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

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

Machiavelli refused wealth and freedom to serve the regime that tortured him — "Machiavellian" self-interest is the exact opposite of who he actually was.

Jun 16, 2026 2:08:20 Difficulty: Intermediate Played

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. 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. The key takeaway: Machiavellian ruthlessness was always in service of protecting Florence, never personal advancement.

#Machiavelli #The Prince #Renaissance Florence #Italian city-states #papal corruption #patronage system #Renaissance justice #Cesare Borgia #history of copyright #political party theory #Discourses on Livy #Renaissance humanism #intellectual history #history of ideas #Florentine republicanism #Renaissance #Florence #patronage #papacy #exile #copyright #Inquisition #Italian politics #political philosophy #humanism #Dante #nepotism #Medici #fortune #political parties #diplomacy

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.

Chapter list
  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

Papal legate
An official representative sent by the Pope on a diplomatic mission to a foreign court or territory, carrying the Pope's authority.
Guelfs and Ghibellines
The two great medieval Italian political factions: Guelfs nominally supported papal supremacy; Ghibellines supported Holy Roman Emperor supremacy. By Machiavelli's era, these labels mostly signified inherited family enmity.
Simony
The practice of buying or selling church offices, sacraments, or positions of spiritual authority — widely practised in Renaissance Italy, as when Machiavelli's family debated bribing for a priesthood.
Signoria
The governing council or senate of the Florentine Republic, drawn from an extremely narrow elite; the institution whose coat of arms bore the word Libertà.
Valentino
The period name for Cesare Borgia, derived from his title Duke of Valentinois; used throughout The Prince and contemporary sources.
Condottiere
A professional mercenary military captain who hired out his forces to Italian city-states; their loyalty to employers rather than polities was a major source of instability Machiavelli analysed.
Usury
Lending money at interest, condemned as sinful by the medieval Catholic Church; widely practised but officially prohibited, making it a prime example of Renaissance society acting contrary to its stated religion.
Index of Forbidden Books
The official Catholic Church catalogue of books prohibited for the faithful to read, established in response to the printing press; The Prince appeared on it within 27 years of first publication.
Imprimatur
The formal permission granted by a Catholic ecclesiastical authority authorising a book to be printed; the basis for the first monopoly publishing licences that Ada Palmer traces to copyright's origin.
Monist
A philosophical position holding that reality is fundamentally one unified substance; Ada Palmer uses it to describe Spinoza's belief that the universe is entirely God's body.
De Rerum Natura
Latin for 'On the Nature of Things,' Lucretius's Epicurean poem presenting atomic theory; Machiavelli hand-copied the entire text, and it surged in influence during the Scientific Revolution.
Deist
Someone who believes in a creator God knowable through reason and nature, but rejects revealed religion and clerical institutions; Ada Palmer describes Thomas Paine as a deist.
Discourses on Livy
Machiavelli's extended commentary on the Roman historian Livy's histories, using them as a frame for his most developed original political theory, including his analysis of republics.
Calvinism
The Protestant theological tradition founded by John Calvin emphasising strict moral purity, predestination, and community discipline — Ada Palmer contrasts its purity focus with Renaissance Catholic acceptance of universal sin.
Pax Romana
The roughly 200-year period of relative peace and stability across the Roman Empire (27 BC to 180 AD); Ada Palmer notes Renaissance thinkers regarded it as the high-water mark of human civilisation.
Hegemony
Dominant political or cultural authority over others; used implicitly in the episode's discussion of which power — Pope, Emperor, or city-state — held decisive influence in Renaissance Italy.
Perfidy
Deliberate breach of faith or treachery; central concept in Ada Palmer's analysis of how Cesare Borgia's spectacular betrayals actually strengthened rather than undermined his authority.
Manuscript
A hand-written book or document, as distinct from a printed book; Ada Palmer discusses the transitional moment when manuscript and print culture coexisted during Machiavelli's lifetime.
Wunderkind
An exceptionally gifted young person; Ada Palmer uses related framing when describing Pico della Mirandola, whom Lorenzo de' Medici went to extraordinary lengths to protect from the Inquisition.
Utilitarian
An ethical framework that evaluates actions by their outcomes and consequences rather than intrinsic rightness; Ada Palmer identifies Machiavelli as the origin of utilitarian political thought.

Chapter 1 · 00:00

How Florence bargained with Cesare Borgia for survival

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.

Claims made here

Machiavelli was tortured and exiled by the Medici regime on suspicion of participating in a coup attempt that he did not actually participate in.

Dwarkesh Patel no source cited

The average length of a papacy in Machiavelli's era was approximately 10 years.

Ada Palmer no source cited

History
Fortune Controls Half of Everything

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

Chapter 2 · 15:08

Machiavelli's analytical innovations

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.

Claims made here

Machiavelli was the first European thinker to propose that two political parties could stably coexist in a state rather than one annihilating the other.

Ada Palmer no source cited

History
Two Political Parties: Machiavelli's Radical Innovation

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

Chapter 3 · 23:58

Why popes became warlords

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.

Claims made here

Machiavelli wrote to relatives about the correct size bribe to secure a priesthood for his brother Toto, treating it as entirely routine business correspondence.

Ada Palmer no source cited

History
Why Popes Became Warlords

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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

Why the common people demanded nepotism

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.

Claims made here

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

History
The Patronage System Was the Justice System

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 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.

Chapter 5 · 47:55

Cesare Borgia brought terror to rulers and justice to the people

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.

Claims made here

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Dwarkesh Patel Edward Gibbon's Decline and Fall of the Roman Empire

History
Cesare Borgia: Terror for Rulers, Justice for the People

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

History
Art as War by Other Means

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

Chapter 7 · 1:06:44

Florence, a city famous in hell

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.

Claims made here

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.

Ada Palmer no source cited

Chapter 8 · 1:16:57

The Prince was a job application to Machiavelli's torturers

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.

Claims made here

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.

Ada Palmer Machiavelli's Discourses on Livy

The Prince was placed on the Catholic Index of Forbidden Books approximately 27 years after first publication, around 1559.

Dwarkesh Patel no source cited

The Prince was first published in 1532, approximately 5 years after Machiavelli's death, by relatives seeking fame for the family.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer Tony Grafton (book on Aeneas of Viterbo)

History
When Machiavelli Became Exciting: Hobbes and the 19th Century

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

History
Original Ideas Had to Be Disguised as Ancient Commentary

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 History

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.

Chapter 10 · 1:41:39

During the Renaissance, original ideas had to be couched in antiquity

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.

Claims made here

The first version of authorial copyright emerged from Catholic Inquisition censorship licensing after 1515, and England subsequently imitated this system.

Ada Palmer no source cited

No indexed bits in this chapter.

Show stoppers

History
The Patronage System Was the Justice System

Ada Palmer – Machiavelli is the most misunderstood thinker … · Jun 16, 2026 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.

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3 / 18 cited (17%)

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.

Ada Palmer no source cited

The average length of a papacy in Machiavelli's era was approximately 10 years.

Ada Palmer no source cited

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.

Ada Palmer no source cited

The Prince was first published in 1532, approximately 5 years after Machiavelli's death, by relatives seeking fame for the family.

Ada Palmer no source cited

The Prince was placed on the Catholic Index of Forbidden Books approximately 27 years after first publication, around 1559.

Dwarkesh Patel no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

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.

Ada Palmer no source cited

The first version of authorial copyright emerged from Catholic Inquisition censorship licensing after 1515, and England subsequently imitated this system.

Ada Palmer no source cited

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.

Ada Palmer Machiavelli's Discourses on Livy

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.

Ada Palmer no source cited

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.

Dwarkesh Patel Edward Gibbon's Decline and Fall of the Roman Empire

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.

Ada Palmer no source cited

Machiavelli wrote to relatives about the correct size bribe to secure a priesthood for his brother Toto, treating it as entirely routine business correspondence.

Ada Palmer no source cited

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.

Ada Palmer no source cited

Machiavelli was tortured and exiled by the Medici regime on suspicion of participating in a coup attempt that he did not actually participate in.

Dwarkesh Patel no source cited

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.

Ada Palmer Tony Grafton (book on Aeneas of Viterbo)