How Machiavelli's Florence bargained with Cesare Borgia for survival – Ada Palmer

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.

This explains the foundational mechanism behind political instability that Machiavelli was diagnosing — a cascade effect that makes a single regime change catastrophic.

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 illustrates how norms around executive power expand incrementally through precedent, a dynamic as relevant to modern institutions as to Renaissance papacies.

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.

This moment of authorial slip reveals that The Prince is not purely theoretical — it is charged with the personal awe of a man who witnessed history's most formidable operator up close.

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 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.'

This is Machiavelli's realism at its starkest — the distinction between surviving and winning, and the cold logic of strategic submission.

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.' 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.'

Machiavelli proposes a counterfactual standard for judging political decisions — separating outcome from quality of reasoning — which anticipates modern decision theory.

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. 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.

Palmer locates the conceptual origin of competitive multiparty politics in Machiavelli, showing how radical an idea peaceful political competition once was.

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.'

This counterintuitive episode shows that nepotism was not merely corruption but a rational trust technology in a world without impersonal institutions.

Even if we spent every penny we have on armies, it would not defend us against France. But we sure can spend it on painting fleur-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 and we are giving him all of this cultural output. If we fought him, we would lose. But if we play the culture victory game, that's cheaper, and we can try to win.

It reframes Renaissance art patronage as rational geopolitical strategy rather than mere aesthetic vanity — a 'culture victory' as a cheaper substitute for military deterrence.

This is a period in which backwards is forwards. That is to say, this is not a period that, like us, thinks of the future as where potential is, and that humanity might get better and better over time. The potential of humanity is recapturing Rome. Backwards is forwards. If we can get more and more like that, that'll be better... For them, cutting-edge technology is imitating the past.

Inverting our default assumption about progress clarifies why Renaissance innovation looked like imitation — and challenges us to examine whether our own faith in forward progress is equally culturally contingent.

When they are trying to create a handbook of what was, what stands out for them is what's different from their present. Their present has plenty of tyrants. Their present has plenty of orgies. Their present has plenty of massacres. Their present does not have 70 years of peace. So that's what stands out as different... they read about the successes and the stability from Trajan, Hadrian, and Marcus Aurelius, and they say, 'That is alien to us. That we haven't had in so long. That is what we want to have again.'

It shows that what any era finds remarkable in history is a mirror of what it most lacks — a methodological insight for how to read historical sources critically.

They all believe in this religion that says, 'If you do this, you're going to go to hell,' and then they all do this. That's something that this period really wrestles with. Everybody is sinning and breaking their rules all the time: killing for honor, committing usury, lending money at interest. They're all sinning all the time... People in the period do bring that up and say, 'Hey, this is not okay.' This is one of the big focuses of Dante's Commedia.

The gap between stated belief and practiced behavior in Renaissance Italy reveals something universal about how moral systems function in societies — and why Dante's project was so radical.

The assumption is everybody sins all the time. There is no such thing as purity. Everybody sins every five minutes... and then you repent of them, and you feel sorry, and you do penance, and you make spiritual progress, and you are forgiven, and then you sin again... So one saint who's super popular in the Renaissance who is not very popular today is St. Julian the Hospitaller, patron saint of murderers... The Renaissance's idea is sometimes you have to commit homicide, and then what's important is that you feel sorry.

The contrast between pre-Reformation and post-Reformation (especially Calvinist) Christianity reveals how fundamentally the concept of moral purity shifted — and how that shapes everything from criminal justice to political ethics.

Machiavelli says, 'No. I'm going to stay, and I'm going to rot, and I'm going to write The Prince, which is my job application begging the new regime to bring me back and let me work for them and demonstrating my loyalty, and I'm going to send it to them and only them, them and my immediate friends. I'm not going to share it with anybody else.' Because Machiavelli is a patriot, and he will not serve any cause that is not his country. No matter whether the pay at a royal court somewhere would be three times what he would ever get at home, that doesn't matter to him.

Knowing The Prince was a private job application — not a published manifesto — completely reframes how we should read it and why it was written the way it was.

Machiavelli becomes exciting first in the aftermath of the publication of Hobbes's Leviathan, because Hobbes's Leviathan hits European thought like a truck full of bricks... in the aftermath of publishing Leviathan, there's a 40-year period where the sole goal of Western European philosophy is coming up with a good way to refute Hobbes. At that moment, they say, 'Okay, Hobbes is using a lot of logics about politics and history that sound like Machiavelli.'... So Machiavelli is suddenly useful not to people who sympathize with him, but to people who see him as an enemy and want to use him to try to defeat what to them is the greater enemy.

It illustrates how ideas gain or lose cultural prominence not on their own merits but based on what questions a given era is urgently trying to answer — and how enemies can accidentally canonize the thinkers they oppose.

if you work for the cardinal or you work for the duke, you can be doing very radical magic, radical philosophy, radical politics, radical sexuality, and nobody in authority can touch you because authority's trumped by a higher authority that is protecting you. This is part of the patronage system.

This crystallizes how Renaissance patronage functioned as a structural shield for heterodox thought and behavior, which reframes how intellectual freedom actually worked before modernity.

the Inquisition needs to please local authorities in order to get to operate at all. So the Inquisition will therefore try to figure out things that will please local authorities. If a book is being presented for publication that has a recommendation letter at the beginning written by an important political figure, the Inquisition will push it through.

It reveals that even the feared Inquisition operated through political negotiation rather than pure doctrinal authority, exposing how enforcement institutions are constrained by the need for local cooperation.

figures like Machiavelli realize we could ask for, 'Hey, you're giving us permission. Can you deny everyone else permission?' The Inquisition immediately realized, this is a great way to get publishers on our side, to get authors on our side, and to get their bosses on our side, because we are protecting the book that is important to the duke because it's dedicated to the duke.

This shows copyright emerging not from authorial rights or moral principle but from the mutual self-interest of censors, rulers, and authors — a strikingly cynical and clarifying origin story for intellectual property.

Sometimes in the history of thought, there are authors who become separated from their work. You have a parallel where there is the actual content of what the person did and said, and separately there is the idea of this person. In the case of Machiavelli, we have Machiavelli the patriot, Machiavelli who did all this work, and separately we have 'Machiavellian' — 'the murderous Machiavel', as Shakespeare calls him. Old Nick, which is a nickname for the devil but became popular because of Niccolò Machiavelli. Old Nick, literally a synonym for the devil.

The bifurcation of a thinker into their real work and a culturally constructed character is a recurring historical phenomenon that distorts how ideas are received and used across centuries.

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. If you have a government and want it to be stable and protect the people's lives, do this.

Reframing The Prince as a manual for stable, protective governance rather than personal ambition inverts the most common popular reading and changes what questions the book is actually answering.

Spinoza is a neat one, because when you actually read Spinoza, he's really warm and sweet. Like Machiavelli, he's passionate and cares about people, and in his case is an incredibly pious theist. He's a monist. He believes the entire universe is the body of God... But a fact about Spinoza was that he was the first person in ages and ages to be targeted with the Jewish equivalent of excommunication... The fact of that spread around, and people had the idea that Spinoza must be even more weird and heretical than any heretic if even the Jews would expel him. The idea of Spinoza the arch-heretic becomes a character.

Spinoza's case shows how a single dramatic biographical event — however unrepresentative of one's actual ideas — can permanently colonize a thinker's reception, making the character eclipse the philosophy.

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... 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.

Palmer elevates the question from Machiavelli specifically to a general cognitive and social tendency — the production of useful fictional doubles from real phenomena — which has broad implications for how ideas, people, and even institutions are understood.