How Machiavelli's Florence bargained with Cesare Borgia for survival – Ada Palmer
In a Nutshell
Machiavelli wrote The Prince as a secret manual to help Florence survive Cesare Borgia’s conquests by buying time through abject loyalty and papal mortality, recognizing that Borgia’s methods—neutral justice after eliminating factions, calculated betrayals, and instilling fear—were strategically correct but ultimately undone by fortune when his father died and the next pope turned against him. Florence’s survival strategy involved betraying allies like Bologna, swearing total obedience, and hoping to be “eaten last” until Borgia’s kingdom collapsed. The work remained private during Machiavelli’s lifetime because he refused to serve any power except Florence, sacrificing career opportunities in exile to remain loyal to his country rather than sell his knowledge.
These notes were generated by AI and may contain inaccuracies.
Machiavelli dedicates The Prince to Lorenzo di Piero de' Medici in 1513. In the final chapter, he states that Lorenzo is the only person who can bring Italy out of its current state of ruin and ravage. Two major factors explain the instability: the city-state structure of Italy and the role of the papacy.
A core political principle holds that long continuity of government creates legitimacy because people are accustomed to its institutions. When that continuity breaks through overthrow or regime change, the new government lacks staying power. One regime change frequently triggers multiple rapid successive changes. This pattern appears in the multiple iterations of the French Republic and in England's Wars of the Roses. When a long stable dynasty ends, repeated overthrows follow because the thread of continuity has been severed.
In Machiavelli's lifetime, that thread of continuity was cut for the majority of Italian cities. When he was born, six or seven city-states had recently had their governments uprooted. By the time he writes The Prince, dozens of places, in fact the majority, had experienced this disruption. Almost no government possessed staying power; every government remained ripe for replacement.
The papacy stands as one of the oldest institutions in the world. Consecutive popes expanded executive power, especially on the military side, and launched more wars while carrying out arbitrary overthrows of governments. City-states directly ruled by the papacy could theoretically have any ruler appointed by the pope. A pope with an illegitimate son could overthrow a city's government to install his son. Successive popes repeated this pattern until the norm emerged that every new pope possessed authority to knock down any pawn on the chessboard.
Because the next pope is elected rather than hereditary, the successor is frequently chosen by a coalition of those who oppose the current pope. With an average papacy length of roughly ten years, a completely unpredictable new monarch arrives who is almost guaranteed to be an enemy of the previous one and will therefore rip up prior arrangements.
Machiavelli sees a perfect storm: nearly every polity has had its thread of legitimacy cut, its institutions lack traditions, and its people have no investment in current rulers. These weakened states remain ready to fall again. The only force that could create stability near the papacy would be one person who gains sufficient power and has staying power through sons and heredity. Cesare Borgia attempted this by acquiring enough power near the papacy to influence the next pope. Machiavelli wants the Medicis not to unify Italy but at minimum to stabilize it by conquering enough territory that the papacy must fear and negotiate with them rather than constantly turning over small weakened powers.
At the moment of writing, the pope is a Medici, which makes this stabilization more plausible.
Before writing The Prince, Machiavelli works as a bureaucratic diplomat and meets many famous figures including King Louis of France and Maximilian of the Holy Roman Empire. He spends much of The Prince attempting to veil how much more he cares about Cesare Borgia than other examples. When discussing Valentino's fall, Machiavelli states that everything Cesare Borgia did was right and that he would have kept his conquests except for fortune. He breaks into first person to report that Borgia told him he had planned for every contingency at his father's death except the possibility that he himself would also be incapacitated.
Machiavelli was physically present in the room beside Valentino through these events and gained an extraordinary first-person view of this uniquely charismatic and terrifying figure. Contemporary accounts range from viewing him as the most incredible charismatic leader encountered to describing him as supernaturally charismatic to the degree that he must be the Antichrist or an incarnation of the angel of death.
Tuscany and Florence's dominion form a notch out of the side of the Papal States that Borgia plans to conquer. Machiavelli advises that Florence cannot permanently bribe or persuade Borgia to pass them by, but they can buy time by abjectly swearing to do anything he wants, giving him forces and money, helping him conquer the rest, and betraying allies such as Bologna, with whom Florence had maintained a 300-year alliance. The strategy is to win favor through loyalty and support so that Machiavelli can constantly whisper that Florence is loyal, thereby earning the boon of Polyphemus: the conqueror's promise to eat them last.
This does not contradict The Prince's warning against rising with the help of greater powers, because Florence is not aiming to rise or gain anything. Florence knows it will lose. If Alexander had lived another year, Valentino would have finished his conquests and taken Florence. Buying time through papal mortality serves as the survival mechanism.
Machiavelli witnesses the massacre at Senigallia. When rumor reaches Borgia that some followers are plotting against him, they abandon the plot out of fear. Borgia meets them, states that he forgives them, that they have renewed loyalty and passed the test, and invites them to a banquet where he massacres them all. The forgiveness proves false and betrayals are punished. Months later, Machiavelli's family in Florence receives word that he survived; they had feared he was caught in the conspiracy because the postal system had broken down.
Machiavelli observes the pattern of encountering conspirators, renewing sacred vows of amity in the cathedral, then slaughtering them at dinner in violation of hospitality laws. Dante would classify such an act as so heinous that a devil emerges from Hell to take the soul, placing the perpetrator already in Hell while the body remains alive. The massacre increases loyalty among Borgia's remaining men, who refuse even to whisper dissatisfaction for fear of death.
Valentino's kingdom falls because he eats the same food that poisons his father and becomes ill at the wrong moment, because the puppet pope Pius III dies too quickly, and because Julius outmaneuvers him. Machiavelli constantly reminds readers that humans control at most half of outcomes; the other half belongs to fortune.
Machiavelli argues that deeds should be evaluated based on the most probable outcome before fortune intervened, not solely on the actual result. People point to the Borgias' fall and the chiseling of their coats of arms from Roman surfaces as proof that one should not imitate them. Machiavelli counters that they fell because of fortune, not because of their choices, and that everything they did was right, so others should imitate them.
Machiavelli is concerned with means because the manner in which power is achieved determines how stable and fruitful that power becomes. Achieving power through mercenaries or great powers that become stronger than oneself creates a precarious position. Achieving power through lying and breaking oaths can succeed because people forget unfaithfulness and take the person at their word the next time.
He distinguishes cases. Savonarola's power rested on belief in his divine inspiration and infallibility, so his flip-flopping on prophecies and promises turned people against him. Cesare Borgia could betray allies because he remained so effective and terrifying that remaining allies became more faithful to avoid being next. Lying is sometimes viable if other conditions of fear and effectiveness are met; otherwise it is not.
The statement that it is better to be feared than loved rests on the view that people will break promises when a ruler's power seems to be weakening. Power based on the expectation of punishment for broken oaths proves more stable. Machiavelli believes people will act as badly as they are allowed to, whether they are tyrants, common people, or nobles.
Machiavelli becomes the first figure in the European tradition to propose that multiple political parties can coexist and compete within a state, venting social tensions through electoral competition. He cites Siena as an example where parties coexist and produce interior adjustments of power that maintain stability. Florence's traditional solution had been to massacre one party entirely, as with the Ghibellines whose houses were burned and the earth salted so nothing would grow.
A ruler's formidability and reputation matter for deterring invasion and extracting concessions. Florence's standard tactic when facing invasion is to determine whether the threatening ruler is serious and then pay a bribe to avoid attack, because paying for safety is more reliable than preparing for battle whose economic costs include trampled lands. Florence maintains an annual bribing-a-king budget allocated to whichever power poses the current threat, whether Maximilian, the King of Naples, the King of France, Milan, or the Venetians.
The pope functions as both spiritual leader and temporal power, with popes and their sons literally fighting wars against other Catholics. Geographic proximity shapes perceptions: distant regions such as Denmark or Iceland encounter the pope only through impressive legates arriving with pomp and circumstance, preserving an abstract respect. Nearby Italian states directly experience the pope's military actions and overthrows.
Italians experienced the pope as a specific, known individual rather than an abstract authority. People knew the pope personally from prior negotiations, knew his family, and understood his political alliances and rivalries. When a new pope assumed power, relatives received promotions while non-relatives were removed from positions. This personal knowledge made it difficult for Italians to view the papacy abstractly.
Italy divided into two factions based on historical beliefs about legitimate authority. Guelphs believed the pope was the rightful successor to Roman emperors and the ultimate political and military power over Italy. Ghibellines believed that when Charlemagne was crowned emperor in 800 AD, the pope delegated political and temporal authority to the emperor while retaining spiritual authority. By Machiavelli's era, these factions functioned as hereditary vendettas where "Those jerks murdered Uncle Tybalt, and we will never forgive them."
When a pope from a hereditarily Ghibelline family was elected, he would promote members of the anti-papal faction, causing the pro-papal faction to unite against him. Florence sometimes fought wars against the papacy to defend papal authority in papal lands against the pope himself, because that individual pope belonged to the anti-papal faction. Italians understood the distinction between the abstract office and the concrete person holding it.
When a new pope was elected, major ambassadors from every polity in Christendom traveled to Rome to deliver oaths of obedience. They waited in line, gave lengthy speeches praising their monarch's power and piety, and then prostrated themselves before the pope, kissing his feet. Florence sent its most prominent citizen for this duty. When Pope Sixtus was elected, Lorenzo de' Medici himself delivered the oration.
Lorenzo de' Medici negotiated with Pope Sixtus to obtain a cardinalship for his brother. Instead, Pope Sixtus organized the Pazzi conspiracy to assassinate the Medici family. The conspiracy killed Lorenzo's brother and several allies while attempting a coup to take over Florence. When the next pope, Innocent, was elected as a known puppet of the same faction, Lorenzo sent his son rather than himself to deliver the oath of obedience.
Lorenzo had his son deliver a message apologizing that he could not come personally: "I could not come myself, but the last time this duty fell upon me, I had a brother upon whom I could leave the burden of the state in my absence. Since now I have no brother, I cannot come in person." The letter was respectful but made clear that Lorenzo would not trust this faction again.
Every generation saw more donations of wealth to the Church. Widows without sons piously left property to monasteries. As the Church grew wealthier, it gained more power, creating stronger incentives for ambitious families to send second sons into the Church. Machiavelli wrote letters debating the correct bribe size to offer for a priesthood for his brother Totto—they avoided offering too much (impoverishing the family) or too little (being outbid by competitors).
Corruption functioned as a prisoner's dilemma: if a duke did not bribe the pope or secure a bishopric for his brother while his enemies did so, he would be disadvantaged. Manipulation of the Church was viewed defensively as necessary for safety. Kings needed the pope to grant marriage dispensations for cousin marriages and to prevent enemies from being made powerful bishops. Bribes and incentives made the papacy more corrupt with each generation.
Every generation for 100 years declared that popes were worse than when they were young. Dante said this in 1300, Machiavelli's grandparents' generation said it in 1400, and Machiavelli said it in 1500. In lived experience, popes became more secular, more military, and more corrupt over time. Machiavelli argued that all institutions gradually corrupt and need periodic reform and return to their foundations, or they collapse. He believed St. Francis of Assisi and St. Dominic had previously reformed the Church and prevented its collapse two centuries earlier.
Patronage was the fundamental basis of political power and social organization, not merely one mechanism among several. When Alessandro Farnese was elected Pope Paul III, he appointed a competent general rather than his illegitimate son to command papal armies. Romans rioted demanding more nepotism, arguing that the pope's son would never betray him and that the system required commanders who rose and fell with the pope. Patronage created multi-generational family entanglements where families rose and fell together, generating trust levels that sustained systems where soldiers swore oaths to commanders rather than polities.
Patronage determined trial outcomes. Medieval and Renaissance law codes prescribed death for theft, adultery, homosexuality, and even setting fire to the prince's beehive. Actual trial records show only one in 100 convictions resulted in capital punishment; most ended in fines or public floggings. A carpenter whose son killed someone in a drunken brawl would approach his Medici patrons to intervene with judges for a lighter sentence. This system was considered proper justice.
The period's justice ideal differed from Enlightenment proportional justice. The trial's purpose was the spiritual correction of the sinner's soul. The ideal outcome involved the accused fearing for their life before a terrifying judge representing God on earth, recognizing their guilt and deserving hell, then receiving miraculous grace and pardon. This process previewed divine judgment and aimed to produce a better person more likely to reach heaven. Religious organizations accompanied condemned prisoners overnight in prayer and walked them to execution holding paintings of the Virgin Mary so their final thoughts would be of heaven.
Giordano Bruno faced multiple Inquisition investigations for radical thought. Earlier trials ended with patrons intervening, resulting in warnings to "be good." His final trial resulted in burning at the stake because he had angered his patron, who turned him in and demanded severe punishment. Without patronage protection, the case proceeded to capital sentence.
Giovanni Pico della Mirandola, more radical than Bruno, received protection when Lorenzo de' Medici and powerful allies intervened. Lorenzo contacted his brother-in-law, an Orsini with enormous Roman influence, securing Pico's release under house arrest with a promise of good behavior. Marsilio Ficino, who recommended a scholar as "the reincarnation of St. Thomas Aquinas" and taught angel-summoning and soul projection, faced Inquisition scrutiny. Lorenzo's intervention through Cardinal Orsini resulted in Ficino being told to teach these practices only to pious people who would use them responsibly.
Patronage was required even for basic activities. Strangers arriving in cities needed letters of recommendation from patrons known to local important people to secure hotel rooms or conduct transactions.
When Cesare Borgia conquered cities in central Italy, he massacred ruling families to eliminate potential rival claimants. He implemented neutral justice because he and his allies had no connections to local factions. Despite being viewed as a cruel, murdering tyrant, he became popular because residents experienced fair justice for the first time in generations.
Before Borgia's arrival, Florence operated under factional control where justice depended entirely on which family held power. A carpenter's son who killed someone in a drunken brawl would receive minimal consequences if his employer belonged to the ruling faction, but would face execution if his employer was out of power. When Borgia conquered these cities and eliminated both ruling families, a neutral judge applied justice equally regardless of family affiliation.
The everyday people who had endured generations of selective justice were delighted by this equitable treatment. Wrongs against the powerless were finally punished, and the previously untouchable elites faced consequences for their crimes. This made Valentino's violent regime popular with ordinary citizens, who willingly joined his armies to defend his conquests.
Machiavelli and contemporaries were surprised because they expected conquered populations to uniformly hate and fear a conqueror who massacred local rulers. Instead, if the conqueror was feared but not hated—because he eliminated oppressive factions and then ruled fairly—the population accepted his authority.
Machiavelli argued that living under a system where someone could arbitrarily point at you on the street and order your execution meant you were not free—you were a slave. True liberty required a system with trials, due process, and public examination, even if that system was unfair or biased. Machiavelli himself was tortured and exiled by Florence's system, yet he valued having a system over arbitrary power.
If Valentino conquered Florence, that system would disappear. A single man could order executions without process. Even if that tyrant were fair and wise, his successor might not be. The uncertainty of monarchical succession made liberty impossible when arbitrary execution power existed.
Despite limited actual political participation, Florentines deeply valued liberty. The LIBERTAS banner represented the coat of arms of the Signoria, a senate drawn from the 1% super-elite minority eligible for government. Citizens would riot in the streets to defend their boss's boss's right to participate in the republic, demonstrating how much they cared about the distinction between having a system versus having a man who could arbitrarily execute citizens.
When Lorenzo de' Piero di Medici took power, he was not equivalent to an external conqueror. The Medici wanted Florence to remain Florence—they wanted to preserve its beauty, treasures, and identity. They would never consider razing city walls or threatening the cathedral as punishment for rebellion.
External conquerors would consider such measures. Florence under a Medici duke retained more of its original character than Milan under the Visconti or Sforza, or Ferrara under the d'Este dukes who could commit atrocities like gouging out family members' eyes with no civic resistance. Machiavelli recognized that if Florence had to fall, falling to the Medici would be the gentlest outcome, though more volatile since internal rulers would not inspire the same fear as external conquerors.
Florence's banking industry generated enormous wealth as the financial center of Europe. The wool industry also created substantial profits in an era when clothing was a major purchase like buying a car today. This surplus funded cultural projects including Lorenzo de' Medici's $30 million library investment for his grandsons.
The art served diplomatic purposes. Since Florence could not afford sufficient armies to defend against France even if all resources went to military spending, cultural diplomacy offered a cheaper alternative. Creating beautiful, expensive gifts and painting symbols like the fleur-de-lis on government buildings made French visitors feel welcomed and allied. When the French king arrived, he encountered friends rather than enemies. Diplomacy through art cost less than warfare.
Renaissance achievements appeared as high-tech to contemporaries as modern skyscrapers appear today. Foreign diplomats from France viewed Florentines as culturally insignificant people not descended from Caesars, yet producing works that either surpassed what Romans could achieve or achieved what contemporaries believed only Romans could do.
The Renaissance worldview saw potential in recapturing Rome's past rather than progressing toward an unknown future. The question was whether humanity could become as powerful as the Romans had been, whether another Pax Romana could be achieved. Imitating classical antiquity represented cutting-edge achievement, not backward-looking nostalgia.
Both Machiavelli and other humanists sought to emulate Roman virtues that made Rome great. They focused on stories from Livy and others about figures like Brutus killing his own sons or Mucius Scaevola putting his hand in fire to demonstrate loyalty. They curated Roman history to highlight what was absent from their present: 70 years of peace under Trajan, Hadrian, and Marcus Aurelius. Their contemporary world already had tyrants, orgies, and massacres; what it lacked was sustained stability.
Medieval and Renaissance Europe grappled with good pagan emperors' fates. The legend emerged that Pope Gregory the Great baptized Trajan's ghost so he could enter heaven despite persecuting Christians. Dante placed Trajan in Paradiso as the ideal Christian ruler. This reflected willingness to claim the best of pagan antiquity while maintaining Christian frameworks.
Machiavelli highlighted Borgia's betrayals because of their strategic effectiveness. Borgia executed Ramiro d'Orco, the deputy he had tasked with harsh rule that brought regional peace, using that deputy's harshness as justification. He also invited potential revolutionaries to a banquet under pretense of goodwill and killed them all.
Despite universal Christian belief that betrayal, lying, and oath-breaking led to hell, these actions were commonplace. Everyone engaged in prohibited behaviors including killing for honor and usury. Dante's Commedia addressed this hypocrisy directly, placing Florentines throughout hell and declaring Florence "a city famous in hell" for its citizens' sins, particularly usury and sodomy.
Renaissance Christianity differed from later Protestant-influenced traditions. The focus was not on achieving purity or expelling sinners from the community. Everyone sinned constantly—envy, lust, sloth were universal. The cycle involved sinning, repenting, doing penance, receiving forgiveness, and sinning again. St. Francis of Assisi constantly self-flagellated despite being considered Europe's most virtuous man.
St. Julian the Hospitaller, patron saint of murderers, had particular significance in Renaissance Florence. His legend involved being tricked by the devil into killing his parents, after which he dedicated his life to pilgrimage and running pilgrim hostels. Icons of St. Julian throughout Florence were commissioned by people who had committed homicide and sought spiritual guidance from someone who had done worse and found a path to repentance.
This contrasted with modern attitudes that treat murderers as permanently stained and requiring removal from society. Renaissance culture viewed homicide as sometimes necessary, with the critical factor being subsequent repentance and spiritual journey.
Society developed sophisticated mechanisms to reconcile religious precepts with practical actions. When Dante and Savonarola condemned putting family coats of arms throughout churches as turning sacred spaces into banking advertisements, the response was that God forgives anything with sufficient repentance. This created a complex hypocrisy apparatus allowing actions to diverge from stated religious beliefs.
Exile was common among intellectual figures including Dante, Voltaire, Rousseau, Thomas Hobbes, and Machiavelli. In Florence, exile functioned differently than Roman permanent banishment. The regime sent you to a specific location to test loyalty. You were expected to serve as an unofficial emissary, receiving diplomatic assignments and delivering trusted letters. Good behavior during exile could lead to eventual recall after years of service.
When Machiavelli is exiled, the Florentine regime does not send him to Bruges, London, Barcelona, or the Germanies—places where he has political contacts. Instead, they send him to a middle-of-nowhere hamlet in the Tuscan countryside outside Florence, where there is nobody important and nothing to do. This is not a "go wait for instructions" exile; it is a "go rot" exile designed to test whether he will faithfully stay, do nothing, and remain forbidden from talking to important people. Everyone expects Machiavelli will respond by running off to work for someone else rather than accept isolation.
Machiavelli possessed the skills of a classicist historian with military and diplomatic capacities, plus political contacts in Rome and France, and he had visited the court of the emperor. He could have worked for any number of cardinals or obtained prestigious diplomatic jobs in a dozen courts. Florentine historians were especially desirable because kings as far away as England had been trying to hire them to write flattering histories of their families. A skilled Florentine historian could easily secure employment writing a commissioned history.
Machiavelli refuses all external opportunities. He declares he will stay, rot in exile, and write The Prince as a job application begging the new regime to bring him back. He intends to demonstrate his loyalty by sending it only to the Florentine rulers and his immediate friends, sharing it with no one else. Machiavelli is a patriot who will not serve any cause that is not his country. Even though royal courts would pay three times what Florence would offer, and even though the regime that arrested, tortured, and exiled him did so despite him not plotting against them, he still wants to work for Florence.
"Machiavelli fundamentally is possibly one of the most patriotic patriots in Earth's history."
He will faithfully sit in the countryside and rot while begging to work for the people who ordered his torture, as long as they will recall him so he can serve his country.
The Prince is secret and proprietary—the secret sauce of how to maintain power. Machiavelli will not let any other power have that knowledge. He compares this to a nuclear scientist with diplomatic secrets who remains faithful to his country and refuses to sell out. Machiavelli knows he possesses the beginnings of a new world of political science, but he will only share it with the government of his country because he wants it to protect Florence. He will not serve any other cause.
It is ironic that the word "Machiavellian" means "self-serving," because Machiavelli himself is one of the most selfless figures in history. He sacrifices career, diplomacy, fame, friends, and even the opportunity to live in a city and have a normal day, choosing instead to rot in the countryside to remain faithful to his country. He would rather serve nothing and no one than give an hour of his time to advancing anything that is not Florence.
The Prince advocates viciousness, realism, and cynicism in service of protecting Florence, not in service of a generic prince of any generic principality. During Machiavelli's lifetime, The Prince circulates only to the rulers of Florence and his immediate scholarly, social, and intimate circle of friends—people he has known for decades who are scholar peers who have discussed his ideas with him. His other works—the Discourses, histories, and comedic play—are written for public circulation and increase his fame.
Writing a book for an audience of one or a very small circle was normal in Machiavelli's era, which was a moment of transition from the manuscript to the print period. It was standard for a major scholar like Pontano to be hired to write a handbook of princes existing in just one copy or three or four copies written for a specific prince. King Alfonso of Naples (Alfonso the Magnanimous), famous for his vast patronage of arts and letters and for cultivated personal anecdotes, paid scholars five times what the Republic of Florence would pay.
King Alfonso once refused to listen to an urgent wartime message until he finished his hour of scholarly contemplation of the soul with his scholar friends discussing Plato. He turned angrily on the sweaty messenger covered in dirt and said, "Get out. This is a place for men in togas, not for men in armor," and lost the battle but won the war. Alfonso commissions scholars to write unique, bespoke handbooks of how to rule and use power for each of his many children. These manuscripts exist in one copy or three copies and are never intended to circulate widely—they are private guidance for the recipient and possibly to pass on to their sons and daughters.
The handbook written for the princess who becomes Duchess of Ferrara addresses her as a prince, because "prince" is a gender-neutral word at this period. It is lexically masculine in terms of ending (like how a table is feminine in some languages), but the term is used for both men and women. Even Queen Elizabeth is referred to as Prince Elizabeth at this stage of her life.
Writing for an audience of one feels alien to modern sensibilities because books are understood as public objects. However, half of the words read on any given day have always been bespoke for one person: emails and letters. In halls of power, book-length reports with audiences of one, five, or a couple dozen have always existed. Historians working for the Department of Defense Intelligence produce book-length research projects with small audiences because they contain bespoke proprietary knowledge needed by government at that moment—sometimes technological, sometimes historical knowledge about important rivers where military events are likely to occur.
The Prince is first published in 1532 when the Medici pope allows its publication. Twenty-seven years later, in 1559, it is censored by that same papacy. Machiavelli's surviving relatives want fame for the family and their dead kinsman, so they ask permission to publish a work that has not yet been published. Because the book is dedicated to members of the Medici family, the Medici also gain fame from publishing it. They do not think as seriously about the power of its contents as its author did.
Every time a new information technology emerges, there is a subsequent wave of censorship. Machiavelli's work is censored in one of these waves but is not a particularly prominent example. The index of banned books carefully differentiates between dangerous books by arch-heretics (printed in all caps) and slightly dangerous books by lesser figures. The all-caps arch-heretic status is reserved for Protestant theologians such as Luther, Calvin, and Zwingli. Machiavelli appears in the index but not in all caps, indicating he is considered less dangerous than the Protestant reformers.
A work with radically unusual ideas may drift along being little read until it answers new questions being asked in a particular decade or century. The Prince first becomes exciting in the aftermath of the publication of Hobbes's Leviathan. Hobbes's work lands like a truck full of bricks with persuasive reasoning that produces a terrifying vision of humanity and God. For a 40-year period after Leviathan, the sole goal of Western European philosophy is refuting Hobbes. Critics note that Hobbes uses logics about politics and history that sound like Machiavelli—utilitarian consequentialist analyses, analyzing the origins of government as if there is no divinity setting it up, and depicting man in a state of nature inventing government rather than God telling Adam how to organize the world.
Critics call Hobbes "the monster" and "the beast of Malmesbury." To refute the monster, they look at "the daddy monster that spawned the baby monster." If they can find holes in Machiavelli, they hope to use those to refute Hobbes. Thus Machiavelli surges in popularity not among people who sympathize with him, but among people who see him as an enemy and want to use him to defeat what they consider the greater enemy.
A different surge occurs in the 19th century, when The Prince becomes a major global staple included in great book series. After the Enlightenment revolutions—the American Republic, the French Republic, and democratic movements elsewhere—people want new ways to think about politics separated from church and state. Most political treatises available at that time have some entanglement of religion with politics at their root, but Machiavelli does not. He offers an early foundational apparatus for thinking about government operating by itself and its earthly consequences without plugging into religion.
The Prince is useful for Italian nationalism, which celebrates Machiavelli as having invented separation of church and state and claims him as "the first modern man." England claims Francis Bacon invented the scientific method, while France claims René Descartes invented logical reasoning and modern principles of logical deduction. This creates a 19th-century nationalist competition among countries to claim their thinker as the first modern man.
In the Discourses, Machiavelli discusses how to maintain republics. He argues that more significant than Romulus in the founding of Rome was Numa, the figure who gave Roman gods and religion legitimacy. This legitimacy and the fear of offending the gods motivates people to defend the republic. After Hannibal destroys Roman armies, the people are about to flee Rome. Scipio, with his sword, makes them swear to their gods that they will stay and defend their homeland. Having given the oath, they conclude that Hannibal cannot be worse than the gods, so they must stay.
Machiavelli separates the institution of religion from the psychological effect of religion on the populace. Thomas Paine, a deist and radical, writes that institutional religion (Catholicism or the Church of England) is a destructive conspiracy to control minds and steal money. Yet Paine argues religion is vital to citizenship because it makes people good, fear laws, and want to obey them. Paine advocates mandatory religious education in schools but is indifferent to which religion it is, as long as people fear God and posthumous punishment.
Machiavelli analyzes how Roman religion, drawing from the Homeric tradition, teaches that a ghost only retains its identity to the degree one is remembered on Earth. If one's name is forgotten, the ghost forgets its name and becomes an empty, mindless, wandering shade. This creates a strong incentive to be remembered by doing great deeds, especially sacrificing oneself for one's country, because then one's name will be honored for as long as the country lasts. Christianity, by contrast, teaches that all that matters for a good afterlife is being pious or martyred, creating no incentive to sacrifice oneself for the state and instead encouraging citizens to sit in a box and be monks.
Machiavelli concludes that Roman religion was much better for patriotism and political stability than Christianity, but adds that Christianity has the advantage of being true.
Both Machiavelli and Thomas Paine think about the utility of religion for forming a citizen in a utilitarian way, not from the position that "this religion is true, we are doing God's work." They treat religion as something to be cultivated or not cultivated based on whether it produces the desired skills in the citizenry—alongside literacy skills or math skills—rather than as an obligation of government to advance because it is true and will bring divine blessings or curses.
Machiavelli's father spent months doing indexing work on Livy in order to obtain a copy of the text. In the early days of printing, books remained scarce. Machiavelli created a manuscript copy of Lucretius by hand from a printed version while incorporating corrections drawn from a manuscript source, producing a hybrid text superior to either original. He added marginal comments throughout. Even when printed copies existed, Machiavelli preferred to invest months creating his own improved personal version rather than wait for future corrected printings.
Print and manuscript technologies operated in parallel during this period. Buyers of early printed books simultaneously produced manuscripts that imitated and were influenced by printed works.
Machiavelli likely had very few books available to him as a youth, making his single copy of Livy especially influential. Unlike modern readers who can consume multiple books weekly, Machiavelli would have reread Livy repeatedly over years, connecting its content to contemporary political events on successive rereadings. This created a different mode of scholarship and intellectual engagement than exists today.
Machiavelli could access additional books through friends or the libraries of his Medici and Soderini patrons, but this differed from having a personal copy at home for constant intimate reference.
Antiquity represented the cutting edge during the Renaissance. Scholars believed that basing society on ancient Roman models would bring peace and inaugurate a golden age. Commentaries on ancient authors were far more popular, prestigious, and commercially successful than original works. Original ideas were considered out of vogue.
Renaissance scholars therefore presented original ideas as commentaries on Livy, Plato, or other ancients to gain larger audiences and greater credibility. Giordano Bruno attributed statements to Aristotle that Aristotle never made, because claiming Aristotelian authority increased serious reception.
Annius of Viterbo fabricated ancient texts and staged archaeological discoveries by secretly burying artifacts and then dramatically excavating them. He created forged antiquities to support his original historical vision, understanding that his ideas would receive more serious attention if presented as ancient discoveries rather than contemporary innovations.
Machiavelli chose to write Discourses on Livy rather than a Florentine history or original treatise on princes because discourses on Livy carried greater prestige, popularity, and commercial viability. The work represented his attempt to produce something widely valued. Throughout the following century, substantial radical political thought—including commentaries on Machiavelli—appeared in footnotes to editions of Seneca and Livy, where the original text occupied a small central square while extensive commentary filled the margins.
Nineteenth-century historians dismissed Renaissance philosophy as lacking original thought because the period's dominant style required original ideas to be presented as commentaries on ancient sources. Historians identified only The Prince and Giovanni Pico della Mirandola's Oration on the Dignity of Man as genuine original works. One philosophy department member characterized the Renaissance as "200 years of people being wrong about Plato."
When Renaissance commentaries are read as genuine attempts to interpret the ancients, they appear mistaken. However, recognizing that the period's conventions required presenting original thought through the form of ancient commentary reveals 200 years of innovative thinking using the ancients as a supporting structure.
Marsilio Ficino, translator of Plato, genuinely believed that his original cosmological and magical ideas were secretly encoded within Plato's texts. He presented his work as commentary on both Plato and Dionysius the Areopagite. This convention explains why Machiavelli framed his political thought as Discourses on Livy—it was the expected scholarly format. Other works by Machiavelli were considered secondary or unusual for a scholar compared to discourses on Livy.
Machiavelli was among the first authors to experience unauthorized printing of his work. A local printer produced an edition containing typos and errors without consulting him. He wrote panicked letters expressing concern that readers would attribute the mistakes to him and damage his scholarly reputation. No legal mechanism existed to address the situation because copyright had not yet been established.
In the manuscript era, discovering an unauthorized copy was welcomed because additional copies reduced the risk of total loss. Creating a single manuscript required six months of labor, making reproduction valuable. Printing changed this dynamic fundamentally.
Copyright and censorship originated together through the Inquisition. After 1515, the Catholic Church required that all texts receive approval from an inquisitor or bishop before printing to prevent heresy. Books were effectively pre-banned until permission was granted. In exchange for this approval process, the approved printer received a monopoly license, creating the first mechanism for enforcing printing rights.
England observed this system and developed its own licensing requirement that granted monopoly rights, which became the ancestor of copyright law in Commonwealth nations and the United States. The initial English system was explicitly modeled on the Inquisition's approach.
During the first half of the 1600s, freedom of the press advocates separated the copyright component of the licensing system from its censorship function. The demand Machiavelli expressed—needing recourse when printers produced unauthorized, error-filled editions—contributed to the conditions that generated copyright law.
The Inquisition had incentive to enforce authorial prerogatives because doing so encouraged authors to participate in the approval process. Individual inquisitors also operated pragmatically, accepting gifts such as wine in exchange for favorable readings and needing to maintain positive relationships with local authorities to secure funding and cooperation.
The Inquisition was not a centralized organization controlled directly from Rome. Individual inquisitors worked in isolated locations with slow communication to the Vatican. They lacked independent funding, officers, and jails, depending entirely on local governments for resources and enforcement power.
Local governments could starve the Inquisition of support or provide generous funding depending on their assessment of the inquisitor's usefulness. The Spanish Inquisition became notorious because Ferdinand and Isabella directed substantial resources toward it for their own political purposes of scapegoating Jewish and Muslim populations.
In Florence under early Medicean rule, the duke protected intellectual radicals at his court, preventing the Inquisition from arresting individuals under his patronage. Inquisitors complained in letters about liberal rulers shielding heretics.
The Inquisition operated similarly to an international organization dependent on local government cooperation. When local authorities collaborated, the Inquisition wielded significant power. When governments withheld support, the Inquisition became nearly impotent, unable to make arrests without local approval.
This system created protected spaces where individuals connected to powerful patrons could engage in radical magic, philosophy, politics, or sexuality without interference from church authorities.
Machiavelli was solidly bisexual, maintaining both male and female romantic partners throughout his life and writing both homoerotic and heterosexual poetry. He had numerous gay friends. When Roman authorities cracked down on homosexuality, scholars and artists sought positions with cardinals because such employment provided protection from prosecution.
One friend who failed to secure cardinal patronage hired two female prostitutes to create the appearance of heterosexuality as a defensive measure. Heresy and homosexuality were policed by the same structures, making patronage relationships essential for protection in both domains.
The Inquisition sought to please local authorities to maintain operational capacity. Books carrying recommendation letters from important political figures received expedited approval. Authors and patrons recognized they could request monopoly printing rights as part of the approval process.
The Medici supported printing The Prince partly because it was dedicated to a family member and celebrated their reputation. They had incentive to control the quality and presentation of the work, including ensuring the dedicatory letter appeared at the front.
Machiavelli became separated from his actual work in historical memory. The real Machiavelli was a patriot who sacrificed wealth, fame, and personal relationships to serve Florence. In contrast, the character "Machiavellian"—the scheming, self-serving, atheistic politician invoked by Shakespeare as "the murderous Machiavel" and nicknamed "Old Nick" after the devil—developed an independent existence.
The Prince functions as a manual for maintaining stable government and protecting citizens rather than a guide for personal advancement. The villainous Machiavelli character proved useful for political discourse, appearing in Spanish discussions that equated Machiavellianism with Jewishness as labels for subversive political thought threatening Catholic Spain.
The modern perception of The Prince as a strategic manual for getting ahead reflects engagement with the fictional Machiavellian character rather than the historical Niccolò Machiavelli who remained in exile to serve his country.
To me, I think even more fascinating than looking at either Old Nick, the fictitious Machiavellian villain, or Machiavelli the patriot, is to look at how did we double-image this? What is the fascinating tendency of our society to take something real, powerful, exciting, intimate, and then say, "But we can also make the character," and the character is itself interesting. So if you take away a main message from this with Machiavelli, it's that Machiavelli, the character of thought experiment, is an important backbone of our society.
We use him as we think about politics. Machiavelli, the actual innovator, is a different backbone of our society and how we think about politics. If Machiavelli can be two such different things, Old Nick and Machiavelli the patriot, so many other things we encounter in life have actually been teased apart by our social utility and made into multiple things which are useful to us in different contexts.
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.
I think that's an excellent place to close. Ada, thanks so much for hopping on. This was a pleasure, as always. I hope it won't be the last time. I hope so, too.
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