standing in for the saint and the judge standing in for God.
This episode
Factual claims made this episode, and whether a source was named.
Machiavelli was the first European thinker to propose that two political parties could stably coexist in a state rather than one annihilating the other.
The average length of a papacy in Machiavelli's era was approximately 10 years.
Machiavelli's hand-written copy of Lucretius's De Rerum Natura, integrating corrections from a manuscript into a printed copy with his own marginal notes, is preserved in the Vatican Library.
The Prince was first published in 1532, approximately 5 years after Machiavelli's death, by relatives seeking fame for the family.
The Prince was placed on the Catholic Index of Forbidden Books approximately 27 years after first publication, around 1559.
Giordano Bruno's fatal Inquisition trial resulted from his patron turning him in after Bruno failed to deliver promised results — not primarily from the radical nature of his ideas.
In Renaissance Florence, approximately 99 out of 100 capital convictions ended in a fine or flogging rather than execution, because patronage networks routinely secured lighter sentences.
Pope Paul III appointed a competent general rather than his illegitimate son to command the papal armies, and this triggered riots in Rome demanding more nepotism.
Cesare Borgia became popular with common people in conquered cities because he imposed neutral justice independent of local factional politics, in contrast to prior rulers who dispensed partisan justice.
The first version of authorial copyright emerged from Catholic Inquisition censorship licensing after 1515, and England subsequently imitated this system.
Machiavelli argued that Roman religion, which tied a ghost's welfare to earthly remembrance, was a better motivator for patriotic self-sacrifice than Christianity, which tied the afterlife to personal piety.
Hobbes's Leviathan triggered a 40-year period during which the sole goal of Western European philosophy was refuting Hobbes, which drove the rediscovery of Machiavelli.
Edward Gibbon, writing in the late 18th century, stated there had never been a better time for humanity than during the Pax Romana and the Five Good Emperors.
Medieval Catholic tradition held that Pope Gregory the Great posthumously baptised the ghost of Emperor Trajan, and Dante placed Trajan in Paradiso as the ideal Christian ruler.
Machiavelli wrote to relatives about the correct size bribe to secure a priesthood for his brother Toto, treating it as entirely routine business correspondence.
Thomas Paine was a deist who believed institutional religion was destructive, yet advocated mandatory religious education in schools because fear of posthumous punishment was necessary to make citizens obey laws.
Machiavelli was tortured and exiled by the Medici regime on suspicion of participating in a coup attempt that he did not actually participate in.
Aeneas of Viterbo fabricated ancient texts and faked archaeological digs — burying and then dramatically 'discovering' artefacts — to lend ancient authority to his original historical ideas.
This episode
Florentine diplomat and author of The Prince and Discourses on Livy; the central subject of the entire episode.
Military commander and son of Pope Alexander VI, described as Machiavelli's dominant case study in The Prince for both brilliant strategy and terrifying personal charisma.
Dedicatee of The Prince and grandson of the elder Lorenzo; also the elder Lorenzo discussed in the context of the Pazzi conspiracy and cultural patronage.
Medieval Florentine poet whose Inferno is discussed as a moral condemnation of contemporary Florentine hypocrisy, including usury and sexual sin.
Florentine religious demagogue whose charismatic preaching Machiavelli analysed as a case study in why lying and policy flip-flopping destroyed a power base built on claims of divine inspiration.
English political philosopher whose Leviathan triggered a 40-year philosophical debate that drove the rediscovery and popularisation of Machiavelli.
Florentine Platonist philosopher protected by Medici patronage from Inquisition consequences for his radical ideas about soul projection, reincarnation, and angel summoning.
Radical philosopher burned by the Inquisition; Ada Palmer argues his execution was caused by losing his patron's protection, not primarily by his radical ideas.
Radical Renaissance philosopher protected from Inquisition trial by Lorenzo de' Medici's patronage; discussed as even more theologically radical than Giordano Bruno.
Ancient Roman poet and atomist philosopher; Ada Palmer discusses De Rerum Natura as a parallel to The Prince in how works drift in obscurity until historical circumstances make them suddenly relevant.
17th-century Jewish philosopher used as a parallel to Machiavelli to illustrate how intellectual figures become separated from their actual ideas by a legendary character that takes on its own cultural life.
American revolutionary thinker cited as a parallel to Machiavelli in thinking about religion's utility for citizenship in purely utilitarian terms, independent of its truth claims.
Roman emperor beloved by medieval and Renaissance Europe; discussed in context of the legend that Pope Gregory posthumously baptised his ghost so he could enter heaven despite being pagan.
Aggressive warrior pope who outmanoeuvred Cesare Borgia after both Alexander VI and Pius III died; discussed as an example of how Machiavelli analyses lying and oath-breaking.
The dominant Florentine ruling family, who tortured and exiled Machiavelli, received the dedication of The Prince, and authorised its first publication in 1532.
Catholic ecclesiastical body for investigating heresy, discussed as structurally dependent on local government and, surprisingly, as the originator of modern copyright law.
Ada Palmer's academic institution, mentioned in the introduction as part of her credentials as a historian.
Machiavelli's political treatise, discussed as a secret job application to the Medici, a proprietary political manual, and one of the most misunderstood books in history.
Machiavelli's major political work framed as commentary on the Roman historian Livy; discussed as the vehicle for his most original political innovations.
The Florentine Republic, Machiavelli's homeland and the central political entity throughout the episode — its survival, liberty, and cultural output are the episode's core concerns.
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