The Battle of Chaeronea: A Father Tests His Son

The Battle of Chaeronea in 338 B.C. was a decisive moment in Greek history. For the first time since the fabled Trojan expedition, the city-states of Greece would unite in common purpose. Not even the wars against the Persians would bring them together as much as the result on this field. Yet, the result and the importance of Chaeronea to history cannot be separated from the most important personality involved. On this field, the future Alexander the Great rose to prominence, and it came because his father, Philip II, wanted him to prove his worth as a man.

Note: this is a preview of sorts for the latest in my Critical Battles Series. You can find the Battle of Chaeronea, along with over a dozen others and counting, at my Patreon page under the “Journeyman” tier.


Every culture has some kind of rite where a boy becomes a man. This was an important concept in the first chapter of Stumped, on masculinity in leadership. Sometimes, these rituals are formalized. In other cultures, like our own, they are unspoken. In comparison to Sparta, Macedon’s ritual was more subdued. Nevertheless, Alexander the Great would get his own personalized test.

Philip II of Macedon was a successful ruler, raising his kingdom to become the first power in Greece. Yet, great rulers don’t live forever. All would come to nothing if he could not secure his dynasty.

Macedonian succession rules are unclear. Alexander was Philip’s oldest surviving son, but it his succession wasn’t set in stone. Unlike in most Western nations, Macedonian kings practiced polygamy.

Nevertheless, Philip treated Alexander as his heir. He famously hired Aristotle to tutor the young prince. At the age of 16, Philip trusted his son as regent of his capital. There, he received ambassadors from the Persian Empire. He also acquitted himself well in command against localized disturbances.

All signs indicated that Philip II had reason to be pleased with his son. Yet, there was one final test he needed to put Alexander through, to see if he would truly be able to command not just Macedon, but all of Greece, and so ensure that his own life’s work would not be destroyed.

Battle of Chaeronea

The Battle of Chaeronea

Philip II had long been master of the northern part of the Greek Peninsula. His rule stretched down to Thessaly. To make a long story short, the Fourth Sacred War broke out when land in a crucial area, which was sacred to Apollo, started to get farmed. This caused hostilities which gave Philip a useful pretext for marching southward. Thebes, close to the area, found it fitting to join Athens in its war against Macedon.

Victory in the ensuing battle would guarantee that long enticing prospect – the unity of Greece. On the other hand, if Philip II lost the Battle of Chaeronea, the opportunity would vanish, maybe forever.

Philip II put his son and presumed heir, the 18-year-old Alexander, in charge of the Macedonian left wing when they arrived at Chaeronea. This was an important post. Not only did it guard the army’s flank, but it also directly opposed the Theban contingent and its elite troops, the Sacred Band, supposedly composed of 150 pairs of homosexual lovers.

It was a place of honor, but Philip II had an insurance policy. The Roman historian Diodorus Siculus notes:

The armies deployed at dawn, and the king stationed his son Alexander, young in age but noted for his valour and swiftness of action, on one wing, placing beside him his most seasoned generals, while he himself at the head of picked men exercised the command over the other; individual units were stationed where the occasion required.

Steven Pressfield elegantly alludes to this situation in his Virtues of War. Phillip II gave Alexander the opportunity to do the job at Chaeronea, but if he couldn’t get it done, his seasoned Macedonian generals would. Either way, Macedonian victory was guaranteed, at least in Philip’s mind.

Alexander’s honor was at stake, and along with it, his claim to the throne. Alexander, no doubt the type to die rather than live in disgrace, prepared for battle.

At Chaeronea, Philip II commanded the Macedonian right wing. His plan was to engage the less-disciplined Athenians and draw them out of formation through a feigned retreat. This would leave the Thebans isolated for Alexander to destroy.

Battle of Chaeronea map

This is what happened. Alexander performed admirably. The popular conception of the Battle of Chareonea is that Alexander commanded the Companion Cavalry, but the ancient sources don’t tell us this. Plutarch says that:

He [Alexander] was also present at Chaeronea and took part in the battle against the Greeks, and he is said to have been the first to break the ranks of the Sacred Band of the Thebans.

We don’t know how Alexander broke the Sacred Band, only that he did. He thus passed the test of his manhood. The battle would prove the start of a stellar career.

“The Strenuous Life”

Theodore Roosevelt’s term describes the essence of good living. Louis XIV noted that those who don’t continually pursue glory, preferring instead to ride high on glory already won, don’t deserve even the honors they already have. This is true on the individual and national level. It’s why Theodore Roosevelt journeyed into the wild west in his youth and into the Amazon in his 50’s.

The first trial is the most important, though. The original hardening, and the confidence that comes with it, instills virtue, and inures one to corrupting ideas. Masculinity must be earned. Men must subject themselves to trials in order to grow. Philip II knew this. He made sure that his son would pass through that first great trial in the Battle of Chaeronea and grow into a true heir, where future glory was possible.

We’ve seen the result of the lack of a “strenuous life” in our citizens over the past year – a neurotic, defeated, hysterical populace. “Weak men create hard times,” as the meme goes.

For many more historical stories on how to attain masculine virtue through a “strenuous life,” read Lives of the Luminaries.

This was also a preview of my Battle of Chaeronea chapter in the Critical Battles serial. You can find the full chapter, and many more, by becoming a patron for $5 a month. You’ll get a new one each month, and much more.

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