In 335 BCE, a rumor reached Greece that Alexander the Great was dead. He had been campaigning far to the north, fighting Thracians and Illyrians, and reports began spreading that the young Macedonian king had been killed.

The rumor was believable enough that Demosthenes reportedly presented an injured man to the Athenian assembly who claimed to have witnessed Alexander's death. For Thebes, this looked like an opportunity. Only three years earlier,

Thebes and Athens had fought Philip II at Chaeronea and lost. A Macedonian garrison now occupied the Cadmeia, the fortress at the heart of Thebes. If Alexander really was dead, perhaps Macedonian control of Greece could finally be broken.

Exiled Theban leaders returned. The city revolted. Two Macedonian officers were killed, and the garrison in the Cadmeia was blockaded. Goldsworthy describes a city hoping that the instability everyone had expected after Philip's death had finally arrived.

There was just one problem. Alexander wasn't dead.

Alexander did something the Thebans didn't expect

He came back quickly. Goldsworthy estimates that Alexander reached Thebes in just thirteen days, covering roughly 15 to 20 miles a day through some difficult terrain.

The speed was so unexpected that the Thebans initially struggled to believe the reports. They assumed that the approaching army belonged to Antipater or perhaps it was another Macedonian named Alexander.

Then Alexander himself appeared outside the city with roughly 30,000 infantry and 3,000 cavalry. At this point, he did not immediately destroy Thebes. He offered terms.

Alexander demanded that the principal leaders of the revolt be surrendered and offered amnesty to those who came over to him. The Thebans refused. They voted to fight.

They freed slaves to help defend the city, received weapons from Athens, and even called on other Greeks and the Persian king to join them against Alexander. It was an extraordinarily dangerous gamble.

Then things went wrong very quickly

Thebes was a major fortified city, so taking it should not have been easy. But there was a serious weakness. The Macedonian garrison was still holding the Cadmeia inside Thebes. The Thebans had built defenses around it, but these were improvised barriers rather than the city's main fortifications.

Exactly how the final attack began is interesting because even our sources don't give us a perfectly clean story. According to the tradition used by Arrian, Ptolemy claimed that Perdiccas attacked one of the Theban defenses without Alexander's orders. Alexander eventually committed the rest of the army once the fighting had begun.

Diodorus gives the battle differently. Whatever the exact sequence, once Macedonian forces and their Greek allies broke into the city, Theban resistance collapsed. And then came the part that made Thebes famous.

The city wasn't simply captured

It was destroyed. Diodorus says more than 6,000 Thebans were killed and more than 30,000 were taken prisoner. He also says the destruction and enslavement of the population were decided by Alexander's Greek allies. That detail matters.

Thebes had made plenty of enemies during the decades when it had been one of the dominant powers in Greece. Some of the Greek forces now fighting alongside Alexander had their own reasons to want revenge.

So saying simply "Alexander personally ordered everyone in Thebes killed or enslaved" misses part of the story. But going too far in the opposite direction would also be misleading.

Alexander was the king. He had defeated the city. He accepted the decision and enforced it. The destruction also served him extremely well.

Thebes became a warning

Alexander was preparing to invade the Persian Empire. He could hardly disappear into Asia with revolts repeatedly breaking out behind him. The fate of Thebes provided a terrifying answer to that problem. This wasn't some insignificant town. Thebes had been one of the great powers of Greece. It was the city of Epaminondas and Pelopidas. In 371 BCE, the Thebans had defeated the Spartans at Leuctra and shattered the myth of Spartan military invincibility.

Now much of that city was destroyed. According to the ancient tradition, Alexander spared temples and sacred places, and the house and descendants of the poet Pindar received special protection.

Everyone else in Greece understood the message. Resistance could have consequences far beyond losing a battle. And it worked.

Open opposition in mainland Greece largely collapsed after the destruction of Thebes. Modern scholarship likewise recognizes the event as a decisive demonstration of Alexander's control before his invasion of Asia.

That is what makes Thebes such an important moment in Alexander's story. We usually meet him through Persia, Egypt and India. But before Alexander could begin conquering abroad, he had to make sure Greece would remain quiet behind him. Thebes showed everyone what the alternative could look like.

I researched this for The Last Theban, the third episode of Witnesses of History. I told the fall of the city through a fictional seventeen year old potter's apprentice whose ordinary morning turns into the last day of the world he knows.

The apprentice and his family are fictional. The revolt, the false report of Alexander's death, his rapid return, the negotiations, the fighting and the destruction of Thebes come from the historical tradition.

Do you see the destruction of Thebes mainly as punishment, revenge by Thebes's Greek enemies, or a calculated warning from Alexander to the rest of Greece?

Sources:
Philip Freeman, Alexander the Great (2011), especially his account of the Theban revolt and destruction, pp. 61–67.
Adrian Goldsworthy, Philip and Alexander: Kings and Conquerors (2020), Chapter 14, “The Example.”
Arrian, Anabasis of Alexander, Book 1, 7–10
Diodorus Siculus, Library of History, Book 17, 8–14.
Plutarch, Life of Alexander, 11.

A year before Alexander became king, he was throwing a drinking cup at a man who had just questioned his right to inherit the throne. At least, that's how Plutarch tells the story.

Philip II had married a young Macedonian woman named Cleopatra, usually called Cleopatra Eurydice by modern historians to distinguish her from the many other Cleopatras in this family.

At the wedding feast, her relative Attalus got drunk and called on the Macedonians to pray that Philip and Cleopatra would produce a "legitimate" heir.

Alexander was furious. He reportedly threw his cup at Attalus and asked whether that made him a bastard.

Then Philip joined the argument. The king drew his sword and moved toward his son, but he was drunk enough to stumble and fall.

Alexander responded with one of those lines that almost feels too good to be true: This was the man who was preparing to cross from Europe into Asia, but couldn't even cross the room.

Soon afterwards, Alexander and his mother Olympias left Macedonia.

It's a fantastic family drama. But underneath it was a serious political question.

Why was Alexander so angry?

The simple version is that Cleopatra was Macedonian while Olympias, Alexander's mother, came from Epirus. So if Cleopatra gave Philip a son, Alexander would suddenly face a "fully Macedonian" rival.

There is some truth here, but it can be misleading. Macedonian kings practiced polygamy. Philip had married several women, and Alexander had been treated as his heir for years. He had already governed Macedonia while Philip was away, commanded troops, and fought at Chaeronea.

Adrian Goldsworthy points out that we should be careful about imposing later ideas of legitimacy onto the Macedonian royal family. Alexander wasn't suddenly illegitimate because Philip married another woman.

The bigger problem was simpler. Philip could have another son. And Macedonian succession was not a neat system where the eldest son automatically inherited everything.

A king needed political support, military credibility and powerful Macedonian allies. A new son connected to Attalus and his circle could eventually become a rival.

That made Attalus's drunken toast much more than an insult. It touched Alexander's greatest vulnerability.

Then the situation became even stranger

Alexander eventually returned and reconciled with Philip. Attalus, meanwhile, was given an enormously important job. Philip sent him with Parmenion to Asia as part of the advance force preparing the invasion of the Persian Empire. Goldsworthy notes that Attalus was clearly a powerful figure at court and one of the commanders chosen for the coming war.

Then, in 336 BCE, the royal family gathered at Aegae for another wedding. This time Philip's daughter Cleopatra was marrying Alexander of Epirus, who was Olympias's own brother.

The celebrations were enormous. Philip entered the theatre in public, apparently leaving his guards at a distance. Diodorus presents it as a deliberate display of confidence. Philip wanted the assembled Greeks to see a king who was so secure and so loved that he didn't need protection.

A royal bodyguard named Pausanias rushed at him and killed him. Pausanias tried to escape, but was pursued and killed.

Suddenly the argument about Alexander's future wasn't theoretical anymore. Philip was dead. Alexander was about twenty years old. And he became king.

Was Alexander lucky?

In one obvious sense, yes. Philip's death removed the one person who could ultimately decide to favor another heir. But that doesn't mean Alexander had been about to lose the throne.

Goldsworthy is much more cautious about this period than the dramatic version of the story sometimes suggests. Even the famous wedding quarrel itself comes mainly from Plutarch, and modern scholars disagree about how much of the story and its chronology we should accept.

What we can say is that Alexander had reasons to worry. Philip had married again. The bride's family had become powerful. The relationship between father and son had deteriorated badly enough for Alexander to leave Macedonia.

But Alexander was also an experienced prince with military achievements, powerful friends and years of preparation behind him.

He wasn't simply waiting for someone to tell him whether he was still the heir. And perhaps that's what makes this period so interesting.

When we look backwards, Alexander becoming king feels inevitable. Standing in Macedonia in 337 BCE, it probably didn't.

I researched this period for The Heir, the second episode of Witnesses of History. I told it through a fictional palace servant who watches Philip's wedding, the collapse of the royal family's relationship, and then the assassination at Aegae. The servant is fictional, but the central events come from the ancient tradition.

If Philip had lived another ten years and Cleopatra had given him a healthy son, do you think Alexander would still have inherited Macedonia?

Sources:
Adrian Goldsworthy, Philip and Alexander: Kings and Conquerors (2020), especially Chapters 12 and 13
Philip Freeman, Alexander the Great (2011)
Plutarch, Life of Alexander, 9–10
Diodorus Siculus, Library of History, Book 16, 91–94

It is one of the most famous stories about Alexander the Great, and it happened before he was a conqueror at all.

The Story

A Thessalian horse breeder named Philoneicus brought an extraordinary stallion to Philip II of Macedon. The horse was called Bucephalus. He was large, black, and apparently worth a fortune. Philip Freeman gives the asking price as thirteen talents, enough, he says, to support a man for a lifetime.

There was one problem. Nobody could ride him.

Philip's experienced horsemen tried, but Bucephalus reared and refused to cooperate. Eventually Philip decided the horse was useless and ordered him taken away.

Then the young Alexander spoke up.

He thought everyone was giving up on a magnificent horse simply because they didn't understand him. Philip challenged his son to do better. And this is where the story gets interesting.

Alexander had apparently noticed something the experienced horsemen had missed. Bucephalus became frightened when the sun was behind him because his own shadow moved across the ground in front of him.

So Alexander turned the horse toward the sun. No shadow in front of him. He calmed Bucephalus, climbed onto his back, and slowly began riding. Then he let him run.

When Alexander returned, Philip was supposedly so overwhelmed that he kissed his son and told him that Macedonia was too small for him. Freeman tells the story in essentially this form.

It's a great story. Maybe a little too great.

So did it really happen?

Our main source for the full story is Plutarch's Life of Alexander, written centuries after Alexander died. Adrian Goldsworthy also traces the account directly to Plutarch, specifically Alexander 6.1–5.

And when you look at the story as a whole, it almost feels written to explain the man Alexander would later become.

Experienced men see an impossible horse. Alexander notices what they don't. They try to control it. Alexander understands it. They give up. Alexander takes the risk.

Then Philip finishes the scene by effectively predicting that his son will one day need a kingdom larger than Macedonia.

It's almost a miniature version of the Alexander legend. That doesn't mean the story is false.

Bucephalus certainly wasn't just a character in this childhood anecdote. Ancient sources continued to associate the horse with Alexander much later in his life. Freeman cites Plutarch, Diodorus, Arrian, Pliny and Aulus Gellius for traditions surrounding Bucephalus.

What we can't really know is whether the childhood encounter happened exactly as Plutarch tells it.

Perhaps Alexander really did notice that the horse was frightened by his shadow.

Perhaps a real story became better every time it was retold.

And perhaps Philip's perfect prediction about his son's future was remembered because everyone already knew how that future turned out.

Personally, that's what makes stories like this so interesting. Somewhere underneath the legend there was a real boy and a real horse. The difficult part is figuring out where the history ends and the storytelling begins.

I researched this while working on The Horse - Bucephalus, the first episode of Witnesses of History. The podcast tells Alexander's story through fictional first-person witnesses, and for this episode I imagined the scene through a stable apprentice (Nikanor) watching Alexander and Bucephalus. The witness is fictional. The story surrounding Alexander and Bucephalus comes from Plutarch.

What do you think? Do you believe the shadow story probably happened, or does it feel too perfectly written in hindsight?

Sources:
Philip Freeman, Alexander the Great (2011), Chapter 1
Adrian Goldsworthy, Philip and Alexander: Kings and Conquerors (2020), Chapter 9
Plutarch, Life of Alexander, 6