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Dwarkesh Podcast

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

16 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What is the main topic discussed in this episode?

0.031 - 20.883 Dwarkesh Patel

Okay, I'm back with Ada Palmer, who is a science fiction author, composer, historian at the University of Chicago. Ada, this time I want to talk to you about Machiavelli. Yes. So he writes The Prince, he dedicates it to Lorenzo de Piero de' Medici, and gives it to him in 1513, and he says in the final chapter, you're the only person who can bring Italy from its current place of ruin and ravage.

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21.504 - 24.469 Dwarkesh Patel

Why were things so bad? What is the historical context in which he's writing The Prince?

0

25.057 - 39.96 Ada Palmer

So I'm going to give a two-part answer to that. Although, of course, with any granular history, there can be many parts. But the papacy is part of it, and then the city-state structure of Italy is another part of it. And I'll start with the city-state structure.

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40.042 - 54.064 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, et cetera.

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54.464 - 70.304 Ada Palmer

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. And so it's very common when there's one regime change for there then be five regime changes, rapid fire over and over.

70.324 - 86.35 Ada Palmer

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.

Chapter 2: What historical context influenced Machiavelli's writings?

86.33 - 110.162 Ada Palmer

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's going to be more and more and more and more overthrows in those governments.

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110.182 - 134.073 Ada Palmer

Because if 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 and, 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.

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134.093 - 154.027 Ada Palmer

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. And the papacy, of course, is a long and evolving organism, right? The papacy is one of the oldest institutions in the world now. It was one of the oldest institutions of the world even then, even though this is 500 years ago.

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154.808 - 168.565 Ada Palmer

And 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. And each one sets norms for the next one.

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168.882 - 194.468 Ada Palmer

And over the course of Machiavelli's lifetime and just before, a bunch of consecutive popes expanded executive power and especially the military side and launched more wars or did more arbitrary overthrow of governments. Because 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. And here is a pope.

194.548 - 195.89 Ada Palmer

He has an illegitimate son.

Chapter 3: How did Machiavelli's diplomatic experiences shape his views on power?

196.391 - 216.287 Ada Palmer

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. And 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.

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216.267 - 237.773 Ada Palmer

Once that is the norm, even a fairly nice pope still inherits the idea that the pope is going to overthrow and replace governments. And 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.

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Chapter 4: Why did the common people support Cesare Borgia despite his cruelty?

237.833 - 258.053 Ada Palmer

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. And 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.

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258.033 - 277.29 Ada Palmer

which means if we assume that the average length of a papacy is 10 years in this period, every 10 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.

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277.27 - 299.486 Ada Palmer

So Machiavelli, when he's writing the last chapter of The Prince, is looking around and saying, okay, we have a perfect storm of practically every polity in this region has just had the threat 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.

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299.526 - 300.848 Ada Palmer

They're ready to fall.

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Chapter 5: What role did art play in the political landscape of Machiavelli's time?

300.828 - 303.973 Ada Palmer

And meanwhile, nothing will stop the turnover of popes.

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304.534 - 327.932 Ada Palmer

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 at heredity, that he can do what Cesare Borgia tried to do and have enough power near the papacy to strongly influence the next pope to create a kind of stability that's otherwise impossible.

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328.216 - 335.267 Dwarkesh Patel

So he wants the Medici's basically to not unify Italy, but stabilize Italy at the very least.

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335.287 - 349.768 Ada Palmer

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.

0

349.788 - 351.531 Dwarkesh Patel

And the Pope now is a Medici, right?

351.551 - 353.093 Ada Palmer

At that moment, yes.

353.113 - 376.345 Dwarkesh Patel

So it makes it even more plausible. Let's lay down a little more historical context. So before Machiavelli writes The Prince, he's a sort of bureaucratic diplomat, and he meets, through his career, a lot of these famous figures. I want to know what he makes, for example, of King Louis of France, of Maximilian of Germany, the Holy Roman Empire. I want to know what he made of Cesare Borgia.

376.626 - 393.347 Ada Palmer

Yeah. He spends a lot of The Prince, in fact, trying to veil how much more he cares about Cesare Morsi 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.

Chapter 6: How did Machiavelli's exile impact his writing of The Prince?

393.367 - 415.437 Ada Palmer

And sometimes he just can't, right? And there's that incredible magical moment when he's discussing Valentino's fall. The moment when he has amassed all this power, he successfully conquered almost everything within Italy. And then suddenly both his father, the Pope, and him fall ill at once. And when Machiavelli describes this and he's saying everything Cesare Borgia did, he did right.

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415.897 - 440.134 Ada Palmer

He conquered this kingdom. He would have kept it. The only reason he lost it was fortune. And 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.

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440.775 - 462.928 Ada Palmer

Our historian cannot veil himself anywhere. He cares too much. He told me, first person, that he had prepared for everything at the event of his father's death, except the possibility that he himself would also be incapacitated at the moment. And it's such a magical moment where the veil between the author and the reader breaks for just that moment.

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462.949 - 482.76 Ada Palmer

And we're like, oh yes, all of these others he observed from a distance. But Machiavelli was in the room next to Valentino. I had Valentino's side through this and 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...

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482.74 - 501.559 Ada Palmer

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. And Machiavelli was in the room.

501.539 - 519.12 Ada Palmer

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, right? Because Machiavelli's job dealing with Cesare Borgia is, it's very clear that the Borgia plan is to conquer the Papal States in the middle of Italy.

519.16 - 526.088 Ada Palmer

And Tuscany, Florence's dominion is this little notch, like a puzzle piece out of the side of the Papal States.

Chapter 7: What were Machiavelli's insights about the nature of power?

526.148 - 549.957 Ada Palmer

And anybody with a map Looking at it as like, you gotta conquer that. You just have to conquer this. You can't have a kingdom without it. You have to. 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.

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551.27 - 575.18 Ada Palmer

And we can absolutely and abjectly swear to do anything he wants. And 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, which Florence had had a 300-year alliance to defend Bologna. And he said, we have to break it. The whole world is broken right now.

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575.22 - 597.274 Ada Palmer

We have to break every promise and every hereditary alliance we had. We must be at the side of this man. And 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.

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597.294 - 621.827 Ada Palmer

I like you, my guest. I'll eat you last. That's the Republic's only hope. And that's Machiavelli's job, is 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.

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622.567 - 631.798 Dwarkesh Patel

Doesn't it contradict what you were saying in The Prince about never rise with the help of great powers for even in success, you have empowered somebody who is stronger than you and whose mercy you're at?

631.978 - 652.101 Ada Palmer

I mean, 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. And Machiavelli is very open about the fact if Alexander had lived another year, Valentino would have finished his conquest and taken Florence and taken it at last and it would have been over.

652.705 - 677.733 Ada Palmer

But popes are mortal, and buying time is sometimes the survival mechanism. And so Machiavelli has this incredible firsthand experience of being with Valentino through all of these decisions, being with him at the massacre at Senegalia, when rumor had reached Valentino that... Some of his people were terrified of him and plotting to overthrow him.

677.794 - 689.48 Ada Palmer

And then they were so scared of him, they decided to abandon the plot. And he heard and he met with them and told them, I forgive you. It's OK. You know, you've renewed your loyalty to me. You've passed the test. I trust you all as well.

Chapter 8: How does Machiavelli's reputation differ from his actual ideas?

689.52 - 713.317 Ada Palmer

And then he invites them to the banquet and then massacres them all. The forgiveness is false. The betrayals are punished. There's this amazing letter that's a couple months afterward where Macchioli's loved ones are writing from Florence because they've received a letter from him after the massacre at Senegal. And they say, oh, thank God you're alive. We had no idea.

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713.478 - 732.28 Ada Palmer

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 because 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.

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732.32 - 750.101 Ada Palmer

He easily could have been on a list of names of people the conspirators intended to recruit and be 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 and it felt to them like a miracle that he hadn't.

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750.121 - 767.982 Ada Palmer

But it meant that he watched these incredible deeds of 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, right? That Dante would say, if you do that,

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767.962 - 786.724 Ada Palmer

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. And that 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.

787.225 - 801.189 Ada Palmer

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.

801.71 - 801.85

Mm-hmm.

802.184 - 825.019 Ada Palmer

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. And 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,

826.045 - 843.805 Ada Palmer

the kingdom would have stood. And indeed, he would have conquered Florence. So 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 maximum half of what causes outcomes. The other half is always going to be fortune, right?

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