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Dwarkesh Patel: evaluation

16 Jun 2026 Dwarkesh Podcast Ada Palmer – Machiavelli is the most misunderstood thinker of all time

“This actually gets to the famous quote in The Prince, “It is better to be feared than loved.”

— Dwarkesh Patel

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Speaker
Dwarkesh Patel
Attribution
Verified speaker
Claim type
evaluation
Recorded
16 Jun 2026
Publisher
Dwarkesh Podcast

Transcript context

…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. This actually gets to the famous quote in The Prince, “It is better to be feared than loved. ” What he’s getting at there is, I think, that he’s very cynical about people’s nature. If people make you a promise, they’ll just go back on it. If your power base depends on people’s promises and loyalties, as soon as your rule seems to be tattering, they’ll go back on it. Whereas if your rule depends on people having the expectation that if they break their oath to you, they’ll be punished, that’s much more stable. He basically thinks people will act as badly as they are allowed to, whether they’re the tyrant or the people or the nobles. This goes back to the thing in The Discourses. His whole justification of checks and balances is not dissimilar to the founders of the US and their reason for wanting checks and balances and wanting to put different factions against each other. He’s just cynical and thinks people will act as badly as you allow them to. 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.…

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