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This episode is brought to you by Choiceology, an original podcast from Charles Schwab. Hosted by Katie Milkman, an award winning behavioral scientist and author of the best selling book how to Change. Choiceology is a show about the psychology and economics behind our decisions. Hear true stories from Nobel laureates, authors, athletes and everyday people about why we do the things we do. Listen to choiceology@schwab.com podcast or wherever you listen to. Adobe Acrobat Studio so brand new. Show me all the things PDFs can do. Do your work with ease and speed. PDF Spaces is all you need. Do hours of research in an instant with key insights from an AI assistant. Take a template with a click now your prezo looks super slick. Close that deal. Yeah, you won. Do that, doing that, did that, done. Now you can do that do that with Acrobat. Now you can do that do that with the all new Acrobat. It's time to do your best work with the all new Adobe Acrobat Studio.
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Very few ideas stand the test of time, and very few works of literature or philosophy are remembered even 50 or 100 years after they were written. What about 500? How many 16th century philosophers do you think you could name? Thomas More? Sure. Francis Bacon? Yeah, but it's high school biology textbooks that are keeping him alive. Montaigne? Can you name a single thing he wrote? If you're a philosophy sicko that listens to this show, maybe. But normies? I doubt it. But then there's Machiavelli. What's up with him? Why, after 500 years, is Machiavelli so famous? Why does his writing, especially the Prince, still resonates so much today? And why, after 500 years of being dissected, analyzed, dissertated, read and re read, is Machiavelli so often misunderstood? What was he really up to? What have we missed? And what can Machiavelli tell us about our world right now? I'm Sean Iling, and this is the Gray Area. Today's guest is Erica Benner. She's a political philosopher and the author of numerous books about Machiavelli, including my favorite, Be like the Fox, which offers a new interpretation of Machiavelli's most famous work, the Prince, which Machiavelli wrote in exile after the Medici family overthrew Florence's fledgling Republican government. For centuries, the Prince has been widely 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. 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. If she's right, Machiavelli is very much a philosopher for our times with something to say about this moment. So I invited her on the show to talk about it. Erica Venner, welcome to the show.
C
Hi, Sean. Thanks for having me.
B
There is the popular caricature of Machiavelli with which I think most people are familiar. You know, the conniving, manipulative, sneaky figure. And then there's the real Machiavelli. Tell me about the gap between those two.
C
It's massive, because if you go and you read Machiavelli's correspondence, they're hilarious. He's the funniest guy on earth. The first kind of literary piece that we've got notes about, but we don't actually have anymore because it was kind of concealed. And then the popes banned everything he wrote. But one of the first things he wrote was a satirical play about the powers that be in Republican Florence. So he's a satirist. I mean, one of the things I just always want to kind of bring out about the gap between this cold, calculating advisor to princes saying, better to be feared than loved, is this guy is hilarious all the time. And he's a dramatist. Like, he's a brilliant writer of plays and dramas. And so that's one gap that when you read, when you come to the Prince, I kind of urge people always to kind of bear in mind that before he wrote the Prince, and then after he wrote the Prince, he was writing political satires. And I think we're in a kind of atmosphere now in the world where that might be easier to see for a lot of people. Because if you imagine somebody who doesn't want to be too direct and preach to people in criticizing the great leaders, but still wants to kind of take the piss out of them, he just does that in a very, very subtle, Florentine way. I don't know if that kind of answers your question.
B
No, no, it does. So, you know, when I was in graduate school for political theory, Machiavelli is introduced as kind of like the first truly modern political scientist, sort of like the Galileo of politics. Is that how you think of them? Is that how we should think of him?
C
No, I absolutely don't think.
B
Say more unequivocally.
C
No, I. Machiavelli was somebody whose main Examples and main interests. When it comes to like, you know, thinking about how politics should work, his main interest is in ancient history. That's clear. He's somebody who's really, really grounded in ancient history, like most of the people who are educated in his times. His second big, big book is called the Discourses on Livy, and that is a commentary on ancient Rome, which is trying to draw from history examples that can serve as cautionary, you know, warnings to people of his own times and for the future, but also help us to think about what is actually, you know, what is a good leader in politics, what is prudent and what kind of sometimes seems like a prudent policy, like something could actually achieve some good. But then if you really, really think ahead and look at history as well and realize what people have done before along those lines, you kind of see the problems.
B
Yeah.
C
I don't think he's a scientist in a political science way at all. Thank goodness.
B
Maybe you could replace political scientists with just political thinker. Maybe that's a little broader. But you're right, he is very interested in the past. And he seems to have a bit of a beef with a lot of these ancient philosophers, the Plato's and the Aristotle's. He seemed to think that they were naive, if that's the right word, that they weren't looking at the political world the way it actually is, but instead they were projecting their own ideals and fantasies onto the political world and then dreaming up a kind of politics in light of that. What was his beef with the ancients? What did he think they misunderstood or got wrong or ignored about actual life?
C
The kind of view that you just outlined. I don't want to get nerdy and too academic about this, but that is.
B
You'Re about to tell me why I'm wrong, aren't you?
C
Out of a couple of lines where he says things like, oh, you know, philosophers have imagined ideal republics. Yes, but in reality that's just one quote. And then there's some other little quotes you can pluck out and you can turn into a big modernist system, which quite a few of my very esteemed Machiavelli scholar colleagues have done. But actually, you know, in context, it's a lot more complicated than that because he also has many quotes elsewhere where he said, the greatest thing you can do if you can't actually create a republic is to imagine one. He has that in one of his pieces that's called the Discourses on Government of Florence, where he's trying to advise them on how to save their flailing, fragile, new non republic, and saying, maybe you should turn this non republic back into a republic. And he says, I'm not in position anymore to help do that in practice like I used to be. So I'm trying to go in the footsteps of Plato and Aristotle and imagine one where you can't have one. There is no sharp contrast in Machiavelli, properly understood, between his ideals and his realism and realism. You know, realism and idealism don't have to be opposite. That idea in itself is something I think people are really waking up to more and more, that if we try to go, you know, if you imagine that you can follow a realistic path towards a better world without having an ideal or two to guide it, you.
B
Know, he sort of has the same problem Nietzsche has in that there's so much irony in so many different voices in his work that it practically begs you to misinterpret it. Or at the very least, it makes it very easy for the reader to project whatever they want onto the work. And so it's his fault, I guess, is what I'm saying.
C
Yeah, but this is what they did. I mean, this is another thing that I hope we will. I mean, I was just reading something today about. About AI and why, you know, somebody like a professor saying, don't we still want students to learn how to read difficult, ambiguous works? And that reading. One of the reasons we want students to keep reading and not to filter everything, to interpret it through a machine, is that reading is like a practice in listening and a practice in hearing things that are subtly off or that you could work with. And that's what you need in politics, right? Especially in a democracy or republic, you need people not just to go by hard rules, but to hear the subtleties and be able to judge for themselves. That's what he's trying to get us to do as part of recovering the republic is. Is readers have to see. You know, he's telling you all these shocking things that you ought to do and that princes ought to do. And readers are supposed to be kind of saying, hang on, hang on, let me judge that for myself.
B
All right, look, let's set about the work of cutting through some of these.
C
You don't believe me, Sean, do you?
B
No, I do, I do. I mean, I think once you get into the business of trying to distinguish what is the wink, wink and what is meant to be taken literally, it's very difficult. But you are. You are a much closer reader of Machiavelli than I am. So I'm not going to challenge you on that. And I think your reading is actually very interesting and very persuasive. Part of what I'm doing here is because the popular image of him is so cemented as this deceptive figure. I'm really trying to set that up so that you can challenge it kind of piece by piece. So let's start, right? I mean, I think one of the, certainly the. The conventional popular view of Machiavelli is that he is someone who wanted to draw this neat, clear line between morality and politics. They wanted to sever these things. But you write in the book that that's not true, right, that he simply wanted to put. And now I'm quoting. He simply wanted to put morality on firmer, purely human foundations. So what does that mean? How is it different from what people think he's doing?
C
Well, what is true is that he often criticizes the morality of the, let's say the hyper. Kind of hyper Christianity or spirituality that, you know, takes morals into the. Puts morals and what, you know, judgments of right and wrong into the hands of priests and popes and some abstract kind of God that, you know, he may or may not believe in, but doesn't think it's something we can totally access as humans. We can't, you know. So if we want to think about morality both on a personal level, but certainly in politics, we've got to kind of go back to basics, think about what is the behavior of human beings, what is human nature, what are the drives that kind of propel human beings to do the stuff that we call good or bad. And that's one of the fundamentals. I think he wants to say 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 until they really behave badly. And then we can call them evil. And sometimes he does. He calls people cruel, inhuman and evil sometimes, but very seldom. But the basic 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 just one too. And then you kind of start from there and say, right, what kind of politics is going to make such people coexist in ways that are not going to aim at some divine order, something that's going to bring higher and higher kind of godly ethics into human life? We've got to be more modest and just talk about. We're all going to be arguing we're all going to be difficult. Let's have rules and laws that help us coexist.
B
Well, let's talk about the Prince. I take it you do not think this book is very well understood in the popular imagination. Is that about right? Do you think most people have this book wrong? And if they do, tell me what you think is the most glaring, obvious misinterpretation of what he's actually up to there. Because I think what people think he's up to is giving this handbook to tyrants. I think that is what most people think. Tell me how that's wrong.
C
I mean, I used to think that too. I used to have to teach my kvadi as part of on lots of different thinkers. And I would just say, well, it's a handbook for tyrants. But then he wrote the Discourses, which is a very, very republican, very openly. So that's the first thing that sets people off, makes you think, well, how could he have switched so quickly from being a super republican as a political actor to writing the Prince to suddenly writing the Discourse? So that's a kind of warning sign. And then that got me thinking and then I kept coming across earlier authors who I trust deeply, like Rousseau, I mean Jean Jacques rousseau in the 18th century, a great, I think a very great philosopher and a deep republican, has a footnote in his social contract saying the Prince has been totally misunderstood. This was Machiavelli, is that right?
B
Yeah, I didn't, I didn't. I mean I've read that book, but.
C
Yeah, yeah, yeah, this is what set me off. So this isn't just me making it up. I mean, I have to say I'm not like. I mean I'm a very, like. I was very uncertain about this too. But then when I started seeing that some of the earliest read 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 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 modern readers. The exciting ones are the ones in the middle about morality and immorality. But like the first ones, you go eh. 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 this is what you should do. Chapter five, wow. It's like how republics fight back and the Whole tone. And remember, he's a literary guy and he's a dramatist. The whole tone changes. Suddenly fire 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.
B
So who is he talking to? Who's he really talking to in the prince? Is he talking to the people or is he talking to future princes?
C
I mean, I see it as, you know, imagine somebody who's been kicked out of his job and has big family to support. He had a lot of kids and who loved his job and was passionate about the Republic. He's been tortured. He doesn't know what's going to happen next. And he's absolutely gutted that Florence's republican experiment, renewing the Republic 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? So, number one motivation is it makes you feel better. You know, I mean, just like 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. It makes you feel a little bit. But I think he's really writing it in a way to kind of expose the ways of tyrants.
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C
He says it's good to be fair to unloved, but if you have to choose, it's better to be fair than love. So that's the context. And then he distinguished. Then he gives you examples of what kind of fear should be used and what he really means. When you look at his examples of the best kind of fear is just, you know, like fear of the laws. You know, he gives examples that actually relate to transparency and legality. I'm sorry, but this is true. If you go to the chapter where he says that it's, you know, he's talking, he says it's better to be transparent and regular and not to do things in an irregular, arbitrary way way. Do not arbitrarily take people's property. Do not take their wives. Do not do this. He gives you these lists. That's the kind of fear you want people to have. And it could be fear of you, the ruler, or it could be fear of a legal constitutional ruler as well. So what he's not saying is you should just use random terror, you know, arbitrarily scaring people. That is a disaster. He's really clear about that in the Prince.
B
Yeah, he says, you know, if you, if you do have to be feared, do not be feared in such a way as to produce hatred. That's a very important qualification.
C
Yeah, yeah, yeah.
B
So, and look, I, I know part of what you do in the book is you're you're driving this. You're resisting this idea that Machiavelli is very simplistically driving a wedge between politics and morality. But, God, there are these incredible lines, you know, like you're. You've been pointing out, right? And here's one. He says, therefore it is necessary for a prince who wishes to maintain himself to learn how not to be good and to use knowledge and not use it according to the necessity of the case. So what is the meaning of a line like that for you? Is he just saying politics is a dirty business and you can't survive it without getting your hands dirty? Or is it more complicated than that?
C
Yeah, I mean, unfortunately, this is what the thing about Machiavelli that makes him so susceptible to the kind of reading that's become popular is he's got these amazing lines.
B
Oh, wow, they're so good, Erika. They're so good and they're so cool.
C
I know. They're so cool. And if you're a teacher or professor who teaches political theory, it is kind of sad to kind of think about my Machiavelli being the right one instead of the one that we've all grown to kind of hate. Love, hate. Because, you know, he's such a different. It's such a different view of politics than what we're used to of ethics. But I'm sorry to tell you that he's fantastic because he really is spelling out how human beings really behave and how leaders often behave. But what he does about Sentence is he's setting the stage for a series of chapters about what do people think is good and are they right? That's what the next few chapters about. And he has discussion of cruelty. What do people think is cruel or harsh and are they right to say and what. And using money. When is kind of using money to get ahead okay, and when is it not okay for you? Because it's actually going to get you in deep trouble. So what he's doing with that is trying to get you to sort of think there's good and there's good is what I. What is what is conventionally thought of as good, the way to go. And sometimes he says that we have this angelic idea of how leaders should behave, which isn't suitable. But that's not saying that you should compromise, like your basic standards of transparency and decent, you know, decent rule.
B
It's just. It's very hard sometimes to know when he's merely describing something and when he's.
C
Endorsing it, he's deliberately ambiguous he's ambiguous on purpose. A lot of ancient writers were deliberately ambiguous. We are the ones who are kind of aberrations, modern people who think that everything has to be straightforward, blunt and clear. In ancient writers, you find loads of. Loads of writers, including Plato and all the historians who were deliberately ambiguous because they're trying to get us to think well.
B
And part of what is very persuasive about your book is that you really get to understand what he's up to. When you see some of his correspondence, some of his private correspondence with letters to friends and that sort of thing where he's being much more honest, and with that context, it gives you a much better insight into what he's actually doing in his. In his work. And that's the work that you do. One of the things he says in the Prince is that the ruler must imitate the lion and the fox. And the book of yours we're talking about is called Be like the Fox. I have it right here. Why that title? What do you mean? What does it mean to be like the fox?
C
Yeah, I mean, fox is. Again, he's playing with us because we think of the classical image of, you know, the trope of the fox is associated with cunning, sly, sneaky, Machiavellian.
B
Hard to pin down.
C
Hard to pin down. Yeah. But if you look at the context, again, you look at what he says. He says the fox recognizes snares. He said, with this should imitate the fox and the lion. The lion because the lion can scare wolves. And the fox because the fox recognizes traps. So the skill of the fox he's highlighting isn't being shrewd and cunning. It's recognizing when someone's being shrewd and cunning towards you and building up defenses, cognitive and physical, whatever you need so that that person doesn't pull you in.
B
Tell me if I'm wrong. I remember. And I don't know where I read this. It was a long time ago, but I recall reading about this story that Machiavelli loved and apparently referenced quite a bit. And the story was of a. Some ruler, I don't know who. Who sends a man to some principality to put down an insurgency with just brutal force, right? And the guy does the job. But the people left behind in that principality are really pissed off and they resent him. So the prince has the guy who did it, the guy that he ordered to do the job, killed and then strung up in the public square. And then he makes a big show of how outraged he is by this man's criminal act of defiance. And Machiavelli apparently is said to have loved that story because it demonstrates how flexible and cunning a prince can and should be, and how effective it can be if he's doing that.
C
Well, I think what you're talking about is chapter seven of the Prince, where he talks about Cesare Borgia, who was the son of Pope Alexander vi, who was a brilliant deceiver, and Cesare Borgia, he's the prince of fortune. Chapter seven is about how to become a prince, not by virtue, but by fortune. And Cesare Borgia is a really ambivalent figure in the prince, but he does something along the lines you suggested. He's got a guy called Ramiro de Orco, and he sets him up in this. In this small town to kind of be the police guy, the big sheriff on the block. And then he scapegoats him, basically. He gets Ramiro to be brutal and kind of suppress all discontent. And then when all the people start getting upset about this, he goes, hey, I'm just going to like. And so he doesn't even. Machiavelli just describes it. He did love telling this story. He told it in several different places, actually. But he says one day the people go into the plaza at dawn, and there's the pieces of Ramiro de Orco, like in pieces with a. With a Coltello, a knife by his side. And, you know, this is the image. And then it says the people were so stupefied that they didn't dare rebel anymore. And that then if you end it there and you say, that's the end of the story. And you say, okay, Machiavellian in that.
B
But that's pretty cynical. It's pretty cynical, Erika. Pretty cynical.
C
Read on. It is. It's very cynical. Read on. Don't get stuck. My one advice. Don't get stuck on one thing. Keep reading on. What were the consequences for Cesare Borgia? What happened to him after that? Well, everyone starts leaving Cesare. Like, all the people who are giving him troops and who supported him, all his allies, they all, like, say, okay, this guy's crazy. He's out of control. They start dropping out. The French pull back their troops that they were giving him all his closest mates, they conspire against him. He finds this out, he brutally slaughters them. And then everyone else hates him. So within a few months, he's, like, really in trouble. And then Cesare is dead. He doesn't actually die immediately, but he's out, and that's it. So if you go to the end of the. You go to the End of the story. You don't just stop and say, wow, what a cool thing. Because I mean, we can see examples of this all over the world today. Wow, that was a cool thing somebody did. That was tough. Wait till the story continues. Because doing that is going to make you feared and hated.
B
And that's what happened. You're mad at me for not finishing the reading, aren't you?
C
Yeah. Oh, you didn't even read that chapter in my book. That was such a good. That is such a good chapter.
B
I read your book all the way through when I read it the first time and I didn't reread it cover to cover this time. I did revisit it, but I didn't reread it, reread the whole thing. But I did at one point read the whole thing. There's clearly a pragmatism to Machiavelli. Would you say that he has something like an ideology or is he just a clear eyed realist?
C
Well, he's a republican. And again, this is something that if you just read the Prince, you're not going to get that. But if you even just read the discourses, which as I say, 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 tyrant or the word tyranny. So if there's a guiding set of political views, whether you call it ideology or not, it's republican. A republican ideology, if you like, is shared power. It's all the people in a city, all the male people. In this case, in Machiavelli's case, he was quite egalitarian. He clearly wanted as broad a section of the male pop situation to be citizens as possible. He says very clearly the key to kind of stabilizing your power is to change the constitution and to have. Give everyone their share. Everyone has to have their share. You might want in the first instance to keep a little bit more for yourself and the rich guys, but in the end everyone's got to have a share.
B
I know you just said he's a republican, he's defending republicanism, but do you think of him as a democratic theorist? Do you think of him as someone who would defend what we call democracy today?
C
If you see the main principle of democracy is also sharing power among all the people equally, which is how I understand democracy? Yeah, 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 tells you you don't want a long term executive. You need to always check power. So anyone who's in a position of like a magistracy, a political office of any kind needs to have very strict limits, needs to be under very strict laws, even stricter laws when they're in the office than they would be as private citizens.
B
Can I pause you for a second? Why is he a critic of people being in power for a long time? Why does he want limits? Term limits?
C
Power corrupts. Simple. He looks at and he's doing this all through Roman history. So he makes his arguments not by just kind of abstract setting that these are the kind of constitutional principles you need. He's saying this is what the Romans did when they got rid of the kings and they started building Republic. They did some really good things and then they did some things not so well. And they had to then kind of go back to the drawing board and rewrite some of the institutions and add some laws that were especially strict for, against people trying to come back and create a dictatorship. So he goes through lots of different, you know, kind of things that the Romans did that are now kind of reflected also in the US Constitution or in, you know, other democracies around the world. Because the founding fathers drew on Machiavelli and others who'd built on him. The rule of law is really super important. If you don't have laws that are kind of constraining everybody and institutions that make sure that the more powerful are not held in check, then you're going to have trouble soon because people are always, always in conflict. This is another thing I think is really more interesting about Machiavelli's view of democracy than a lot of democratic theories you get today. He stresses how much democracy is turbulent. Even in a stable democracy, people are going to be fighting all the time about what kind of, you know, where do they want to go, what kind of values do you want in their rich and poor? You know, how much should people get taxed? That's an eternal problem of democracy. Eternal. And he says you need to have institutions where everyone can debate that. And you know, checks on people getting too powerful also economically.
B
Why did he think rule of law was so perilously fragile?
C
Because people don't want to be equal all the time. And that's just a thing. That's where he's. This is where I would say Machiavelli is a realist. It's this kind of human nature realism that isn't. It's not, you know, good and evil. That's the wrong lens to read Machiavelli. He's going back to this old ancient pre Christian, you know, traditions that say, look, human beings are bloody messy. We're always doing these things that upset the orders we create with all our great ideas. And people don't all want to be equal. You know, you're not going to turn people into angels who are happy just saying, let's all just share power. You've got to have institutions and laws that do that for them. And if you're going to talk about what kind of democracy would help us, you know, get more stability, he thinks it would make sense just to have it up front that we're not idealizing human nature. We're not idealizing what a democracy is. Democracy is like hard work. It's hard work and it means that some people are not going to be happy all the time but fight for it because it's a lot better than the alternatives.
B
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B
If we were looking at Machiavelli for for insights into, well now where do we start? What do you think makes him a useful, relevant guide to understanding contemporary politics, particularly American politics?
C
This is a really Machiavellian moment. If you read the Prince kind of looking not just for those outstanding great Course quotes. But look for the criticisms, and sometimes they're subtle. You start to see that he's often exposing a lot of the stuff that we're seeing today. And Chapter nine in the Prince, where he talks about how you can rise to be the kind of ruler of a republic and how much resistance you might face. And he says that the resistance that you're going to. People might be kind of quite passive at first and not do very much, but at some point, when they see you start to attack the courts especially and the magistrates, that's when you're going to clash. And he says that's when you, as leader, he's playing like, I'm on your side leader. That's when you got to decide, are you going to get really, really tough, or are you going to have to kind of find other ways to kind of soften things up a bit?
B
What would he make of Trump?
C
He would put Trump in two categories. He's got different classifications of prince. He's got the prince of fortune, who's somebody who relies on wealth and big impressions to get ahead and on other people's arms. He would say Trump has a lot of qualities of that because of the wealth question, relying on a massive wealth to help him campaign. But he'd also call him, what Machiavelli has this word, astutes, Astuteness, which doesn't really translate in English because we think of that as a good quality. But he means like calculating, shrewdness. Somebody who has great talent is being able to kind of shrewdly manipulate and find little holes where he can kind of. And people's weaknesses and dissatisfactions and exploit them. And that's what he also thought the Medici were good at. And his analysis of that is that it can cover you for a long time. People will kind of see the good appearances and hope that you would be able to achieve the things that you can. But in the long term, people who do that don't know how to build a solid state. That's what he would say on a domestic front, let's also say, like, if people are interested, chapter 21 is the most Machiavellian chapter, in a way, for our times, because it's about foreign alliances and people's behavior on the international stage. And he's got this example of Ferdinand of Aragon of Spain, who was like, super hyperactive. Like, he comes to power and he's immediately going out and, like, doing things that shock and, you know, horrify everyone. Beating up Jews, beating up Arabs, beating up, doing this and that and taking neighboring countries around him. And Machiavelli kind of is very, very funny in the way he describes his behavior. But then he ends up in the chapter saying, look, if you don't have stable alliances, you're dead. Stable alliances, thick and thin transparency. That is the key to kind of steady long term government.
B
Just going back to Trump.
C
I didn't mention him directly.
B
We're not running away from this, Erica. I'm sorry. No, look, I think there's an unsophisticated way to look at the Trump administration as Machiavellian. There are these lines in the Prince about knowing how to deploy cruelty, knowing when to be ruthless. But to your point, I don't think Machiavelli ever endorses cruelty for cruelty's sake. And this is my personal opinion, but I think with Trump, cruelty is often the point. And that's not really Machiavellian, it's just cruel.
C
Exactly. I wouldn't say Trump is Machiavellian. I mean, quite honestly, since the beginning of the Trump administration, I've often felt like he's getting advice from a lot of young people who haven't really read Machiavelli or put Machiavelli into ChatGPT and got some pointers and got all the wrong ones because the ones that they're picking out that he and his guys are acting on, especially at the beginning, were just so crude. They're crude, but they sound in Machiavellian. But cruelty, you're absolutely right. Cruelty is, I think for me too, it's been the thing that made me most, wow, this is something that's very hard to process. And Machiavelli is very, very clear in the Prince that cruelty is not going to get you anywhere. You're going to get pure hate. So if you think it's ever instrumentally useful to be super cruel, think again.
B
Again. I'm being a little American centric here, but obviously one of the problems of our time is polarization and negative partisanship. Did he have a lot to say about the dangers of partisanship in democracies?
C
Oh, yeah. Oh, yeah. And that was again, something that the Romans talked about a lot. So he's drawing on a whole history of talking about partisan ship. He talks about divisions developing to such a point that it doesn't even really matter that much if the other side is telling the truth or introducing a specific policy that is justifiably going to annoy the other side. It's just that there's so little trust that conflict is bound to escalate. And he calls this kind of thing a sickness that you've got to catch as early as possible, because if you let it grow too big, it's going to be really, really hard to. To pull back.
B
Something I hear a lot in my life from people around me is some version of the argument that, you know, the system is so broken, things are so messed up, we need someone to come in here and smash the system in order to save it. We need political dynamite. Trump and I bring that up because I. Machiavelli says repeatedly that politics requires flexibility and maybe even a little practical ruthlessness in order to get done what has to get done in order to preserve the republic. Do you think he would say that there's real danger in clinging to procedural purity?
C
Yeah, this is a great question, and again, this is one he does address in the discourses quite a lot. And he talks about how the Romans, when their republic started kind of slippery, slidy, you know, going in a wrong way, and great men were coming up and saying, I'll save you, I'll save you. And there were a lot before Julius Caesar, final saved, and then it all went to pot. He really 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 long, excessively long offices, but also creating some emergency institutions where if you really face an emergency, that institution gives somebody more power to take executive action to solve the problem. But that institution, the dictatorship, it was called in Rome. It wasn't like a random dictator can come and then do whatever he wants. It's like this dictator has executive special powers, but he is under strict oversight, very strict oversight by the Senate and the plebs, so that if he steps. Takes one step wrong out and maybe serious punishment. So he was really into being very severe in punishing leaders who took these responsibilities and then abused them.
B
Anytime we do these sorts of philosopher episodes, or looking back on some important thinker, I try to close with some sense of their legacy and what they left us and why they're important still matter. And Machiavelli is such a unique case because his influence is everywhere. I mean, he's really one of the few philosophers that have sort of seeped into the mainstream culture. And, you know, whatever. Whatever you think of him and whatever he may have believed privately, he did lay out a vision of politics that is easily recognizable today. It's our politics in lots of ways. Did he help make the world that way or did he just see it clearly before most others? I don't know. Maybe a bit of both. How do you think about his ultimate legacy?
C
I'm. I mean, you know, obviously, because I think that what he was really trying to do was to criticize exactly the kinds of actions and leaders that we often see as his, his children, you know, his, his brainchildren. And a lot of politicians have, have cited him as their kind of intellectual grandfather and given an intellectual respectability to a lot of positions, which I consider and I think he would consider really, really cheap and amateurish and bad. So I'm confident about this legacy and I think it would be great if more people would maybe in the times we're living in, start to kind of think, hang on now I'm kind of getting this idea that maybe Machiavelli was being kind of cynically funny, but also trying to kind of steer people to criticize what's going on and maybe pick up the prints and find some of these passages and realize that maybe this is a kind of satirical warning signal, a serious satire that's saying, you know, wake up people. This is what they're doing. These are the tricks. But these are also, in a way, he's empowering citizens, I think, also who read the Prince because he's saying these guys are actually vulnerable. I'm spelling out what they do. And I'm also, if you read properly to the end of their story, I'm showing you where they ended up by using these so called hardcore realist methods. So that means that it's not lost. All is not lost. They are vulnerable. Recognize that. Find ways to build up your own power and do it well.
B
We're doing the important work here of setting the record straight. And look, Machiavelli is endlessly interesting and your book Be like the Fox is fantastic. Thanks very much for coming in.
C
Thank you so much for having me.
B
All right, I hope you enjoyed this episode. You know I did. As always, we want to know what you think, so drop us a line at the gray areabox.com or you you can leave us a message on our new voicemail line at 1-800-214-5749 and if you have some time, please go ahead. Rate Review subscribe to the show. This episode was produced by Beth Morrissey, edited by Jorge Just engineered by Christian Ayala Fact Checked by Melissa Hirsch and Alex Overington wrote our theme music. New episodes of the Gray Area Drop Drop on Mondays. Listen and subscribe. The show is part of Vox. Support Vox's journalism by joining our membership program today. Go to Vox.commembers to sign up and if you decide to sign up because of this show, let us know.
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Episode: Machiavelli on how democracies die
Host: Sean Illing
Guest: Erica Benner, political philosopher and Machiavelli scholar
Date: May 26, 2025
This episode of The Gray Area tackles the enduring legacy and misunderstood nature of Niccolò Machiavelli, focusing especially on how his insights illuminate the vulnerabilities and threats facing democracies today. Host Sean Illing is joined by political philosopher Erica Benner, author of Be Like the Fox, who upends the popular image of Machiavelli as a ruthless advisor to tyrants. Instead, she argues Machiavelli was a subtle republican satirist, offering lessons on power, morality, conflict, and institutional decay that remain urgently relevant.
[03:51 - 05:22]
[05:22 - 06:56]
"His main interest is in ancient history...trying to draw from history examples that can serve as cautionary, you know, warnings." — Erica Benner [05:50]
[07:48 - 10:54]
"Reading is like a practice in listening...you need people...to hear the subtleties and be able to judge for themselves." — Erica Benner [09:53]
[12:08 - 13:54]
"We should see human beings not as fundamentally good or evil...let's have rules and laws that help us coexist." — Erica Benner [12:08]
[14:22 - 17:39]
"He's really writing it in a way to kind of expose the ways of tyrants." — Erica Benner [17:09]
[20:21 - 21:37]
[22:22 - 24:37]
"He's deliberately ambiguous...because they're trying to get us to think well." — Erica Benner [24:12]
[25:23 - 26:14]
[27:13 - 29:39]
[30:16 - 33:49]
"He says very clearly the key to kind of stabilizing your power is to change the constitution and to have. Give everyone their share." — Erica Benner [30:16]
[33:54 - 35:19]
"Democracy is like hard work...fight for it because it's a lot better than the alternatives." — Erica Benner [33:54]
[37:02 - 40:17]
[40:23 - 41:49]
[42:04 - 42:45]
"He calls this...a sickness that you've got to catch as early as possible..." — Erica Benner [42:24]
[43:24 - 44:45]
[45:37 - 47:18]
"Maybe this is a kind of satirical warning signal, a serious satire that's saying, 'wake up people.'...All is not lost. They are vulnerable. Recognize that. Find ways to build up your own power and do it well." — Erica Benner [46:54]
Erica Benner’s reading of Machiavelli invites us to shed the caricature of the ruthless power-broker and instead see a satirical, republican critic of tyranny. Machiavelli's works remain a vital warning about how democracies die—through slow erosion of laws, unbridled partisanship, and the failure to see through the cunning manipulations of those who would rule alone. His message? Beware those who seek unchecked power, stay vigilant, and continually renew collective republican institutions.