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Machiavelli judges historical actors like Cesare Borgia not simply by whether they succeeded, but by whether their choices were the most probable route to success before chance (fortune) intervened — so the Borgias' fall does not prove their methods were wrong.

Ada Palmer explains Machiavelli's distinctive method: he judges actions not merely by ultimate outcome but by what the most probable outcome would have been absent bad luck — meaning Cesare Borgia's actions were correct even though fortune later doomed him. ✦ AI generated

Ada Palmer · Dwarkesh Podcast · 2026-06-16 · original ↗

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Doesn’t it contradict what he was saying in The Prince about how you should never rise with the help of great powers, for even in success you have empowered somebody who is stronger than you and at whose mercy you are?

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.

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0:00– How Florence bargained with Cesare Borgia for survival

0:00– How Florence bargained with Cesare Borgia for survival

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