Dwarkesh Podcast · AI Research & Frontier Labs · June 2026
His own synthesis of several threads from the conversation, offered rather than asked. The setup is Machiavelli's Rome, where generals months away on the frontier commanded the same men for decades and collected their loyalty personally. The argument is that institutions we think of as welfare or justice policy were first of all solutions to the problem of divided loyalty.
turns out like a surprisingly effective solution is
for the viewers, you can leave your solutions in the comments. And if this is the kind of puzzle you enjoy, go to jane street.com/slash ThwarCash to check out their open ML positions.
Okay, so to tie a couple of threads we were talking about together. The prince is painting a picture of just regime is incredibly unstable. You had to worry about foreign powers. You had to worry about rival factions within your own country. You had to worry about mercenaries. You had to worry about lots of different things. And so any given regime is very unstable. And so what had to happen for things to get more stable, basically. And we're talking about a couple of the ways in which people owed their loyalties not to the regime, but to others within the regime, which created instability. So in Discourses on Livy, Machiavelli talks about the Roman Empire. One of the reasons that its fall was instigated is that these generals who were months away in the frontier fighting these wars because the empire was so big had to amass for the periods of years or in some cases for Caesar, of course, decades, the command of so many men who have for decades just basically been listening to this guy tell them what to do, who to fight next. This is the person who they're loyal to. As opposed to, say, if the consuls could be giving dictates every single day, then the loyalty could be to the regime in Rome. And same with patronage, if there's not a system of both deterministic justice that we have in the modern world today. So a lot of the prince is dedicated in discourses on Livy on, well, how do you make sure that some family is not pissed off that their son got killed and it wasn't avenged or whatever. And if we just have a reliable criminal justice system, that problem goes away. And same with the welfare state and getting rid of the patronage system. Basically, if you don't have to rely on this family, then this intermediates them and the state can have your loyalty. So it's interesting to connect all these threats together of communication time, impartial justice system, impartial welfare state as being what is required for the regime to have enough legitimacy and then as a result, enough stability. To have modern nation states.
Yeah. One thing that everyone is surprised by is that when Valentino Borgia is that when Cesare Borgia, Valentino is much more what he's called in the period, when Cesare Borgia conquers these cities in central Italy, and he goes in and he massacres the ruling family and 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. And 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. And when they implement justice, they do so neutrally because they aren't interested in the local backstory of factions. And 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. And everyone says, why are they like this man? He is a cruel, murdering tyrant. And the answer is, for the first time in generations, they have had something close to fair justice. Meaning, it used to be that there was one faction in power and there was another faction out of power, which meant in our scenario where a carpenter's son gets drunk and kills someone in a broken brawl, if that carpenter's son is the carpenter of the power that's in power, then there will be no justice and there will be no consequences for this murder, maybe the smallest of fines. And if that carpenter works for the families that are out of power, then throw the book at him, he'll be executed for that death. And there will be no fair justice. The outcome of the sentence will be entirely who's in power and out of power and 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. And the people who have lived in generations of there is 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 were in power are finally being punished for the crimes they commit. And 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. So
why would it have been so bad if Valentino took over Florence and he had survived? And he would have massacred maybe the ruling regime at the time, the Republic. But I don't know what Machiavelli is especially concerned about, but like the cultural treasures of Florence and everything. I
know it. So again, in the discourse, isn't that? I think the cultural treasures of Florence would potentially have been okay. There's two answers to that. One of them is 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 of where there is an arbitrary power who can have you put to death, you are a slave. And 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, right? 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, and 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. And 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 could say, execute him. That meant a lot to Machiavelli. And it meant a lot to the Florentine people. And 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, right? And the banner, libertas, is the coat of arms of the senioria, 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. And 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, right? And 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.