October 25, 2021

Alexander the Great (Part 1)


 Alexander the Great (Not Philip)

Hello and welcome to How To Take Over The World. This is Ben Wilson.

This episode has been a long time coming. It’s one that I’m very excited for. 

What can you say about Alexander the Great? He’s one of the most impactful men of history. He’s possibly the greatest conqueror of all time, he established an enormous empire the likes of which the world had never seen - from the Balkans in the west to India in the east, from Armenia in the north to Egypt in the south. 

As the Greco-Roman biographer Arrian would later say “One can point to no other man, Greek or barbarian, who performed exploits so numerous and so momentous.” I am inclined to agree.

It’s also just a great adventure story. One of the reasons that I love the life story of Alexander the Great is that he was the last great military leader who swung his own sword. He was himself a gifted horseman and powerful warrior who was an integral part of his own battles and fought from the front.

The final reason that I’ll mention that I love this story is that he inspired so many other greats. Napoleon studied his campaigns, and Julius Caesar famously had his life changed by Alexander. As you’ll recall, Julius Caesar was a young-ish man in Spain who hadn’t accomplished much of anything. And he came upon a statue of Alexander the Great and burst into tears. Plutarch tells us that - quote  -

“His friends were surprised, and asked him the reason of it. ‘Do you think,’ said he, ‘I have not just cause to weep, when I consider that Alexander at my age had conquered so many nations, and I have all this time done nothing that is memorable?’”

He then of course proceeded to found the Roman Empire. I hope that some of you will have your “Caesar moment” when listening to this podcast and be inspired, like Caesar, to greater things.

So let’s jump into it. But first, one thing: I want to make a small note on my sources.

I used three books as my primary sources: 

Alexander the Great and His Time by Agnes Savill.

Philip and Alexander: Kings and Conquerors by Adrian Goldsworthy. I really enjoyed that one and highly recommend it. 

And the Landmark Arrian: The Campaigns of Alexander. Arrian was a Greco-Roman, born in 86 AD, he was the only man to be both a consul in Rome and the Archon of Athens, the highest civic office of that city. 

He wrote his history of Alexander the Great as basically an account of his life and a critical analysis of his virtues and vices. His biography of Alexander is essentially a 2,000 year old episode of How to Take Over the World. 

I think I’ve talked about the Landmark series before but it really is so good if you like ancient history. For the Landmark Arrian, they have produced a really good translation that is very readable, with tons of clarifying footnotes to help you understand it, and tons of pictures and maps to help you make sense of where the action is taking place.

If you’re a casual fan, it might not be super interesting, but if you’re even a casual history fan I really recommend it.

Anyway, I also mention it because I’m going to be quoting a ton from Arrian throughout this series. He wrote a very faithful history, he had plenty of access to firsthand accounts so it’s pretty cool to read these accounts, it really transports you back to Alexander’s time.

Okay, so that’s it for sources, and finally before we get started, a word from our sponsors.

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Alexander was born in 356 BC. This is about 100 years after the golden age of Athens. So the Greeks are still dominant throughout the Mediterranean in terms of trade, art, philosophy, and culture - but they had lost some of their luster.

The greatest world power at the time - at least as far as they knew - was Persia. The Persian empire extended from modern day Turkey all the way to India, and included most of the Middle East, Egypt, Armenia, and more. But like the Greeks, the Persian empire was also viewed as somewhat past its prime.

And while it was the twilight of Greek political power, he was born at the time of what is considered a golden age of Greek philosophy. One of the greatest Greek philosophers, Aristotle, was alive at the same time as Alexander and in fact the two knew each other, as we shall soon see.

And one of the things these philosophers loved to philosophize about was this question of what has happened to Greece? And how do we make Greece great again?

Well one philosopher, Isocrates, basically said that the Greeks had run out of places to expand to and settle. And so they just squabled among themselves. And what they needed to do, according to Isocrates, was invade Persia. That would give them plenty of land and riches.

The only problem was that this would take Greek unity. And the Greeks were famously fractious. They were constantly infighting. And it seemed unlikely that they could rally around a leader because they didn’t want to elevate a single city-state. In other words, Sparta would never follow an Athenian or a Theban or a Corinthian leader, and vice versa.


It was fitting then, that the person who eventually united Greece in this cause came from outside of Greece.

Philip, Alexander’s father, was a Macedonian. 

Macedonia was an undomesticated backwater just north of Greece. Rich in resources like timber and gold, Macedonia was a region to be fought over by larger players like Athens, Thebes, or Sparta, not a kingdom that ever exerted influence or dominion over others, especially not the Greek world.

Macedonians were kind-of sort-of Greek. They spoke a Greek dialect and worshiped the same gods as the Greeks, but they were not as developed economically, technologically, or culturally, and didn’t live in city-states as the Greeks did.

But Philip was an unbelievably gifted statesman and military leader and he managed to raise Macedonia up, conquer its neighbors, and eventually bring all of Greece under his dominion. And when he did, with his first act he got them all to agree that they would participate in a combined invasion of Persia.

Alexander’s Childhood:

As Philip’s oldest able-bodied son, Alexander was the heir apparent to the Macedonian kingdom when he was born.

And he soon showed himself to be worthy to be Philip’s heir. He was short but strong and a good sprinter. He was a gifted musician and orator. He was intelligent, strong-willed, impatient, curious, and charming.

And we know this isn’t just propaganda, because we have documented proof of ambassadors and diplomats visiting the Macedonian capital at Pella and being charmed by this precocious young prince.

The most famous story from Alexander’s childhood occured when he was twelve or thirteen years old. He’s with his father when they come across a horse breeder who wants to show a magnificent horse to Philip. 

And supposedly this horse is beautiful. Tall and strong with a beautiful dark coat and a white mark on its forehead. The man wants to charge King Philip an unprecedented 13 talents for the horse. Philip scoffs at this price, especially when his groomers are completely unable to tame it. He declines to purchase and is getting ready to leave when Alexander protests. And says they can’t pass on such a magnificent prize of a horse.

And Philip kind of says “Oh, you think you can do better than all of my trained, professional stable hands?” And Alexander basically says “Yeah, I think I can.” So they make a bet. If Alexander can tame the horse, Philip will buy it for him. So Alexander carefully approaches the horse.

He had noticed that when the king’s men had tried leading the horse, it was spooked by its own shadow. So Alexander turns him toward the sun, and starts soothing him and speaking softly to the horse. Soon he calms to Alexander’s presence - who is then able to hop on his back and gallop around, with the horse eventually really letting loose and astounding everyone with his unbelievable speed.

It’s a great story, almost certainly an exaggeration, but the horse, named Bucephalus, was real, and he is probably the most famous horse of all time. Bucephalus would accompany Alexander on nearly all of his conquests and Alexander would even end up naming a city Bucacephala after him.

So Alexander was this naturally gifted young boy, but he also had the best education that money could buy. And it’s interesting because he had two distinct types of education. He received a traditional Macedonian education - which was more martial in nature. He learned to ride, to hunt, to swing a sword, and every other skill he would need to know to be an effective warrior.

His primary tutor for this phase of his education was a guy named Leonidas, like the famous Spartan king. He’s a relative of Alexander’s mother. And he’s your stereotypical hard-nosed drill-master tough guy teacher. He would go through Alexander’s stuff and throw out any treats  or gifts that his mother had given him.

Alexander would later say that “Leonidas’s idea of breakfast was a night march, and his idea of dinner was a light breakfast.” He was extremely cheap. He would always butt heads with Alexander over sacrifices. Alexander was very religiously observant, always scrupulous in his observation of proper rituals, sacrifices, prayers, and things like that.

And he was always generous in his sacrifices and offerings. Well this bothered Leonidas, who would always tell him he was wasting too much incense in the offering.

Later, after a big victory that made Alexander a bunch of money, he sent 18 tons of frankincense and myrrh, ya know, multiple shipping containers full of incense, and essentially as a practical joke he had it dumped on Leonidas’s front step with a note that said “In the future I hope you will not be so miserly in your offerings to the gods.”

At age 13, Philip finds Alexander a new tutor, Aristotle. Aristotle is of course one of the great philosophers of the ancient world. And whereas his teacher and mentor, Plato, was more of a purely theoretical philosopher in the tradition of HIS mentor, Socrates, Aristotle was more grounded in reality. In observing nature. He made many important discoveries and observations in biology, geology, and astronomy, in addition to the more typical philosophical field of politics and metaphysics.

And it is obviously very intriguing that these two had such a close relationship. Unfortunately, we don’t have access to Aristotle’s curriculum. Wouldn’t you love to know what he taught him and how he taught him? If I could be a fly on the wall in any place at any time, seeing Aristotle tutor Alexander the Great would be way up there.

But one thing that you can say is that Alexander had an insatiable curiosity, a love of learning and discovering new things. And I think it very likely that he learned some of that from his famed tutor.

Home Situation:

Now I said that Alexander was Philip’s heir apparent. But it’s a little more complicated than that. 

Macedonian kings were polygamous - meaning they had multiple wives - and Alexander was born to Philip’s fourth wife, Olympias. She was the daughter of a nearby king, Neoptolemus of Epirus, and she was a very intelligent, strong-willed woman. 

And Macedonian royal polygamy was a double-edged sword. It meant that there were plenty of heirs around. But it also meant that there was often conflict for the throne. There was a lot of court intrigue, a lot of plotting, secret murders and poisonings, rebellions - it was very rare for a Macedonian king to die peacefully in his bed.

And so Olympias and Alexander are both quite paranoid about Alexander’s position as heir, especially when Philip marries his seventh wife. Everyone knew that he was planning a big invasion of Persia. And it was anticipated that it would take years to carry out this invasion. So okay, if you’re going to be gone for years you really need to make sure that your homefront is secure. Philip usually took a new marriage to seal political alliances, and this was no different.

So for the first time, Philip takes a native-born Macedonian for his wife. Many Macedonians, especially the nobility, are thrilled about this. But it’s not a great thing for Alexander because a son born to this marriage would automatically have a strong claim to the throne.

Well this situation is made worse at the wedding. One of Philip’s top generals, a man by the name of Attalus, proposes a toast. And by background, Attalus was one of the most powerful men in Macedonia, perhaps the most powerful outside of the king himself, and for this reason Philip was marrying Attalus’s niece, so their families are getting united through this marriage, which is a big win for Attalus. 

And so in his toast, Attalus says “may this union bless Macedonia with a legitimate heir.” 

Ooh. Ooohhh. So that is clearly an insult - a direct shot at Alexander, who does not take it well. He throws a cup of wine at Attalus and yells “Are you calling me a bastard?”

Philip stands up to try to break up the fight. But by this time he’s in his mid 40s and he has been through a lot of fighting and has a whole bunch of injuries. Including a permanent limp that he developed when he was stabbed through the thigh with a spear. He’s also been at a wedding all day and presumably has had a few drinks so when he stands up to try to break up this brewing fight, he trips, and falls flat on his face.

And  Alexander, still heated, points at Philip and says “Look everyone, this man was planning to cross from Europe to Asia, but he cannot even cross from one couch to another.”

This enrages Philip. A royal wedding was an opportunity for him to cement and reaffirm his power in front of the most important subjects in his kingdom. And instead he’s humiliated by what is - let’s face it - a pretty sick burn from Alexander. I mean he really got him with that one.

So Philip stands up and he is spitting mad, he draws his sword and wants to kill Alexander. But luckily his friends restrain him, giving Alexander the time he needs to escape.

Alexander goes and spends some time with his mother’s family in Epirus - waiting to see how things will shake out. And all of Philip’s friends are telling him, look man, you have to make peace with the kid. You can’t leave for this invasion of Persia  without an adult male heir who is capable of ruling in case you die on campaign.

And to his credit, Philip takes their advice. He extends the olive branch, brings Alexander back home, and makes peace.

Having said that, there is still a little unease between Alexander, his mother Olympias, and Philip. But, needing a strong heir in place, Philip really bends over backwards to accommodate them. As part of that, he has a big monument constructed that has a statue of him and standing right behind him are Olympias and Alexander. Philip is making every effort to re-emphasize that hey, Alexander is my one and only true heir.

Another thing he does to assuage their fears is arrange a powerful royal marriage between his daughter and Olympias’s brother.

This wedding is really supposed to be Philip’s final act before heading off for Asia to invade the Persian empire. It’s basically a very elaborate way of saying “Hey everyone, I’m super cool and powerful. And by the way, if I die, Alexander is in charge.”

But as we know if you listened to the Philip episodes, Philip is assassinated at this wedding.

Alexander acts very quickly. He’s obviously in the strongest position to take over his father’s kingdom, but he needs to worry  about rebellions. If the Greeks see even a hint of dissension in the Macedonian ranks or get a whiff of weakness from Alexander, they’re sure to rebel. So Alexander acts very quickly and is ruthless to consolidate power.

One of Philip’s top nobles and commander, a guy named Antipater, brings the soldiers together at a place called Vergina and carries out the necessary ceremony where the soldiers declare Alexander king as they clash their spears on their shields. Alexander is 20 years old when this happens and he becomes king.

After this, Alexander has all other potential rivals killed, including the infant daughter of Philip’s seventh wife. Women couldn’t sit the throne, but I guess he must have feared that she could have legitimated the claims of a man by marrying him. At the time, many claimed that Olympias was behind the killings and that she did it out of pure spite and jealousy. It’s impossible to say now with certainty who ordered the killing and why.

In any case, there were three top commanders who Alexander had to reckon with. The first, Antipater, was with Alexander in Macedonia and as we just saw, was immediately loyal and declared him king. One down.

The other two were together in Asia Minor, leading Philip’s advance guard for his invasion force of Persia. Their names were Attalus and Parmenion.

Attalus was the same guy who Alexander had thrown the wine at - at the wedding, and he immediately knows that he’s in danger. There are two stories, one is that he writes to Athens, asking them to join him in rising up against Alexander, but then changes his mind. Attalus of course tells a different story. He claims that Demonsthenes of Athens wrote to HIM but he rejected the offer to rebel.

For Alexander, who hates Attalus, it probably wouldn’t have mattered either way. He writes to Parmenion and basically says “Hey could you do me a solid and prove your loyalty by killing Attalus?”

Attalus was actually Parmenion’s son-in-law, but Parmenion could see which way the wind was blowing, and he does have Attalus killed.

Consolidating the Kingdom:

So with that, the internal danger of a Macedonian challenging Alexander for the kingship is over. But before Alexander can carry out his father’s dream and invade Persia, he needs to make sure that his broader empire is obedient and his borders secure.

For his first act, Alexander calls together all the Greek city-states, in something called the League of Corinth. This was an organization established by Philip that was essentially a puppet state for him to control all of Greece. Except for Sparta, who refused to join. But basically all the other Greek city-states belonged to this League of Corinth.

And Alexander calls them together at Corinth to affirm him as the heir to his father’s throne and essentially the master of Greece. So they all show up and say Alexander, you are totally king, you’re very powerful, you’re very cool, your jokes are funny, we love you.

While visiting Corinth, many of the city’s exceptional residents came to Alexander with their congratulations. However, one significant absence was the philosopher, Diogenes the Cynic.  

Diogenes was a controversial figure.  He accused everyone of corruption. He critized society and lived outside of society. He lived in a barrel outside the city, only wore one simple roughspun garment, and basically lived as a homeless vagrant. That is why the school that he founded is known as cynicism which literally means dog-like. In other words implying that Diogenes lived like a dog.

Alexander, called on Diogenes, but he was basically given the response that “if Alexander wants to meet me, he knows where to find me.”  Alexander trekked to the philosopher’s barrel outside the city where he found Diogenes sun-bathing.  The philosopher took little notice of Alexander and after the king offered Diogenes his greetings, Alexander proceeded to ask Diogenes if he wanted anything.  Diogenes is said to have raised himself up a little and remarked, “move a little to the side, you’re in the way of the sun.”

As they walked away, members of Alexander’s retinue were making fun of Diogenes but Alexander silenced them, saying, “if I were not Alexander, I would wish to be Diogenes.”

The Destruction of Thebes:

So Alexander returns from Corinth with his empire firmly in control.

He then turns his eyes toward securing his borders in preparation for carrying out the invasion of Persia. He also wants to try out his new army. This is his first time in command of the entire Macedonian army, and you’d like to have some battles before the big one. You don’t want your first game to be the Super Bowl, so to speak.

So he marches around to Thrace and Illyria and beats up on some barbarians for a bit. During one of these battles, Alexander receives an injury. Nothing major, but combined with the fact that he’s been away from the capital for a few months now, this injury snowballs into a rumor that Alexander is dead.

Well, when this rumor reaches Greece, Thebes, one of the major city-states there, starts celebrating and they declare their freedom from Macedonia. 

Alexander leaves Thrace and force marches his troops all the way to Thebes.  He gets their with astonishing rapidity. Weeks before anyone would have believed he could have done it. As you’ll recall, fast marching is a hallmark of great conquerors. And Alexander could march with the best of them. He was lightning fast. 

When the Thebans see his advance guard, they think that there is no way this is Alexander, who was just in Thrace. They literally refuse to believe it’s him. We heard he’s dead and besides, there’s no way he could have marched that quickly from Thrace to here.

Alexander besieges Thebes, and there’s actually a battle outside the city walls, the Thebans think they have a chance in open combat so they bring their men outside the city walls. Alexander’s men see an opportunity and commit themselves without his explicit command. But in their haste they overextend and are counter charged by the Thebans. But the Thebans make the same mistake and are counter-counter-charged by Alexander’s forces.

The Thebans retreat so hastily that they are unable to close the city gates behind them, and Alexander’s men flood into the city and lay waste to it, massacring thousands of Thebans. In the end, Alexander decides that the city has been so thoroughly destroyed by his men that it’s beyond saving - plus it had been rebellious besides. So he destroys it and enslaves the remainder of the populace.

Now there is some awkwardness. Some of the city-states had expressed willingness to aid Thebes or had at least expressed encouragement at the rebellion. This included Athens, and I love this quote from Arrian, who was an ancient Roman who wrote a biography of Alexander. He said “the Athenians sent ten envoys to Alexander to say that the people of Athens were delighted by his safe return from the Illyrians, even if they had not expressed this sentiment at the time.”

That’s some really good A+ back-pedaling right there. Hey we were super glad you were alive, even if we forgot to show it.  I was happy to see you, I just forgot to smile.

The Invasion of Asia:

With Thebes destroyed and all of Greece pacified, Alexander finally decides he is secure enough to carry on his father’s legacy, complete his vision, and invade Persia. The ostensible reasons for the invasion were due to some Persian invasion 200 years prior and some temples they had destroyed when they were there.

It was also supposedly for the liberation of some Greek city-states in Anatolia that were under Persian rule. But the thing is, the Greeks actually didn’t really mind Persian rule for the most part. They were known as pretty laid back rulers.

In addition, they were also known as very good paymasters when it came to hiring mercenaries. And the number one place they liked to hire mercenaries from was Greece. As a consequence, though Alexander was supposedly fighting a crusade for Greek liberty, in the end more Greeks ended up fighting for his enemies than for him.

It was a pretty flimsy pretext, and everyone knew that it had more to do with winning glory and riches. And frankly because he thought he could.

But why did he think he could? Why was he so sure that  he could just march into the biggest empire on earth and beat them on their home turf? 

Remember, Persia was past its prime, but it was still THE dominant power in the known world to these people. They would have armies many times the size of Alexander’s. 

Well the reasons were supreme self-confidence in his abilities as a commander on the part of Alexander and Greek chauvinism on the other hand. The Greeks truly believed that they were better than everyone else. And to their credit, they were some of the fiercest fighters in the world, especially when it came to their heavy infantry.

Alexander’s father, Philip, had created a new infantry tactic that was virtually unbeatable. Traditional Greek hoplites wielded spears about 7 or 8 feet long, but Philip had trained his men to use great long pikes called sarissas that were more like 15 feet long.

With these pikes you could have 4 or more ranks of men jabbing the enemy. Philip and Alexander typically used them to hold the enemy in place and then strike with their cavalry to finish them off.

So it’s with great optimism that Alexander invades Persia.He crosses the Hellespont - that’s the narrow little strip of water in modern day Turkey that separates Europe from Asia - and he starts marching toward the interior of Asia Minor, that’s modern day Turkey.

Alexander’s opponent, - The King of Persia -  was named Darius. He had a number of generals and advisors. One of the senior ones was a Greek by the name of Memnon. Memnon advised Darius to go scorched earth strategy. He said that the Macedonian infantry was far superior to their own, and they shouldn’t risk open warfare.

He advised they burn all of the crops and all of the towns. Don’t give Alexander a chance to gain a toehold or gain supplies. It’s a great strategy, and it probably would have worked, but the native Persian advisors of Darius prevailed. 

They say in effect, Darius, you’re the king of kings, this is THE GOSH DANG PERSIAN EMPIRE, and you’re expecting us to cower before this upstart kid from nowhere? C’mon. Be serious.

We’re not going to burn one stalk of grain. We’re going to go beat him in battle.

So against Memnon’s counsel, they march their army to the border of the Granicus river.

Alexander meets them there. The two armies camp on either side of the river, and Alexander’s chief advisor, Parmenion, advises him to wait. It’s risky to attack over a river, they’ll suffer casualties, and he’s sure that if he just waits overnight, they can attack them at dawn and surprise them. In fact I’ll just read the exact quote:

P28 of Arrian.

We can see that Alexander was very focused on the psychology of his men. And great generals are always focused on morale. On momentum. As Napoleon is purported to have said, more battles are lost by loss of hope than loss of blood. So for Alexander it was no small thing  to hesitate, he wanted his forces to feel that they had his confidence, wanted them to feel aggressive and confident.

And so he attacked immediately.

He forms up his troops with his infantry in the center, Parmenion leading the cavalry on the left wing, and he himself leading the cavalry on the right wing, including the elite companion cavalry.

They form up and there is a quiet before the storm.

“For a time both armies held their position at the river’s edge, shrinking from what lay ahead. There was a great silence on both sides. The Persians were waiting for the Macedonians to enter the river, intending to attack them when they climbed out.”

You can imagine this moment. Years of planning, hundreds of miles of marching, hundreds of thousands of men, have all led up to this. Alexander’s entire life has all led up to this. And he’s going to risk it all by marching up hill out of a river, right at the greatest army in the world.

You can feel the heaviness of the moment.

And then Arrian tell us “Then Alexander, leaping onto his horse and urging those nearby to follow him and show themselves true men, ordered the Scouts to charge into the river with one infantry battalion. ALexander himself, leading the right wing to the sound of war trumpets and the men raising their cry, entered the stream.”

Now Alexander is leading the right wing, which attacks first. But he doesn’t make first contact. A different detachment of the right wing does. And they’re like the first ones to land on Normandy beach in WW2. Here’s what Arrian says happens to them.

“Where the first troops touched the bank, the Persians shot at them from above, some hurling javelins into the river from the bank, others descending to the lower ground at the water’s edge. There was a shoving match between the two cavalries - one emerging from the river, the other barring its way - and a dense shower of javelins hurled by the Persians, while the Macedonians assailed the enemy with their spears. But the Macedonians, far outnumbered,  suffered in the first assault; they were defending themselves from a low and insecure position in the river, whereas the Persians were assailing them from above. What is more, the strongest contingent of the Persian cavalry had been stationed at this spot. Thus the first Macedonians to engage the Persians, though they showed themselves brave, were cut to pieces.”

Alexander, seeing this massacre, doesn’t retreat, but hurries to the spot with the rest of the cavalry of the right wing. “Bringing up the right wing, Alexander now drew near and himself launched an attack on the Persians at the point where the mass of their cavalry had been posted and where the Persian commanders had been stationed.”

This would be a hallmark of Alexander’s style. He always went straight for the jugular.  He himself would take his best troops and attack their command. In this case, one benefit of this is that it serves as a distraction. Everyone is watching as Alexander attacks the Persian high command.

“A fierce battle was joined around Alexander, and meanwhile, battalion after battalion of Macedonians succeeded in crossing the river with no difficulty.”

Arrian tells us that though this is mostly a cavalry battle, it resembles an infantry battle because of the tight space around the opposite bank where all the fighting is occurring. It becomes something of a shoving match. Alexander himself exposes himself to great danger.

P30, paragraph 6.

Now remember, the Macedonians fight with sarissas. These big 15 foot pikes. This has advantages and disadvantages. But one advantage is that this fighting style tends to wear down the enemy over time.

Imagine you’re a Persian cavalryman during this battle. You charge in, and at first things are going alright. The Macedonians have these big long pikes, but they can’t get much thrusting force because they’re so long. They’re more of an annoyance than anything else.  They’re more poking and pushing than they are truly thrusting  to kill. And you’re knocking aside these sarisas and trying to get a good stab in at your enemy.

And then as time goes on, these sarissas keep just swinging and poking around your face like flies. Remember, they’re long enough that multiple ranks can have their sarissas going at once.  You find that you’re constantly occupied blocking the and knocking them aside. And then one glancing strike gets through your defenses and cuts your cheek. It’s not much of a cut, but it’s not nothing.

And then a few minutes later, another pike swings by and hits your mouth. You think it might have knocked out a tooth but you don’t have time to check. And then a sarissa that you don’t even see cuts your arm. And now another blow hits you on the forehead. And now you’re tired, you’re sick of constantly trying to fend off these blows, there’s blood in your eyes, blood in your mouth. And you start looking around, and seeing that the men to your left and to your right are looking every bit as tired as you.

And then you see one sarissa hit a guy square in the face, and his nose is half dangling off. And you start to back up a little. In fact, you realize, everyone is backing up a little. And then someone starts to turn and run. And before you know it you’ve turned your horse around. All  you know is you don’t want to be the last man off the battlefield.

This is exactly what Arrian tells us happened. He says “And now the Persians, their faces, and those of their horses, torn by the lances striking them from all sides, were thrust back by the Macedonian cavalry. They gave way first where Alexander was bearing the brunt of the battle. When their center collapsed, both cavalry wings also broke and a desperate flight began.”

The Persian cavalry flee, and the Greek mercenaries who served as infantry are left standing dumbfounded in the middle of the battlefield. Alexander surrounds them and begins to slaughter them, though he eventually takes two thousand prisoners who he sends back to Greece as slaves.

The Persian army is shattered completely. Now the war isn’t over. This was a regional army, not the full Persian army. Darius himself wasn’t at the battle. But it’s a huge victory. In a single day, Alexander has won all of Asia minor, most of modern day Turkey.

Alexander’s Administration

Alexander then does something interesting. He takes a Macedonian man by the name of Kalas, and appoints him as satrap. Satraps were the Persian governors of the various regions throughout the empire. 

This is Alexander, a Macedonian, at the head of a combined Macedonian and Greek army, in the cause of Greek liberty, and he’s full on borrowing Persian institutions.

It’s basically the opposite of what the USA did in its invasions of Iraq and Afghanistan. Instead of replacing the administration, he’s keeping it entirely intact and only replacing the man at the top.

Partially this reflects the centrality of the Persian empire to the Mediterranean world. It was the only real empire around. The Persian king was THE king of kings. In fact in Arrian’s campaigns of Alexander, when he simply says “The King,” he isn’t referring to Alexander, but to Darius. So this is the only real model that Alexander has for how to run an empire.

But it’s also a clever propaganda move by Alexander. He’s basically saying “Look at me. I’m the captain now.”. I’m the king of kings. I’m the one with the power and authority to appoint satraps.

And that would be his official position ever after the Battle of the River Granicus. That he was the rightful King, and that he was only temporarily being dispossessed by Darius, who was stubbornly refusing to let Alexander take his rightful throne. And on a certain level, this was effective in portraying a sense of inevitability that he would eventually win.

The one place where he does change the administration is in any Greek city-states in Asia minor, of which there were many. He abolishes the oligarchies, establishes democracies in their stead, and cancels their taxes.

Despite all of this, capitulation to Alexander is not total And he has to march around and attacking or besieging holdout towns in order to subdue them. This goes on all fall. In the winter, Alexander sends home any recently married troops so that they can go take care of their business and frankly impregnate their new wives. Alexander himself remains with his older troops - the poor guys who don’t get to go home to  get laid, and together they conduct more mopping up operations in Asia Minor.

It is during these mopping up operations that Alexander comes to the city of Gordian. They had a legend that an old farmer had a wagon and long story short, there’s a rope at the end of the wagon that had tied it to a post but the rope got impossibly tangled into this huge tight ball of a knot, and the old farmer prophesied that whoever could untie the knot would be the king of all of Asia. Supposedly the knot sat there, unsolved, for a hundred year.

So Alexander comes to this city and finds this knot. He’s 22, he’s just won this major victory, he’s styling himself as the King of Asia, and he feels like he has to solve it, and prove that he’s the one to rule all of Asia. According to one legend, he stays up all night carefully picking at the knot and eventually is able to untie it.

But according to the more famous version of the story, he stares at the knot for a while, takes out his sword, and CUTS THE KNOT IN HALF, declaring “Now it is undone.”

This is probably a later invention, but it’s a great story. And a gordian knot is a common expression now for an extremely difficult or unsolvable problem, and cutting the gordian knot is an expression that means solving such a problem with a clever or incisive solution.

And true or not, the story is a great symbol of Alexander’s nature. He always found the direct route to solving the problem and shed all extraneous consideration.

After cutting the knot, Alexander is rejoined in Gordian by his fresh recruits who had gone home from the winter to spend some alone time with their wives. His army once again at full strength, Alexander marches toward Syria. 

A Clash of Kings:

But he was not going to be able to march through the rest of the Persian empire unchecked. Darius himself had not been present at the Battle of the Granicus River, and he was now leading the full force of the Persian army, and he was pursuing Alexander.

When Alexander hears that Darius is in the area, he marches straight for him. In fact, Darius and Alexander are both looking for each other, and they pass each other. This is dangerous for Alexander because it cuts off his supply line.

So he turns his army around and meets Darius and the Persian army at Issus. 

He’s in a very familiar position. Once again, he has to be the attacker, and must attack over a river. Unlike at the Granicus, where the forces were pretty close to equal, his army is VASTLY outnumbered this time.

The night before the battle, Arrian tells us that Alexander “said everything a brave leader would naturally say to hearten brave men on the even of a dangerous venture, and his troops approached him from all sides, clasped their king by the hand one by one, and with encouraging words urged him to lead them out at once.”

The next day, Alexander leads them out to the battlefield, only to find that Darius has begun to build rudimentary defensive fortifications on the opposite bank. This is a sensible thing for Darius to do, since he knows that Alexander has to attack. But Alexander uses it to his advantage, telling his men “This made it clear that Darius, in his own mind, had already been humbled in spirit.” In other words, he knew he couldn’t face Alexander in open battle, and was too afraid to attack. 

Once again the armies line up. Alexander rides up and down the line, we imagine he must have looked stunning riding on bucephalus, sporting his armor, and looking very active. While Darius was at the battle, situated in the center, behind the front divisions, you don’t get the impression that he was as involved, or that he was quite the fighting man that Alexander was. So he’s drawing a contrast.

Finally the time comes for the battle to begin. Once again, Alexander leads the right wing, Parmenion leads the left wing, and the infantry are stationed at the center. And once again Alexander leads the initial charge. This charge is largely successful. But it’s unfortunately too successful. Alexander leads too far out and becomes separated from his infantry.

They try to attack the Greek mercenaries at Darius’s center, and are largely unsuccessful. In fact, they’re faring pretty poorly.

At the same time, Parmenion’s forces on the left wing are attacked by the Persian cavalry on that wing and are also looking like they are losing.

So Alexander is winning on the right flank, but it’s looking like it won’t be enough since his center and his left flank are being beaten. 

But that’s when Alexander pulls out his signature move. His stone-cold stunner, his RKO, his PEOPLE’S ELBOW.

He takes the men with him, the companion cavalry, essentially the special forces of the Macedonian army, and he charges straight at the back of the Persian infantry, right where Darius and the Persian command are located. 

Darius, who is in a war chariot as was the Persian tradition, flees the battlefield. And when the rest of the Persian army sees the King of Kings, a god among men, fleeing before ALexander, they too turn and run. 

Alexander was a genius at this. He understood the one thing he needed to achieve in order to win, and then he assembled an extremely strong, highly concentrated force to achieve it. 

He is once again cutting the gordian knot, so to speak. He realizes he doesn’t actually have to untie the knot, just undo it. Similarly, he doesn’t necessarily need to beat all of Darius’s hundreds of thousands of men, he just needed to beat Darius.

Don’t be like Darius. Be like Alexander. Don’t try to win everywhere, try to identify the one thing that you need to achieve that will unlock everything else. Then concentrate all of your energy and your best resources on achieving that one thing.

I see this happen to me all the time when I’m planning out my week. I’ll have this big long list of things I need to get done. And there’s nothing wrong with that, I do need to get a lot of those things done. But it’s actually much more effective to focus 80% of my energy on the one or two things that are really going to make a difference.

Now after Darius flees, Alexander would like to pursue him but there’s a problem. Parmenion is still getting owned by the Persian cavalry, and about half of the Macedonian infantry are also in trouble. So rather than pursuing, Alexander has to wheel around and save the rest of his army.

The battle is won, but Darius escapes. Though he leaves his chariot, his shield, his cloak, and his bow in his haste to get away.

Alexander tries to catch up with him, but he’s too late. But in the Persian camp he does find Darius’s mother and wife.

And Alexander’s men are wondering, what are you going to do? Are you going to execute them? Are you going to have them publicly humiliated? Hold them for ransom? Imprison them? Cut off their hair? I mean this is ancient warfare, there were plenty of nasty options.

But Alexander says what I want you to do, is take them, put them in a royal tent, refer to them as your highness, bring them the nicest food we can spare, and in all ways, continue to treat them like the queens of Persia. Which seems like an odd choice at first. I mean, aren’t these the people he’s supposed to be overthrowing?

And it actually reminds me of a story from the life of Julius Caesar.

When Caesar won his final battle in the civil war, his men go to the tent of the enemy general Cato, and they find a chest with all of his letters. Now this is a juicy find because it was a dirty civil war with lots of people switching sides and professing to support one side but secretly supporting another and all this sorts of stuff.

And so with these letters, Caesar and his supporters can finally find out who were really their friends all along, and who had only been pretending. Over the previous decades, there had been a series of bloody murders and executions, what were called the proscriptions. And so the assumption was hey, we’re going to look at these letters and find out who was really opposing you this entire time.

And his men are giddy at this find and they come back to Caesar and say “What do you want us to do with these?”

And Caesar says, thank you for these letters, now kindly put them on a pyre and burn them all. Because the war was over. All Romans were his subjects now. It didn’t matter. There was no opposition. To take retribution on his enemies would be to admit that he still had enemies. 

And in his view he didn’t. He was the one legitimate ruler of the Roman empire.

And Alexander is doing the same thing. He’s essentially saying look, I just beat Darius. I’m the King of Kings now. These women are not only my subjects, but they’re essentially my family now, since they were related to the old king of kings.

He’s establishing continuity with the old rulers. Look, it’s the same kingdom, there’s just a new guy at the top, but you’re going to keep paying your same taxes and obeying the same laws. It’s a genius strategy.

In a matter of weeks, Darius manages to make his way back to the heart of the Persian empire. Many of his forces having survived, he feels beaten and humbled, but not completely defeated. And so he writes to Alexander and makes a request and a proposal.

Arrian summarizes what Darius wrote, quote:

“Their battle’s outcome had doubtless accorded with the will of some god, and as a king he was now asking a king for his wife, mother, and captured children, and was also ready to form a friendship and an alliance with Alexander.”

In a followup letter, Darius offers Alexander all of Persian territory from the Euphrates to the Greek sea, that’s modern Iraq, Syria, Turkey, Jordan, Palestine, Israel, and Egypt. And his own daughter’s hand in marriage.

So… Alexander has made it. Darius is offering him intermarriage with the most powerful family in the world and oh yeah, HALF THE PERSIAN EMPIRE. Alexander is 23 years old. He could accept the deal and go down in history as one of the greatest conquerors of all time. His empire would be 1A and 1B with the Persian empire, they would basically co-rule the world together. He’d be, along with Darius, the most powerful and wealthy man in the world.

This is like being 23 years old and having someone offer to acquire the company that you own  100% for $200 billion dollars. You won! Okay maybe you’ll have slightly less money than Elon Musk, by a couple billion but you just played the game of tech and won. Cash out baby, this is the moment you’ve been waiting for.

Alexander shows the letter to his advisors. Parmenion tells him c’mon man this is a no brainer. I would accept that deal if I were you.

But, quote “Alexander replied that if he were Parmenion, he would do likewise, but since he was Alexander, he would answer Darius as he did in fact answer him.”

Alexander does not accept. He says in essence this: Hey Darius, first of all if you want your wife, mother, and children back, come to my court and ask for them. You will not be harmed, you will be given your family back, as well as anything else that you can convince me to give you. Secondly, I will marry your daughter if I choose to. Even if you don’t offer her. That is my prerogative as king of kings.

And lastly, Darius, stop referring to me as your equal. You are not my equal. I just defeated you in battle and proved as much. In the future, please refer to me as the king of Asia.

X o x o - Alex

Arrian tells us “When Darius heard this, he gave up hope of coming to terms with Alexander, and again set about preparing for war.”

For Alexander, being the most accomplished Greek king of all time was not enough. Being co-emperor of Persia was not enough. He had set out to conquer the entire Persian empire. And nothing less than total victory would do.

There is something powerful about that clarity of vision. Knowing exactly what you are trying to achieve. It allows you to see through all the fluff. All the extra stuff. It sharpens your thinking and keeps you focused.

And as I read this story it got me thinking, what is my Persian empire? What is the thing that I won’t stop until I have achieved.

I think everyone should find that for themselves. And should know it and always keep it in mind.

So anyway, that’s it for part 1 of Alexander the Great, stay tuned for part 2 next week!

Until then, thanks for listening.


The feeling you get is that he was very similar to his father, but one key difference was that Alexander never felt quite as  confident or secure… and part of that probably had to do with how he felt about his body.

People often mention the Napoleon Complex which ironically, Napoleon doesn’t actually seem to have had.  Napoleon was never bothered by his height.  I can’t say for sure whether Alexander was ever bothered by his own height. There don’t seem to be any stories in which he gets mad at anyone for mentioning his height.  Indeed, there’s at least one story of him being good natured about it.  

But for whatever reason, where his father was confident and comfortable in his body, Alexander was not.  Philip’s comfort can be observed with his sexual conquests. By contrast, Alexander was almost completely asexual.  We know he had at least a couple lovers, but that was probably it. Still Alexander spoke about not enjoying sex because of a lack of control.  

In fact, Alexander hated sex and he hated sleep because he felt those were the times when he was not in control of his body.  All of this is to state that he possessed this slight insecurity to him where his father did not.

So Alexander is the heir apparent when he’s born.

Alexander was similar to his father in many ways.  He was just as brilliant and just as energetic. Just as charismatic and charming.

But Alexander was also different in a few key ways.  Whereas Philip was tall, Alexander was short. And where he was bearded and dark-haired, Alexander was always clean shaven and was known for his notable light hair. This sometimes gets embellished to him having white or platinum blond hair but one the more reliable accounts say that  his hair was “tawny like a lion’s” which seems much more likely.  

To think about a lion’s hair color - that could range from dark blonde to light brown or even a little reddish. 

Alexander had light eyes. Probably light blue or greyish blue. And a ruddy complexion.

He was presumably well-built, as he was athletically gifted and a great sprinter.

And as I said earlier, he’s intelligent and charismatic, and he demonstrates as much from an early age.

He’s a talented musician, orator, athlete, and diplomat.

It’s said that this experience moved Philip to tears who declared, “my son, Macedonia is too small a kingdom for you.”

Alexander was eager to prove this to his father and often responded poorly at the news of Philip’s victories.  With each success, Alexander complained there would be nothing in the world left for him to conquer.  He proved impatient embarking upon mini campaigns, disputably unnecessary.  

In one instance, Alexander traveled to a community just outside the kingdom where excitement was mounting among the tribesmen.  Alexander identified trouble and questionably set to depopulate the society.  Re-populating the land with Macedonian settlers and setting it about his way, Alexander renamed the community Alexandropolis after himself.  Alexander was anxious to model his father’s success who Alexander did not feel close to per Philip’s frequent absence away on campaigns.

It seems important to note that Olympias and Alexander carried a sort of insecurity throughout their lives toward their relationship with Philip the II.  But it is also worth noting that when Philip immortalized himself as King of Macedon in a stone rotunda?, he only chose to include Olympias and Alexander though he had significantly more wives and family. 

Like Father Like Son:

It’s a worth a moment to compare Philip and Alexander.  Philip was a truly remarkably gifted man.  His life and success are worth taking a detailed review of as Philip was extremely accomplished.  We know Philip was tall. He was handsome.  He was gifted in terms of interpersonal skills.  He made friends extremely easily.  Many were charmed by him.  It all made sense because Philip was intelligent and exceptionally capable.

Philip was also exceedingly skilled as a military commander.  He governed his domestic affairs really well.  He was great at accumulating wealth. He built Macedon into a prosperous kingdom which elevated its reputation abroad.  Philip seduced a lot of women and likely had many bastards.  He seduced a lot of men, because hey, these were Greek times.  He could be labled a Rockstar, a man’s man, the ultimate chap.

Alexander acquired his most famous tutor at the age of 13 or 14 years old when his father secured Aristotle.  Philip bargained the rebuild of Aristotle’s hometown for the trade of Alexander’s education.  As the product of direct tutoring of one of the greatest philosophers of the classical enlightenment era, there are strong arguments to be made for the progressive philosophic thought experiments these philosophers employed.

One could argue that Aristotle’s philosophical contribution was the argument for practicality beyond the employ of pure reason.  Where Socrates and Plato explored intuition, experience, and reasoning, Aristotle employed a practical methodology resembling something akin to what we call science.  His keen observation gave way for the reasoning of the mind to influence its application in the world.  Throughout Alexander’s campaigns, he often sent Aristotle exotic specimens to inspect as Alexander continued under the guidance of Aristotle.

Alexander received the quintessential Greek classical education.  Not only an education focused on thought and reason but also prioritizing physical fitness.  Proper Greeks from Athens or Phoebes or Corinth prioritized physical education similar to what we would witness in a gym today.  They would strength train and body build and prioritize a purely aesthetic development of the body.  However, the Macedonian training focused on martial education such as wrestling, fighting, horseback riding, and other skills useful in combat.

About Episode

Alexander the Great took his father's kingdom and made it the greatest empire the world had ever seen. Part one covers his childhood, education, rise to power, and early conquests.

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