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in: Ancient Greece, Military History, Podcast

• Last updated: September 8, 2020

Podcast #588: The Audacious Command of Alexander the Great

Alexander the Great became king of Macedonia at age 19. By age 30 he controlled an empire that spanned from Greece to India. In the two thousand years after his early death, his influence has persisted. Military leaders from Caesar to Napoleon studied his campaigns and imitated his strategies and tactics, and without Alexander, the influence of Greek culture on the world wouldn’t have been the same. 

My guest today has written a very readable, yet academically authoritative biography of this legendary king, commander, and conqueror. His name is Philip Freeman, and he’s a classics professor and the author of Alexander the Great. Today on the show, Philip takes us on an engaging tour of Alexander’s life, beginning with the myths surrounding his birth, and his education under the great philosopher Aristotle. Philip then explains the cloak and dagger intrigue of Macedonian politics and why Alexander’s father was assassinated. We then dig into Alexander’s political reign and military command and highlight the most famous battles during his decade-long campaign to conquer the ancient world. Along the way, Philip shares the leadership lessons we can learn from Alexander.

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Show Highlights

  • How did Alexander become “great”? What was his impact on the world?
  • How Alexander’s father set the stage for his rise
  • The legends of Alexander’s birth 
  • The influence of his mother 
  • Did Alexander’s childhood foreshadow his future power?
  • How ancient Macedonia was basically a real life Game of Thrones scenario
  • The strategic and tactical innovations of Alexander
  • Alexander’s unparalleled campaign against Tyre 
  • The administrative successes of Alexander
  • Injury, illness, and the mystery of his death 
  • What happened to his vast empire?
  • The lasting impact of Alexander the Great

Resources/People/Articles Mentioned in Podcast

Book cover of Alexander the Great by Philip Freeman.

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Read the Transcript

Brett McKay:

Brett McKay here and welcome to another edition of The Art of Manliness Podcast. Alexander the Great became king of Macedonia at age 19. By age 30, he controlled an empire that spanned from Greece to India. In the 2,000 years after his early death, his influence has persisted, military leaders from Caesar to Napoleon studied his campaigns and imitated his strategies and tactics. And without Alexander, the influence of Greek culture on the world wouldn’t have been the same. My guest today has written a very readable, yet academically authoritative biography of this legendary king, commander, and conqueror. His name is Philip Freeman. He’s a classics professor and the author of Alexander the Great.

Today in the show, Philip takes on an engaging tour of Alexander’s life, beginning with the myths surrounding his birth and his education under the great philosopher, Aristotle. Philip then explains the cloak and dagger intrigue of Macedonian politics, and why Alexander’s father was assassinated. We then dig into Alexander’s political reign in military command, and highlight the most famous battles during his decade-long campaign to conquer the ancient world. Along the way, Philip shares the leadership lessons we can learn from Alexander. After the show’s over, check out our show notes at aom.is/alexanderthegreat.

All right, Philip Freeman, welcome to the show.

Philip Freeman:

Thanks. It’s great to be here.

Brett McKay:

You got a biography out about Alexander the Great. Now, there are a lot of books and biographies about Alexander the Great. Ancient Ones, we’ve got Arrian’s, Campaigns of Alexander. Why did you think that we needed another Alexander the Great biography?

Philip Freeman:

Well, there are, you’re right. There are a lot both ancient and modern. Arrian, of course, I think is the very best of the ancient biographies, and there’s some very good, modern biographies. When I wrote this a few years back, there really weren’t any that had been done recently. There have been a couple that have been done since. But my goal in writing this was really just to tell the story of Alexander for a modern audience. I wanted to be accurate, I wanted to be academic and all of that, but I really wanted to put it in the form of a story that people could read and feel like they could really get to know this man.

This is a book about more than just battles, although I do talk about the details of battles and such, but it’s really much more of a book about the person of Alexander, who he was, what motivated him, as best that we can tell, looking back over 2,000 years.

Brett McKay:

Yeah, I love the way you wrote it, because it does read like this, like Game of Thrones or the Godfather, completely in that early part. And we’ll talk about that sort of the succession between Philip, Alexander’s dad and Alexander. And there’s a lot of assassinations and killings that’s going on.

Philip Freeman:

Yes.

Brett McKay:

But I loved how you wrote that, it just, it read like this like a really good murder mystery novel.

Philip Freeman:

Oh, I had so much fun with it. Thank you.

Brett McKay:

Before we talk about Alexander the Great, let’s talk about why we call him Alexander the Great. How big of an empire did he mass? How long did it take him? Why are we still talking about him 2,000 years later?

Philip Freeman:

Well, he’s a fascinating character because what he did was really amazing, it really was great. He started off being a struggling king of a very small Kingdom in Northern Greece. And he conquered the world, basically, all the way from Greece to Egypt, across what’s now Iraq and Iran, all the way to what’s modern India. No one had ever had an empire that big before. He conquered the Persian Empire, which made up most of his realm, but he did more than that. It was an enormous empire. Imagine starting off in Seattle, and conquering the United States all the way to New England and Florida, 2,000 years ago, that’s what Alexander did. It was an enormous geographical area, an area very populous, made up of incredibly diverse people, languages, cultures, many of them very warlike, and Alexander was able to do this in a period of about 11 years, when he was very young.

He started this when he was about 20 years old, and he finished just before his 33rd birthday when he died. He was able to conquer most of the known world of the Mediterranean, Eastern Mediterranean and Near East, at a time when nobody had ever done anything like that before, and especially had never done it so fast.

Brett McKay:

Yeah, when you realize how young he was, it makes you feel like a slacker.

Philip Freeman:

Well, Julius Caesar, when he was in his early 30s, came across a statue of Alexander, when he was in Spain. Julius Caesar was really just starting off and he wept because Alexander had conquered the world at a time when Julius Caesar was still a junior officer. So, yeah, it made me wonder what I’ve done with my life.

Brett McKay:

In the beginning, you make the case, as well as a general of Alexander the Great, that Alexander wouldn’t have been able to do what he did, without the foundation that his father, King Philip of Macedonia, laid. Let’s talk about this first, let’s talk about the Macedonians. Because as you said, there was this northern city state or call… I don’t know what you’d call it, just an area in Greece, sort of the backwoods, the back country, but somehow it managed to rise to power. So, his background, what was Macedonia? What was the role in Greek culture at the time of Alexander, or before Alexander the Great?

Philip Freeman:

Right. Well, Macedonia had been a part of ancient Greek history for a long time. They run the northern fringes, though. The Athenians, the Spartans, the Thebans, all of the civilized Greek people to the South, saw them as their barbarians to the north. And at a time when the Athenians were inventing democracy, and you had the rule of the people spreading across Greece, the Macedonians were still a kingdom, ruled by a king with pretty much absolute power, very much like a warlord, somebody from Game of Thrones, which you mentioned. So, the Greeks always looked at the Macedonians as their back country cousins, always look down on them, but they were a powerful kingdom, but they really, until the time of Philip, they were always being threatened with war, always being threatened by being torn apart.

And what Philip did was Philip was able to take the Macedonians, take these wild people, who were natural great warriors, but he was able to form them into an army, using the techniques that he had learned from the Greek cities to the South. And when you combine that sort of natural talent and bravery and force of the Macedonians with the discipline that Philip learned in military, discipline that he learned from the Greek city states, they were an incredible force to be reckoned with. And Philip was able, not only to survive when he rose to power in Macedonia, but he was able to take over, really, most of Greece, except for Sparta, and make it part of his own Macedonian Empire, with the aim, ultimately, as he always said, of invading the Persian Empire, which everybody thought was a pretty ridiculous idea.

Brett McKay:

And why did Philip want to take over Greece? What was his goal there?

Philip Freeman:

Oh, I think he was like many kings and tyrants and rulers through the ages, he wanted power. And also, he lived in a society that was, like, think of the Middle Ages, and you had to conquer, you had to push forward, or you were falling back. And you always had to press forward, you always had to give your warriors something to fight for. You always had to give them loot from sacked cities. It was a military society, so, it had to have some sort of a military purpose to it. And I think that was a big part of it. I think he also wanted legitimacy. He wanted to be recognized that he was Greek, and he wanted to be accepted by the Greeks to the South.

Brett McKay:

And he’s also, he took advantage of the tumult that was going on in a lot of the Greek city states. I think, a lot of times when we think of ancient Greece, we think of the white statues and the pillars and these all, but it was a very chaotic time, particularly around this time, just couple of generation before Socrates was assassinated, there was this whole political intrigue and tumult going on in Athens, and this sounds like Philip was able to take advantage of that.

Philip Freeman:

He was. What happened in the generation before Philip, really, at the end of the 400s B.C., was a great Peloponnesian war between Athens and Sparta, a 30-year war, which was just, imagine World War II lasting for 30 years. It was that level of devastation and death and destruction. And so, Greece was exhausted when Philip came to the throne. So, that helped him, he was able to step in. They were exhausted, but they were down but not out. They were still very powerful warriors, especially the city of Thebes, which rose to power after Athens and Sparta had exhausted themselves. So, they were formidable enemies, they really were, but Philip was able to step into this power vacuum, and take advantage of it.

Brett McKay:

All right, let’s just talk about Alexander. The birth of Alexander was sort of shrouded in legend.

Philip Freeman:

It is.

Brett McKay:

Talk about that.

Philip Freeman:

Yeah, when you read about heroes in the ancient world, things often get put in mythological terms.

Brett McKay:

There’s always legends that he was born of a god or there was thunder and lightning. It was like weird stuff going on.

Philip Freeman:

Right, there was. The night that he was born, there was supposedly a thunderstorm. At his conception, Philip was never quite sure, according to the stories, if he was actually the father, because there was a claim that Zeus was really the Father. That was a fairly standard sort of thing to do. You wanted to have an ancestor who was a god. If you could be the actual son of a god, that was great propaganda. That was something maybe most people wouldn’t believe it, but some people would. And so, I think Alexander himself, really wasn’t quite sure. But his mother told him that he was divine, that he was special. His mother, Olympias, was a tremendous influence in his life.

Brett McKay:

Well, talk about the influence that Olympias had on him.

Philip Freeman:

Yes, she was a princess in an ancient country called Epirus, which is basically modern Albania, and she came into the court of Macedonia and became one of many of Philip’s wives. She was fairly young at the time. She was a very smart, very determined woman. And her goal in life was to get her son, Alexander, on the throne, because there were other contenders, both children of Philip and other members of the Macedonian nobility. So, she fought very hard. She had some rather exotic ways. There’s a story that one night Philip came to crawl into bed with her, and he found a giant snake wrapped around her. She was doing some sort of a strange wild ritual with a snake.

And the sources say that after that, Philip really was a little bit intimidated and didn’t go back to bed with her. So, she was exotic, certainly, but a very determined woman, who lived all throughout. She outlived her son, Alexander, and was there all the time pushing for him.

Brett McKay:

Well, that religiosity of Olympias seem to rub off on Alexander as well. Throughout his life, he was very pious or devout or religious.

Philip Freeman:

He was. And it’s very easy for us from a modern point of view to be cynical and say, “Oh, he was just manipulating religion, he didn’t really take it seriously.” And to a certain extent, he was manipulating it. But I think he was also very serious and very devout. The Greeks really tended to be quite serious about their religion. They asked questions, philosophers did, some of them even questioned the existence of the gods. But for the most part, the Greeks were really quite serious in their religion, and I think Alexander certainly followed that model.

Brett McKay:

And we’ll talk a bit about more into that, in the experience he had in Egypt when he began his campaign. But, let’s talk about Alexander as a child. Were there signs when he was a boy that he would grow up to become Alexander the Great?

Philip Freeman:

Well, there were. And again, when you have stories about great people of the ancient world, you often have childhood stories of great things that they do. But I think with Alexander, some of these were quite true. When he was a young man, he wanted a horse, and there was this great horse that was brought before Philip named Bucephalus, and it was untamable. This magnificent beast, nobody could control it. But Alexander was smart enough to notice that what seemed to upset Bucephalus was seeing his own shadow. So, Alexander, very calmly, went up to him and took Bucephalus, and turned him to face the sun, so that he couldn’t see his own shadow. And then, after he calmed him down, he jumped up on top of him and rode Bucephalus across the plain and he came back.

And Philip said, “My son, you need to find new kingdoms, Macedonia isn’t going to be big enough for you.” So, there’re some wonderful stories like that, some of them might not be true, but I think some of them are.

Brett McKay:

And then also is he had a unique education because his personal tutor was the great philosopher, the philosopher, the teacher, Aristotle.

Philip Freeman:

Yes. I mean, what more could you want? As a teenager, for several years, first of all, Alexander was tutored by several excellent tutors who taught him Greek, he knew Homer, he knew mathematics, he knew all the subjects a man should know. But Aristotle was his tutor. The great Aristotle, the one Dante called the master of all who know, he was certainly one of the most intelligent men ever. And like Aristotle’s own teacher, Plato, he explored a wide variety of subjects. But Aristotle also was a great experimental scientist, really one of the first. Whereas, Plato would theorize about things, what animals were like, Aristotle would be out waiting in the swamp collecting tadpoles to dissect. So, he was a wonderful teacher and a great influence on Alexander.

Brett McKay:

Do we know why Aristotle decided to take that role? I mean, because he was in Athens, he was a student of Plato, but he decided to go to the backwoods of Macedonia to tutor this king’s kid.

Philip Freeman:

Yes. I mean, Aristotle actually wasn’t from Athens, Aristotle grew up in Macedonia. His father was the court physician in Macedonia. So, he was very familiar with the wild and crazy ways of Macedonia, but also, things were getting a little difficult in Athens, and so, he, I think, left, just to avoid problems and anti-Macedonian feelings. And so, I’m sure he was also very well paid. So, he went up and he taught Alexander and his small group of friends. You can still visit the site, it’s on the side of a mountain, and it’s a beautiful place. I can just imagine learning from Aristotle at that setting.

Brett McKay:

Well, according to lore, we don’t know if this is true, but that Alexander, during his campaigns, supposedly sent stuff back to Aristotle, like animals and furs and things for him.

Philip Freeman:

Right, samples and things that he found. Aristotle practically invented biology, and so, Alexander was always sending back unique animals and plants and such things to his old teacher, Aristotle, all throughout his 11-year campaign.

Brett McKay:

Well, another interesting part of Alexander’s childhood, would call childhood now, is when he was a teenager, his dad actually put him in charge of military. He was a captain in the military at 16 years old.

Philip Freeman:

Right. 16 years old, he was put in charge. Alexander learned a lot of wonderful theory in biology and mathematics and literature, but he was also trained from the very beginning by Macedonian soldiers, some of the toughest soldiers in the world, he was trained in the practical arts, the practical arts of fighting in leadership. And so, from an early time, Alexander was put in charge of leading men in battle. And so, when he was 16 years old, he was serving as a captain in the army of Philip, and getting very much on-the-ground training in military matters.

Brett McKay:

The part in your book that started reading like a mafioso or like a Game of Thrones is the succession between Philip and Alexander. The interesting part first is that, at first, Philip, he wasn’t always sure that Alexander was his son, and there was actually a moment where Philip says, “No, you’re not going to be my heir, Alexander.”

Philip Freeman:

Right. And this was when Alexander was in his late teens, and Philip was getting ready to go off on the invasion of Persia, and there was a lot of pressure on Philip to… He had had daughters, he had had one son who was mentally handicapped, but he didn’t have, aside from Alexander, he didn’t have a healthy son, who he could leave the throne to. And that bothered some of the Macedonian nobility because they saw Alexander as a half-Macedonian, not really one of them. And they really wanted Philip to marry and sire a son with an old Macedonian family. And so, Philip listened to them and he sent Olympias and Alexander away, and removed Alexander, at least temporarily, from the line of succession.

But then, after he was unable to have another son, and he was just getting ready to leave on the military expedition, he realized he couldn’t just leave without nobody as an heir, and so, he brought Alexander back and reinstated him as his heir. Which, I imagine, made Alexander a bit resentful.

Brett McKay:

Yeah, I can see that being really awkward. Like, “Do you think this Thanksgiving dinner is awkward?” Imagine being like, “You’re not going to be the heir. Oh, yeah, you are going to be the heir again.”

Philip Freeman:

Exactly, exactly.

Brett McKay:

And then, all during this time, before Philip was going to go off to Persia, he was worried about having a successor in case he died out there. But there was also this inner intrigue going on, people wanting to assassinate Philip. Why were there conspiracies to get rid of Philip? What was going on in Macedonia?

Philip Freeman:

Well, Macedonia, truly, reading about its history is reading the Game of Thrones. There was plots, counter plots, murders, intrigue, treachery. Most Macedonian kings were assassinated. That’s how most of them died. And it was unusual for one to live and die in old age. And so, there were always plots, there were always factions. And so, people from the Athenians to the Persians themselves, the Persians knew what was going on, they were keeping a close eye on things. There were factions within the Macedonian nobility. So, there were plenty of people who might want to see Philip dead. And so, in the end, one of them killed him.

Brett McKay:

And do we know who that guy was?

Philip Freeman:

Well, we know something about the man who killed him, at least, he was the assassin. He was a very minor figure. But the real question is, who was behind him? That’s what people have struggled with and nobody has really figured it out. Was it the Athenians? That’s what some people say. Was it the Persians? Was it just an angry, jilted former lover of Philip, who was behind it all? So, nobody really knows. But the upshot is that Philip was murdered just before he was getting ready to leave on his great Persian expedition. And Alexander was there. A lot of people, of course, in later years, thought that Olympias maybe was behind it, or maybe Alexander himself.

Brett McKay:

That period when Alexander became the king, in any moment there’s succession, there’s always the possibility that the succession won’t go as planned. There’s all these people fighting for, “No, actually, he’s not this heir, I’m the heir.” Was Alexander able to galvanize the Macedonians to say, “Yes, I’m the guy, come follow me”?

Philip Freeman:

He was. He had proven himself as a military leader already, but he was 20 years old. A lot of them saw him as a half-Macedonian kid, who was trying to step into his father’s very big shoes. And so, there were a lot of people who were against him, and certainly, whether or not, the Athenians or other Greeks or Persians were behind it. They certainly took advantage of the assassination of Philip and tried to thwart Alexander at the very beginning. But through matters of persuasion, through proof of his military and organizational ability, Alexander showed them that he really was worthy to take over the Macedonian throne, and he established himself, and he showed the Greeks that he was serious, he was not afraid to knock some heads together.

And so, he consolidated his power to the South in Greece, and then he launched a campaign in the North, up in the Danube River Valley, which was a great training session for his invasion of the Persian Empire. It showed his military skill, his leadership, and it secured his northern borders, before he would head out East and invade Persia.

Brett McKay:

What I was impressed during this time with Alexander was his political astuteness. He understood that there were people in his father’s court or in his military leadership that were probably against him, but he kept them on anyways. But then there were some people he knew he had to get rid of right away. He knew the right people to fire and the right people to quit, or keep.

Philip Freeman:

Right. Yeah. I mean, he was very smart. I mean, plenty of people have looked at Alexander for lessons of business leadership, and there are good lessons there, and knowing who you have to get rid of. But if you do just a general purge and get rid of everybody, then you remove all the talent that you need. And that’s certainly not a way to develop loyalty to you in the future. And so, Alexander was sparing and he used violence like a surgeon’s knife, rather than like a club to hit people with. Sometimes, he did have people killed, sometimes, he had them executed. But he really preferred to try to win them over and to try to make good use of their talents, if he could.

Brett McKay:

So, he did that initial like training ground, securing his northern borders and the Daniel River Valley. But then, he started turning his attention towards Greece and some of these city states that have been belligerent and getting in the way, and one of his initial campaigns was against the Thebans. Tell us about these guys and why were they such a formidable foe? And why did Alexander feel like he had to put them in check?

Philip Freeman:

Well, the Thebans had filled the power vacuum in Greece just after the Peloponnesian War, when Athens and Sparta were down but not out, they were weakened. And the Thebans were a tremendous military force. They were the very first ones to beat the Spartans. The Spartans really had never been seriously defeated in battle, until after the Peloponnesian War, the Thebans were able to meet them on the field of battle and beat them. They were incredible, incredibly trained professional soldiers. Philip had learned so much, he was a hostage. A young man among the Thebans, and that’s where he learned a lot of his military skills.

The Thebans had something called the sacred band, which I’ve never seen anything like it in history. It was a group of 150 male couples, who were same sex couples who were lovers, who fought together. So, you had 300 men, who were superbly trained. Probably one of the best military forces ever. And they fought all the harder because they were fighting beside people that they loved. And so, Alexander was able to, he marched on Thebes and he said, “Surrender, I’m the boss now, my father’s gone.” The Thebans said, “No, we’re not going to surrender to a kid.” And so, Alexander, by using his skill and siege warfare and other things, he took the city of Thebes and destroyed it.

And he gave a very specific object lesson to the rest of Greece, by basically killing or enslaving everybody in Thebes, so that the Athenians, the Spartans, and the rest, would think twice before rebelling. While he was off in Persia, he would simply send back a message and say, “Remember Thebes.” And so, he used violence on a grand scale, but a very selective scale, in order to impress the people of Greece.

Brett McKay:

Yeah, that was his modus operandi. If there was a city that just didn’t give up or didn’t surrender right away, he would make sure that he would teach a lesson to them, but everyone else.

Philip Freeman:

Absolutely.

Brett McKay:

You mentioned, he used siege warfare during his time, and he made some innovations there. Besides that, what sort of other innovations did Alexander introduce strategically, tactically, that made him such a formidable military leader?

Philip Freeman:

Well, really, organization on the battlefield and off the battlefield. One thing that he was able to do which is something I share with my students in class, the Greek hoplite army. The heavily armed infantry men, who were in Athens, Sparta, Thebes, Macedonia, they were a very tough bunch, and they had these spears. In the ancient world, you really didn’t throw your spear. That was a last resort. So, they would have spears that were maybe eight feet long, that they would use to poke and stab their enemy. Well, what Alexander came up with was the idea of what he called a sarrisae. He and his father came up with it. It was an 18-foot long spear.

And you can imagine a spear that’s 18 feet long, can reach through just about any military line. The problem is, if you have 100 men carrying 18-foot spears, they have to be superbly trained, so they don’t get entangled with each other. But if you can get 100 men who can move like a machine, with 18 foot spears, then you can press your way through just about any heavily armed infantry line. That was just one of the innovations of Alexander. But he had a great many others. And really, one of his main ones was speed. Nobody ever moved as fast as Alexander. You’d be getting ready for a battle in three days with him, and then find out as he was right there on your doorstep.

And in battle, one of his tricks was to rush in very fast with his horsemen, before anybody could even get their arrows ready, to get underneath the range of the archers. So, speed, in all of its different aspects, was a major factor of Alexander.

Brett McKay:

And now, back to the show. So, he gets Greece under control, the Peloponnesian peninsula under control, then he moves over to Persia. And it seemed like initially, he was just focusing on Greek cities that were under Persian control. Correct?

Philip Freeman:

Right, the Greek cities on the western coast of what’s now Turkey, they had been Greek for 1,000 years, the Greek settlers, all on both sides of the Aegean. And they, the ones on what’s now the Turkish coast, had been a part of the Persian Empire for a couple of hundred years, and they were generally fairly happy, sometimes they weren’t, sometimes they were. But people thought that Alexander was going to restrict his invasion of Persia, to just trying to take the Greek cities of Asia Minor, Ephesus and all of the rest along the coast, and he did. And when he finished, they thought that probably he would stop. But that’s the thing about Alexander, he never stopped. He always kept going.

Brett McKay:

Yeah, why did he keep going? After he got that under control, why did he keep going after Persia?

Philip Freeman:

It’s funny, I don’t think it was that he wanted money, that he wanted to sack cities or anything like that, I think he wanted power, like many people through history. So, I think it was certainly about power, I think it was about reputation. His hero was Achilles from the Trojan War. And Achilles gloried in the fact that he was the greatest warrior ever. And Alexander, I think, aspired to be like that. He slept with Homer’s Iliad underneath his pillow every night, with the stories of Achilles. And so, I think a lot of it was that, I think a lot of it was just wanting to prove that he could do it, that this kid from Macedonia could actually do it. And so, he kept pushing farther and farther along the coast, the Mediterranean coast, and then, eventually, England.

Brett McKay:

Speaking of his admiration of Achilles, one of the first things he does when he gets to what’s now Turkey, he goes to Troy and visits the grave of Achilles.

Philip Freeman:

Right. You can still visit it today. It’s a beautiful sight that the Turkish government takes very good care of. And he went there and he sacrificed to Achilles and to the gods. And he and his friend, Hephaestion, stripped off their clothes and raced three times around the city of Troy, an invitation of Achilles and Hector in Homer’s Iliad.

Brett McKay:

So, he takes back control of the Greek city states in Persia, starts turning inland. The king of Persia this time was Darius. So, Darius, when did he realize that Alexander posed a threat and then he had to do something about this guy?

Philip Freeman:

Well, Alexander fought a battle on the Granicus River near Troy, the first few weeks that he invaded, and the Persians thought, and that was just fighting a little local Persian army, the Persians thought that that would take care of things, they would kill Alexander and that would be it. And they almost did kill Alexander, it was a very tough battle. But, I think after Alexander took the Greek cities of Asia Minor, that’s when Darius knew that this was something different, and that’s when he began to gather his army. He didn’t invade Asia Minor, Darius didn’t with the Persian army, but he was waiting for him there. It took a long time to gather together the force of the Persian army.

And so, Darius let Alexander basically take the rest of Asia Minor and go down the coast of what’s now Syria, and Israel, Palestine, into Egypt. But he was waiting for him after he came into the area of what’s now Iraq.

Brett McKay:

Let’s talk about his before. He met Darius twice. The first time-

Philip Freeman:

He did.

Brett McKay:

… there was a rally, he basically routed Darius, and Darius had to flee.

Philip Freeman:

Right. Yes, the first time he fought him at a place called the Issus, which is now just on the border of Turkey and Syria. It was a great battle. Darius didn’t even bring his entire army to this battle, but it was huge. And Alexander was certainly outnumbered. And so, Darius is heading towards Alexander, Alexander is heading toward Darius. They end up actually missing each other. In the fog of war, they get lost in different valleys. And so, it turns out that Darius ends up on the north of Alexander, Alexander’s to the south. And so, they’re in a narrow valley. And one thing I tell my students is, if you’re ever in a situation where you’re fighting a battle with an army that outnumbers you, especially when it outnumbers you greatly, try to restrict them to a small area, because it negates somewhat their power. And this is what Alexander did.

He fought the battle of Issus on a narrow coastal plain, so that Darius wasn’t able to spread out his whole army and envelop Alexander. And so, there at the Issus River, Alexander struck against Darius very fast and used the speed and used his flanking maneuvers and all of his different tricks, and routed Darius. He drove Darius away. He was able to capture the tent of Darius, where all of his wives were, where his mother was, and he treated them very, very well. That was one thing about Alexander is that he… it was, I think, an act of chivalry, but was also a very practical act, that he treated them very well and sent them back to Persia unharmed and untouched. And he was able to win the first great battle at Issus, and then eventually go forward from there, down into Syria and Egypt.

Brett McKay:

Well, that’s kind of interesting thing you mention throughout the book about Alexander’s relationship with women, he seemed to have a soft spot for them. He wasn’t interested in them romantically, it seemed like.

Philip Freeman:

Not to a great extent, and not really. And sexual orientation in the ancient world is always a difficult thing to try to look at because we look at it in modern categories. But Alexander, he did get married, eventually, he did have a child. He married more than once, actually. But I don’t think women were his obsession, certainly, like they were with his father, Philip, who would pretty much sleep with anything wearing a skirt. But Alexander was more restrained, certainly.

Brett McKay:

But, yeah, he had a respect for them. He was very respectful particularly to older women.

Philip Freeman:

Yes, he was, very much so.

Brett McKay:

So, he continues down. He routes Darius, Darius flees, and he’s like, “I’ll take care of you later. I’ve got other stuff to take care of.” He continues down the coast, and he used to wear modern Lebanon’s art. And there’s this island, Tyre, which is one of the craziest campaigns probably ever in world military history. Tell us about what happened at Tyre.

Philip Freeman:

Well, Tyre was an island about a mile off the coast of what’s now Lebanon. It had been a commercial center of the Phoenicians, the great trading people, the Phoenicians. They were an important part of the Persian Empire. They were the main naval base of the Persians in the Mediterranean. They had this walled Island, as I said, about a mile off the coast, and it had never been conquered. You could not take something like this. It had never been done before. So, Alexander sends a embassy to them. He’s standing on the shore, basically says, “I want to come over and worship in the temple of Hercules. And by the way, I want you to surrender.” And they say, “Nope, sorry, not going to do that.” Because they are pretty sure that Darius is going to come back and crush Alexander with his entire army.

So, they say, “No, we’re not going to surrender.” And if Alexander, maybe he should have just moved on and left them there. But the problem is that they still controlled a very powerful navy. And so, he would be heading south into Egypt, with a powerful Persian navy still in force. And he couldn’t do that. He had to take Tyre, he had to find some way to subdue this island city. And so, what he did was something just astounding. He built a causeway between the mainland and Tyre. And this is not some shallow sort of tidal bottom land between the mainland and the island, it was deep. And so, he spent months, his men spent months pouring rocks into this channel. And the Tyrians, the people of Tyre, would just stand up on their walls and laugh at him for this. But as the months went by, and the causeway got closer and closer, they stopped laughing.

And eventually, Alexander was able to complete the causeway and roll his machines of war right across it along with all his soldiers and ladders, and they took the city of Tyre. And because the Tyrians had resisted, he did the usual thing where he ended up killing or enslaving most of them.

Brett McKay:

And it’s no longer an island. You can still see the causeway there that Alexander built.

Philip Freeman:

Right. There’s a picture. You can look at it online and you can see that Tyre is now connected to the mainland, as it has been for the last 2,300 years, because of Alexander. It’s a physical feature in the geography of the Middle East that Alexander created.

Brett McKay:

Talking about this spiritual aspect of Alexander, an important part of his campaign was when he went to Egypt. Now, Egypt today is like, we think of Egypt sort of this land of mystery, it was the same thing in Alexander’s time, Egypt was seen as this land of mystery and magic and spirituality. And he gets to Egypt, and he decides to go on this month-long detour to the middle of the desert, so he can go talk to an oracle.

Philip Freeman:

Right, he conquered Egypt without any resistance. The Egyptians never particularly liked the Persians. So, they were happy to proclaim Alexander as pharaoh and to show him around. And like everybody, Alexander was very impressed with Egypt. He went to the pyramids. And we have to realize that the pyramids were older to Alexander than he is to us. So, there’s an enormous antiquity to Egypt, and mystery to it. So, he left the Nile Valley, and he went far to the west, to the oasis of Siwa, which is now on the border of Libya, where there was a great oracle of Amun-Ra, now which the Greeks called Zeus. And so, he went there on this dangerous journey, that I think only a young man and his buddies would do, crossing the Sahara Desert. And he went there, though, to consult the oracle.

And we don’t know exactly what happened when he went into the oracle’s temple. The story seems to be that Alexander wanted to know if Philip was his real father. And when he came out, people say that he seemed to change. And so, the supposition is that the oracle told him that, “You are actually the son of Zeus.” And so, he went forth at that point, believing maybe that there was some actual truth to the story, that he was the son of a god. And so, he went back to Egypt and then headed inland to invade the heart of the Persian Empire.

Brett McKay:

Well, supposedly he asked also, if he would conquer the Persian Empire.

Philip Freeman:

Yes, yes. And the oracle said, “Yes, indeed you will.”

Brett McKay:

Yeah. And that seemed to change him. He left that profoundly affected and it gave him more gustar to keep doing what he had started to do.

Philip Freeman:

Right, because Alexander had gotten a message from Darius, the king of Persia, saying, “Let’s work out a deal. You can keep the Mediterranean parts of my empire, which are really quite small and not particularly wealthy, and just stay there. And I will recognize you as king of the Mediterranean coast, and that’s it.” I think Darius probably intended to still conquer Alexander, but he wanted to buy some time. And Alexander, a lot of people said, “Alexander, this is incredible. This is more than any of us could ever have hoped for. You’ve conquered Asia Minor, you’ve conquered Syria, you’ve conquered Egypt, stop, this is enough.” And Alexander said, “No, I am going forward.”

And so, his army, who were very loyal, followed him inland to the heart of Mesopotamia, to the Tigris and Euphrates Valley.

Brett McKay:

Yeah, as I read about that experience of Alexander, it made me think of like, if you look back in history, a lot of what we’d call great individuals, individuals who had a great impact on history, they had that in common with Alexander. They had a very powerful sense of purpose and identity, and that they used that for good or evil. It could just depend on how you look at it.

Philip Freeman:

Right. I mean, there’s the modern theory, the great man theory of history, which is, many historians poopa, they say, “No, it’s not individuals who change history, it’s economic and social forces.” And of course, there’s a lot of truth to that. But I disagree, I think, with them to a certain extent. I think that there are certain men and women who really do change history, that change everything. Julius Caesar was certainly one of these, Alexander was one of them, Napoleon was one of them. Certainly, religious leaders, Muhammad, Jesus, the Buddha, these are individuals who changed history. And so, Alexander was one of those.

Brett McKay:

As he was conquering these Persian cities, his empire was growing. Taking over things is easy, managing is a lot harder. How did Alexander start managing his growing empire? What did he do?

Philip Freeman:

It’s a part of Alexander’s life that really isn’t focused on very much, but he was a great administrator. What he did first of all, was he kept most of the Persian apparatus for administering the empire intact. So, the taxation, the administration of the individual provinces, he kept the Persian civil servants and the other natives there. So, he didn’t disrupt thing, he didn’t come in and try to make everything Macedonian. He adapted it, very happily adapted it. And he also kept a constant flow of correspondence. So, all of the time, all of these 11 years when Alexander was tromping across the mountains of Afghanistan, he was getting constant reports about what kind of crops were growing in Phrygia, or how things were going back in Macedonia.

So, he was able to dispatch and rule and administer the empire very effectively. And that was really the key. Conquering an empire is hard enough, but keeping it can be impossible. We’ve seen many examples in history of people who do that, and just, you watch their empires fall apart when they die. Charlemagne, for example, he leaves his empire to three sons, and then it just collapses gradually after he dies. So, Alexander was a great administrator.

Brett McKay:

But another thing that Alexander did besides maintaining the current Persian apparatus, political and religious and things like that, he also started adapting Persian customs and clothing.

Philip Freeman:

He did. He started wearing Persian clothing, which I think, one sense it was practical, because it’s really hot in Persia. So, he started wearing pants, which Macedonians wouldn’t do, Greeks would never do that. So, it was practical. But also, a part of it was that the people of the Persian empire that he conquered, wanted a king who looked like a Persian king. And so, he started dressing, at least, in public displays, like a Persian king, which got some of his Macedonians, who were very much a rough and ready bunch of cowboys sort of people, thinking, “Why is Alexander starting to act like a Persian?” That created some tension.

Brett McKay:

Yeah, the Macedonians, they were a kingdom, but they were a lot more democratic than say the Persians.

Philip Freeman:

They were. I mean, when I think of the Macedonians, I think about Vikings, I think about a hall full of Vikings with a king up front. And all the warriors gathered around him, proudly fighting for him, but doing it by their own will. And so, it was a more democratic kind of institution than the Persian Empire, which was very much a hierarchical top-down administration.

Brett McKay:

So, he continues just steamrolling through Persia, does he eventually kill Darius?

Philip Freeman:

Well, he doesn’t eventually kill Darius, somebody else does. But after the great battle at Gaugamela, in what’s now Northern Iraq, where Alexander faced the entire Persian army, vastly outnumbered and was able to defeat them by, again, by just sheer daring and speed. Then, the army collapsed. And after that, Darius was a king on the run, with just a few men with him, one of which eventually killed him. Alexander didn’t want to kill Darius, he wanted Darius to surrender to him. So, he was very disappointed when he found the body of Darius somewhere in Iran at an oasis at a caravan stop. And so, eventually, somebody else killed Darius, and eventually then, Alexander was the undisputed king of his new empire.

Brett McKay:

All right. So, he’s taken over the Persian Empire, what does his men think? Is it, “All right, let’s go home, we’ve been gone probably…” What? I don’t know how they’ve been long, I mean, seven, eight years at this point?

Philip Freeman:

Yeah, at this point, they’ve gone through what’s now Iran, they got stuck in Afghanistan, like pretty much every army does in history, for that was the toughest time that Alexander had was in Afghanistan. And then he goes down into what’s now Pakistan, and just across the border into modern India, and he’s going to keep going. He says, “All right, boys, let’s go. We’re going down the Indus River, all the way to Cafe to China if we can.” And they say, “No, it’s been almost 10 years, we want to go home, this is far enough. Make an end to your ambition.” And so, Alexander, when he hears this speech, he goes into his tent and sulks for three days, and then finally says, “Okay, boys, you’re right. It’s time to go home.”

So, he heads back to his new capital at Babylon, in what’s now Southern Iraq.

Brett McKay:

Yeah, the sulking thing, he’s done that before and it worked. This time, it didn’t work.

Philip Freeman:

This time, it didn’t work. This time, the men are just not going to follow him any farther. And so, there’s really not a whole lot Alexander can do at this point. He just, he has to turn around. And so, he does and he’s not giving up his ambitions at all. But he is heading back, at least, for a while to Babylon.

Brett McKay:

And what’s interesting on his quest back, instead of going back the way he went, he decided to go this hard route, because he heard that no one else had done it before, and it was that whole idea of Alexander, “I’m going to do something that no one else has done before, even if it might kill me, I’m going to do it.”

Philip Freeman:

Yeah, he did. He went across this great Gedrosian desert, which is really like Death Valley. He led his men across and some of them didn’t make it. But I think Alexander did it. Some people have said Alexander did this to punish his army. I don’t think so. I think he did it because, like you said, it hadn’t been done before. And most of them made it. He made it back across the desert back to Persepolis, and then back eventually to Babylon.

Brett McKay:

And that’s where his story ends. How did Alexander die? Did he meet the fate of like other previous Macedonian kings and get assassinated?

Philip Freeman:

Well, that’s the question. Alexander had been sick before, and nobody really certain exactly what it was, maybe malaria. But he had been sick a number of times and recovered. He was also injured many times. He said, “Look at my body, I’m covered with scars.” He was stabbed with swords and spears and always managed to pull out of it. So, he’s 32 years old, and he’s in Babylon. And all of a sudden, he comes down with a great fever, and doesn’t last all that long. And people ever since then have said, “Oh, he was poisoned, or something happened. Somebody killed him.” Maybe, it’s possible, but it’s also very possible that Alexander, there was a lot of sickness in the ancient world, and it’s very possible that Alexander was just weakened after all of these years of campaigning, and just simply died of disease there in Babylon.

Brett McKay:

Now, just like there’s legends around his birth, there’re also legends around his death, particularly about who would succeed Alexander.

Philip Freeman:

Right. That’s the great story, which I think is probably true. Alexander had married a princess from the area of Afghanistan, and eventually had a young son. But, that he was just an infant, he wasn’t able to take over the empire. So, people wanted to know, his generals wanted to know, “Who are you leaving in charge of your empire, this vast empire you’ve created?” And so, they’re all gathered around his deathbed, and Alexander whispers to them his last words, when they say, “Who are you going to leave it to?” He says, “To the strongest,” and then he dies. That’s the story, which may be a little dramatic, but I think is probably true.

And so, after that, as you can imagine, there was chaos about who was going to take over Alexander’s Empire.

Brett McKay:

And so, what happened at the empire?

Philip Freeman:

Well, his generals divided it up. What happened was, one of them took the eastern part, the parts of India and Persia, another took Asia Minor area, another took Macedonia, and then his old friend or his best and oldest friend, Ptolemy, took Egypt, which was probably the smartest move of all because it was a very wealthy and very contained and easy to defend kingdom. And so, Ptolemy and his descendants ruled Egypt for several hundred years until his very last descendant, Cleopatra, was taken over, surrendered to Rome.

Brett McKay:

And what happened to Macedonia itself?

Philip Freeman:

Macedonia itself fell back. It was given to one of Alexander’s generals, but it continued to exert a lot of influence. It was still powerful, but it really, it started to fall apart at that point. Certainly, the empire part did. And it wasn’t that long afterwards, until Rome was a rising power in the West, and they certainly did their best to bring down Macedonia if they could. And so, Macedonia itself reverts to being what it had been before, which is a fairly small kingdom, and all the rest of Alexander’s empire is divided up into among different generals who found dynasties.

But the thing is, Alexander’s influence continued. Alexander not only conquered, but he established cities, he established libraries, he settled his veteran soldiers in colonies, all the way to Afghanistan and India. So, these little centers of Greek civilization, all in these cities, basically named Alexandria, after himself, he founds all across his former empire, and they become a great center for Hellenic, for Greek culture, that greatly influenced the area for centuries thereafter.

Brett McKay:

Yeah, how did it set the stage for Western civilization after that point, do you think?

Philip Freeman:

Well, what Alexander did, before Alexander, Greek civilization was pretty much contained in Greece, the Aegean area. But Alexander spread Greek civilization, the stories of Homer, the philosophy of Plato, across the ancient world, to Egypt, to Mesopotamia, to India. And so, when we think about the golden age of Greece and the wonderful plays and books and histories and all, Alexander is really responsible for spreading that. And then the Romans took it up and they helped spread it even more. But Alexander founded the cities, the greatest of which was the Alexandria of Egypt, which became the intellectual center of the ancient world, where people from all over the place came, where this great library for the collection and dissemination of knowledge was founded.

And so, Alexander spread civilization really, Greek civilization, at least, all across the ancient world. And so, that people spoke Greek, and not everybody, they still spoke their native languages. But, we look at the New Testament, for example, written in the first century of our era, it’s written in Greek. It’s not written in the Aramaic of Jesus, it’s written in Greek, the Greek of Alexander.

Brett McKay:

You mentioned that people often looked Alexander for leadership lessons, for business or for military. And so, Alexander the Great, he’s an interesting character because, as I was reading your biography of him, I’ll be like, “Wow, this is really cool.” And then he would just basically commit genocide, and you’re like, “Ooh, that’s not good.” So, you walk away ambivalent about him, but what do you think are the lessons that people can take from Alexander the Great on leadership?

Philip Freeman:

Well, I mean, it’s a tough question. It’s a question we deal with in college courses all the time, when we study people from the past, and then we find out something terrible about them, that they owned slaves, for example, what do we do with somebody like that? What do we do with George Washington, who did all these amazing things and yet owned and oppressed individual people? It’s a tough question. So, what I try to do is I say, “Try to look at the context of the times.” Because, otherwise, we’re going to end up ignoring everybody from history. We’re going to end up canceling everybody.

So, look at Alexander in his own times and what he did, he did some pretty horrible stuff, but he did some amazing stuff, too. And learning leadership lessons from him, watch how he fought. He was never an armchair general, he was always there in the front. There was a city he invaded in India, he was the first one over the wall into this hostile city. So, he always was in front, always facing physical dangers, always taking care of his men before himself, always very well organized, but also very daring. So, I think those are some lessons that all of us can apply to our lives.

Brett McKay:

And his overlooked idea of he was a good administrator. There’s probably lessons from that as well.

Philip Freeman:

Right, absolutely.

Brett McKay:

Well, Phil, this has been a great conversation, where can people go to learn more about the book and the rest of your work?

Philip Freeman:

Well, they can go to philipfreemanbooks.com. I have a nice little website that some very kind people put together and that talks about all my different books. I’ve got books on Julius Caesar, Alexander the Great, Sappho, St. Patrick, and some other things too. So, I would welcome people to go there. I’m also on Facebook, under Philip Freeman Books.

Brett McKay:

All right. Philip Freeman, thanks so much for your time, it’s been a pleasure.

Philip Freeman:

My pleasure. Thanks very much.

Brett McKay:

My guest today was Philip Freeman. He’s the author of the book, Alexander the Great. It’s available on amazon.com and bookstores everywhere. You can find out more information about his work at his website, philipfreemanbooks.com. Also, check out our show notes at aom.is/alexanderthegreat, 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 at artofmanliness.com, where you can find our podcast archives, as well as thousands of articles we’ve written over the years. And if you’d like to enjoy add-free episodes of the AOM Podcast, you can do so on Stitcher Premium. Head over to stitcherpremium.com, sign up, use code, Manliness, and checkout to get a free month trial. Download the Stitcher app on Android or iOS, and you can start enjoying new episodes of the AOM Podcast ad-free.

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