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

I'm going to give a two-part answer to that, although of course with any granular history there can be many parts. The papacy is part of it, and then the city-state structure of Italy is another part of it. I'll start with the city-state structure. There's a principle in politics that when there's long continuity of a government, and the government has been in power a long time, that government has a lot of legitimacy. People believe in its institutions. People are used to it. Even if you complain about it, it's the government. When you break that—when you overthrow the ruler, when you dissolve the republic, when you put in a new thing—it doesn't have that same staying power. So it's very common when there's one regime change for there to then be five regime changes, rapid fire, over and over. We see this with how many iterations the French Republic goes through: the French Republic, and then restored monarchy, and then republic, and then monarchy. When a long thing cracks—boom, boom, boom, boom, boom—you get chaos. England's Wars of the Roses are similar. There was one stable dynasty for a long time. The moment that a king is overthrown, then you have overthrow, 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 are going to be more, and more, and more overthrows in those governments. When Machiavelli was born, there were six or seven city-states in Italy that had had their governments uprooted recently. By the time he's writing The Prince, it's dozens, in fact, the majority of these places. So it's volatile. Almost no government has staying power. Almost every government is ripe for yet another replacement, yet another replacement, yet another replacement. That's half the answer of why he perceives there to be this urgency and this guarantee that there cannot be stability. The other half is the papacy. The papacy, of course, is a long and evolving organism. The papacy is one of the oldest institutions in the world now. It was one of the oldest institutions in the world even then, even though this is 500 years ago. As we all know, when you have power centralized in an authority, especially an executive, there can be changes in how that executive uses that power. Each one sets norms for the next one. Over the course of Machiavelli's lifetime and just before, a bunch of consecutive popes expanded executive power, especially in the military side, and launched more wars, or did more arbitrary overthrow of governments. You have a number of city-states that are directly ruled by the papacy, and in theory, the pope can appoint anybody to be ruler of that city. Here is a pope. He has an illegitimate son. He wants his illegitimate son to be ruler of something, so he overthrows the government of a city and puts in his son. The next pope does it to three cities. The next pope does it to five. Soon we have a precedent that every new pope feels he has the authority to knock down every pawn upon the chessboard if he feels like it. Once that is the norm, even a fairly nice pope still inherits the idea that the pope is going to overthrow and replace governments. This creates a unique instability within Italy that no other part of Europe is subject to, because there is no predictability to who's going to be pope next. It isn't hereditary. You can't plan for it. The next pope is elected. As is often the case with elections, very frequently the next pope will be elected by a coalition of all the people who hate the current pope. One of the things that electoral politics does is that it tends to swing, in which those outside of power work hard to get into power with the next regime. Let's assume the average length of a papacy is ten years in this period. So every ten years, you suddenly have a completely unpredictable new monarch who's almost guaranteed to be one of the enemies of the old monarch, and will therefore rip up and replace all of the things that that monarch tried to do with new things. So Machiavelli, when he's writing the last chapter of The Prince, is looking around and saying, "Okay, we have a perfect storm. Practically every polity in this region has just had the thread of legitimacy cut. Its institutions have no traditions. Its people have no investment in its current rulers. These are all pawns that have been knocked over before and barely stood up again. They're ready to fall." Meanwhile, nothing will stop the turnover of popes. The only thing that could stop the turnover of popes would be one person gaining enough power and ascendancy near this region, who has staying power, who has sons and heredity, that he can do what Cesare Borgia tried to do: have enough power near the papacy to strongly influence the next pope to create a kind of stability that's otherwise impossible.

Exactly, by having conquered enough of a chunk that the papacy fears them and must negotiate with them, as opposed to the papacy being surrounded by small, weakened powers that will constantly be turned over and turned over and turned over.

At that moment, yes. So it makes it even more plausible.

He spends a lot of The Prince, in fact, trying to veil how much more he cares about Cesare Borgia than everyone else. It's so interesting. He tries to be balanced. He tries to talk about this example, and this example, and this example, and Valentino, and this example. Sometimes he just can't. There's that incredible, magical moment when he's discussing Valentino's fall. It's the moment when he has amassed all this power, he's successfully conquered almost everything within Italy. Suddenly both his father, the Pope, and him fall ill at once. When Machiavelli describes this, he's saying, "Everything Cesare Borgia did, he did right. He conquered this kingdom. He would've kept it. The only reason he lost it was fortune." What Machiavelli should say is, "Valentino had planned for every contingency at his father's death, except the possibility that he would also be on death's door." But that's not what Machiavelli says. What Machiavelli says is, "He told me that he had planned." The first person breaks in. Our historian cannot veil himself anymore. He cares too much. "He told me", first person, that he had prepared for everything in the event of his father's death, except the possibility that he himself would also be incapacitated at the moment. It's such a magical moment where the veil between the author and the reader breaks for just that moment. We realize that all of these others, he observed from a distance. But Machiavelli was in the room next to Valentino, at Valentino's side through this. He had the most incredible, life-changing, first-person view of this man so unique, and charismatic, and terrifying, that when you read accounts of him, they range from "This was the most incredible, charismatic leader I've ever met," to "This man was supernaturally charismatic to the degree that he must be literally the Antichrist or an incarnation of the angel of death on Earth, because I have no other explanation of how he could be so persuasive and charismatic." Machiavelli was in the room. And every so often you just feel that he's still in the spell of this incredible figure at whose side he had the scariest job in the world. Machiavelli's job dealing with Cesare Borgia… It's very clear that the Borgia plan is to conquer the Papal States in the middle of Italy. Tuscany, Florence's dominion, is this little notch, like a puzzle piece out of the side of the Papal States. Anybody with a map looking at it is like, "You've got to conquer that. You just have to conquer this. You can't have a kingdom without it." There is no way to stop it. So what do you do? Machiavelli's advice to his polity is: this time we're not going to succeed in persuading this conqueror to pass us by. We can't bribe him into doing something else permanently. But we can buy time. We can absolutely and abjectly swear to do anything he wants. We can give him our forces, and we can give him our money. We can pay him and help him conquer the rest of it, and betray our allies. Betray Bologna. Florence had had a 300-year alliance to defend Bologna. He said, "We have to break it. The whole world is broken right now. We have to break every promise and every hereditary alliance we had. We must be at the side of this man." The only possible survival mechanism is to win from him through loyalty, through support, and through Machiavelli being at his ear whispering forever, "Florence is loyal. Florence is loyal." By that, we buy the boon of Polyphemus, the terrifying promise of the conqueror: "I like you, my guest. I'll eat you last." That's the republic's only hope. That's Machiavelli's job: to stand next to the scariest man who has lived in Europe since Frederick Barbarossa and whisper constantly in his ear, "The Florentine Republic will support you and will give your grace anything you ask. Just eat us last."

This is not Florence aiming to rise. This is not Florence expecting that it will gain anything by this. This is Florence knowing it will lose. Machiavelli's very open about the fact that if Alexander had lived another year, Valentino would have finished his conquests, and taken Florence at last, and it would've been over. But popes are mortal. Buying time is sometimes the survival mechanism. So Machiavelli has this incredible firsthand experience of being with Valentino through all of these decisions, being with him at the massacre at Senigallia when rumor had reached Valentino that some of his people were terrified of him and plotting to overthrow him. They were so scared of him, they decided to abandon the plot, and he heard. He met with them and told them, "I forgive you. It's okay. You've renewed your loyalty to me. You've passed the test. I trust you. All is well." He invites them to the banquet, and then massacres them all. The forgiveness is false. The betrayals are punished. There's this amazing letter a couple of months afterward where Machiavelli's loved ones are writing from Florence because they've received a letter from him after the massacre at Senigallia. They say, "Oh, thank God, you're alive. We had no idea. All we heard was that he had massacred a large number of the people who were with him. We didn't know if you were alive." It took months in the chaos, the postal system had completely broken down. It took months for them to get word that Machiavelli was still alive. They didn't know whether he had been caught up in the conspiracy. He easily could've been on a list of names of people the conspirators intended to recruit, and been gone. So his wife and his loved ones back at home, his children, had to wait months to find out whether he too had been slaughtered. It felt to them like a miracle that he hadn't. But it meant that he watched these incredible deeds: you encounter them, you forgive them, you renew vows of amity—sacred vows taken in the cathedral—and then you slaughter them at dinner, violating the laws of hospitality. Dante would say if you do that, you've committed such a grave sin that you're not just regular damned. A devil comes up out of Hell and takes your soul out of your body and inhabits you. You're actually already in Hell even though your body is still alive on Earth, because that's how heinous a sin this is. And yet, it works, and all the rest of Valentino's men are more loyal to him afterward than ever before, and won't even whisper to each other about dissatisfaction, because even the faintest whiff of conspiracy might result in death. So why does Valentino's kingdom, for which he did everything right, ultimately fall apart? Because he happens to eat the same thing that gives him food poisoning as his father, and happens to be ill at the wrong moment. Also the puppet that he manages to get in power, Pius III, dies too fast, and then he's outmaneuvered by Julius. If all those things hadn't gone wrong in a row, the kingdom would've stood, and indeed, he would've conquered Florence. Machiavelli is constantly reminding us that, yes, we have all of these things we can try to do. We can remember it's better to be feared than loved. We can remember not to be hated. We have power over, at maximum, half of what causes outcomes. The other half is always going to be fortune. We look at Machiavelli. We know he's the origin of utilitarian thought, and that he says we need to evaluate people's deeds based on outcome. But he doesn't just say we need to evaluate their deeds based on outcome. He says we need to evaluate their deeds based on what the most probable outcome was before fortune intervened. So he says people look at Valentino Borgia and say, "But the Borgias fell. They were feared, and then they were hated, and then they fell, and then their enemies took power and chiseled their coats of arms off of every surface in Rome, so that to this day you're walking through Rome and you sit down at a pizzeria and there's a weird scar on the wall, and that scar is where the Borgia bull is no more." People want to make the moral of that be, "Don't do what the Borgias did. They fell." Machiavelli's like, "No, they did not fall because of their choices. They fell because half of what happens in the world is never in our control. You can do everything right, and it's out of your control. But we have to evaluate what would have happened, and therefore we should imitate them, because everything they did was right."

It's even subtler than that. Because if you are someone who breaks your word and you break it this way, it'll bite you in the ass. If you break it these ways, it'll be okay. He also does analysis of figures like Savonarola, who would make prophecies and promises, and then some of them would happen and some of them wouldn't. He would then make new ones and correct what he said yesterday. He handled his manipulation and untruths badly, in Machiavelli's analysis, in a way that did turn people against him and make him lose power. Partly because Savonarola, as a religious demagogue, the core of his power was people believing that he was divinely inspired and that he wouldn't make mistakes and wouldn't err. So his power base was fragile vis-à-vis untruth. For him, because of the specific shape of his power and then the specific way he handled his contradictions, that did hurt him. Whereas if it's somebody like Cesare Borgia, who will make an alliance and work with that ally for a while and then betray them—because meanwhile he was such an effective conqueror and he was so scary and everyone was so afraid of him—even when he would betray an ally, his other allies would say, "I've got to be more faithful to him so that the next person to be betrayed isn't me, and try to work hard to be in the good graces of the prince so that I'm not next", as opposed to turning on him, because he was so scary. Savonarola was not scary. Savonarola was charismatic and persuasive and had one of these voices that made crowds thrill and women swoon. Decades later, when people asked Michelangelo what Savonarola had been like—when Savonarola had been dead for decades—Michelangelo's answer was, "I still hear his voice." He had one of those charismatic presences. That wasn't enough when he started flip-flopping on policy and truth. Whereas Valentino was so scary that he could betray his top general and seize his lands and overthrow his city, and all of his other generals would say, "Better step even further into line." So it's not just that lying is okay, it's that lying is sometimes okay if you check these other boxes, and it's not if you don't. So this is even more reinforcement of how much he zooms in on the means. If you do A and B, you're okay, but if you do A and C, you're not. He's looking at the minutiae of different ways you can wield power and different reasons people can have to follow you. If you're a prince who's decided to invest in being loved, you have to keep it up, or cultivate being feared alongside it. If you've invested heavily in being feared, there are things you can then do that you can't do if you're a prince whose power depends on being loved.

On that topic, Machiavelli is the first person that we have ever in the European tradition to suggest that it could be viable for there to be more than one political party in a state at the same time, and that they would compete against each other and vent the society's tension through competition and vie to try to dominate an election and then the next one. This is what we're used to, but this is innovative in Machiavelli. He talks about how competition within a city, if the parties are kind of stable—he's observing Siena as one of the examples of this—can vent local tensions and allow interior adjustments of who has power, and be stable. I'm going to come back to interior adjustments of who has power in a second. The standard attitude toward political parties is that if there are two political parties in a polity, it will not be stable until one of those political parties is dead, and their heads have been cut off and put on spikes, and their houses have been burned down and paved over. That has been Florence's solution to political parties before. Florence massacred its Ghibellines and killed all of them, and rubbed salt into the earth where the houses used to be so nothing can grow there. Nothing still grows there. Then when the Black Guelphs and the White Guelphs split into two sub-parties, they immediately started slaughtering each other as well. The standard was that one party must wipe out the other party for there to be stability. There are comparatively few examples, although Florence's neighbor Siena is one, where political parties managed to not only coexist side by side but be politically helpful.

Very much so. He and his son are literally fighting wars against other Catholics, but the other Catholics are fighting them back.

Here is where geographic proximity is everything. If you're far from Rome—when you're Denmark or Iceland, and the pope is all the way over there—the way you interact with him is that occasionally an incredibly impressive papal legate will visit. There'll be vast pomp and circumstance, and the city will rename a street in honor of the fact that somebody sent by the pope has visited. He has this great power to say yes or no to petitions, and different countries have been trying to petition for specific things for ages, and the pope's legate is here to interview the emperor, to judge whether the queen can be queen or not, and it feels like a big deal, and the pope is very abstract. It's easy to have a lot of respect for that pope, because what do you see that pope do? You see that pope in pomp and circumstance. You see that pope make judgments about fates of popes and kings. You see that pope put out papal bulls and edicts that give theological answers to questions. You see that pope exercise judgment of life or death over people at a distance. He's very abstract, and the difference between one pope and the next pope is kind of small from your perspective. You don't see their policy differences. If you're in Italy, the pope is that asshole who went to college with your brother and beat him up when they were at college, and then was drunken and irresponsible at middle age, and you've been negotiating with him in these other jobs, and you know this jerk. You know his family. You know the other jerks who are also competitors for this. You're allied with him, you're not allied with him. His ancestors are allies of yours or not allies of yours. He's a specific dude. You're much more likely to judge a pope based on, "He's that guy." This is not Pope Julius II. This is Giuliano della Rovere, and I judge him based on his uncle who put him in power, and the actions of his friends, and the actions of the city he's from. You know all of his dirty laundry. You are subject to the fact that when he moves into power, everyone who's related to him is going to get promoted within Italy, and everybody who's not is going to get removed from Italy. So it's much easier for an Italian to see this pope, and it's actually quite hard to see the papacy. That's how you have these fascinating wars where even the cities that are hereditarily incredibly loyal to the papacy will sometimes be fighting a war against the papacy. All Italy is divided into these two factions, the Guelphs and Ghibellines. Theoretically, what these two factions mean is that Guelph powers, Guelph families, Guelph cities believe the correct successor to the Roman emperors is the pope. The pope is the emperor. He has the right to be the ruler of Italy, and indeed of everything that was once Rome's. He is the ultimate political and military power, and he is the rightful and only rightful overlord of Italy. The Ghibellines believe that in 800 AD, when Charlemagne conquered a bunch of stuff and made the empire that we now refer to as the Holy Roman Empire, when the Pope crowned Charlemagne, he delegated the political and military side of his authority to that emperor, and made himself the spiritual authority, but the emperor the political and temporal authority. Therefore, the rightful ruler of Italy is the emperor, the successors of Charlemagne. These are the two factions for which these parties fought originally, 300 years ago. These days, what these factions actually mean is, "Those jerks murdered Uncle Tybalt, and we will never forgive them." They are the team that is our enemy, and we are this team. They are that team, and we hate them. We want to crush them because they want to crush us. This means that sometimes a pope will be elected who's from a hereditarily Ghibelline family, and the pope will start promoting people from the anti-papal faction, and the pro-papal faction will unite against the pope. It makes no rational sense until we remember that they are serving the pope abstractly. So you get multiple situations where there's a war between Rome and Florence over the fact that Florence wants to defend papal authority in papal lands against the pope itself, because that individual pope was from the anti-papal faction.

Yes and no. Again, when you're far away, yes. When you're close up, you know too much of the dirty laundry of these people. So let me use a fun example: the most passive-aggressive letter ever written in the entire history of time, in my opinion. There's a type of ceremony that happens when a new pope is elected, which is the giving of oaths of obedience. A major ambassador from every polity in Christendom comes to Rome. They wait in line for a long time, and then they give a long-winded speech about how great the monarch is that they're there to represent, and how vast his power is, blah, blah, blah, and how pious he is, and how glad he is, Your Holiness, that you're the pope now. Congratulations on behalf of my wonderful king. And you're supposed to send the highest-status possible person who can leave your polity without it falling down. You might send a younger son of the king. You might send a lord chancellor. In the case of Florence, you're going to send the most prominent citizen you can. So when Pope Sixtus was elected, it was Lorenzo de' Medici himself—not the dedicatee of The Prince, the grandfather and namesake of the dedicatee of The Prince—who went to deliver this oration of obedience, which means literally prostrating yourself in front of the pope, literally kissing his feet, and giving this oath. Lorenzo did this for Pope Sixtus, with whom he was negotiating to try desperately to get a cardinalship for his brother. Pope Sixtus instead organized the Pazzi conspiracy to try to butcher the Medici family, killed Lorenzo's brother, killed a number of his allies as well, and attempted to have a coup to take over Florence. Then the next pope was elected after Sixtus, Pope Innocent, who was as everyone knew, a puppet of the same faction that Sixtus was from. So we go from this very dangerous pope who had tried to wipe out Lorenzo's family to a puppet of the same faction. Lorenzo sent his son, instead of himself, to give this oath. He had his son deliver the message, apologizing to His Holiness that, "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." It's a very respectful letter, but it's also very overt about the fact that he does not trust and will not again trust this faction. So they negotiate very carefully how to deal with the fact that the popes have this great spiritual power, but sometimes the popes are acting as horrifically selfish warlords. That's also something which has worsened over time, and it's important for us to remember that the papacy becomes gradually more corrupted over time. This is because with every generation, more people leave donations of wealth to the Church. A widow who has no son and has property decides to piously leave this to a monastery. The Church gets wealthier and wealthier. As the Church gets wealthier, with wealth comes power. More and more power is in the state. This makes a stronger and stronger incentive for every ambitious family to send their second son into the Church. And this goes all the way down. We have personal letters of Machiavelli writing to and from relatives of his, where they're debating the correct-sized bribe to offer to buy a priesthood for his little brother, Totto. They don't want to offer too big a bribe, because it would impoverish the family. They don't want to offer too small a bribe. They've heard that another family that's after this priesthood offered an extra big bribe. That's kind of not fair. How do they respond to being out-bribed? They just write about this as the most everyday, normal thing in the world. This is a wealthy merchant-prince-level family. They are in the top 5% of wealth and power in Florence, but not in the top 1%. But for them, too, it's normal to talk about paying a bribe to get a priesthood. That's just how it works. Every generation sees the Church get wealthier and have more power. Therefore the incentives to corrupt it are even greater. It even becomes a kind of prisoner's dilemma system. If you're the duke and you don't manipulate the papacy, if you don't bribe the pope, if you don't work hard to get your brother to be bishop, and your enemies do, you're screwed. So you even see it as defensive: "I must manipulate the Church. It's the only way my people will be safe. If I don't manipulate the Church, my enemies may manipulate the Church, and then there's danger." This happens all the way up to the scale of kings, where popes can make your enemy the most powerful bishop in your kingdom or can deny you the right to marry, because inevitably the person you want to marry is a cousin, and you're going to need a special dispensation to marry them. The pope can prevent that and mess with your marriage alliances. You need the pope very desperately if you're a king. You also need the pope all the way down. That means bribes and other kinds of incentives make the papacy more corrupt with each generation. So the papacy is worse in everyone's lived experience than it used to be even a few popes ago. You see every generation for 100 years say, "Popes are much worse now than popes used to be when I was young." Everybody says that. Dante says that in 1300. Machiavelli's grandparents' generation is saying that in 1400. Machiavelli is saying that in 1500. In everybody's lived experience, the popes are getting more secular, more military, and more corrupt over time. It's a gradual accumulation, and it comes to a peak, as such things do, triggering the reformation, when it becomes so bad that there has to be a massive move against it. Machiavelli, in an interesting way, anticipates this, because Machiavelli says, "All institutions are gradually corrupted and need to be reformed and returned to their foundations, or they will collapse under the weight of their corruption." He thinks that the papacy has been undergoing this, and that Christianity has been undergoing this. And that, if not for the fact that St. Francis of Assisi—and also to some extent St. Dominic a couple of centuries before his time—reformed the Church and brought in a lot more popular support, Christianity would already have cracked under the weight of its own corruption 200 years before, and that it will need such a restoration again—as any institution needs, as city governments need, as republics need—as corruption accumulates over time.

It's not just that it was more prominent, but that it was the fundamental glue of the society, as opposed to one of several glues of the society. Patronage, which was also familial and therefore entangled with nepotism, was so fundamental. For example, when Alessandro Farnese was elected Pope Paul III in the middle of the 1500s, he didn't corruptly make one of his kinsmen commander of the papal armies. He instead appointed a really competent, experienced general instead of his own not very competent, illegitimate son. And there were riots in Rome. "Your Holiness, 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. We don't know that about this other commander. He might turn against Your Holiness. There might be a rift between the Pope and the papal armies if he's not somebody who rises and falls with you the way your son does. Therefore, by popular demand, the people want more nepotism, because the system depends on it." That's how you see how the system depends on it. There are levels of trust that the patronage system creates, because it involves multi-generational entanglement of families. If these families rise, they rise together. If they fall, they fall together. That creates levels of trust that can sustain things like this world where the oath of a soldier is to his commander, not to the polity that he serves. In modernity, we realize another solution to that. The oath of the soldier is not to the commander, but to the Constitution, or to the country, or to the people. But in this period, the oath of the soldier is to the commander, mostly because communications are so slow that the commander has to be able to give speedy field commands. But it means you're creating an army and handing it to a man. If you cannot trust that man, then the people will be terrified that there could be a rift between Rome and its own armies, or between Rome and its treasurer, or between Rome and its other allies. Patronage is the glue that makes things work all the way down. All the way down to the level of, if you need a defense attorney, that's done through patronage. The outcomes of trials are a really great way to see patronage. We're all familiar with the fact that law codes in the Middle Ages are really cruel: death for everything. Death for theft, death for adultery, death for homosexuality, death for setting fire to the prince's beehive. Whatever it is, that's the sentence on the books. You look at the actual trial records and maybe one in 100 convictions for that crime actually ends in a capital sentence. Almost all of the other ones end in a fine or a public flogging, but not in the sentence that's on the books. We say, "Why and how is that happening?" Patronage is the answer. So say it's the Middle Ages or the Renaissance, and you're a carpenter, and your teenage son gets drunk and punches somebody in a brawl, breaks the guy's nose in a way that makes him die. He accidentally kills a guy in a drunken brawl and your son is now on trial for murder. You're a carpenter. You have worked for the rich family whose family carpenter you are. Let's say it's the Medici family. Whenever they need new pews for the family church or new furniture or repairs for the family gates, they go to you. So you go to them and say, "My son is in danger. He's on trial. Please put in a good word." Your patron has the ability to influence the judges, and they will put in a good word for you, and you will get a lighter sentence. This is an ancestor of having a character witness to say, "So-and-so is such a good person, they should have the milder punishment, not the more severe one." The norm is: you're accused of a severe crime, you're put on trial for your life, your patron intervenes, and you get a lighter sentence. This is how justice is supposed to work. This is a very severe line that changes in the 18th century with the Enlightenment. Because we now think of proportional justice: the sentence for the crime should be this, and ideal justice is that everyone who is guilty of the crime gets that sentence. That is fair. It doesn't matter who you know. It doesn't matter whether you're rich or poor. The sentence should be the same. This is the ideal of Enlightenment justice. The ideal of this period's justice, which is much more shaped by Christianity, is that the purpose of the trial is the spiritual interior correction of the soul of the sinner. Therefore the ideal outcome is for them to fear for their life. They're before a terrifying judge who is the earthly representation of God. They know that they're guilty, and they deserve to be thrown into the pits of hell. But miraculously, they are given grace, and they are pardoned. The process of being put on trial, fearing for your life, begging to the patron, and then receiving mercy is supposed to be an earthly preview of the process your soul will undergo when you are before divine judgment. Therefore it should make you come out the other end a good person. The goal of the justice system is the spiritual improvement of the sinner and the hope that they will come out the other end better and more likely to go to heaven. Even when people are being sentenced to death, there are religious organizations who sit with them overnight, having a final prayer group, and walk with them to the gallows, holding their hand and holding a painting of the Virgin Mary in front of their face, so that to the very last moment, the person who's about to be executed is thinking about heaven. The ideal outcome of the execution is that the soul goes to heaven. So the whole structure of the justice system expects the intervention of a patron, who represents the intervention of a patron saint, persuading the judge, who is God, to give you mercy. So when we see 100 trials end with 99 where the person paid a small fine, and one where the person was executed, what that actually means is that in 99, their patron stepped in. Somebody persuaded somebody who put in a good word, and they got the light sentence. In one, that person had fallen out of the patronage network. That person had angered their boss, their protector. That's why it went all the way to being a capital offense. Probably a lot of people listening are familiar with Giordano Bruno, very famous as a martyr for science because he was burnt at the stake by the Inquisition. Fewer people know that that was not his first Inquisition trial. He was investigated a number of times by the Inquisition for doing various radical forms of thought. The earlier trials had the usual outcome for that kind of trial. He had a patron, there were rich people that he worked with or for, the university was hosting him. They put in a good word. He's fine. The Inquisition tells him, "Be good," and things continue as they are. That time, he had angered the person he worked for. He pissed off his patron. It's his patron who turns him into the Inquisition and says, "This guy is a charlatan. He promised he could teach me these things, and he can't. I don't trust him. He's no good. Throw the book at him." The reason that trial goes all the way to a capital sentence is that he doesn't have a patron. He's the 99th case that time. If he had had a patron protecting him, despite how radical his stuff was, he would've been okay. We see that in the trial of Giovanni Pico della Mirandola, who was candidly substantially more radical than Giordano Bruno. But when Pico is on trial, Lorenzo de' Medici and other powerful people really care about Pico, and they pull out all the stops. Lorenzo talks to his brother-in-law, who's an Orsini. The Orsini have enormous influence in Rome. They get permission for Pico to be let go and sent home to Lorenzo to sort of live under house arrest, under Lorenzo's promise that he'll be good from then on. Or you have Marsilio Ficino who is this radical Platonist who publishes a book on how to project your soul outside of time and summon angels, arguing for the existence of reincarnation, and is very clearly being extremely theologically weird. This is the man who wrote the best letter of recommendation ever written in the history of time when he was recommending a young scholar for a job with the King of Hungary. He writes in the recommendation letter, "This young man is the reincarnation of St. Thomas Aquinas, so you should give him a job." Now, that is a letter of recommendation. But you think, "The reincarnation of St. Thomas Aquinas, huh?" And the Inquisition comes knocking on Ficino's door and is like, "Hmm, reincarnation?" Ficino's like, "Oh, no. Help. Talk to Lorenzo." Lorenzo talks to his brother-in-law, Cardinal Orsini. Cardinal Orsini shuts it down, and Ficino is told, "Maybe lay off talking quite so overtly about the reincarnation." Ficino says, "Yes, of course, and I will only teach very pious people how to summon angels and project their souls out of their bodies. I promise I won't teach it to anybody who will use these powers irresponsibly." The Inquisition is like, "Okay," and goes home. Because patronage kicked in. Patronage is the glue that makes everything work. You can't even stay in a hotel or buy an apple—I'm not kidding—without a patron. You arrive at a city. Nobody knows you. You're a stranger. What you have is a letter of recommendation from your patron who's friends with some important person there. You present that at the hotel. That's why they let you stay.

Yeah. One thing that everyone is surprised by is that when Cesare Borgia—Valentino is much more what he's called in the period—conquers these cities in Central Italy, he goes in, and he massacres the ruling family. He works hard to kill every member of them that he can so that there isn't a potential rival claimant to come displace him. He implements neutral justice, because he and his cronies have no side in that city. They aren't connected with one group of families against another. When they implement justice, they do so neutrally because they aren't interested in the local backstory of factions. As a result, to everyone's surprise, he moves into a city, he massacres the rulers, he implements an authoritarian regime, and he's incredibly popular and beloved by the people. Everyone says, "Why are they liking this man? He is a cruel, murdering tyrant." The answer is, for the first time in generations, they have something close to fair justice. Meaning, it used to be that there was one faction in power and another faction out of power. In our scenario where a carpenter's son gets drunk and kills someone in a drunken brawl, if that carpenter's son is the carpenter of the power that's in power, then there will be no justice and no consequences for this murder. It'll be maybe the smallest of fines. If that carpenter works for the families that are out of power, then throw the book at him. His son will be executed for that death. There will be no fair justice. The outcome of the sentence will be entirely who's in power and out of power, not the fairness of the case. But when both of those ruling families have been wiped out, and an outside power is here, and a homicide takes place, the neutral judge hears this neutrally and gives the same answer regardless of whose family's carpenter that is. The people who have lived in generations of "justice for some and injustice for others," suddenly having equitable justice, are delighted by this and find that wrongs are finally being punished. The people that they've resented and hated for so long who are in power are finally being punished for the crimes that they commit. This makes Valentino's conquering and violent regime incredibly popular with the everyday people of these cities, who are therefore willing to sign up for his armies and help defend his conquests and keep them in power and man his fortresses. So Machiavelli and others are startled by this. They had expected that if a conqueror moves in and massacres the rulers of a city, everyone in the city will hate and fear that conqueror. But if the conqueror is feared and not hated, because he wiped them out but then was fair toward the people, then it works.

The cultural treasures of Florence would potentially have been okay. There's two answers to that. One of them is that Machiavelli is very adamant that 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 where there is an arbitrary power who can have you put to death, you are a slave. If instead you live in a system where there must be a trial, and there must be a process, and this must be examined and public, if there is a system, then you have liberty. That system may be unfair. It may be biased. It may be, in Machiavelli's case, the very system that tortured and exiled him. But there was a system. He considers that difference to be enormously important. So if Valentino conquers Florence, it's not going to be that system anymore. There will be a man who can walk down the street and point at a Florentine citizen and say, "Kill him," and they will kill him. Will that tyrant be fair? Maybe. Will that tyrant exercise this power well? Perhaps. Will his successor be worse or better than him? We don't know. We can't predict. It's a monarchy. It's vulnerable to good successors and bad successors. But the people of Florence are not free if there exists a man who can say, "Execute him." That meant a lot to Machiavelli, and it meant a lot to the Florentine people. It's kind of hard for us to see how few liberties and how little franchise they had and yet how much they cared. Florentines are constantly willing to go into the street and risk their lives flying the banner that says "Libertas" across it: liberty. The banner LIBERTAS is the coat of arms of the Signoria, the Senate, which is selected from the 1% super mega elite, tiny minority of the city that is eligible to be in government. They aren't rioting to defend their right to participate in the republic. They're rioting to defend their boss's boss's right to be in the republic. Yet they care so deeply about it, and they consider it fundamentally different from the situation in which there is a man who can walk down the street and point at you and say, "Him, kill him." That tradition of liberty means a lot and would be gone even if the most beneficent tyrant in the world took the city. So that's half of the answer.

That's the second half of the answer. There is a huge difference between when the conqueror is from your city, loves your city, and wants to take care of your city, and when the conqueror is from the outside. When the Medici take over Florence, they want Florence, and they want Florence to be Florence. They want all of its beauty and all of its treasures to still exist and be theirs. They would never consider razing important parts of it to the ground. They would never consider threatening the Florentines with, "We will destroy your city walls," or, "We will destroy your cathedral if you rebel." Any outsider would. So Florence looks more like Florence under a Medici duke than Milan looks like Republican Milan under a Visconti or Sforza duke, or than Ferrara, which has no remnants of its republic, does under the dukes d'Este, who can do anything they want, including murderously gouging each other's eyes out and the city will never take one step against them. So Machiavelli is aware that if Florence has to fall, falling to the Medici is gentlest. It's most volatile perhaps, because they aren't going to be feared as much as an outside conqueror would be feared, but certainly gentlest. You preserve some important rights when you're conquered from inside that you don't when you're conquered from outside.