There are very few philosophers who become part of popular culture, and often, if their ideas become influential, people don’t know where they came from.Niccolò Machiavelli, the great 16th-century diplomat and writer, is an exception.I don’t know how many people have actually read Machiavelli, but almost everyone knows the name, and almost everyone thinks they know what the word “Machiavellian” means. It’s someone who’s cunning and shrewd and manipulative. Or as one famous philosopher called him, “the teacher of evil.”But is this fair to Machiavelli, or has he been misunderstood? And if he has been, what are we missing in his work?Erica Benner is a political philosopher and the author of numerous books about Machiavelli including my favorite, Be Like the Fox, which offers a different interpretation of Machiavelli’s most famous work, The Prince.For centuries, The Prince has been popularly viewed as a how-to manual for tyrants. But Benner disagrees. She says it’s actually a veiled, almost satirical critique of authoritarian power. And she argues that Machiavelli is more timely than you might imagine. He wrote about why democracies get sick and die, about the dangers of inequality and partisanship, and even about why appearance and perception matter far more than truth and facts.In another of his seminal works, Discourses on Livy, Machiavelli is also distinctly not authoritarian. In fact, he espouses a deep belief in republicanism (the lowercase-r kind, which affirms representative government).I invited Benner onto The Gray Area to talk about what Machiavelli was up to and why he’s very much a philosopher for our times. As always, there’s much more in the full podcast, so listen and follow The Gray Area on Apple Podcasts, Spotify, Pandora, or wherever you find podcasts. New episodes drop every Monday.This interview has been edited for length and clarity. The popular view of Machiavelli is that he wanted to draw this neat line between morality and politics and that he celebrated ruthless pragmatism. What’s incomplete or wrong about that view?What is true is that he often criticizes the hyper-Christian morality that puts moral judgments into the hands of priests and popes and some abstract kind of God that he may or may not believe in, but in any case doesn’t think is something we can access as humans. If we want to think about morality both on a personal level and in politics, we’ve got to go back to basics. What is the behavior of human beings? What is human nature? What are the drives that propel human beings to do the stuff that we call good or bad? He wants to say that we should see human beings not as fundamentally good or evil. We shouldn’t think that human beings can ever be angels, and we shouldn’t see them as devils when they behave badly.But the basic point is if you want to develop a human morality, you study yourself, you study other humans, you don’t put yourself above other humans because you’re one, too. And then you ask, What kind of politics is going to make such people coexist?I take it you think his most famous book, The Prince, is not well understood?I used to have to teach Machiavelli and I would just say, It’s a handbook for tyrants. But he wrote the Discourses, which is a very, very republican book. So that’s the first thing that sets people off and makes you think, How could he have switched so quickly from writing The Prince to being a super-republican writing the Discourses? So that’s a warning sign. When I started seeing some of the earliest readers of Machiavelli and the earliest comments you get from republican authors, they all see Machiavelli as an ally and they say it. They say he’s a moral writer. Rousseau says, “He has only had superficial and corrupt readers until now.” If you ever pick up The Prince and you read the first four chapters, and most people don’t read them that carefully because they’re kind of boring, the exciting ones are the ones in the middle about morality and immorality and then you come to chapter five, which is about freedom.And up to chapter four, it sounds like a pretty cruel, cold analysis of what you should do. Then you get to chapter five and it’s like, Wow! It’s about how republics fight back, and the whole tone changes. Suddenly republics are fighting back and the prince has to be on his toes because he’s probably not going to survive the wrath of these fiery republics that do not give up.So who is he talking to in the book? Is he counseling future princes or warning future citizens?It’s complicated. You have to remember that he was kicked out of his job and had a big family to support. He had a lot of kids. And he loved his job and was passionate about the republic. He was tortured. He doesn’t know what’s going to happen next. He’s absolutely gutted that Florence’s republican experiment has failed and he can’t speak freely. So what does a guy with a history of writing dramas and satire do to make himself feel better? It’s taking the piss out of the people who have made you and a lot of your friends very miserable, in a low-key way because you can’t be too brutally satirical about it. But I think he’s really writing to expose the ways of tyrants.Would you say that Machiavelli has something like an ideology or is he just a clear-eyed pragmatist?He’s a republican. And again, this is something that, if you just read The Prince, you’re not going to get. But if you read the Discourses, which was written around the same time as The Prince, it’s very, very similar in almost every way except that it praises republics and criticizes tyrants very openly. Whereas The Prince never once uses the words “tyrant” or “tyranny.” So if there’s a guiding political view, whether you call it “ideology” or not, it’s republicanism. And that’s an ideology of shared power. It’s all the people in a city, all the male people in this case. Machiavelli was quite egalitarian. He clearly wanted as broad of a section of the male population to be citizens as possible. He says very clearly, The key to stabilizing your power is to change the constitution and to give everyone their share. Everyone has to have their share. You might want to speak a little bit more for yourself and the rich guys, but in the end, everyone’s got to have a share.Should we treat Machiavelli like a democratic theorist? Do you think of him as someone who would defend what we call democracy today?If you think the main principle of democracy is that power should be shared equally, which is how I understand democracy, then yes. He’d totally agree with that. What kind of institutions would he say a democracy has to have? He’s pretty clear in the Discourses. He says you don’t want a long-term executive. You need to always check power. I realize we exist in a very different world than Machiavelli, but is he a useful guide to understanding contemporary politics, particularly American politics?This is a really Machiavellian moment. If you read The Prince and look not just for those provocative quotes but for the criticisms, and sometimes they’re very subtle, you start to see that he’s exposing a lot of the stuff that we’re seeing today. Chapter nine of The Prince is where he talks about how you can rise to be the ruler of a republic and how much resistance you might face, and he says that people might be quite passive at first and not do very much. But at some point, when they see you start to attack the courts and the magistrates, that’s when you’re going to clash. And he says, That’s when you as a leader — and he’s playing like he’s on the leader’s side — that’s when you’ve got to decide if you’re going to get really, really tough, or are you going to have to find other ways to soften things up a bit?What would he make of Trump?He would put Trump in two categories. He’s got different classifications of princes. He’s got the prince of fortune, somebody who relies on wealth and money and big impressions to get ahead. He would say that Trump has a lot of those qualities, but he’d also call him this word “astutia” — astuteness, which doesn’t really translate in English because we think of that as a good quality, but he means calculating shrewdness. Somebody whose great talent is being able to shrewdly manipulate and find little holes where he can exploit people’s weaknesses and dissatisfactions.This is what he thought the Medici were good at. And his analysis of that is that it can cover you for a long time. People will see the good appearances and hope that you can deliver, but in the long run, people who do that don’t know how to build a solid state. That’s what he would say on a domestic front. I think there’s an unsophisticated way to look at Trump as Machiavellian. There are these lines in The Prince about knowing how to deploy cruelty and knowing when to be ruthless. But to your deeper point, I don’t think Machiavelli ever endorses cruelty for cruelty’s sake, and with Trump — and this is my personal opinion — cruelty is often the point, and that’s not really Machiavellian.Exactly. I wouldn’t say Trump is Machiavellian. Quite honestly, since the beginning of the Trump administration, I’ve often felt like he’s getting advice from people who haven’t really read Machiavelli or put Machiavelli into ChatGPT and got all the wrong pointers, because the ones that they’re picking out are just so crude. But they sound Machiavellian. You’re absolutely right, though. Machiavelli is very, very clear in The Prince that cruelty is not going to get you anywhere in the long term. You’re going to get pure hate. So if you think it’s ever instrumentally useful to be super cruel, think again.This obviously isn’t an endorsement of Trump, but I will say that something I hear often from people is that the system is so broken that we need someone to smash it up in order to save it. We need political dynamite. I bring that up because Machiavelli says repeatedly that politics requires flexibility and maybe even a little practical ruthlessness in order to preserve the republic. Do you think he would say that there’s real danger in clinging to procedural purity if you reach a point where the system seems to have failed?This is a great question. And again, this is one he does address in the Discourses quite a lot. He talks about how the Romans, when their republic started slipping, had “great men” coming up and saying, “I’ll save you,” and there were a lot before Julius Caesar finally “saved” them and then it all went to hell. And Machiavelli says that there are procedures that have to sometimes be wiped out — you have to reform institutions and add new ones. The Romans added new ones, they subtracted some, they changed the terms. He was very, very keen on shortening the terms of various excessively long offices. He also wanted to create emergency institutions where, if you really faced an emergency, that institution gives somebody more power to take executive action to solve the problem. But that institution, the dictatorship as it was called in Rome, it wasn’t as though a random person could come along and do whatever he wanted. The idea was that this dictator would have special executive powers, but he is under strict oversight, very strict oversight, by the Senate and the plebians, so that if he takes one wrong step, there would be serious punishment. So he was very adamant about punishing leaders who took these responsibilities and then abused them.Listen to the rest of the conversation and be sure to follow The Gray Area on Apple Podcasts, Spotify, Pandora, or wherever you listen to podcasts.See More: