Leadership Lessons From Alexander the Great, Hannibal, and Caesar

Alexander the Great, Hannibal, and Julius Caesar. Three of the greatest generals of antiquity. But what made them great and what can we learn from them about leadership? My guest explores those questions in his book Masters of Command: Alexander, Hannibal, Caesar, and the Genius of Leadership. His name is Barry Strauss and he’s a classicist and military historian at Cornell University. Today on the show we discuss the traits all three of these men possessed that made them such military geniuses, including audacity, ambition, and a little luck. Barry walks us through the five stages of war that each of these legendary commanders navigated and where each thrived and floundered.

Barry then makes the case that while Alexander, Hannibal, and Caesar each experienced success in the short-term, in the long run all of them failed to achieve their ultimate aims because they became victims of their own success. We end our conversation discussing what these commanders’ shortcomings can teach modern leaders in any kind of field, and whether it’s possible to be both a bold visionary leader and a great manager.

Show Highlights

Why Barry decided to focus on Alexander, Hannibal, and Caesar
How each of these men rose to great power
Why Alexander the Great decided to take on the Persian Empire
What was Hannibal’s aim in taking on Rome?
Why Caesar goes to war agains his own country
The mixture of personal ambition and grand national aims in each of these men
The personal and military strengths of each
The incredible role luck in the careers of Alexander, Hannibal, and Caesar
The 5 stages of war
Common problems of conquerors
How each of these conquerors ended up floundering in the end
Is it possible to have ambition and great leadership skills, and also know when to stop?
How these ideas can carry over into modern realms

Resources/People/Articles Mentioned in Podcast

Connect With Barry

Barry’s website

Barry’s podcast

Barry on Twitter

Listen to the Podcast! (And don’t forget to leave us a review!)

Available-on-stitcher.

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Recorded on ClearCast.io

Podcast Sponsors

Wrangler. Whether you ride a bike, a bronc, or a skateboard, Wrangler jeans are for you. Visit wrangler.com.

Indochino. Every man needs at least one great suit in their closet. Indochino offers custom, made-to-measure suits for department store prices. Use code “manliness” at checkout to get a premium suit for just $359. Plus, shipping is free.

Shapr. Take networking from awkward to awesome with Shapr: the number one professional networking platform that uses your experience, interests, and goals to help you make the right connections.

Click here to see a full list of our podcast sponsors.

Read the Transcript

Brett McKay: Welcome to another edition of The Art of Manliness Podcast. Alexander the Great, Hannibal, and Julius Caesar, three of the greatest generals of antiquity, but what made them great, and what can we learn from them about leadership? My guest explores these questions in his book Masters of Command: Alexander, Hannibal, Caesar, and the Genius of Leadership. His name is Barry Strauss, and he’s a classicist and military historian at Cornell University. Today on the show, we discuss the traits all three of these men possessed that made them such great military leaders, including audacity, ambition, and a little bit of luck.

Barry walks us through the five stages of war that each of these legendary commanders navigated and where each thrived and floundered. Barry then makes the case that while Alexander, Hannibal, and Caesar each experienced success in the short term, in the long run, all of them failed to achieve their ultimate aims because they became victims of their own success. We end our conversation discussing what these commanders’ shortcomings can teach modern leaders in any kind of field, and whether it’s possible to be both a bold visionary leader and a great manager. After the show’s over, check out our show notes at aom.is/mastersofcommand.

Barry Strauss, welcome to the show.

Barry Strauss: Thank you, great to be here.

Brett McKay: So you are a classicist, a military historian, and you’ve written this book, Masters of Command: Alexander, Hannibal, Caesar, and the Genius of Leadership. And you use these guys, these great generals, to explore what makes a great military leader. How did you decide on these three guys and compare and contrast them?

Barry Strauss: Well, it was kind of easy to choose them. They really are the big three of ancient military history, and most famous generals, I would say, and also, they come as a set. Hannibal looked back on Alexander as his role model, and so did Caesar. Each of them, in a way, measured himself against Alexander, so the three of them really are a set of great generals. They’re very famous, they have fantastic authors write about them from the ancient world, they’re remembered today, they still influence generals today, soldiers, they’re still studied. So it was kind of easy to choose them.

Brett McKay: Another thing that you did really well is you … As you compared and contrast them, their military careers, there was a pattern to it that was very similar amongst all three of them.

Barry Strauss: Yes, so I chose them because each of them was a risk-taker. Each of them loved mobile warfare. Each of them started a war against an enemy who, in principle, was unbeatable. The enemy in each case outnumbered them greatly, had more financial resources, and had a much greater navy. They either had no navy or a much smaller navy. And yet each of them defeated his enemy. In Hannibal’s case, of course, in the end he lost, but he won some spectacular victories. Alexander and Caesar did indeed defeat his enemy. And each of them, in spite of great military success and a certain amount of political success, none of the three of them was able to achieve his final goal. None of the three of them was able to achieve the settlement that he wanted, so there’s something sad about them as well.

Brett McKay: And we’ll get into why they didn’t achieve their final goal, but let’s kind of do just some rough thumbnail sketches of these guys, because we’ve heard lots about them. I mean, they’re sort of icons of Western history, Western culture.

Barry Strauss: Right.

Brett McKay: We have cultural references to them, you know, Caesar crossing the Rubicon, Hannibal, you know, the elephants through the Alps.

Barry Strauss: Right.

Brett McKay: So let’s talk about Alexander. All these guys were risk-takers, but what else about Alexander that often gets overlooked about him?

Barry Strauss: Alexander was a king, and he was the son of a great conqueror. His father was Philip of Macedon, the man who really put Macedon on the map, and took Macedon from being kind of a wreck, a messed-up, chaotic state, but a lot of potential, on the outside of the Greek world. He brought it to the center, he unified it, he created a new military system, conquered all of the Greek city-states, and prepared Macedon for what he saw as his life’s work, which is to be going to war against the Persian Empire, this giant, but … Giant to the east of Macedon, but one that seemed to have been past its prime.

So Alexander inherited this as a young man, at the age of 20, when his father was assassinated, and not many people were convinced that Alexander was up to the task and could equal what the great man had done. But in fact, he was every bit up to the task, and did what his father wanted to do, and then some. He’d been prepared all his life for war, he’d already commanded the Macedonian cavalry in a battle when he was 18, and now he showed himself to be every inch a king, and ready to take his country to the next step. So he had a great preparation.

Also, his father had prepared him all the way; he had given him the greatest tutor imaginable. His tutor was none other than Aristotle, the premier philosopher of the ancient world. Alexander was highly intelligent. His mother was a stormy, brilliant woman named Olympias, who convinced her son that he was unstoppable. He believed that through his mother, Alexander believed that he was descended from none other than the Greek hero Achilles, the hero of epic. Alexander took Achilles as his role model in a way. In some ways, a great role model; Achilles was Greece’s greatest warrior and the hero of its most important literary work, the Iliad. But Achilles was also a tragic figure, somebody who died young and never succeeded in conquering Troy, so a somewhat paradoxical choice on Alexander’s part. But like Achilles, he was geared for greatness.

Brett McKay: Why did he … Why did his father, and why did he decide to conquer the Persians? Like, what was it that they hoped would happen after they conquered the Persians? And then, not only did Alexander want to conquer the Persians, but he also wanted to go on and conquer the rest of Asia. Why?

Barry Strauss: So, the Persian Empire was the greatest empire that … Not only the Greek world, but the world period, the greatest empire that the world had ever seen. And it controlled an empire that stretched about 3,000 miles, from what is nowadays western Turkey all the way to what is nowadays the Indo-Pakistani border, so enormous empire, enormous wealth, enormous power. But it was weak, you know, it had had a series of revolts over decades. A Greek mercenary army had fought its way through the empire, defeated a Persian army, and made its way home successfully. The Persians, by the same token, had interfered in Greek wars over the decades as well, so the two sides, the Greeks and the Persians, had been at war with each other.

And for Philip and Alexander, it just looked like it was ripe for the taking. They believed that they could conquer this empire, or at least part of it, and bring it under their control. If you wanted to look at a more noble motive, well, the western part of the Persian Empire, much of it consisted of Greek speakers who were under Persian control, and Philip, Alexander, the Macedonians and the Greeks could have thought, “Well, we can liberate these people from the Persians.” It’s a bit more complicated, because some of them were perfectly happy under Persian rule and didn’t want to be liberated, and some of the Greeks felt that they were the oppressed ones, because now the Macedonians controlled them.

But mostly, it was the power, the wealth, the glory, the possibility of expanding, being a great conqueror. This was something that, for kings in the ancient world, was a no-brainer. Conquest, you wanted to be a great conqueror.

Brett McKay: Okay, and that will come back also to bite him in the butt, possibly, later on. We’ll talk about that. But let’s move on to Hannibal. Hannibal’s an interesting character because he is from Carthage, and a lot of people, they know of Carthage in the ancient world, but they don’t know really what role it played in the ancient world. It’s in Africa.

Barry Strauss: Right.

Brett McKay: So tell us about Hannibal and what he was trying to do.

Barry Strauss: Like Alexander, Hannibal was the son of a great general. His father, Hamilcar Barca, was Carthage’s leading commander. He successfully commanded the Carthaginian forces in the First Punic War; although the Carthaginians lost that war to Rome, Hamilcar himself was undefeated. Then he came back to North Africa and put down a rebellion by the mercenary troops in Carthage’s army, and then he left Carthage, left North Africa, went to Spain, and carved out a new empire for Carthage in the south of Spain.

He brought his young son, Hannibal, with him to Spain, and raised him to be a great soldier. He also raised him to hate Rome. There’s a story, we don’t know if it’s true or legend, that at the age of nine, his father made Hannibal swear on an altar to not rest until he won revenge on Rome. Carthage and Rome were the two greatest military and political powers of the central Mediterranean, and they clashed in the middle of the third century BC in a war for control of the island of Sicily. For centuries, Carthage had controlled the western part of Sicily and was eager to take over the eastern part. Rome jumped into the Sicilian waters in the middle of the third century, and decided to try to push Carthage out of Sicily. It was a very audacious thing to do, but the Romans succeeded in a war that lasted a generation. They finally succeeded by winning this war on sea, and as I said, Hamilcar, Hannibal’s father, bounced back, undefeated himself in this war, and bounced back by winning Carthage a new empire in the south of Spain.

Now, he’s killed in battle when Hannibal’s still a young man. He’s succeeded, replaced by Hannibal’s brother-in-law. When Hannibal’s brother-in-law in turn is killed, the army turns to Hannibal as their new commander, and Hannibal has been groomed by his father to be a great general, and he himself is a brilliant, talented, charismatic, visionary leader who is utterly up to the task.

Brett McKay: Give us some background here, or some context. So this was Rome, they were fighting Rome when Rome was a republic, correct?

Barry Strauss: Yes.

Brett McKay: Okay, and this was not too long after Alexander. I mean, one thing that was interesting is that these guys were within just a few hundred years of each other.

Barry Strauss: Yeah, so Alexander dies in 323 BC, and Hannibal takes … Hannibal’s born in 247 BC, so less than a century later. The first war between the Roman Republic and the Carthaginian Republic, they’re both republics, takes place in the years 264 to 241 BC, and then in 218, the new war between Rome and Hannibal, Second Punic War, as it’s called, or Hannibal’s War, as it’s sometimes called. That’s when that war breaks out, so a little over a century after the death of Alexander.

Brett McKay: And what was Hannibal’s military aim by taking on the Romans?

Barry Strauss: Hannibal’s military aim was twofold. First of all, the Romans threatened Carthage’s new empire in Spain. Hannibal wanted to secure that empire and get the Romans out of his hair. Secondly, he wanted to destroy the Roman confederacy. Rome’s power rested on its alliance system in central Italy; Carthage’s power rested on its alliance system as well, but the Roman alliance was particularly formidable, particularly strong. And what Hannibal wanted to do was to break this alliance up, to wedge the … To drive a wedge between Rome and its allies, to pry them apart, and to deprive Rome of the ability to threaten Carthage ever again in the future. He didn’t want to destroy the city of Rome; that wasn’t his plan. That was beyond him, he knew. He simply wanted to break Roman power. I say “simply”; it was a huge undertaking. But he wanted to make sure that Rome could no longer threaten Carthage.

Brett McKay: Let’s move on to Caesar, and this … Again, Caesar wasn’t too long after Hannibal, so what’s interesting … Caesar’s an interesting case because he was an individual who actually invaded his home country. Tell us about that for those who aren’t familiar.

Barry Strauss: Yes, so Hannibal dies in 183 BC, and Caesar’s born 83 years later, in 100 BC. Caesar was a member of the Roman aristocracy; unlike Hannibal or Alexander, he didn’t have a father who was a great general. His father was a politician and a commander, but not absolutely of the first rank. But Caesar burned with ambition. Even as a young man, he was a soldier, and he won a very high military honor, and he started a political career early on, and he wanted to become top dog in Rome. He wanted to succeed both in politics and in the military, and his career is successful in both of those areas.

In his 40s, he takes on a great undertaking. He decides he wants to conquer Gaul, and Gaul is basically France and Belgium in our terms. He undertakes a war against the various peoples of Gaul. They are warlike, but disorganized, and they don’t have the discipline or the managerial skill, the political skill that the Romans have. Nonetheless, it is not an easy thing to conquer them, and Caesar carries it off in a series of lightning campaigns. They take about a decade, he becomes the conqueror of France and Belgium, as well as a little bit of Germany, and even invades Britain, although he doesn’t conquer it for Rome, he’s not able to keep it.

It makes him one of Rome’s greatest generals ever, in all the history of the Roman Republic. It also makes him the wealthiest man in the Roman world. His ambition is to go back to Italy and to win every honor there is, and to win the height of political power, and to be recognized by the other members of the nobility that govern the Roman Republic, to be recognized as the First Man in Rome. His political enemies think that Caesar is just too much. They think he’s too ambitious, too egotistical, that he will never respect them or share power with them equally, so they decide to try to get rid of him. The Roman Senate actually takes his command away from him, they fire him as general and say, “Put down your arms.”

Caesar instead decides to go to war against his own country. He begins a civil war to defend what he says both of all the rights of the Roman people, because he’s a champion of the poor, but also to defend his own status, his own dignity, his own rank, and his own honor.

Brett McKay: One thing that’s already popped out to me as you describe these three guys and their aims, it was both a mixture of just personal ambition, personal glory, but they also, I don’t know, presented it as they were doing something for something larger, for the greater good for everyone else.

Barry Strauss: Absolutely. That’s absolutely true. Alexander said that he was invading the Persian Empire, actually he said he was doing it to get revenge for the Persian invasion of Greece 150 years earlier, when the Persians had taken the city of Athens for a time and burned the temples of the gods on the Acropolis. And he also said he was going to liberate the Greeks under Persian rule. Hannibal wanted to get revenge for his own country for what Rome had done, bring the country national security, and when he got to Italy, he also said he was there to liberate the Italians. “Italy for the Italians” was Hannibal’s motto.

And Caesar, of course, said that he was fighting both for the rights and freedom of the Roman people, but also for the rank and honor that were important to him, and that were actually the cement of the Roman political system. Just as an American today might, for example, fight for freedom more generally, so a Roman might fight for honor and rank.

Brett McKay: So let’s talk about these attributes these guys shared, and that led to their success, and also their failure. You mentioned already that all three of them were incredible risk-takers, but you also say there’s other attributes that they all shared in varying degrees.

Barry Strauss: Sure. Well, you know, they were all immensely ambitious. In Ancient Greek, the word for “ambition” is “love of honor,” and I think that really works for all three of them. They were also what the ancients called a great-souled man. They had enormously high opinions of themselves, and they aimed at great things. Abraham Lincoln spoke about these kind of men as members of what he called “the tribe of the eagle,” and he said that members of this tribe achieved great things, but they can be destabilizing to their own society, and I think that’s true of all three of them.

They had some other qualities as well. First of all, they had great leadership skills, both in politics and in war. They had very good judgment, and they were able to make decisions on the fly. That’s also tremendously important for them; they did not need to take a lot of time or to agonize over their decisions. Risk-takers, as I mentioned. They also showed great agility. They were flexible, they were able to roll with the punches. They excelled in more than one form of warfare; for instance, they were all great commanders in set battles, but they also had the ability to engage either in unconventional warfare or in sieges. They all had access to great infrastructure, to great resources, money, and manpower. None of them could have done what he did without access to a great military.

They were strategists, both in the literal sense of the term in Ancient Greek — a strategos is a general — but they also had the vision thing, as the late George Bush put it. They were able to think big, and they had a grand strategy as well. Sad to say, they were all capable of terror. They were all capable of killing innocent people in order to make their point, and they all engaged in terror. On a lighter note, they were geniuses at branding, at marketing, at selling themselves, and taking simple themes, putting them forward so that the mass of their soldiers could understand it, and the masses at home could understand it as well.

And they were all lucky. Napoleon said that he wanted to have lucky generals; I would say that their luck was so extraordinary that we have to call it something else, fortune, or if you will, divine providence. Nothing else can explain the way things just broke right for each of them at various points in his career.

Brett McKay: What are some examples of that, of things breaking right for them, just because of dumb luck, for these three guys?

Barry Strauss: So, Alexander had a very dangerous enemy whose name no one has ever heard of. His name is Memnon of Rhodes. He was a Greek general who was a mercenary in service of the Persians, and Memnon came up with the brilliant strategy of taking the war home to Greece. The Persian king gave him the resources to have an enormous navy that outclassed Alexander’s puny navy, and Memnon launched an offensive to cross the Aegean Islands, to island-hop the Aegean and land a large army back in Greece that would have forced Alexander to turn around early in his campaign and go fight in his homeland. Immensely successful strategy, and then suddenly, Memnon dies in the midst of the campaign. It’s really unexpected, so unexpected that a modern novelist claims he was poisoned by a Macedonian plot. But in fact, he probably dies of a stroke or a heart attack, natural causes, but that’s just immensely lucky for him to happen at this particular time.

Caesar has a number of moments when he is almost killed in battle, but he survives it, and that’s lucky as well. Hannibal’s immensely lucky in that the Romans play exactly into his strategic hands. Hannibal wants the Romans to fight pitched battles against him. Wiser heads tried to prevail in Rome and got them to say, “We can’t do this. Instead, we should adopt the scorched earth policy and not give Hannibal what he wants by fighting in a battle.” But instead, in the end, they lose out in the political debates in Rome, and the Romans decide to field the biggest army they’ve ever put onto the battlefield, and use this to fight Hannibal. He couldn’t have asked for something better, this playing exactly into his hands. So that’s an example of dumb luck really helping him.

Brett McKay: So all these guys had these attributes in varying degrees, but did some of them possess more of them than the other? For example, was someone more ambitious or more willing to take risks than the others?

Barry Strauss: I don’t think that … I think they were all equally ambitious and risk-takers. I would say that Caesar has a remarkable ability to be strategic about his risk-taking. In strategic terms, Caesar was actually fairly cautious strategically. One of the reasons he’s so successful is that he balances tactical risk with strategic caution. For example, after crossing the Rubicon and conquering Italy, he was tempted to cross the Adriatic and follow his leading enemy Pompey’s army to the east to fight a battle in Greece. But he knew that Pompey had tremendous allied armies in Spain, on Caesar’s western flank, so instead of doing the ultra-risky thing and crossing into Greece, Caesar instead decides to march against Pompey’s armies in Spain, and protect his flank before turning eastward for the climactic battle. So Caesar is really good at balancing risk with calculation.

In other terms, I would say that Hannibal is by far the best battlefield commander. All three of them are really great battlefield commanders, but nobody quite has the really amazing agility that Hannibal shows on the battlefield, the ability to know just how to calculate the use of force. For example, so the battle of Gettysburg famously begins when Robert E. Lee loses control of his army. He tells them, “Don’t start a fight with the Union army,” but they don’t listen to him, and they do, and so Lee is forced into this battle. Hannibal faces a similar situation in northern Italy when his men disobey his command, they try to provoke a battle with the Romans. Hannibal pulls them back, and Hannibal punishes them, and manages to make sure that he doesn’t have to fight a battle unfavorable terms. It’s that kind of fingertip control of his military that really makes Hannibal outstanding.

And as far as branding, well, Alexander really is the great master of branding. He makes sure that he has the greatest sculptors of his day present his image to the other Greeks in a series of statues, and these statues of Alexander are still immensely famous. We see them in all the great museums of the world. On top of that, he has himself proclaimed a god, and this has some resonance. He comes up with a new title for himself, the King of Asia. Persian kings had never called themselves the King of Asia before, and his men expected him to be the mere King of Macedon.

And finally, when he gets into Persian lands, he strategically takes on certain items of Persian dress in order to appeal to his new subjects. So he’s able to look both ways, to both be a Greek hero, but also be someone who would appeal to Persians. He’s very flexible when it comes to marketing, and very, very cunning as well.

Brett McKay: Maybe I’m remembering incorrectly. Didn’t Alexander go visit the grave of Achilles, or where they thought the grave was?

Barry Strauss: Yes, he did. So, the Greeks had set up a colony at what they thought was Troy. They called it Ilium, it was a Greek city. And one of the first things that Alexander did when he crossed the Hellespont and went into Persian territory was he made a pilgrimage to the tomb of his ancestor Achilles. This was also something that would resonate well with the Greeks and show how much he respected Greek culture. There were some Greeks who said that as a Macedonian, Alexander wasn’t even a Greek, and he had no claim to Greekness, but this was a way for Alexander shrewdly to show that he was every inch a Greek. Thanks for bringing that up.

Brett McKay: Yeah, the branding, the personal branding there. Throughout the book, besides highlighting these different attributes that all these guys had, you also talk … There’s five stages of war that all three of them saw, and that each stage has its own dangers to it. So what are these stages? And then we can talk about where these guys excelled at or floundered at afterwards.

Barry Strauss: Sure. So, what I call the five stages of war, the first is attack. You have to have a battle plan, and you have to have a way of beginning. The second is resistance. As the saying goes, no battle plan survives contact with the enemy, and so they had to decide what to do when the enemy struck back. The third is clash. They had to come up with a way to force the enemy to confront them on the battlefield and to win. But it’s not enough to win a battle victory or a series of battle victories; that brings us to the fourth stage, which is closing the net, or sealing the deal, if you will, getting the enemy to admit that he has been defeated and to be willing to make terms for peace. And then finally, the last stage, knowing when to stop. Knowing when to stop, and this is in some ways the most difficult stage for a conqueror, because the same reasons that make men join the tribe of the eagle makes it very difficult for them to step down and go into a cage, as it were.

Brett McKay: Well, let’s walk through these five stages with, say, Alexander, so we can see that in action there.

Barry Strauss: So, Alexander’s plan is to take the Macedonian army and to cross the Hellespont with the help of his small navy, and then to get the Persian army to agree to fight him in the thing that he’s really good at, which is a pitched battle. The Macedonian army is the greatest army in the world when it comes to battlefield confrontation. Luckily for him, the Persians play right into his hand. Instead of doing what would have been wiser for them to do, to engage in a scorched earth policy and not fighting, they agree to fight a battle, in fact, a series of battles against him. Three great battles in which Alexander is able to defeat their resistance and to carry out the clash, which is defeating the Persian army in set battles.

But Persia still is a very strong country, and it still has military resources. Alexander has to know how to close the net, which he does by invading Iran, going after the remaining Persian army, and defeating them. Now comes the more difficult stage. The Persians retreat until their Central Asian redoubts. He decides to convince his army that they now have to march into the stans, if you will — Uzbekistan, Tajikistan, even Kyrgyzstan — in order to defeat the Persian army, and to engage in unconventional tactics and asymmetric warfare. They’re no longer fighting pitched battles; they are engaging hit-and-run raids, they’re fighting in terrain that Alexander’s not used to, and he has to retool his army to fight in these conditions, and he also has to accept rather large casualties. But he pulls all that off.

Then, unfortunately, Alexander decides this is not enough. He wants more. He wants to cross the Hindu Kush and to invade what the Greeks called India; for us, that’s Pakistan as well as India. This is dragging his men much further than they want to go into climactic conditions, the monsoon that they don’t want to deal with. And although Alexander does win a pitched battle there, his men mutiny, and he is forced to go back to what has now become his base, which is Babylon, the Persian capital in Mesopotamia, in southern Iraq.

At this point, you would say, “Okay, Alexander, you’ve conquered the Persian Empire, you’re in your early 30s, you’ve had your fun. It’s time to settle down, to put your stamp on this empire, and to create a dynasty that can succeed you.” But Alexander does not agree; instead, he is planning a new military expedition to conquer Arabia, which would probably mostly be the coast of Arabia, the Arabian Peninsula. It’s a joint land-sea operation. And he is hatching plans to go to war, to turn west and go to war both against Carthage and against the Roman Republic. So for Alexander, there is no limit. He wants to carry out a war without end.

But just before he launches the Arabian expedition, he dies unexpectedly, just before his 33rd birthday in June of the year 323 BC. Probably he died of a virus, a virus that might have been made worse by the fact that he had had seven battle wounds in his years of fighting, some of them serious. But there is a minority opinion in ancient sources that says that he was poisoned. Minority opinion in ancient sources that says that he was poisoned by his own men, because they were terrified of him, and they didn’t want to keep fighting. There’s an outside chance that that’s true. So Alexander is a supreme example of somebody who didn’t know when to stop.

Brett McKay: And then also, the other thing that upset his men, talk about, is that he was becoming too much of a Persian. That upset that he’s taking Persian wives, Asian wives, dressing like a Persian, kind of thinking of himself as a Persian. Everyone’s like, “Wait, you’re a Macedonian. Why are you doing that?”

Barry Strauss: Right. Yeah, this is a problem that conquerors often have. It’s not just Alexander. When you conquer a new territory, you can’t simply crush the new people that you’ve conquered. You need to somehow make your peace with them. This is especially true of ancient armies, because they don’t have the technology, either communications or military anyway, to control these areas without getting some degree of cooperation from the people that they have conquered. They need to get buy-in. And Alexander’s way of getting buy-in was to be able to say to his new subjects, “I’m one of you guys. I’m not just a Greco-Macedonian who’s come in to make your life miserable, but I respect your customs, I’m going to meet you halfway.”

Alexander meets them halfway and then some. As you said, he takes Persian wives, or Iranian wives. He takes wives who come from the East. And he also recruits Iranians to serve in his new army, and he forces his men to take Iranian wives as well, who are going to give birth to sons who, from the point of view of Macedonians, are half-breeds, they would have called them. They were racists, and they would have looked down on them. Many people in the ancient world were racists; it’s not specific to the Macedonians or the Greeks.

But Alexander is looking on a broader canvas, and in a way, he’s remarkably un-racist. He wants to create this new army, this new ruling group that will be a mixture of Greeks and Macedonians. He actually famously gives a banquet in which he prays for peace and harmony, peace and harmony, between the Macedonians and the Persians. To us, this looks like a noble ideal. To the Macedonians, this is, “Whoa, we went to war for Macedon, to conquer these people. We didn’t go to war to make friends with them, or to mate with them, or to create sons who will be half Persian.” Alexander’s taking his men farther than they want to go.

Brett McKay: And so this is a great example of, you know, Alexander, he was successful in the short term with his military aims. He did invade Persia, and conquered most of Asia, a lot of Asia. But after he died, that thing just collapsed, because he was so busy conquering and expanding that he didn’t really spend time building infrastructure for the newly acquired territory that he got.

Barry Strauss: No, exactly right. I mean, Alexander, what he needed to do was to create a dynasty, and to ensure that he would have heirs who would follow him, who would be able to keep this vast new empire together. And he also needed to work on the ideology of the empire, the rationale for it. He needed to build up a ruling group that was going to be loyal to him. Instead, he dies just before his 33rd birthday. Supposedly, on his deathbed, when asked who he wanted to leave his empire to, supposedly he said, “To the strongest,” meaning that he knew that there was going to be a civil war. And there was, and those civil wars last for 50 years. They’re very bloody. By the time they’re done, the Persians haven’t come back; his empire is in Greco-Macedonian hands, but it’s split up into a series of successor kingdoms. No one is able to hold together this thing that Alexander had conquered.

Brett McKay: And that paved the way for the Roman Republic to rise. Let’s talk about Hannibal first. Where did he flounder out in this five stages? Because he did well, it seems like, in a lot of them.

Barry Strauss: Yeah, he did. I mean, the attack was brilliant. He marched a land army 900 miles from southern Spain over the Pyrenees, over the Rhone river, including taking elephants over the Rhone, and then over the Alps in the winter, and lands in northern Italy. He loses most of his army, so, to desertion, to the weather, to resistance from tribes who he meets along the way. So he’s not there in northern Italy with the big army he wanted, but he immediately gets new allies and wins a series of victories over the Romans, and he defeats them in this cavalry battle in northern Italy, then a combined arms battle in northern Italy, then a crushing defeat in central Italy at Lake Trasimene. And finally, his greatest victory of all, the one that went down in history books, the battle of Cannae, August 2nd, 216 BC, in which he crushes a Roman army in the plains of southern Italy.

And he’s convinced that the Romans are now going to give him what he wants, that they’re going to surrender. Northern Italy and southern Italy have risen in revolt on the side of Hannibal against the Roman Republic and against the Roman alliance, but as one of Hannibal’s commanders says to him afterwards, “You know how to win a victory, Hannibal, but you don’t know what to do with it. You don’t know how to use a victory.”

Hannibal, for instance, refused to march on Rome after the victory at Cannae, as one of his advisors wanted him to. He said his army was too battered, too bruised, they needed time to recover, and the defenses of Rome, in any case, were too strong. But in later years, he looked back on this as a mistake, that he should have stuck the knife in, that he should have marched on Rome, however difficult it was, and that he might have terrified the Romans into surrender or terrified some of their allies into leaving them.

The problem for Hannibal is that the Romans are a bit like Britain in 1940 against the Germans, after Dunkirk. They say, “Well, we’ve lost, it’s true, but we don’t announce that we’ve lost, we don’t acknowledge it, because we believe that strategically, the odds are pretty good for us. We’ve got the British Navy, there’s the potential of allies, particularly in the United States, so we’re going to keep on fighting.” The Romans are somewhat similar. They say, “Yeah, well, we’ve lost really great battles, but we still have all our allies in central Italy. We still have our fleet to come and get us, and we still have our walls. You can’t win.”

And they go on to rebuild, the Romans go on to rebuild. The allies in central Italy are tied to the Romans very closely. The Romans have not only defeated them, but they’ve used a combination of carrots and sticks to bring those allies into the Roman alliance, to make ties with the ruling classes of all these cities. In some cases, they’re blood ties, because the ruling classes intermarry with the Roman elite.

Hannibal’s not good at breaking these bonds that hold central Italy into the Roman alliance. To do so, he would have had to lay siege to the cities of central Italy. Hannibal’s not a siegecraft kind of guy. His sieges in Spain have not gone well. They’ve been frustrating, he was badly wounded. He’s a mobile warfare kind of guy. So Hannibal wants to take the war to Sicily, to Sardinia, he wants to recapture these cities, he wants to get new allies in the Greek world, where he does have an alliance with the Macedonian king. But not much comes of it, and the Romans are able to rebuild. They rebuild their army, they defeat the Carthaginians in Sicily.

And worse for him, all along, the Romans have been wanting to open a second front in Spain, with limited success, but finally pull it off, because the other problem that Hannibal runs into is that in warfare, if you have a brilliant new way of doing things, and you don’t defeat the enemy, if the enemy’s any good, the enemy’s going to figure out how to do this brilliant new way as well. Case in point, the Second World War, the Germans have Blitzkrieg, and their enemies eventually figure out how to do Blitzkrieg of their own.

So Hannibal’s worst nightmare is a Roman survivor of the Battle of Cannae. It’s a man named Scipio, a general named Scipio, who comes from one of the first families of Roman warfare, and Scipio understands that Hannibal is able to run ring around the Roman army because of the professionalism of his troops, and the ability of his troops to carry out combined arms tactics in which the infantry and the cavalry work well together, something the Romans were never good at. Scipio rebuilds the Roman army to be able to do this sort of thing.

Hannibal is also good at tricks and ambushes, and Scipio is as well. And Hannibal portrays himself as kind of a god, or at least someone who has the favor of the gods, in particular of Hercules, who is a god for the Carthaginians as well as for the Greeks and Romans, and Scipio does something like this as well. He leads an army to Spain, and through an ambush, he captures the Carthaginian capital city of New Carthage, modern Cartagena in southeastern Spain. And then he goes on to defeat the Carthaginians in battle and force the Carthaginians out of Spain, so they lose the jewel in the crown of their empire.

Hannibal’s still in Italy, but he’s not able to get the Romans to admit defeat, he’s not able to dislodge the Romans from their alliance in central Italy. The attempt to reconquer Sicily fails; the Romans inflict a bloody defeat on the Carthaginians there. The Carthaginian home government, which has never been without its suspicions of Hannibal, and suspicions of his family and what they want to do, has not given him the kind of support that he would absolutely want either.

At this point, Scipio proves that he is truly a master of warfare, because he’s not just a great battlefield general, but he is also a great diplomat as well, and he now launches his most impressive coup. It’s years in the making, it takes years of cajoling. One of Hannibal’s aces was his alliance with Numidia. Numidia is the equivalent of what is today Algeria. The Numidians are superb horsemen. They’ve got one thing that the Carthaginians absolutely need: They’ve got a light cavalry. This light cavalry is incredibly fast and mobile, and it’s absolutely key to Hannibal’s battlefield victories.

What Scipio’s able to do is he is able to convince the Numidians to defect from Carthage and to join Rome. It is not an easy process; it’s very long, and it’s very complicated. It’s got its own set of plots and almost operatic connections involving a Numidian princess who tries to save the day for Carthage, but is forced in the end to commit suicide. But with the help of Numidia, Scipio is able to bring the war back to North Africa, to force Hannibal to leave Italy, and force him to roll the dice on one final great battle in Tunisia, a battle that, because Scipio now has his Numidian ally, because he’s pried this away from Carthage, that Scipio’s able to win, and finally force Hannibal and the Carthaginians to win defeat.

So this is an epic warfare, a war that goes back and forth. It’s got these two stunning commanders, Hannibal and Scipio, if you will, the Napoleon and Wellington of the Second Punic War, and it finally ends in a Roman victory.

Brett McKay: So it sounds like for Hannibal, he was a fantastic combat commander, but long-term strategy, even the politics, the diplomacy, that was a slight blind spot for him?

Barry Strauss: Yeah, I would agree. Maybe not a blind spot, but he didn’t have the absolute mastery that Alexander and Caesar had. I think that was his difficulty. I mean, there are those who would say Hannibal’s problem was that he should never have started the war in the first place. This was a bit of vanity on his part to think that he could have defeated the Roman Republic. I’m not sure. I think there’s a lot to be said for his decision to go to war against Rome. Rome really was threatening Carthage’s empire in Spain. But I think that after having defeated … After having inflicted great defeat on Rome, I think Hannibal should have gone back to Spain, declared victory, and built up his resources there.

Brett McKay: Didn’t do it, but he wanted to continue on.

Barry Strauss: Yeah.

Brett McKay: So Hannibal clearly, he lost, he got defeated.

Barry Strauss: Yeah, yeah.

Brett McKay: Alexander, he won, but lost in the long run.

Barry Strauss: Yeah.

Brett McKay: The same thing happened with Caesar, so this is a man who climbed up the ranks in the Roman military, conquered his home country, became the First Man of Rome, the first Caesar.

Barry Strauss: Right.

Brett McKay: But it seemed like a victory, but it also didn’t last for him either. I mean, he ended up getting killed.

Barry Strauss: No. He ends up getting killed, he’s assassinated, of course, on the Ides of March, March 15th, 44 BC. And he’s assassinated in a way because the … He wins too much. I mean, he wants to become the First Man in the Roman Republic, but instead, he destroys the Roman Republic, and he proclaims himself dictator for life, a position which was completely illegal. You couldn’t be dictator for life; it’s a new constitutional position. On top of that, he’s a famous lover, a Latin lover, if you will, and his most famous conquest happens to be a queen, a queen of Egypt, Cleopatra, by whom he has a son, at least she claims it’s Caesar’s son, Ptolemy XV, the next king of Egypt, who everybody calls Caesarion, or “Little Caesar.”

And he himself flirts with royal affectations, he wears royal robes and gets honors such as no Roman had ever had. On top of that, he’s trying … He has the same … A problem similar to Alexander. He’s trying to balance the loyalty of his old supporters with the new ones who he brings into his army. Like Alexander, he says, “You can’t just crush the people you conquer; you need to win their loyalty.” So Caesar famously, after winning the Roman civil war, instead of executing his former opponents, he pardons them. He gives them clemency, as he calls it.

But this doesn’t work for two reasons. First of all, it offends, alienates his old supporters, who say, “Hey, wait a minute, what about us? Why are you being so nice to these new guys?” And secondly, the way he gives them clemency is kind of offensive. He makes them beg for it. “Please, oh great Caesar, please forgive me for what I have done,” as if there was something wrong with defending their country against a would-be dictator.

So Caesar just sets up a sea of enemies against him, and they decide to plot against him. Caesar’s not doing well in the city of Rome. He doesn’t really like Roman politics, he’s more successful in the battlefield. And so he plans to leave Rome yet again, after the civil war, and start a new war, this time against the enemy in the East, the Parthian Empire, a revived Iranian empire that controls Iran, Iraq, is extending into the Roman province of Syria. They’ve clashed in the past, Parthians have won, Caesar says he wants to go now back to the East and avenge former defeats. But before he can leave Rome, he is, of course, assassinated on the Ides of March.

To add to the mix, Caesar was not a healthy man. He was suffering either from epilepsy or perhaps a series of mini-strokes, it’s not entirely clear, that might have weakened him on the Ides of March, and probably did not bode well for his long-term longevity. He was a man in his mid-50s. But he thought he was going to be able to pull off this military campaign and at least win some victories. Who knows what would have happened in the end? But his opponents were convinced that he was a threat both to his old supporters and to his former enemies, who defended the Roman Republic, so they joined together in a conspiracy and managed to take him out in the Senate on the Ides of March, 44 BC.

Brett McKay: What happened to Rome after that, after-

Barry Strauss: So, what happened to Rome after that. Caesar had an eye for talent. He already had begun the process of concentrating power in the republic that used to belong to the nobility, concentrating power in his own hands and that of his family. He didn’t have any legitimate children of his own; he had a daughter, but she had died. But he had some nephews and cousins, and he began to share power with them. The most promising was an 18-year-old grand-nephew, the son of his sister’s daughter. This is a guy named Gaius Octavius. Gaius Octavius had been brought to Caesar’s attention by his mother and his grandmother, and Caesar had given … Paid a lot of attention to him while the kid was growing up. He was fatherless, his father had died when he was young. And Caesar has sent young Gaius Octavius to the East to be part of this new campaign.

But when Caesar dies, in his will it turns out that Caesar has adopted him posthumously, which is not something you did in Rome, by the way, as heir, and left most of his enormous fortune to him. This young man was incredibly clever and talented. He comes back to Rome, and he starts a campaign to capture all of the honors and power that Caesar had. It is a long struggle that lasts almost a generation and leads to a new civil war. To make a long story short, this young Gaius Octavius, who becomes another Julius Caesar, ultimately defeats everyone and becomes Rome’s first emperor. We know him as Augustus.

So Caesar does leave a dynasty behind him, not in the way that he had planned, and it’s a very iffy thing, but in the end … He leaves behind him another civil war, just as Alexander leaves behind him another civil war. But in the case of Caesar, one man manages to win the whole thing. The Roman Empire might have split up into a series of smaller realms, just as Alexander’s empire did, but young Gaius Octavius, the future Augustus, is so successful, so competent, and so fortunate, that he wins the whole thing. And the Roman Republic becomes what we call the Roman Empire, the Roman monarchy, in fact.

Brett McKay: I mean, one of the big takeaways I got from this book was that all three of these men, crazy ambition, crazy audacity, brilliant, but that idea that they, a lot of them … None of them knew when to stop. I’m curious, do you think it’s possible to be a part of the tribe of the eagle, like Abraham Lincoln said, and know when to stop, have that balance? Has there ever been a military leader who’s been able to do that, or do you have to have like two people sort of balance each other off?

Barry Strauss: It’s a great question. It’s really hard to do, and most people, most of us are good at one thing, and we’re not immensely versatile. That’s why it’s really important, by the way, to have a second in command. And one of the reasons that Augustus wins is that he’s not a great warrior, and he has a second in command who is a great warrior, and he doesn’t want to knock him off. Agrippa, Marcus Agrippa. So when you got that situation, then you can have someone who knows how to stop, as Augustus knows how to stop.

George Washington is somebody who knew how to stop. He didn’t become king after winning the American Revolution; in fact, he goes home and retires. It takes a really remarkable personality who has a kind of modesty and humility that allows him to stop. Another person who knows how to stop is William the Conqueror. After conquering England, he doesn’t say, “Hey, this was just beginning. Let’s keep on going.” He knows when to stop. He figures, “Hey, this is a great thing to win. I’m going to spend the rest of my life trying to absorb it.” So it’s possible, but it’s really rare, really difficult to do.

Brett McKay: Yeah, and what I loved about this book, I mean, while it’s about military history, you can see this, this can transfer over, these same ideas, to business.

Barry Strauss: Yeah.

Brett McKay: You see businesses that are just so hellbent on growing and growing and growing that in the end, it bites in the rear and they collapse, immediately and fast.

Barry Strauss: Yeah. And also in business, you often see someone who’s the genius, who figures out how to start a new business, but rarely is that person also going to be the manager and administrator who can bring it to the second generation. So it’s really common: You have a founder, “Great, bye, see you,” now we have somebody who is going to codify the whole thing and do the slog of making it work. These guys didn’t like doing the slog work, they really didn’t. I mean, I think that’s something they have in common.

Brett McKay: So you’ve got a new book out. I’m curious, how is this a continuation of this book, Masters of Command, or is it a continuation, or is it something different?

Barry Strauss: It is a continuation, thank you. So, the new book is called Ten Caesars: Roman Emperors from Augustus to Constantine. It takes the story through Caesar’s successor, Augustus, and asks, how does he win the whole thing? What’s his ambition, what’s his … How does he … What makes him so successful? And then how does he pull it off? Caesar can’t get the Romans to accept him as dictator for life. How does Augustus pull it off? And having done so, what kind of government, what kind of regime does he leave, and how are the Romans able to continue it? Particularly because they continue with the fiction that it’s still the Roman Republic. We call it the Roman Empire, but they never did, and we say they have emperors, but they never said that at all. They said, “Oh, no, no, no, no, no, it’s just a republic. Nothing has changed. Who are you going to believe, me or your lying eyes? Pay no attention to the man behind the curtain. Nothing has changed.”

How do they pull it off? And in fact, not only is it not true that nothing was changed, but the Romans have this problem that the world doesn’t stand still. The world keeps changing enormously, in big ways, and in a way, the Romans are the victims of their own success, because they have a successful empire; the empire starts changing. How are you going to adapt when that happens? How do you make change your friend, which you need to do if you want to stay in power? Nobody stays in power by saying, “I’m not changing anything, I’m going to keep everything the same,” because you can’t keep things the same. So I’m really fascinated by this question, how do the Romans have this balance in change, in continuity? And they do, and they manage to keep the empire for a very, very long time. It’s partly because of this flexibility.

Brett McKay: It sounds like there’s lot of lessons there that can transfer over to other areas of life as well.

Barry Strauss: Indeed.

Brett McKay: Well, Barry, where can people go to learn more about your work?

Barry Strauss: People can learn more about my work in two places. First of all, on my website, barrystrauss.com, but also I have a podcast, which I started in the fall, and I’m really excited about. It’s called ANTIQUITAS: Leaders and Legends of the Ancient World, and you can find it on all the major podcast platforms, on iTunes, for instance, or Google Play, or Stitcher, as well as on my website. And the first season is called The Gods of War, and it takes you from Achilles to Julius Caesar. The second season, which I just recently launched, is called The Death of Caesar, and you can read about that, you can hear about that as well on the podcast. I encourage you to listen to it, and if you like it, please rate it on iTunes.

Brett McKay: Well, Barry, this has been a great conversation. Thanks so much for your time. This has been an absolute pleasure.

Barry Strauss: Thank you, thank you, thank you. It’s really been great pleasure for me as well.

Brett McKay: My guest today was Barry Strauss. He’s the author of the book Masters of Command. We discussed that book today. It’s available on amazon.com. Also, check out his new book, Ten Caesars, also available on amazon.com and bookstores everywhere. Find out more information about his work at his website, barrystrauss.com, and while you’re there, check out his podcast, ANTIQUITAS: Leaders and Legends of the Ancient World. You can also check out our show notes at aom.is/mastersofcommand, where you can find links to resources where you can delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Check out our website, artofmanliness.com, where you can find our podcast archives. Got over 480 podcasts up, evergreen, they’re still good; even if they’re like five years ago, they’re still quality. Also, you can find thousands of articles we’ve written over the years about personal finances, physical fitness, how to be a better husband, better father. Check it out, artofmanliness.com. And if you haven’t done so already, I’d appreciate if you take one minute to give us a review on iTunes or Stitcher. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it.

As always, thank you for your continued support. Until next time, this is Brett McKay reminding … As always, thank you for your continued support, and until next time, this is Brett McKay reminding you to not only listen to the AOM podcast, but put what you’ve heard into action.