Italy during the Renaissance suffered from a severe lack of political stability. Ada points to two primary causes for this chaos: the collapse of institutional legitimacy in city-states and the unpredictable power of the papacy. When a long-standing government is overthrown, the thread of continuity is cut. This makes subsequent overthrows much more likely because the people no longer believe in the permanence of their institutions. By the time Machiavelli wrote The Prince, most Italian city-states had experienced multiple rapid-fire regime changes. This left them volatile and ripe for further replacement.

The moment that a king is overthrown, then you have overthrow, overthrow, overthrow for a long time because the thread of continuity was cut. In Machiavelli's lifetime, that thread of continuity is cut for the majority of cities in Italy. And that guarantees from his perspective that there's going to be more and more overthrows in those governments.

The papacy added a unique layer of instability. Unlike hereditary monarchies, the papacy was an elected office. Successive popes expanded their executive and military power. They often overthrew local governments to install their own family members. Because each new pope was often elected by a coalition of the previous pope's enemies, the political landscape would be violently reshuffled roughly every ten years. Ada explains that this created a perfect storm where no institution had tradition or public investment. Machiavelli hoped the Medici family could consolidate enough power to create a stable core that could withstand this constant turnover. This was not necessarily about unifying all of Italy. Instead, it was about creating a power significant enough that the pope would have to negotiate with it rather than simply knocking it over like a pawn.

Machiavelli had a unique firsthand perspective on Cesare Borgia. In his writing, he often struggles to stay objective because he was so impressed by Borgia power. There is a moment where the narrator veil breaks and Machiavelli admits he was in the room when Borgia confessed his failures. Borgia was an incredibly charismatic and terrifying figure. Some saw him as a leader and others saw him as the Antichrist. Machiavelli job as a diplomat was to stand next to this scary man and buy time for Florence. He knew Florence would eventually be conquered. His only hope was to offer total loyalty so they would be the last ones destroyed.

He told me that he had prepared for everything at the event of his father death, except the possibility that he himself would also be incapacitated at the moment.

Borgia used brutality to ensure stability. At the massacre of Senigallia, he invited men who had plotted against him to a dinner. He told them they were forgiven and then had them all killed. While this violated every social law, it was effective. His remaining followers became more loyal because they were too afraid to whisper a single word of dissent. This highlights the idea that it is better to be feared than loved. Fear is stable because it relies on the leader power to punish. Love is fragile because it depends on the unreliable promises of other people.

We have power over maximum half of what causes outcomes. The other half is always going to be fortune. You can do everything right and it is out of your control, but we have to evaluate what would have happened.

Machiavelli argues that we should judge leaders by the logic of their actions rather than the final results. Borgia did everything right but lost his kingdom because of bad luck. He and his father both fell ill at the same time. If fortune had not intervened, his kingdom would have likely survived. This perspective suggests that the means of achieving power are vital. Dwarkesh points out that rising with the help of great powers is risky because it leaves you at their mercy. Machiavelli agrees and notes that breaking promises is only useful if a leader is scary enough to prevent backlash. Every choice must be tailored to the specific type of power a leader holds.

Machiavelli was the first thinker in the European tradition to suggest that a state could survive with more than one political party. Before his time, the standard belief was that stability required the total destruction of any opposition. In Florence, this often meant massacres and the literal destruction of a rival party's homes. If two groups disagreed, one would kill the other and rake salt into the earth where their houses once stood. Machiavelli looked at examples like Siena and argued that having stable, competing parties could actually help a society. Instead of constant violence, competition could vent local tensions and allow for peaceful adjustments in who held power.

The standard attitude toward political parties is that if there are two parties in a polity, it will not be stable until one of those parties is dead and their heads have been cut off and put on spikes and their houses have been burned down and paved over.

Dwarkesh and Ada also discuss how reputation and diplomacy worked during this period. For Florence, the primary way to handle a threat was not through war, but through bribery. Preparing for a fight was risky because soldiers would trample lands and damage the economy. Instead, Florence maintained a budget specifically for bribing kings and invaders. Machiavelli’s job as a diplomat often involved assessing whether a person was a serious threat. He had to decide if a leader was worth paying off or if the city should save its money for a more formidable enemy like the King of France.

Geographic proximity shaped how people viewed the Pope during the Renaissance. For those far away in places like Denmark or Iceland, the Pope was an abstract and holy figure. They saw him through grand ceremonies and theological edicts. However, for people in Italy, the Pope was often a specific person they knew personally. He might be the man who went to college with your brother or a rival from a competing family. This familiarity made it much easier for Italians to judge the man rather than the office.

If you're far from Rome, the Pope is very abstract. It's easy to have a lot of respect for that Pope because you see him in pomp and circumstance. If you're in Italy, the Pope is that asshole who went to college with your brother. You know his family and you know all of his dirty laundry.

This personal familiarity led to complex political conflicts. Two major factions, the Guelphs and Ghibellines, originally fought over whether the Pope or the Emperor should rule Italy. Over centuries, these labels turned into tribal family feuds. People would fight against a specific Pope because he belonged to a rival family, even if they theoretically supported the authority of the papacy. Ada explains that political loyalty often came down to local grudges rather than religious ideology.

The church became increasingly corrupt as it accumulated wealth and land over generations. As the church grew richer, it became a more attractive target for ambitious families. This created a cycle where families would bribe officials to secure positions for their relatives. It even became a prisoner's dilemma for rulers. If a Duke did not bribe the Pope to install a friendly bishop, his enemies would. This forced everyone to participate in the corruption just to stay safe.

Every generation sees the church get wealthier and have more power, and therefore the incentives to corrupt it are even greater. It even becomes a kind of a prisoner's dilemma system. If you don't manipulate the papacy and your enemies do, you're screwed.

Machiavelli observed that all institutions naturally collect corruption over time. He believed they must be periodically reformed and returned to their original foundations to avoid collapse. He argued that the church had survived previous centuries only because reformers like Saint Francis of Assisi brought back popular support. Without these regular restorations, the weight of accumulated corruption eventually leads to a breaking point, such as the Reformation.

Patronage was the fundamental glue of society 500 years ago. It was not just a side feature but the primary way things functioned. People even demanded nepotism because it created trust. For example, when Pope Paul III appointed a competent general instead of his own son, people rioted. They believed an illegitimate son would never betray his father, whereas a professional commander might. This system relied on family entanglement where people rose and fell together.

The people demand more nepotism. You must appoint your illegitimate son to command your armies, because your illegitimate son will never betray you. And we will know we can trust the papal armies not to turn on Rome if the Pope's son is the commander.

Military loyalty was tied to commanders rather than a constitution or a country. Communication was slow, so a commander needed immediate authority. This required a deep personal trust between the ruler and the general. Without a patronage link, the public feared a rift between the city and its own military. This relationship of trust was the only thing that kept the army from turning against the people it was meant to serve.

The justice system also relied on patronage. While laws were incredibly harsh, the actual punishments were usually light. A carpenter whose son committed a crime would ask his wealthy employer to intervene. The patron would influence the judges to secure a lighter sentence. This was seen as a spiritual process. The trial was meant to make the sinner fear for their soul before receiving mercy. This mirrored the way a person hoped to receive grace from God through the intervention of a patron saint.

Famous figures like Giordano Bruno were executed because they lost their patronage. Bruno had angered his employer, who then turned him over to the Inquisition. In contrast, other radical thinkers like Marsilio Ficino were protected. When the Inquisition questioned Ficino about his belief in reincarnation, powerful friends like Lorenzo de Medici intervened. The system was so pervasive that a person could not even stay in a hotel or conduct basic business without a letter of recommendation from a patron.

Machiavelli’s works show that historical regimes were often unstable due to shifting loyalties. People often owed their allegiance to powerful generals or patrons rather than the state itself. Dwarkesh notes that for a regime to become stable, it needs an impartial justice system and a welfare state. These institutions remove the need for personal patronage. When the state provides these services directly, it earns the loyalty of the citizens.

Cesare Borgia provides a famous example of this principle. When he conquered new cities, he would often eliminate the old ruling families. He then established neutral justice. Before his arrival, justice was often biased toward whoever was in power. If a crime happened, the punishment depended on your family’s connections. Ada explains that Borgia was an outsider with no local ties. He applied the law equally to everyone. This fairness made his authoritarian rule popular among common people who had suffered under biased systems.

If you live such that there is somebody who can have you summarily executed, he can walk by you in the street and point at you and say, "Him, kill him," and it happens, then you are not free. In his vocabulary, in the text, if you live in a state of where there is an arbitrary power who can have you put to death, you are a slave.

Machiavelli argues that liberty depends on the existence of a legal system. Even if a system is flawed, it provides more freedom than the arbitrary whims of a ruler. Florentines valued their republic because it offered a process for justice. They preferred a system of laws over a ruler who could kill on sight. The identity of a conqueror also matters. A local ruler like a member of the Medici family is more likely to preserve a city’s culture and treasures. An outside conqueror is more likely to use the threat of destruction to maintain control.

The Renaissance produced incredible art and architecture despite constant warfare. This was possible because banking and the wool industry generated massive wealth. However, spending on art was also a strategic choice. Diplomacy is often cheaper than war. Florence used cultural output to build relationships with more powerful nations. If a city could not defeat the King of France in battle, it could use expensive gifts and artistic symbols to win him over as a friend.

And that dollar for dollar, diplomacy is cheaper than war. They are using the art to do diplomacy. In one sense, if you are not doing the art, you would have to spend more on the war. It is not that the art is being made from a surplus of the war. It is, oh no, we cannot afford enough armies to actually defend us against France. But we sure can spend it on painting fleurs-de-lis all over our seat of government and creating beautiful expensive gifts for the King of France so that when the King of France comes, he will feel like we are friends.

At the time, these artistic feats were seen as high-tech achievements. People today look back at the Renaissance as a historical period, but for those living in it, backwards was forwards. Their goal was to recapture the height of Roman power and stability. They debated whether it was even possible to surpass the Romans. For them, cutting-edge technology meant imitating the past.

Renaissance thinkers curated Roman history to find the heroes and stability they lacked. They focused on figures like Trajan and Marcus Aurelius because they provided the peace and order missing from the present. This admiration was so strong that medieval legends emerged about Pope Gregory the Great baptizing the ghost of Emperor Trajan so he could enter heaven. Even though Trajan had persecuted Christians, he was seen as the ideal ruler.

The medieval and Renaissance Europe are very good at having their cake and eating it too, in terms of getting to pick and choose the best parts of the pagan world and the best part of the Christian world when constructing their imagined antiquity to have both and celebrate both at once.

In the Renaissance, people often acted against their religious beliefs despite a genuine fear of hell. Dwarkesh asks if the brutal betrayals of the era were rare. Ada explains that everyone was sinning all the time. People committed usury and murder even though they knew these were sins. Dante wrote his Inferno to show the reality of these consequences. He even placed popular romantic figures like Paolo and Francesca in hell for adultery. This was shocking to a public that celebrated their love story.

Dante is making this painful point of, guys, it says that if we do this, we go to hell. I'm gonna make a book where that's literally true.

Ada points out that Renaissance Christianity was different from modern Puritanism. It did not focus on leading a pure or unspotted life. Instead, it assumed that everyone would fail. People would sin, feel sorry, do penance, and then sin again. This cycle was a normal part of life for everyone from bankers to saints.

The figure of Saint Julian the Hospitaller shows this mindset. He is the patron saint of murderers. Today, society views murder as an unforgivable act that requires permanent exile. In the Renaissance, homicide was seen as a sin one could live with and repent for. Many icons of Saint Julian in Florence were commissioned by people who had committed homicide and wanted to seek spiritual recovery.

The Renaissance's idea is sometimes you gotta commit homicide, and then what's important is that you feel sorry, and you need to have a patron saint whose job it is to be a spiritual mentor for you.

This sophisticated hypocrisy allowed society to function even when actions contradicted religious rules.

Machiavelli's experience in exile was unusual compared to other Florentine intellectuals. In Florence, exile often served as a test of loyalty. The government would send a person to a major city like London or Bruges to act as an unofficial diplomat. If the person followed instructions, they were eventually brought home. Machiavelli was sent to a small hamlet with nothing to do. Despite his skills as a diplomat and historian, he refused to work for other European courts that would have paid him much more. He chose to stay in the countryside and write as a way to beg the new regime to let him serve his country again.

Machiavelli fundamentally is possibly one of the most patriotic patriots in Earth's history. And he will faithfully sit in the countryside and rot while begging to work for the people who ordered his torture so long as they will recall him so that he can serve his country.

The Prince was not written for the public. It was a secret document intended only for the rulers of Florence. Ada compares it to a nuclear scientist keeping diplomatic secrets for their own country. In the Renaissance, it was common for scholars to write bespoke handbooks for specific rulers. These books were like proprietary technology. They were never meant to circulate widely. They were private guidance for a prince or princess. Dwarkesh observes that this concept of writing for an audience of one still exists today. Modern intelligence experts still write long reports for a handful of government leaders, just as AI can now generate content for individuals.

A work containing radically unusual ideas often drifts through history without being widely read until society hits a moment where it needs specific answers. This occurred with Lucretius and his ancient theory of atoms, which became essential centuries later during the development of germ theory. Machiavelli followed a similar pattern. His family first published his work to gain fame after his death. It was later caught in waves of censorship following the invention of the printing press, though he was considered less dangerous than the major Protestant theologians of the time.

Machiavelli became a central figure again when thinkers tried to refute Thomas Hobbes. They viewed Machiavelli as the intellectual father of the secular and utilitarian logic found in Hobbes's Leviathan. By the nineteenth century, his work became a global staple. Modern republics needed a way to think about politics that was separate from the church. Machiavelli provided a foundational framework for analyzing government as a system that operates by its own earthly consequences without needing to plug into religion.

The vast majority of political treatises available to humanity at that point have some sort of entanglement of religion with politics at their root. But Machiavelli doesn't. He is this early foundational— what if we think about government in a box without plugging into religion? What if we just think about government operating by itself and its earthly consequences?

Dwarkesh notes that Machiavelli still saw religion as a vital tool for state legitimacy. In his view, the Roman religion was superior to Christianity for building a stable republic. Roman belief suggested that a person's soul depended on being remembered for great deeds on earth, which motivated citizens to sacrifice for their country. Christianity, by contrast, focuses on interior piety and the afterlife, which Machiavelli argued encourages people to become monks rather than defenders of the state. This perspective treats religion as a psychological tool for shaping citizenship rather than a matter of theological truth.

Machiavelli lived during a time when printing was new and books were still scarce. This scarcity forced scholars into a relationship with texts that is very different from our own. Ada describes a manuscript in the Vatican Library where Machiavelli hand-copied the entire poem of Lucretius from a printed version. He did not just copy it. He integrated corrections from other manuscripts to create a superior version for his own use.

He is from this moment when print and manuscript are parallel technologies that we are using at the same time. The very people who are buying the first printed books are also producing manuscripts imitating those printed books.

This deep engagement with a single book defined the intellectual life of the era. Dwarkesh notes that Machiavelli's father worked for months just to obtain a copy of Livy. Machiavelli then spent decades writing his discourses on that single text. While modern readers might finish an audiobook every week, Machiavelli read the same book repeatedly over his entire life. This led to a psychological mode of scholarship where every event in his life was filtered through his tenth or twentieth reading of a single classic.

During the Renaissance, the most cutting-edge way to present an idea was to frame it as an imitation of antiquity. People believed that imitating ancient Rome would end the chaos of the previous world and usher in a new golden age. Because of this, original ideas were actually out of vogue. A scholar would go to great lengths to pretend their original insights were actually the words of Plato or Livy. Framing a book as a commentary on an ancient text ensured a larger audience and more prestige than presenting it as original thought.

If you claim it is Aristotle, people will take it more seriously. The most extreme version of this is Aeneas of Viterbo. He had a radical vision of how he wanted to rethink history and faked ancient texts. He made them up. He faked archaeological digs. He would secretly bury artifacts and then dig them up to great drama. He forged antiquities to create this book that advanced his visionary original idea of ancient history.

Ada notes that Machiavelli's Discourses on Livy was his attempt at a high-status, prestigious project. While modern readers focus on The Prince, it was considered a niche work at the time. The real innovations in political thought throughout the 1600s often occurred in the massive footnotes of editions of Seneca and Livy. This scholarly style created a misunderstanding in the 19th century. Historians from that era valued the idea of the lone philosopher creating original treatises in a cabin by the sea. They looked at the Renaissance and dismissed it as a period where people were simply wrong about Plato or Aristotle for 200 years.

If you think Ficino is what he says he is, a commentary on Plato, then indeed the Renaissance is 200 years of people being wrong about Plato. But if you realize that what it is is their style guide requires original thought to be presented in the form of a commentary on an ancient. What it is is 200 years of original thought using the ancients as the trellis up which the rose climbs in order to bloom.

To understand the true innovation of the Renaissance, one must look past the outliers like The Prince and examine the commentaries. Scholars like Ficino may have sincerely convinced themselves that their original cosmology was secretly coded in ancient texts. In reality, they were using ancient foundations to build entirely new visions of the universe.

Machiavelli experienced the transition from the manuscript era to the age of print. In the past, every new copy of a book was a relief because it meant the text was less likely to be lost to fire. But when local printers began mass-producing his work without permission, Machiavelli was horrified by the typos and errors. He worried that these mistakes would destroy his reputation as a scholar, yet he had no legal recourse because the concept of copyright did not exist yet.

Ada explains that copyright and censorship were actually born together through the Inquisition. After 1515, the Catholic Church required authors to get permission from an inquisitor or bishop before printing. While this was designed to prevent heresy, it offered a benefit to printers and authors: a monopoly license. The record of censorship became the legal document used to prove ownership and sue others for unauthorized editions.

The very first version of copyright is the Inquisition. And places outside the Catholic world then, like England, look at this, and there is actually popular demand in England for censorship. They saw the Inquisition as a way to let printers have a monopoly on printing a book and let authors deny print permission.

The Inquisition was not the centralized, all-powerful monolith that historical propaganda suggests. Ada compares it to an organization like Doctors Without Borders. Individual inquisitors were often isolated and lacked their own funding or jails. They relied entirely on the cooperation of local governments. If a duke or a republic refused to provide resources, the Inquisition was powerless. This created bubbles of protection for intellectual and personal radicals. If you worked for a powerful figure like a cardinal or a member of the Medici family, you were often untouchable. Machiavelli and his friends noticed that those working for the church hierarchy could avoid prosecution because their local authority trumped the Inquisition agents. This patronage system eventually fed back into copyright, as the Inquisition used monopoly licenses to please the powerful families who wanted to control the quality and legacy of books dedicated to them.

Ada explains that some historical figures become separated from their work. A dual image often forms. There is the actual content of what the person said and the separate idea of who that person was. Machiavelli is a perfect example of this split. On one side is Machiavelli the patriot who served his country. On the other side is the Machiavellian villain. This character is often called Old Nick, which is also a nickname for the devil.

The idea of the scheming politician who is probably atheistic, definitely self-serving, and who wants nothing but to advance himself in power... isn't the real Machiavelli if you read the work. The real Machiavelli is not about advancing yourself. It's not a manual for getting ahead. It shouldn't be shelved next to 'How to Win Friends and Influence People' because it's a manual not of how to gain power, but of how to keep power.

This process happened to other thinkers like Thomas Hobbes and Spinoza. Spinoza was labeled an arch-heretic and was even excommunicated from his community. People imagined him as a dangerous figure. Yet when you read his actual work, he is a warm and pious writer who believes everything in the universe is part of God. The fictional character of the heretic was simply more useful for social debate than the real man.

Society often creates these characters because they are useful thought experiments. The villainous Machiavelli allows us to discuss strategic advancement and rationalism. This character has a separate life from the real man who was willing to give up his wealth and society to serve his country. Recognizing this split helps us see how social utility often teases apart real things to make them useful in different contexts.

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.