in: Character, Knowledge of Men, Podcast

• Last updated: September 29, 2021

Podcast #375: The Misunderstood Machiavelli

The ends justify the means. It’s better to be feared than loved. Politics have no relation to morals. 

These are just a few of the maxims the Italian writer Niccolo Machiavelli is well known for. The cynical and duplicitous advice he offered in The Prince has made Machiavelli’s name synonymous with manipulative self-interest and deceitful plays for power.

But what if Machiavelli wrote The Prince not as sincere advice for would-be leaders, but as a work of irony and satire that’s meant to shine a light on the futility of manipulative deception and the need for leaders of virtue. 

That’s the argument my guest makes in her book Be Like the Fox: Machiavelli in His World. Her name is Erica Benner and she’s a professor of political philosophy. Today on the show, Erica and I discuss why Machiavelli is misunderstood and what he actually was trying to accomplish with his writing. Instead of being an advisor for tyrants, Erica argues that Machiavelli was an impassioned supporter of republicanism and spent his life trying to foster republican virtue in Florence. And she argues that if you look at Machiavelli’s life and all of his writing, you’ll find a man who didn’t think politics had no relation to morals, but rather firmly believed the only way for free republics to last for centuries was to develop citizens and leaders of virtue. 

You’re not going to read The Prince the same way after listening to this episode.

Show Highlights

  • Why Erica took it upon herself to redeem one of the most loathed characters in world history 
  • Where did Machiavelli’s poor reputation come from?
  • Is The Prince actually a work of satire and irony?
  • The world that Machiavelli was born into
  • Why it was hard for Machiavelli to get into politics
  • Machiavelli’s military and citizen militia views 
  • The ancient writers who most influenced Machiavelli’s ideas
  • What did Machiavelli mean by “fortune”? 
  • What makes Machiavelli so timeless?
  • How the newcomer should read The Prince and Machiavelli as a whole
  • Why virtue is more important in leadership than nearly any other trait 
  • How to be more like the fox 

Resources/People/Articles Mentioned in Podcast

Book cover of "be like the fox" by Erica Benner.

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Read the Transcript

Brett McKay: Welcome to another edition of The Art of Manliness podcast. The ends justify the means. It’s better to be feared than loved. Politics have no relation to morals. These are just a few of the maxims and ideas the Italian writer Niccolò Machiavelli is well known for, the cynical and duplicative advice he offered in his book The Prince has made Machiavelli’s name synonymous with manipulative, self-interest and deceitful plays for power.

But what if Machiavelli wrote The Prince not as sincere advice for would be tyrant leaders, but as a work of irony and satire that’s meant to shine a light on the futility of manipulative deception and the need for leaders of virtue. That’s the argument my guest makes in her book Be Like the Fox: Machiavelli in His World. Her name is Erica Benner. She’s a professor of political philosophy and today on the show Erica and I discuss why Machiavelli is misunderstood and what he  actually was trying to accomplish with his writing. Instead of being an advisor for tyrants, Erica argues that Machiavelli was an impassioned supporter of Republicanism and spent his life trying to foster Republican virtue in Florence. And she argues that if you look at Machiavelli’s life, in all of his writings, you’ll find a man who didn’t think politics had no relation to morals, but rather firmly believed that the only way for free republics to last for centuries was to develop citizens and readers of virtue.

You’re not going to read The Prince the same way after listening to this episode, after the shows over check out the shownotes at And Erica joins me now by phone.

Erica Benner, welcome to the show.

Erica Benner: Thank you. Thanks for having me.

Brett McKay: So you published a book called Be Like the Fox and it’s sort of … You’re trying to redeem one of the most loathed men in at least political history, Machiavelli. His name’s become synonymous with duplicity, amorality, evilness.

Before we get into that, what … You’ve sort of made a career for yourself writing about Machiavelli, how did you get drawn to him as a subject.

Erica Benner: Yes, this is a question that still puzzles me quite a lot. If anyone had told me about 10 or 12 years ago that I’d end up writing three books about Machiavelli in that space of time, I don’t know what I would have done. I would have been horrified. I mean it was kind of an accident. I was working on something completely different, nationalism in the 18th and 19th century and Machiavelli is somebody who a lot of kind of theorists of nationalism like Rousseau and Hegel would mention a lot in a favorable way.

So I thought, “Well I’ll just have a closer look at Machiavelli and see why he’s so interesting.” Of course, I heard his reputation. I’d been teaching one segment of a course on political history and political theory. Machiavelli had been a character, but I hadn’t read him closely. As soon as I started looking more closely at what he wrote, not just in The Prince, but in his other works like the Discourses, I just realized he was a lot more confusing and interesting than I ever realized.

The main thing was that he contradicted a lot of the things that he’s famous for saying over and over in his works. He’s famous as you said for being a teacher of evil for saying, “It’s better to be feared than loved.” For seeming to promote princes as heads of republics. But when I read closely it looked to me like he wasn’t always saying that, and basically I got hooked on trying to crack him. Trying to kind of work out what’s the bottom line of this confusing, bewildering writer.

Brett McKay: So how did he get the rep? I mean the reputation that he has, as you said favors princes or monarchies over republics. He’s all about political duplicity, and he’s sort of synonymous with that The Prince is a work of satan and he’s evil. Where did that reputation come from?

Erica Benner: Well, at the time that he wrote, he says a lot of very irreverent things about the Catholic Church and also about monarchs. And, at the time that he wrote both of these things were becoming stronger and stronger. And they didn’t like somebody who was going in audaciously, or in some cases very subtly, kind of satirizing them. A lot of other Republican authors at the time, actually, a Republican reader sorry, at the time, thought that Machiavelli was criticizing the Catholic Church and monarchs and they approved of him for doing that. But that’s the main reason at the time why he started being the poster boy for the church and defenders of the, of strong monarchies, of somebody’s whose evil, who ought to be, who’s teaching things that were subversive, not to be avoided.

But the reason why he continues to sound like a teacher of evil is that he really does say some pretty shocking things, if you just gloss through The Prince, and just skim without reading every line very closely.

You do come up with some take away quotes that are pretty horrifying. I mean he says things like, “Sometimes if you’re a ruler, you sometimes have to be prepared to do evil. You have to enter into evil ways in order to protect your state,” and that kind of thing even now, even when we’re not so divested in Catholic and the nautical values. It still worries us.

Brett McKay: So what he was doing, so would it be safe to say that The Prince is sort of work of satire? It’s a very subtle argument for Republicanism?

Erica Benner: That’s what I think and that’s what, and there I’m not claiming to be holy original. I actually was inspired in that reading by early readers like Rousseau and Benedict de Spinoza and others who saw The Prince as a work of very subtle irony. And in some cases of outright satire. I mean the difference is satire is kind of more in your face. I’m making fun of you. And you usually recognize satire when you see it. Irony can be a lot subtler where the victim of an ironic remark doesn’t always kind of realize it or know it. Are you teasing me or not?

And The Prince has a lot of both those things about princes, basically about princes, and subtly between the lines says lots of very positive things about republics while claiming up front, Machiavelli says that at the beginning, “I’m not going to say that much about republics.” But if you keep on reading The Prince really carefully you’ll notice all sorts of things he says and republics always come up a lot better than princes. They’re stronger. They’re much better at fighting wars, and winning them. They’re much better at making the subjects or citizens love their state and feel committed to it, and hold it up through thick and thin. So yes, there is this kind of subtle message all the way through.

Brett McKay: You know what I love? I love the argument because whenever I read The Prince and I looked at some of the advice he was giving, I would look at it and I would think, “If someone followed this advice, this is a recipe for actually diminishing your power,” right? Because there’s only so long that people would be like are going to take that very authoritarian bully like or duplicity that he promotes and they revolt. So when I read that this is actually kind of sly of Machiavelli, he writes this manual that is supposedly for princes or cardinals or whatever. If they follow this advice it will actually lead to their ruin and actually promote republicanism.

Erica Benner: Yeah, I mean and this is kind of an odd thing to me, kind of always puzzled me. Why would someone as intelligent as Machiavelli and he clearly is as soon as I started really reading him closely I was … I’ve been so impressed by the analytical or the sharpness of this guy, and the understanding of human nature he had. Why would someone who’s that intelligent and subtle think that everyone else is so stupid that they just fall for this kind of trick? That princes just so easily just kind of step all over whoever they felt like conquering. He often says, “Yeah, men are easily taken in.”

People, one thing about human beings is they we are easily taken in by snares and traps and that’s the kind of weak point that human beings have unlike foxes. That’s hence the title, Be like the Fox. “Foxes,” he says, “are really good at seeing through snares and that makes it harder to trap them.” Human beings are kind of easy to trap because they’re kind of vulnerable and they’re thinking about their present interest and not very much about the future. But once you’ve got them, if you’re stupid enough to think that you can hold them easily, then you’re going to get, you’re going to have another thing coming.

In The Prince that’s exactly what he says the Prince is about trying to hold republics. You can get them by being sneaky and people are kind of going to let you maybe be taken in by some of your tricks, but once you’ve got people conquered if they’re used to freedom they’re not going to like it and they’re going to fight back and your life will not be fun as a ruler. Your life as being the most powerful man in Italy or wherever is not going to be as rosy as you thought it was going to be.

Brett McKay: So I think to fully understand the context of Machiavelli’s work, not just The Prince but his Discourses, it’s important to at least have a rudimentary understanding of Italian and European politics. I’ll admit when I was reading the book, you had that list of cast of characters at the beginning. I had found myself having to go back over and over because there’s so many different people involved, and people would rise to power, and fall to power, and then they would rise back to power. So what was the political world like that Machiavelli grew up in?

Erica Benner: Yeah, that’s a good … just on that point about … When I first started getting into Machiavelli about 10 years ago, I had no clue about this history. I’m a political philosopher. I didn’t know much about it. I knew nothing about Italian history really and so I completely sympathize with anyone who just says, “Ah, too hard to get everybody straight.”

When you pick up The Prince you also might have that thought, I used to. I’d read The Prince and I’d think, “Oh, I’m not going to really be able to get into this because there are too many names of people that I don’t know.” But I just say it’s really rewarding once you do.

About the context, I mean well there’s this political world in Europe that Machiavelli lived in. The basic fact about it I think is that borders were always changing. There was no territorial stability and states were constantly expanding and trying to take bits of other states. So it was very unstable in that sense, constantly in upheaval. The other fact about this is most of this kind of expansion was happening with big monarchies. So there were kings and queens who were hereditary trying to take bits of each other’s states, and the easiest way to do that was just to marry somebody from another royal family and then you could make a claim on their state.

Now Machiavelli and Republicans like him thought this is a very … this is not a recipe for stability in Europe. If you want to have the more stable kind of set up wouldn’t it be better to have not ruling families running states, but to have people running them on a kind of more permanent basis. That was one of the good arguments that they had for republics.

A specific context of Florence where it was also upheaval, because there was a constant struggle that had been going on for about 80 yeas when Machiavelli was born between like the old republic Florence was, had unusually in Europe, very unusually a Republican Constitution based on a white male franchise.

But the very powerful families, the Medici, a banking family had cropped up in the last 60 or 70 years before Machiavelli was born trying to take control of the state. And they come to dominate Florence even though Florence remained in name a Republic, in fact it was run like a principality of the Medici family.

So Machiavelli came into the scene at this crucial point when there was this life and death struggle for this old vulnerable proud republic.

The only one really of its kind in Europe at the time, which had a lot of people that by that time sort of saying, “Wouldn’t it be better for Florence if we just went the way of everyone else and became a monarchy? I mean the big powers were all monarchies, France, Spain, Habsburg Empire, England. Why shouldn’t we try this form of a monarchy? Wouldn’t that make us stronger?”

And Machiavelli was one of those rebellious people who said, “No, I don’t think so. I don’t think this is best for Florence and I don’t think it’s best for Europe.”

Brett McKay: Well despite that opposition to monarchy he still played the political games, even when there was sort of a monarchy put in place effectively. He went along with it and tried to find ways he could change things from within.

Erica Benner: Yeah, that’s right. And that wasn’t unusual at the time because if you think about it. I mean what happened … Machiavelli worked as a civil servant in a short period when Florence was in a very strong.

There was a popular republic set up, and the Medici, the princes, had been kicked out for a while. When they came back, when Machiavelli was in his 40’s, he did try to work with them but it was, this is a tiny, tiny city where everyone knows each other, everyone of a certain class is friends with each other. And somebody like Machiavelli couldn’t go and be invisible. There was just no way he could just go and hide because the Medici Princes had already singled him out as a troublemaker. He was somebody who was known to have supported the republics that they had expelled. And the only way for him to kind of live, to have employment of any kind was to try to work for them. So he did try, he failed for a long time of getting any notice from them at all. So he had to make a living in other ways.

But yeah, he did keep trying to get back into government because A, that was the only way he could make a living. And B, he wanted to influence politics. He still wanted to try to steer his country back into the form of a republic.

Brett McKay: But getting into politics was hard for him because of his family background, correct?

Erica Benner: Yes, I mean he … Well he and his father and brothers were actually not allowed to be full citizens. They had the status of people who could participate as civil servants in a kind of bureaucratic level of the state. But they couldn’t vote. They couldn’t run for public office. So Machiavelli’s posts when he had them were not elected posts, and they were not the kind of posts that he had as magistrates. They were kind of civil servant appointments of the lowest status so that’s what he was allowed to have in his family, because of his family. His father had been a tax debtor. He owed money to the state. That’s the main reason he and his sons could not be full citizens.

But there’s also a kind of darker story behind that, that kind of Machiavelli’s father’s cousins had been involved in a coup attempt against the Medici before Machiavelli was born. And this put them on the blacklist and made it much harder for the Machiavelli family to be trusted as long as the Medici Princes were in power.

Brett McKay: Yeah, the coups, the assassinations. As I was reading, this is like Godfather stuff, right? I think there was one instance they were at a church I forget what it was, but they were escorting this guy and they just stabbed him with a dagger and he died there in the church.

Erica Benner: Yeah, yeah, let me just say the kind of reputation of the Renaissance and Italian politics at the time for being so much worse than it is today and being so bloody. I think you can overstate it. Because yeah, there was this Pazzi conspiracy and I think that, that was headed by the pope. That was somebody sent by the pope to make trouble for the Medici ruling family. The popes were especially bad at this and that’s one reason why the church didn’t like Machiavelli because he brought this out. He talks about this in his writings.

But their every day politics, especially in Florence was actually run under the rule of law as much as possible. They really, when the Medici were not in power there were very strict rules about who could and what happened to whom. Assassination was extremely rare. When people were indicted for treason the law said, the law actually gave rather soft penalties. They were going to be sent into exile rather than be killed.

So yeah, it’s a bloody world, but it’s also a world where there were a lot of people struggling to hold up the rule of law and to apply very ancient and clear cut rules to kind of deal with political conflicts, and this is also the kind of thing Machiavelli was fighting to uphold something people don’t realize. If you read his writings all the way through this is a man who cares about political order and order based on clear rules. Clear and equal transparent rules, more than anything. And that’s something that the reputation of Machiavelli doesn’t let you in on at all. It’s all dark and yeah very-

Brett McKay: I was going to say how did he go about doing that, right? Like promoting that end? Was he like the ends justify the means that he’d use conniving and duplicity in order to promote the rule of law in this sort of weird political world that he existed in? Or was he pretty straight forward, a straight shooter?

Erica Benner: Well yeah, and again this depends on when. Because there’s Machiavelli when he was in the anti-Medici Republic, the republic that had thrown these Medici Princes out and this lasted for 15 years. And that’s the time when Machiavelli was a civil servant and actually politically active. Under that sort of system of government he was really promoting the rule of law very hard and working with other citizens who did the same. And it was easier for them because the Medici were out of the picture for a while.

But then when the Medici had their crew and came back that’s when Machiavelli had to become cunning in a way. But his cunning wasn’t political cunning in the sense that he was going out and kind of trying to plot and scheme and stab somebody in the back. His scheming took the form of writing because he was no longer allowed to take part in politics. The Medici banned him from political activity completely. So what does he do? He goes off and just starts writing, and writing, and writing.

And he writes The Prince first of all, which that I think is a kind of subtle critique of Medici power, and also an attempt to kind of warn other citizens about how princes actually operate.A lot of the stuff he says that we take as advice to princes, what if he’s actually just saying, “Look this is what princes do to get into power. A lot of it isn’t very nice, be careful,” you know? “Be careful what you wish for if you’re wishing for princes because this is what you’re going to end up getting,” you know? And so he’s writing in this cunning way because it wasn’t actually safe for him to say outright, you know ? The princes and the pope are lying, cheating conceiving self-seekers that free people need to be careful about.

Brett McKay: Was Machiavelli ever able to implement some of his reforms that he thought would help bolster republicanism in Florence.

Erica Benner: Yes, I mean this is one of his big dreams from the time he enters political office was to create a citizen militia to replace the mercenary system of military defenses that most Italian states had. In most Italian states they brought foreign soldiers from somewhere else. France, Spain, wherever, to fight their battles for them. And the battles were very anemic because people were not … The soldiers didn’t like to, they didn’t want to lose their life because they’re not losing their life for their own country. They’re just out there being paid, hired fighters, so because of that the wars ended up being really fast, you know, step-step-step. “I’m around your enemy try not to actually hurt them too much, ” and then hope that there’s going to be a stalemate and they’re call it off.

And Machiavelli was up for a full blooded battle by ideally, by people who really, really cared about the outcome of the battle. And that was going to be for him citizens whose lives were at stake, and whose freedom was at stake in a territorial war. So he thought the best way to defend Florence was to get on citizens, ordinary people in the countryside, in the city, and get them to fight their own battles. Now the aristocrats in Florence didn’t like this idea at all because they were afraid that if you armed the ordinary people they might use the arms against us.

The Machiavelli’s just tiredly, tirelessly fought for this citizen militia idea and worked with a lot of high up political people to get it realized and it came to pass while he was holding his civil service post and it worked. They fought a war against a city, Peza, that had left the Florentine cycle, won Peza back. And Machiavelli was herald by a lot of his friends as being the kind of author of this great concept. Unfortunately, a couple of years later when the Medici came back it’s the first reform that they basically obliterated. They just wiped it off the map and that was the end of Machiavelli’s dream.

Brett McKay: Yeah, I think that’s a perfect example of Machiavelli’s actions contradicting advise he gives in The Prince. One of the things that people always point out in The Prince. A piece of advice is that a prince, one of the first things they should do is disarm the subjects. But there his actions, Machiavelli’s like, “No, I’m going to arm the subjects, that is how you defend a republic.”

Erica Benner: Absolutely, and this is the key I mean that’s the one point where I think all Machiavelli scholars agree that this militia was the heart and soul of Machiavelli’s project. We disagree about lots of other things, but everyone agrees on that. And like you just said I don’t understand why if they realize how ready he was to arm the citizens and then fight.

He also says very clearly in The Prince, if you want to arm the citizens you have to actually give them some political power too. You can’t just give them arms and then leave them politically powerless because then of course they’re not going to like you. And yeah, then the threat is going to be definitely might use the arms against you, so if you want to be of faith in arming them. You have to give them more political power. You have to give them employment. Economic employment that gives them some sense of dignity. And he actually uses this militia, not just as a way of trying to find better military defenses, but also as a kind of argument for making Florence into a deeper, more democratic republic where people actually have more economic equality and more sense of mutual respect. That’s a pretty strong argument against the idea that he thinks principalities are the best way to go.

Brett McKay: And Machiavelli was influenced substantially by, significantly by ancient writers from Greece and Rome. Were there any writers in particular that influenced his ideas about democracy, republics etc.

Erica Benner: Yeah, I mean the writer he mentions most often is the historian Livy, Titus Livy. And Livy wrote this massive, massive history of Rome at the end of the Roman Republic just when the republic had collapsed after years of being corrupt and been replaced with emperors. Livy regretted this. He was very sorrowful and he writes this big long history of the republic and how great it had been in the past. Tries to diagnose the reasons why the republic fell. And Machiavelli mentions him a lot as a force of lessons on how you can save republics from internal decay and internal corruption that makes themselves combust. Tacitus is another Roman author he uses a lot. Tacitus was a very sly, subtle, subtle, critic of the Roman Empire when he lived under it. He writes very subtle critiques without quite showing his cards, so it’s hard to kind of … Nobody could really easily persecute him because he didn’t … You can’t really pin down what he’s really saying sometimes. I think Machiavelli was very influenced by his style of writing.

Brett McKay: And yeah, you talked about the book this is when the printing press was first invented at the same time. So he had access like … How does he make trips just to buy these books for his own personal library?

Erica Benner: Yeah that was actually Machiavelli’s dad who was a really interesting guy. That was Machiavelli’s dad who got … He’s the one who … He didn’t have a full time job because he was a very highly trained and respected lawyer by education. He hardly ever practiced law, probably because he thought the Medici system he was in was too corrupt, or they didn’t want him to practice.

But what he did do was spend a lot of time reading. And he offered to copy out a whole index of Livy’s many, many works if he could get the book for free from his friend the printer. And so this is the book, the great first 10 books of Livy that Machiavelli wrote his Discourses about. In his book, the Discourses actually called The Discourses on Livy.

And he uses Livy as his main inspiration talking about how … And the themes are again, the themes that are so topical for us today too. It’s how do great republics decline? What goes wrong? And how can you … He was looking back as Livy was on the glorious history of republics that never the less come to end and sometimes by their own hands, right? By their own mistakes and so I think Machiavelli’s main point was trying to teach future generations as well as Florentine’s how to see the dangers before they get too big. How to try to protect your freedoms, your good institutions that we tend to take so much for granted. And to spot the kind of diffuses before they become lethal.

Brett McKay: So another theme in Machiavelli’s work, a big one is this idea of fortune. And I’ve heard people say that The Prince is a sort of a guide book on how to master fortune. First, what did Machiavelli and his contemporaries mean by fortunes? I think we use that word differently than people say in the Renaissance did.

Erica Benner: Yeah, I mean fortune is basically, it’s a word that signifies the unpredictable in human life. What is incalculable, unpredictable. What you cannot entirely control. That’s what it means for Machiavelli and for the ancients that he is drawing on. I mean it’s a concept that you find in all the ancient Greek, Roman writers too. Now the thing about talking about fortune being something you need to master, the thing about fortune the way I just defined it is you can’t master it. I mean by definition fortune is something that is not masterable. So when modern people say, “Yeah Machiavelli’s teaching you how to master fortune.”

“Uh-huh. No he’s not.” He’s teaching you, first of all remember that fortune is not something you can master it’s, there’s always going to be some unpredictability in life and politics, whatever that might be. So get used to it. Bite the bullet and understand that.

Second point is, if you decide that you’re going to try to master fortune and waste a lot of time at that rather pointless end, you’re not going to get very far because fortune is unreliable. You might actually manage to get a good string of luck and to think, “Okay now I’m really getting this. I’ve got, I’m controlling things now. By one way or another I’ve got it.” You get too confident. You start to rely on luck and that’s going to make you work a lot less hard at what you actually need to do to make a stable state, or to consolidate your own personal power.

Fortune is unreliable and you’ll be surprised if you think that you’re doing really, really well. And you find a lot of politicians who to everyone’s surprise seem to be kind of flying really high to massive successes. Whether it’s Napoleon, or Cesare Borgia in Machiavelli’s own time or many people we don’t have to name in our own time. Why is this happening? This is amazing. Well Machiavelli says, “If they’re not doing the things you need to do in order to consolidate your power, to consolidate power takes this tool, virtue.” It’s how it’s translated. And virtue is hard work. That’s one of the main qualities of virtue for Machiavelli. It’s very hard work. Looking way ahead, foresight. Knowing your own limits. Getting friends, allies, because you can never do everything all by yourself. So you need stable friends, not just fair weather ones. And getting this kind of building political orders and institutions and power bases in those ways is a much better guarantee than relying on fortune.

Brett McKay: Yeah, as you said how in the book he uses Borgia right as an example. It was sort of a subtle dig. It makes it sound like when he wrote that he was praising this guy, but if you read between the lines what Machiavelli was saying, “This guy is only in power because he just got lucky.”

Erica Benner: Yeah, I mean, did you get that reading it? Because it’s hard. This is one of the hardest bits of Machiavelli and you’ll get really, really excellent life long Machiavelli scholars who still don’t see that. And others who do, but nowadays not so many. But there is this kind of … It’s a hard thing to do wonderful satire. He uses all these very good words for Cesare Borgia. He says, “I would always present him as a model to be imitated by anyone who wants to win power through fortune.”

So here it is, here are these wonderful things he did. But you go it, right? As you would say, I would hold him up as an example to anyone who wants to get power through fortune but a few pages only Machiavelli has just told us, he says in black and white, “If you want to get power and hold it, fortune is not the way to go. Don’t rely on fortune. Rely on virtue, which is the opposite of fortune because fortune is-

Brett McKay: Yeah.

Erica Benner: Fortune is easy. Virtue is hard work. Fortune is quick and fast, virtue is long and hard.” You know these are all classical themes that Machiavelli just saying on again.

But yeah he does seem to praise Cesare Borgia, but between the lines he tells you what how did Cesare get to power? It’s not precisely just luck because fortune here, Machiavelli breaks it down being a very concrete minded guy, he says, “Fortune is money.” I’ve got a lot of money and so I can buy my way to power. It is other people’s weaknesses. Oh good, I’m an opportunist. I see a chance to jump in there and make myself powerful because somebody else is in trouble. And fortune is relying on other people’s strengths and resources, not my own talents and hard work.

And he shows you in this little chapter about Cesare, exactly how he operates. And he never stops working with money and depending on fortune for your money, and other people’s weaknesses, and other people’s resources. So that’s what fortune is and he leaves it to the reader. Does the reader get it? If they’re not gonna get it, then you can read Machiavelli The Prince and think, “Do I get this or not?” Well if you don’t get it, then you might try to imitate Cesare, and good luck to you. You’ll end up in the same way he did. Flying really high, everyone being in a terror of Central Italy for a long time and then within a few years, crash, fall. His empire breaks up and he’s dead

Brett McKay: Right. That was one of my favorite take aways from reading your book and the critique of Machiavelli may … Because I think even if you’re not in a position of power that being fooled by fortune can lead to a lot of heartache. Sometimes you think you’re doing great and it’s all you, but it’s really not. And then when something bad happens because it’s just fortune, you feel terrible you say, “Well this is my fault.” No, it’s not entirely your fault, there’s an element of fortune there. I thought that was a really, really …. that’s the one thing I’ve been thinking about since I finished reading our book.

Erica Benner: Well you see a much more virtuous character than Cesare because Cesare Borgia contrary to saying, “Oh I fell, that must be my own fault.” He did the opposite he said, “Oh I fell, that’s everybody’s else’s fault but mine.” That’s what a really fortune dependent character does. They blame everybody but themselves and we won’t mention any politicians who do that. We don’t know any like that. But that’s Cesare. And, obviously you’re a good person because you said you blame yourself.

Brett McKay: Yeah, so focus on virtue rather than fortune, or luck, or whatever you want to call it. That is a key to life and I guess the challenge to is assessing now what is fortune and what is based on your own virtue, that’s another challenge.

Erica Benner: Yes. That is and that’s something that again Machiavelli following his classical orders, he doesn’t want to give you simple answers. He doesn’t want to do like a modern text book would do. And say, “Here’s fortune. Here’s virtue. Go and pass a test telling us what’s what.”

He actually wants, he’s kind of mixing these things up in his examples of individuals and invites readers to say for themselves, “Where is Cesare’s virtues here? Why is he being too reliant on fortune?” Because that’s the only way in practice ordinary citizens can start to judge their political leaders as well. You see it on paper. You see these examples of somebody and you judge for yourself what’s working, and what’s not, and why. And then you can go out into the political arena and see how people are operating there, and judge for yourself

Brett McKay: He wrote his stuff, The Prince, the Discourse in Livy, over 500 years ago. People are still reading it. What do you think it is about Machiavelli that’s so timeless?

Erica Benner: Well I think the simplest level, it looks so simple and clear. His writing style on the surface looks just so beautifully readable and simple. It isn’t once you look more closely like we said. And it’s got these wonderful maxims that just stick out but also resonates so strongly. Whether the maxims are the kind of nasty Machiavelli ones about salt, conceiving politicians. Or whether it’s his more uplifting points about republics and how to save them from decline, these are problems that are always with us. Politics and human nature as he says don’t change as long as human beings are human beings there’s no real progress in lets say the way that human beings function in their relationships with each other, which is what politics is. We might get progress from medical, science, or more knowledge of the broader universe, but this is one area where things don’t change much and Machiavelli really, he’s truthful. He’s intriguing because it’s not always clear what he’s getting at. He hits the nail on the head.

Brett McKay: Yeah, I like, I love that portrait, that famous portrait of Machiavelli where he’s sort of got this sly smile on him. And after reading this is … His whole work is sort of a work of slyness and I like that picture it makes me wonder what he was thinking-

Erica Benner: Yeah.

Brett McKay: … when he had that portrait done of himself.

Erica Benner: Yeah, but don’t you think he looks, he looks like, it’s a kinder kind of-

Brett McKay: Right.

Erica Benner: … a kind sort of slyness. It’s not, it’s slyness not in the interest of, “Oh, let’s just get ahead-

Brett McKay: Exactly.

Erica Benner: … which is what people think. It’s more a slyness in, “Hang on, let’s defend ourselves and better all of us.” 

Brett McKay: Right.

Erica Benner: “Not just me. Not just me, me, me, but all of us.”

Brett McKay: That’s all of us. So my last question is how would you … What advice would you give to people who want to revisit The Prince and they want to look at it with fresh eyes. So they see these insights into how he’s promoting virtue. How he was promoting freedom, and republicanism, and getting over that idea that he’s just showing you how to be the conceiving con artist.

Erica Benner: Yeah, I mean first I’d say, well first as a rule of thumb, realize that it’s not as easy as it looks. It’s not as straight forward as it looks. I think that’s pretty important because it can be seductively deceptively clear Machiavelli prose. Realize it’s harder, and then I would say although I’m in favor of reading books like The Prince all the way through. Maybe counter balance the reputation that is in all of our heads about Machiavelli, counter balance it by doing the opposite of what most people do reading The Prince. Most people go straight for the kind of stand out, jump off the page, Machiavelli quotations. And say okay, “That’s Machiavelli,” the rest they kind of skim or at least I used to do that when I, before I really got into him. Instead of that, look for the things where he talks about republics, starting with and when he mentions the word freedom or republics go for it and really look at what he’s saying and feel, feel the passion even.

In chapter five of The Prince which is where he first really talks about republics, they just burst on the scene in a heated way. Everything that’s happened before it in the first four chapter is cold princes, cold. This is how they operate. Suddenly there’s a public and what are they doing? They’re resisting the prince. They’re resisting very hard and then they can raise absolutely hell for the prince.

And I would really go for that, and then go to the Discourses too and look at a couple of chapters where he does the same thing. Where he talks about republics in ways that’s very hard to make you, to resist the thought that hang on he’s so … This is somebody whose not just saying that republics are sometimes the best form of government pragmatically speaking. This is someone that believes it as a matter of deep principal for human beings at all times, this is the best way to go and not princes.

Brett McKay: And the other thing I’ve done is look, highlight the word fortune. That’s so I’ve been on the look out for that. That-

Erica Benner: Fortune? Oh, but does that really help? Does that help you get to republic in Machiavelli ?

Brett McKay: No, not really but the idea that virtue is more important, right? Don’t just rely on sort of like the Borgia guy, like don’t be like him. He might, when he mentions fortune it doesn’t mean it’s really a good thing.

Erica Benner: Yeah, yeah, yeah, yeah, good point. Yeah, that’s … Highlighting, I mean my mind, if I could show you some of my Machiavelli texts the highlights … I’ve got highlights and highlights of all kinds of words that stick out. If you want to get a nice little guide to how I read The Prince, I’ve got a whole book on Machiavelli The Prince, right? It’s kind of chapter by chapter, and I even set out at the beginning a list of keywords and how he plays with them, so there’s that book too which is, it’s called Machiavelli’s The Prince: A New Reading. So not to promote my other books-

Brett McKay: No that’s-

Erica Benner: But it’s at least it’s my way of … It shows how I tried to come to terms with all these difficulties in a very, I think honest way. So that’s controversial but Machiavelli’s one of those authors who is always going that’s be controversial because that’s just inherent in the way he writes. He writes in a tricky way. I don’t think he wants readers to say, “Oh this is like a good lecture where we can always says professor Machiavelli tell us how to do X and Y,” that’s the wrong way to read him. The right way is he’s testing, he’s testing our political intelligence by giving us examples that are confusing, or you might judge in different ways, and I think that’s the starting point. If anyone tells you Machiavelli is so easy and so simple. You know they haven’t really engaged with him.

Brett McKay: So you have to Be Like The Fox to catch a fox?

Erica Benner: Yeah. And then you learn to be a fox, but a good kind of fox, not one whose trying to get one over somebody else, but someone whose trying to do what Machiavelli says foxes do in The Prince. What he praises them for is seeing through snares. They see through traps. They don’t try to cheat other people. He’s very curious of animals, other animals non human animals generally are not as cunning. We’re not, they’re not cunning in the same way. They’re a lot more, there’s a lot you can learn from them without taking on these human defects that we’ve projected onto foxes and not hens.

Brett McKay: Yeah, so Erica this has been a great conversation. Is there someplace people can go to learn more about your work?

Erica Benner: Well since you ask, I’ve just been struggling with setting up a new personal website. It doesn’t seem to be really showing yet, but I hope it will be soon.

Brett McKay: Fantastic. Well Erica Benner, thank you so much for your time. It’s been a pleasure.

Erica Benner: Thanks, Brett.

Brett McKay: My guest today was Erica Benner. She’s the author of the book Be Like The Fox. It’s available on and in bookstores everywhere. Also check out our shownotes at And find links to resources where you can delve deeper into this topic.

Well that wraps up another edition of The Art of Manliness podcast. For more manly tips and advice make sure you check out the Art of Manliness website at If you enjoyed the podcast and got something out of it, I’d appreciate if you take one minute to give a review on iTunes or Stitcher, it helps out a lot. And if you’ve done that already, thank you. Please share this show with your friends. Word of mouth is how this show rose.

As always thank you for your continued support and until next time, this is Brett McKay telling you to stay manly.

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