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Published · transcript-backedDwarkesh Patel: evaluation
16 Jun 2026 Dwarkesh Podcast Ada Palmer – Machiavelli is the most misunderstood thinker of all time
“I think one misconception of Machiavelli that I had, because I had not read these books before, is that he says the means don’t matter, the end matters.”
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- Dwarkesh Patel
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- evaluation
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- 16 Jun 2026
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- Dwarkesh Podcast
Transcript context
…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.” I think one misconception of Machiavelli that I had, because I had not read these books before, is that he says the means don’t matter, the end matters. There’s a virtue ethic sense in which maybe he doesn’t think the means matter, but he is way more concerned about the means than I would’ve naively thought. He thinks the means are incredibly important, because the means by which you achieve power determine how stable and how fruitful that power will be. In the context of military conflicts, he says if you achieve some power with the help of mercenaries or with the help of great powers—people who become stronger than you as a result of you achieving power—that is a very precarious spot to be in. But speaking of Julius, he makes another point that if you achieve your power by lying, by breaking oaths, by being unfaithful, that this is okay, because his view is that people will forget that you are not faithful. They will just take you at your word the next time they encounter you. It’s actually a very interesting meditation on by what means you can achieve power that will make that power stable versus not. The fact that he thinks breaking your word is totally fine… 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.…
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