November 19, 2021

Alexander the Great (Part 2)


Alexander Part 2 Script

HELLO, and welcome to How to Take Over the World. I’m back, with part 2 of the life of Alexander the Great.

I’d like to start with an analogy, if that’s alright. In Chelyabinsk Russia, the 15th of February, 2013, started just like any other normal freezing winter day. It was a Friday, and many people were still on their way to work when they saw a bright light in the sky.

As it streaked across the sky, it got brighter and brighter until it was brighter even than the mid-morning sun. It then winked out.

Several minutes later, there was a deafening boom and people standing outside felt a wave of heat wash over them. All across the city, people were knocked over by an unseen wave and thousands of windows shattered.

And then it was over, the only evidence that anything had happened was a slight odor that people described as smelling like gunpowder or sulphur. Hundreds of people were injured but miraculously, no one was killed.

It turned out that miles above them, an asteroid had hit the atmosphere with such speed that it released an explosion over 30 times greater than the nuclear bomb that destroyed Hirsohima. It was the largest asteroid to hit earth in over a hundred years.

And luckily for the residents of Chelyabinsk, the blast happened so high in the atmosphere, that they only felt the very edges of that explosion.

But it must have been an incredibly bizarre thing to experience. Something brighter than the sun suddenly appears in the sky. A phenomenon that no living human had experienced. And then boom and then it’s over. Go about your life like nothing ever happened, I guess.

The life of Alexander the Great is kind of like that. He explodes onto the world scene, conquers everyone in sight, establishes the largest empire the world has ever seen and then right as he is coming into the height of his powers, he dies.

And sorry, spoiler alert, the empire basically disappears.

And just like the residents of Chelyabinsk in 2013, we are left wondering how to account for it. So on this episode I’ll try to explain how such a magnificent empire could arise so quickly, and obviously what personal attributes of Alexander enabled him to be the one to do it, and then how it all came apart so quickly.

But before we get into it, here’s a brief word from our sponsors.

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Quick recap on where we’re at: Alexander grows up in Macedonia, takes over as king when his father dies, mops some things up back home, then invades the Persian empire. He scores a major victory at the Battle of the Granicus River which wins him all of Asia minor, modern day Turkey, and then he wins another large battle, the battle of Issus, and for the first time he has defeated the fully assembled army of the Persian empire, and now appears to be a significant threat.


After winning the battle of Issus, Alexander’s most important task was to ensure that the Persian could no longer threaten him from the sea.

He had beaten them at Granicus, and beaten Darius himself at Issus, but the whole time a Persian fleet had been harassing his Greek allies and threatening to link up with the Spartans, who never joined Alexander’s League of Corinth, and potentially join them in an invasion of Greece or Macedonia.

So you can imagine that there is a scenario where Alexander is winning battle after battle in Persia, but it doesn’t matter because his home territory is invaded by sea because he basically doesn’t have a navy.

Well it turns out that most of the Persian navy operated from Phoenicia, which is basically modern day Lebanon. So after Issus, Alexander marches through Phoenicia. And without the Persian army there to protect them, most of the Phonecians surrender to Alexander, and turn over their cities, including their pots and their fleets.

But they have one city that doesn’t do this, called Tyre. And Tyre is in fact the wealthiest and most important city in Phoenicia, so it’s a big problem that they won’t surrender to him. They won’t surrender because they want to remain neutral, and because they basically think that their city is impossible to besiege, so there’s nothing Alexander can do about it anyway.

Tyre was on a little island just barely off the coast, and it was wealthy, well-supplied, and had big walls surrounding it. And so legitimately, if you’re Alexander, what do you do? How do you besiege a city that has enough supplies to last for years, is able to resupply itself from the sea, and has no land around it where you can bring up battering rams or siege engines? What would you do?

This is a difficult circumstance, and every proposal is going to seem crazy, but Alexander’s suggestion is perhaps the craziest of all. He wants to change the literal landscape.

His plan is to shovel and build and connect the island to the mainland. Not just by building a bridge, mind you, but by actually connecting it with stone and dirt so that it’s no longer an island.

So he sets his men to building this what’s called a mole. Basically a land bridge. And Tyre is about a kilometer from the shore, so they have to build a kilometer long mole. And at first the soldiers and sailors in Tyre are just laughing at them. But day after day they’re making progress and the Tyrians start to think: Okay this is still probably crazy, but maybe we should start to take this seriously.

A game of chess ensues where each side is coming up with new tactics every day to match and beat out the other side. A game of cat and mouse. We’re going to shoot arrows at your workers so they can’t keep building this mole. Okay, then we’ll build wicker walls for the builders to work behind. Okay, then we’ll set our arrows on fire to burn the wicker walls. Alright, then we’ll douse the wicker in water. Then we will launch a surprise raid to destroy your work. Then we’ll start building towers along the mole and post guards. And so on and so forth. This goes on for seven months. And throughout it, this land bridge is slowly getting longer and longer. And at the end of it they’re able to roll up some siege engines, and in conjunction with an assault by sea, get over the walls and destroy and subdue Tyre.

Now this story is remarkable to me because it’s almost the opposite of what we came to expect from Alexander based on the first episode. The main theme that I pulled out of episode 1 was cutting the Gordian knot. Finding the simple solution that cuts through the noise and gets the end objective accomplished FAST.

Well this is the opposite of that. Here he is literally moving heaven and earth. It’s a slow and technically complicated solution that uses brute force rather than cleverness.

It reminds me of Edison. His early inventions all hit him like a bolt of lightning. They’re new, clever ways to solve problems that no one could have ever imagined. But then he gets to the lightbulb, and he has no flashes of brilliance. He actually thinks he does early on but it doesn’t work.

And so his process for solving the problem of a lightbulb is to just try thousands of designs to see what will work. He just brute forces a solution through trial and error.

And that’s similar to what Alexander does here. You’ve got to be able to have that dual approach, of saying okay, I’m going to look for a clever, novel solution here. But if I can’t find that or if it doesn’t exist, I’m just going to sit here and chip away at it and be patient and solve the problem through sheer grit and by bringing more resources to bear than my opposition.


After conquering Tyre, Alexander turns his eye toward Egypt. Egypt was always important, it was a wealthy territory, it was basically the bread basket of the middle east and eastern mediterranean, the Nile river valley was extremely fertile and provided a lot of grain.

And luckily for Alexander, they’re basically inviting him in. He just has to go collect it. The Persian kings had disrespected the local religious traditions, and so the Egyptians were ready to be done with them.

Plus there was really nothing that King Darius could do at this point, Alexander was between him and Egypt and there was nothing he could do to stop Alexander from taking it.

Alexander is of course over the top in his observance of their religious rites. As part of that, he becomes not just king of Egypt, but pharaoh. And that title is a deitific, meaning he is considered not only a ruler, but a god.

As I’ve noted before, Alexander made these religious observances, not just for cynical reasons, but it appears that he was a genuinely pious and religious person himself. When he first comes to Egypt he of course does all the necessary stuff of installing a satrap and doing some basic government reforms, but he soon takes a journey to a tiny little Oasis town called Siwa in order to visit a very famous oracle there:

The god of Amūn or Ammon. Siwa was famous for their god Ammon, even though it was an insignificant town. I mean it’s literally in the middle of nowhere. NOTHING around.

It’s on the border of modern day Egypt and Libya, and if you look at it on a map you’ll see that it’s just sand for hundreds of miles in every direction. So this town had no military, political, or economic significance

Because Siwa was so remote, they had been separate from Egyptian civilization and culture for millenia, and that is why they had their own gods. And I think that made their gods seem kind of exotic. They were foreign, from this weird little civilization that was on the one hand pretty close but on the other hand really weird and foreign because they were these desert people.

Of course over the years the Egyptians had recognized Ammon as similar to their sun god Ra and had combined the two, which they referred to as Amun-Ra.

And if you ever see any old movies like the mummy, you’ll see an old-timey Egyptian priest in a very serious tone invoking “in the name of Amun-ra I summon you from your grave.” or something like that. This hybrid god Amun-Ra was very important and still survives on in pop culture.

Similarly, the Greeks were very impressed by Amun and they saw him as similar to Zeus so they referred to the combined deity as Amun-Zeus.

So Alexander goes to see the oracle of Amun-Zeus at Siwa and he has to march through days in the desert to get there. His party almost gets lost and dies in the desert. And again, there is no strategic advantage to this. He’s risking his life because he really wants to see this cool thing and have this cool experience.

And some historians try to say that there must actually be some political reason why he did this. He’s making this visit to legitimize his rule in Egypt or for future propaganda use among the Greeks.

And I just think that that’s way off. And I hate the attempt to imbue every action in history with this monomaniacal pursuit of geopolitical power. Humans were humans and they did things for power, but they also did things for other reasons: For wonder or curiosity or love or loyalty or  lust or hate or simple enjoyment and all other manner of reasons.

And that’s especially true of Alexander’s story. He was someone of really strong emotions and strong will. I definitely think it’s a mistake to just see him as a force of nature - the manifestation of economic and geopolitical forces greater than himself. He had a human will and he was able to impose it on the world.

So Alexander goes to Siwa and is able to ask the oracle a question. We don’t know what he actually asked the oracle, though later reports would claim that he asked if his father’s murderer had been avenged, and the oracle responded that he was asking the wrong question, since his father was not a mortal. That he was not the son of Philip, but of Amun-Zeus.

While this is probably a later invention, he does apparently have a deeply affecting visit to the oracle. And ever-after, he would refer to himself as the son of Amun-Zeus.

Now some people think that this mean’s Alexander considered himself a son of a god, that he believed that Philip was not his true father. That he believed that a thunderbolt from Zeus had actually come down from Zeus and impregnated his mother.

But this is not true. Alexander always referred to Phililp as his father. When he called himself the son of Amun-Zeus, he was referring to a more distant connection. Through his family history he was supposedly descended from Hercules, who was the son of Zeus. So his allusions to being the son of Amun-Zeus is more a reference to that genealogy, and not any belief that he was in any real sense divine.

Afterwards, after this visit to Siwa, he returns to Egypt proper, finishes settling his affairs, and founds a new port city which he would name Alexandria, after himself. So while he may not have believed that he was the literal son of god, there was still plenty of ego.


While in Egypt, Alexander hears that Darius has been busy fielding a new army. From the Persian perspective, Granicus was nothing more than a skirmish, and the battle of Issus could be explained away as the Persians having under-estimated Alexander and being hasty and sloppy.

But now, well NOW the Persians had the full force of their army. They were bringing in soldiers from Afghanistan, Uzbekistan, Armenia, and Iraq, they were bringing the full weight of the Persian cavalry, they were even bringing fearsome war elephants all the way from India.

And furthermore, they are waiting for Alexander. This time they are committed to fighting on friendly territory in a setting that will be advantageous to them. They are sitting in an open plain in northern Iraq near a tiny village called Gaugamela, near the modern-day Iraqi city of Mosul.

With an open plain, they could use their superior numbers to surround and overwhelm Alexander’s much smaller army. We don’t know exactly how much smaller it was, but most modern scholar’s estimate that it was about half the size of Darius’s. Probably 100,000 Persian soldiers to 50,000 Macedonians.

Alexander takes the bait. He promptly marches his army from Egypt to Babylon. Unlike the previous battles, you can tell that Alexander is slightly intimidated by this massive Persian army. Because unlike the other battles, he doesn’t immediately attack. He takes a few days to draw  up plans and prepare, which is a little unlike him.

The Persian plan was obvious to Alexander and his commanders. They would use heavy chariots to break up the Macedonian infantry, and then use their numerical advantage of cavalry to surround and flank them.

Parmenion, seeing how difficult it would be to beat this massive army on their own chosen ground, encouraged Alexander to launch a night attack. But Alexander doesn’t go for it. He didn’t want anyone to be able to say that he had stolen the victory and illegitimately won the Persian empire through trickery.

Like all great generals, he’s always thinking beyond the X’s and O’s. He’s thinking not just about the tactics, but the psychology. And it’s going to be hard to rule an empire if everyone thinks you stole it by being conniving and sneaky. So he arranges a much more straightforward strategy.

Alexander arranges his troops much as he did at Issus, with the infantry in the middle and his cavalry on the wings, with his most elite troops  - the shield bearers and the companion cavalry  - on the right side, with him personally leading them companions.

Unlike at Issus, Alexander kept a second line of infantry in reserve in order to meet any flanking maneuvers. Alexander attacks, having his men move at an angle to the right.

The Macedonian infantry dealt with the chariot charges well, opening up their ranks when necessary to allow the chariots to pass harmlessly through.

A lot of the details of this battle are missing, because even at the time, people didn’t know what was happening. It was a big flat battlefield on a dusty plain and the horses running around are kicking up dust so no one can really see what is happening from an overall cohesive battle perspective.

You have individual squadrons of cavalry charging and counter-charging each other on both the Macedonian and Persian sides. You can imagine it must have been terrifying, you can’t see anything but you hear the clash of steel, men’s battle cries and horses running around in every direction. And you never know what a squadron are going to come screaming out of the dust right on top of you before you even know what’s happening.

But despite the overall uncertainty, we do know some things that happened in the battle of Gaugamela. And the battle unfolded in a very familiar way if you can think back to the battle of Issus.

Alexander’s left flank, led by Parmenion, is seriously threatened and fairing poorly when Alexander on the right side of the line, notices a weak spot in the Persian line, and charges straight through it with the companion cavalry. They burst through, and head straight for King Darius, who turns and flees AGAIN.

And just like at the Battle of Issus, this flight of their king and leader sends the Persian army into a general retreat. Once again, Alexander is unable to pursue Darius for as long as he would like because he needs to turn back and support Parmenion’s left wing from being overrun.

Alexander had lost very few men, perhaps 500. And while we don’t have accurate numbers of the Persian casualties, it’s in the tens of thousands. The Persian army was crushed. While Darius would still need to be pursued and captured, the war was basically over. After the battle of Gaugamela, Alexander was the new master of the Persian empire.

I just need to point out that this strategy of taking advantage of the pivotal moment is really common among great generals. Napoleon was really great at it, he generally won his battles late in the day after the other side was tired and he would charge his most elite units against the weakest part of their line and break through and break the enemy army.

Julius Caesar was also great at it, and in fact, the Romans basically systematized and institutionalized this style of fighting. Whereas most armies would deploy the vast majority of their forces right from the beginning, the Romans would typically have three rows to their army, and only deploy the first at the beginning, so that they had plenty of reserves that they could hit their enemy with throughout the battle and kind of shock them.

And last thing, and I know I’ve brought this up before, the basketball team the Golden State Warriors circa 2015-2016 had this lineup that was called the death lineup. And it was unstoppable. When they played these five players together, they would just demolish teams. But the would never play the lineup until the second half of games, late third quarter and for most of the fourth quarter.

And lots of people, myself included, would criticize their coach, Steve Kerr, saying if this lineup works so well, why don’t you just play it for the entire game.

But you know he won multiple championships and coached some of the greatest teams of all time because he’s smarter than people like me, and I doubt he was intentionally mimicking Alexander the Great and Napoleon but he was very much using the same strategy as them.

There does seem to be something about wearing your opponent down first, keeping some fuel in the tank, something in reserve, and then unleashing it on them once they’re tired. It’s really demoralizing when it happens, and a great way to break the competition.

Taking Persia

After Gaugemela, Alexander quickly establishes control over the main power centers of the Persian empire. He enters Babylon and takes control.

Archaeologists have found some pretty funny temple records from this time. Darius is described as the king of the world on the morning of Gaugamela. A few days later, the record reads “Alexander, king of the world, entered Babylon.”

So you can see how Alexander’s strategy of continuity was paying off, it was very easy for people like the Babylonians to just accept that there was now a new king of the world.

He then marches to Susa, the administrative center of the Persian empire, and captures it without resistance, and seizes their treasury., but otherwise leaves it untouched and undamaged.

He then marches to Persepolis, which was the ceremonial seat of the Achaemenids, the ruling dynasty of the Persian empire. Remember he’s basically running for king of Persia, if you want to think of it as an election, on the platform of continuity. That’s why he left Susa completely untouched, it was the administrative capital of his new empire.

But Perspeolis was different, it represented, not the actual empire, but the dynasty of Darius, the Achaemenids, the guys that had ruled before Alexander.

And so Alexander lets his men run amok and completely pillage the city. He has the treasury completely emptied and taken back to Susa.

And then Alexander does one of the most controversial things of his entire reign and burns the city down. Arrian says that Alexander made a calculated decision to burn Persepolis as revenge for past Persian incursions into Greece.

Diodorus relates that Alexander was up partying with his companions - and he had a few drinks in him - when he was convinced to light the city on fire by a prostitute.

In either case, it seems that Alexander soon regretted the decision. While it did damage Achaemenid prestige, and really made the idea of Darius somehow making a comeback as king impossible, it also created a rift with his Persian subjects. He was disrespecting their traditions and their sacred symbols in the most egregious way possible.

The Chase

In any case, word soon came that Darius was gathering forces in the far eastern reaches of the empire. He was no longer able to muster a force that could even come close to challenging Alexander, who was for all intents and purposes now the king of Greece, Macedonia, and the entire Persian empire. But the fear was that if he continued to hang out on the periphery with a ragtag group of forces, perhaps that might inspire other areas to eventually rebel and join him.

So Alexander furiously pursues Darius through these northern regions in modern Afghanistan, Uzbekistan, and Tajikistan. It’s interesting, he really pushes his men hard, force marching them, having them charge headlong into defensive enemy positions instead of waiting.

You can tell he’s really impatient to capture Darius and have this thing 100% done with. I think there’s a lesson there about never leaving a thing mostly done. Even if it’s 99%. You gotta wrap it up 100%. Eventually Darius is betrayed by one of his top generals, a man by the name of Bessus. Bessus stabs Darius and leaves him for dead.

This really upsets Alexander, who wanted to capture Darius alive so that he could get the official handoff. So that he could basically force Darius to tell everyone “Hey guys listen up. Alexander is the new king.”

So Alexander is really upset at this Bessus guy, and when he eventually catches up and captures Bessus, he has his ears and nose cut off, and sends him off to be executed. And with that, Alexander is really and truly the unchallenged king of Persia.

A Melting Pot

With the war won, Alexander’s men prepare to head home. But Alexander wasn’t done. And he’s frustrated that his men aren’t as enthusiastic about the prospects of further conquest as he was.

And he’s got other issues. He’s now got this international, multicultural, diverse empire. And problematically, it’s got two centers of power. The Greeks and the Persians.

He couldn’t rule as a purely Greek ruler if he meant to maintain the loyalty of his eastern subjects. The methods of ruling were just way too foreign.

Greece was very egalitarian compared to Asia. In Greece Alexander was first among peers, but in Asia, he was expected to be above everyone else. Almost a god. The Persian king actually wasn’t technically considered a god but it was pretty close.

And you might think, well okay but are they really going to care if he treats them better. If he acts more humble, as the Greeks wanted. Surely everyone would want that, right?

But I’m going to give another basketball comparison, let’s say you play a guy one on one, and he just smokes you, beats you 21 to nothing. And the game ends and you go “Man, you’re really good,” and he says, “actually, not really. I’m pretty bad at basketball.” Well, okay, that’s nice that you’re being humble I guess but what does that say about me???

And that’s how everyone in the Persian empire felt, it’s okay if you get beat by someone who’s a regal, semi-divine, force of nature. But if this Greek comes over and beats all your armies and starts acting like, actually, I’m just a guy like everyone else, I’m not that special… it’s actually insulting.

But alternatively Greeks were very egalitarian, very democratic, and they did not take well to anyone lording power over them. Greek states were built on the idea of sharing power, and they were very sensitive to tyranny or despotism.

So Alexander is in a real pickle. His first instinct is to try to split the difference. He began dressing in a mixed way, combining Macedonian and Persian garments.

He took an eastern style harem with a different concubine for every day of the year, but he didn’t actually make use of it. He also allowed certain Persian nobles to continue to serve as administrators and advisors, but mostly kept his senior positions filled with Greeks.

Most troublingly to the Greeks, Alexander was flirting with the practice of proskynesis. This was the traditional greeting to a Persian king. If you were a commoner, it meant fully prostrating yourself on the ground, and if you were of a more elevated background, it meant bowing. This was viewed as worshipful to his Greek and Macedonian men, and mocked by them.

Alexander doesn’t fully make them observe proskynesis, but he does sort of skirt around it by setting up a shrine of Zeus next to him and making his Greek subjects worship when they come to visit him. You can imagine how that would go over. Basically he’s saying, I’m not Jesus, but I’m going to set up a picture of Jesus behind me and every time you come to speak to me you have to say “Thank you for blessing me this day, Jesus.” and I’m going to say “you’re welcome.” But to be clear, I’m not saying I’m Jesus.

So his Greek and Macedonian men think this is troubling but also kind of funny. And then Alexander is getting mad at them because they’re mocking and putting down some of his most important subjects, some of his newly gained nobles and advisors from Persia.

In one incident, Callisthenes, a close friend of Alexander and his official biographer, won’t let the thing go. He’s openly mocking Alexander and his Persian subjects who bow to him. And so when a group of pages conspire to kill Alexander, Callisthenes is also arrested for having inspired them, and he is either executed or dies of natural causes while imprisoned, depending on the source.

Well all of this is creating a pressure cooker environment where Alexander’s Greek and Macedonian subjects are feeling very disgruntled.

One young aristocrat hears of a plot to kill Alexander and tells Philotas, the son of Parmenion. When nothing happens, he goes back and tells Philotas a second time. Finally, the young man takes a different route and makes sure that Alexander finds out by other means about the plot. The conspirators are summarily executed.

And now the question arises what Alexander should do with Philotas. As a son of Parmenion, he had served in important roles in all of Alexander’s major battles, and he was a strong leader, a capable military commander who had done much to help Alexander win his victories. But did his failure to notify Alexander of the plot mean that he hoped the plot would succeed?

Philotas claimed that he simply didn’t take the threat seriously. That these were the imaginings of a young man and didn’t constitute a real threat.

But egged on by nobles who were jealous of Philotas’s lofty position, Alexander had Philotas tortured until he extracted a forced - and almost certainly false - confession.  He was then executed, either by stoning or being stabbed with spears. Alexander then sent swift riders to assassinate Parmenion before he could learn of his son’s execution.

It is an ignominious and ungrateful end for a man who had served Alexander and Philip well for decades, and who had contributed much to both of their successes. Perhaps Philotas was negligent in his reporting of the conspiracy. But it’s easy to see a much simpler motive.

With dissatisfaction roiling all around him, Alexander did indeed need to worry about conspiracy. And while Parmenion and his son were almost certainly not conspiring at this time, they were the only two Macedonians with enough prestige and stature to replace him.

By having them removed, Alexander truly removed any possible threat to his rule.

We really just don’t know what the motives are. Some historians are inclined to see it as a conspiracy by other nobles to have Parmenion and his son removed.

Also around this time, there’s another troubling incident involving Alexander. He’s at a party, he’s had a few drinks, which is a situation that seems to frequently get Alexander in trouble, and he gets into an argument with a friend named Black Cleitus. Black Cleitus is the one who saved Alexander’s life at the Battle of the Granicus. He was a good friend and a close companion.

But they were both drunk and they started quarreling, with Cleitus saying that Alexander was forgetting where he came from and that he owed all of his victories to his father, Philip. Alexander gets mad and ends up throwing a javelin through Black Cleitus’s heart, killing him.

By all indications, this was not intentional. Alexander was immediately horrified by what he had done, and refused to eat for three days afterwards in mourning.

But I think it’s just another sign of the pressure that Alexander was under. Fusing the two ends of his empire was going to prove as difficult as winning any battle.

Alexander’s early attempts to combine Greek and Persian customs were ultimately clumsy and  mostly unsuccessful.


After a year or so of this, Alexander decides that his conquest of Persia is not actually finished.

Darius I, the founder of the Persian empire and the Achaemenid dynasty, had conquered the western part of India - the Indus river valley - more than 200 year previously. Since then, the Persian kings had not really ruled it, they hadn’t exercised any control over any part of India, and had not really tried to. But they nominally asserted that they were the rulers of this territory.

And when Alexander takes the throne, Indian exiles start coming to his court to see. These are men who just like in Greece or Persia, had lost civil wars or struggles for power, and were now seeking allies to put them back on the throne.

And Alexander did not want to see anything undone. He wanted to make sure that the entire Persian empire was under his control, even those parts that hadn’t previously complied with the Persians.

And Alexander was more than happy to oblige.

But let’s be honest, I don’t think that any of this gets at the real reason why Alexander invaded India. Here’s how I think about it: Running the Persian empire doesn’t sound fun, to me. You are constantly meeting with delegations from various regions who are complaining about your policies or appealing for some change or another.

You’re constantly worrying about back-stabbing and court plots. You’re mostly sitting in the same throne in the same court as you take meetings and hear petitions day after day after day.

Contrast that with what life was like when Alexander was on campaign. You’re basically camping in a new cool place every single day. And not just camping, but glamping because you have this huge nice tent that is well heated and you’ve got good food being brought to you. And speaking of food, Alexander was a light eater, of course, but he really enjoyed trying different kinds of meats and especially different kinds of fish that he was able to find and enjoy as he went on these various conquests to all these new areas. This is before refrigeration so you couldn’t just sample the food from all over the empire.

So you’re in nature in your nice tent, you get food that’s delicious and new and exciting, you’re hanging out with your top commanders all day, who also happen to be your best friends.

And oh yeah, anytime you have a decent-sized victory you throw a festival where the best athletes in the world come to compete in games, the best actors come to put on plays, the best musicians come to play, and you get to drink and party and enjoy all of this.

And if you enjoy sight-seeing today, oh man. The globalized world that we lived in is actually extremely homogeneous compared to Alexander’s day. Each new city brought new languages, new customs and manners, new gods, new histories and stories, new temples and architecture.

So look, it’s clear that Alexander was addicted to being on campaign, to being at war - but it wasn’t just because he liked gaining more power, it was also because I think the act of being on campaign must have been very fun.

So he goes to India. He fights a number of battles, the biggest and most famous of which is the Battle of the Hydaspes River. Once again Alexander is fighting against overwhelming odds, attacking over a river, and this time he is facing a large contingent of great war elephants. You can only imagine the shock that his soldiers must have felt facing such giant beasts.

Supposedly there was very hard fighting at the river, but eventually Alexander is able to encircle the army of his opponent, an Indian king named Porus, and force him to surrender.

Alexander was extremely impressed by Porus. He was a fierce warrior who stood 6’7” and looked very impressive. And Alexander actually befriended him after the battle and allowed him to keep his kingdom, so long as he promised to submit to Alexander in the future.

Return Voyage

Now according to some sources, Alexander expected that he would soon reach the edge of the world. Not that he believed the world was flat but the classical Greeks believed that the whole world was basically one big landmass and that it was surrounded by one great ocean.

And Alexander thought he was close to that ocean. And so when Porus tells him, that actually no, there are more even greater Indian kingdoms as you travel east, Alexander says “okay let’s go fight and conquer them.”

But supposedly his men mutiny. They hear that this Indian kingdom, now known as the Nanda empire, was massive with a huge army, thousands of war elephants, and hundreds of thousands of men. And at this point the longest serving of the veterans have been on campaign for TEN YEARS since they left Macedonia. And so they say we’re not going.

Alexander says fine all you ingrates who don’t want gold and glory can go back but I’m going to press on with those who will follow me. But after a few days it becomes clear that basically no one will follow him. Alexander sulks for a bit. Upset that he can’t go on, but he eventually agrees to turn around. And so his conquests end in Western India.

He sends much of his army back to Persia with his general Craterus, but he leads the rest of them down the Indus river on barges and boats that they build or otherwise acquire, and then leads them home through the desert, along the coast of modern day Pakistan and Iran.

This is one of the most controversial decisions of Alexander’s career. Because it’s extremely dangerous, it’s basically unknown, unexplored territory, and it benefits him nothing. There are no kingdoms or even cities on this coast that he can conquer.

But according to Arrian, he did it to outshine other conquerors, none of whom had explored this territory. Well unfortunately for him, they never explored it for a reason. And that is that it’s extremely dry and barren territory. There was very little food or water for his men and his army suffered crushing casualties in this desert crossing. Many of them died of thirst or diseases brought on by malnutrition.

Conditions get truly desperate, men are dropping like flies, when they finally make it through to Carmania, a Persian region that was much more fertile and settled, and that contained many of his troops and supplies.

The End

When Alexander comes back, he has to purge a number of officers who had got up to nonsense while he was gone, some were cruel to local populations and others had dabbled in corruption, so he sets about reforming his government.

He’s also still trying to marry the Greek and Persian halves of his empire, so he does something very curious. He goes and gets Persian wives for his nobility and has them all married in a mass wedding for hundreds of people. He himself takes two Persian wives, the daughters of the two most recent Persian kings.

These marriages largely did not work out and most of the Macedonians just left their Persian wives behind and headed back to Macedonia, but it showed that he was still trying to marry the two cultures to create a single cohesive political unit, in this case by literally marrying the two populations.

Once again, this fusion is making people uncomfortable. At one point, he decommissions his older and wounded veterans, and this really throws the Macedonian soldiers into a fit. They’re worried that Alexander is trying to replace them with Persian soldiers. They’re thinking “We just conquered this whole empire for you with our sweat and blood, and now you’re turning around and handing it on a silver platter to the people who we conquered.”

Alexander responds:

“I will speak not to quell your longing for home, Macedonians, for you may go wherever you wish as far as I am concerned, but so you may realize, as you depart, who we are, you and I, that you should act toward me in this way. I will begin, as is appropriate, with Philip, my father, who took you up when you were helpless wanderers, most of you dressed in skins, pasturing a few flocks in the mountains and fighting ineptly to protect them from your neighbors, the Illyrians, Triballoi, and Thracians. He gave you cloaks to wear instead of skins, led you down from the mountains to the plains, and made you able to hold your own in battle against your barbarian neighbors, so your safety depended not on your mountain strongholds but on your own courage.”

On and on he goes, recounting how he has risked everything, made his men rich, taken nothing for himself, given them glory and honor and comfortable homes to go back to. And how dare they betray him after all this! How dare they be so ungrateful~

The speech basically works. There is a big reconciliation with his men, and he has a big banquet with his Macedonian men and his new Persian soldiers to try to build a spirit of harmony between the two.

Alexander administers his empire for a year or so, conquering some mountain tribes, and settling some disputes, before moving his court to Babylon.

At Babylon, Alexander makes plans for his next big invasion: He plans to invade Arabia.

But one night, Alexander is out partying when he comes down with a fever. He continues to make plans for his invasion, believing that he will soon recover, but his condition only continues to get worse. His fever gets worse and he weakens until he could barely even speak.

Many have speculated that Alexander was poisoned, but the duration of the sickness and the slowly worsening symptoms seem to point to an illness, perhaps malaria.

As his condition worsens, people start to worry about who might take over the empire if he should die. At this point Alexander did have an infant son, who could be expected to reign eventually, but someone would need to administer the empire in the meantime.

As it became clear that Alexander would not recover, his top generals and friends crowded around his bed and asked him to whom the crown should go.

With the little energy that remained in him, with his last words, Alexander whispered “to the strongest.”


You can imagine how those men must have felt standing around Alexander’s bed as they realized that they were all now at war with each other.

I’ll get more into what did eventually happen to his empire in the endnotes episode.

But, I’ll leave that as the end of the narrative portion of the story.

So what are we to make of the second half of Alexander’s life? What lessons can be learned?

First of all, from the siege of Tyre we learned that sometimes there is no clever solution. Sometimes even the greatest commanders just have to grind out victories with long, arduous effort.

From his battle at Gaugamela we learned the power of the pivotal moment. Of keeping your best strategy, your best effort, in your back pocket until your enemy is worn down and then overwhelming them and breaking their spirit.

From his pursuit of Darius we learned to never leave a thing mostly done. Never take your victory lap until the thing is 100% finished and no opposition stands in your way.

We can also learn to, and I mean this unironically, follow your passion. Can’t you just imagine little Alexander in elementary school, and asking him what’s your passion, young Alex? “Gaining glory, putting my enemies to the sword and destroying their cities, going where no man has gone before and doing what no man has ever done.”

The last lesson I would draw is to just bask in his greatness. Alexander never lost a battle. He built an empire more powerful than any that had ever existed. He was absolutely restless and insatiable in his desire to see more, experience more, do more.

He was the original man to receive the “great” monicker. He served as the inspiration for Pompey, Caesar, Hannibal, Napoleon, and others.

I think that, when another man worthy to be called great is born into the world, he will take inspiration from Alexander.

He has been dead for 2300 years, but somehow he is still alive in the hearts of those who revere his life.

When Octavian, better known as Caesar Augustus, was in Alexandria, he asked to see the tomb of Alexander the Great. He stayed in the tomb for a long while, contemplating Alexander’s long shadow and his incredible legacy.

His guides then asked him if he wished to see the tombs of the other Egyptian kings in the city.

“No,” he said, “I came to see a king. Not corpses.”

Thank you for listening. I’ll be back soon for the Alexander the Great endnotes episode. As always, you can follow me on Twitter or Instagram at H T T O T W. That’s the first letter from each word in How to Take Over the World. HTTOTW. Or you can email me at Ben@httotw.com.

And if you feel like helping out the show, please leave me a five star rating and review on apple podcasts.

Thank you. Bye.

About Episode

Alexander the Great took his father's kingdom and made it the greatest empire the world had ever seen. Part two covers the apex of his powers, plots against his life, the unification of his empire, and more.

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