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The Time When Alexander the Great was ‘Defeated’

The Time When Alexander the Great was ‘Defeated’

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Alexander the Great is widely known as one of the greatest military generals and conquerors of all time, and his name became synonymous with greatness and invincibility throughout the ages.  Alexander was also the man who expanded Greek culture and Western civilization around the then-known world.

As a boy growing up, Alexander was blessed to have as his teacher, Aristotle, one of the greatest philosophers who ever lived.

The great philosopher was the one who inspired Alexander to show so much interest in philosophy, even though as every young Greek male who was destined to be a warrior king—whether he was Athenian, Spartan, Corinthian, or Macedonian like Alexander—his first priority was to receive a military education and discipline. This was the main factor as to why later Alexander’s accomplishments didn’t revolve strictly around the battlefield and warfare, but had a deep cultural, political, economic, and social perspective.

Aristotle teaching Alexander the Great

Aristotle teaching Alexander the Great (public domain)

The harmonic coexistence between different and distant peoples became Alexander’s main focus, while he pursued the “marriage” of opposing cultures and civilizations, which he achieved to a certain degree through the spread of Greek culture, language, art, and science, a fact that signaled the beginning of a new era in which Hellenism and Western civilization became the center of a global civilization, which would later be continued by the Roman Empire.

On the other hand, Diogenes the Cynic—who, according to Plutarch, was born on the same day Socrates died—was one of the founders of the philosophy of Cynicism, and arguably the greatest ever from the specific movement of philosophy. He mainly focused on and almost exclusively raised awareness of social and moral problems. His teaching was essentially revolutionary and subversive to the political regimes that then prevailed. He openly doubted and questioned the local authorities and used philosophical arguments to change the corrupt society he lived in. Diogenes deeply believed that a better world was possible only if people returned to Mother Nature and accepted it (nature) as the only absolute authority and ruler. He believed that the true happiness of men lies in the natural life and that only self-sufficiency, frugality, self-awareness, and exercise can secure it. He literally lacked respect for any form of political or military power.

So the question is, how could two such different types of men as Alexander and Diogenes ever have competed with each other and on what basis?

Diogenes used to get in trouble pretty often because of his rebellious teachings and lifestyle. He got arrested and exiled a couple of times from a few Greek city-states.  In one of his various adventures and trips he got captured by pirates and sold into slavery. This way he ended up in Corinth, where Xeniadis, a local wealthy aristocrat charmed by Diogenes’s spirit and intellectuality, bought him so that he could educate his sons.

During the same period, Alexander the Great had already launched his campaign to unite all of Greece under one kingdom and expand Hellenism all over the world. Alexander had a trainer named Leonidas, who was privy to the philosophy of Cynicism, and so Alexander was already aware and a fan of Cynicism and of Diogenes’s teachings and spirit. So when Alexander arrived in Corinth, the first thing he requested was a meeting with Diogenes.

Diogenes, however, was not easy to find. He believed that no man needed much, and so he did not own any property nor live in a house, but instead slept in a barrel, which he rolled about from place to place. He spent his days sitting in the sun and teaching his theories to the many people who wanted to be introduced to Cynicism.

Diogenes living in his barrel.

Diogenes living in his barrel. Painting by Jean-Léon Gérôme, 1860 (public domain)

Thankfully, one of the greatest historians of antiquity, Plutarch, provides a detailed version of the story, which allows us to know what happened and what was said between Alexander and Diogenes when they finally met,

“Thereupon many statesmen and philosophers came to Alexander with their congratulations, and he expected that Diogenes of Sinope also, who was tarrying in Corinth, would do likewise. But since that philosopher took not the slightest notice of Alexander, and continued to enjoy his leisure in the suburb of Craneion, Alexander went in person to see him; and he found him lying in the sun. Diogenes raised himself up a little when he saw so many people coming toward him and fixed his eyes upon Alexander. And when that monarch addressed him with greetings, and asked if he wanted anything, “Yes,” said Diogenes, “stand a little out of my sun.” It is said that Alexander was so struck by this, and admired so much the haughtiness and grandeur of the man who had nothing but scorn for him, that he said to his followers, who were laughing and jesting about the philosopher as they went away, “If I were not Alexander the Great, I would like to be Diogenes.”

The meeting between Alexander and Diogenes

The meeting between Alexander and Diogenes (public domain)

Throughout the years many (slightly) different versions of the specific dialogue appeared, with the origin of pretty much all of them being the original account of the dialogue given by Plutarch. Of particular interest, however, is the version of Dion of Prusa, who gave a new dimension to the whole meeting. According to Dion, Alexander the Great and Diogenes had a long discussion of great significance that influenced the king’s way of thinking. Diogenes appears to have explained to Alexander when it is that a king can be beneficial to and loved by the people. More specifically, Diogenes supposedly said to Alexander,

“If you conquer all Europe but you won’t benefit the people of this region, then you’re not useful. If your conquests throughout Africa and Asia won’t benefit the people of these regions, again you’re not being beneficial or useful.”

Judging from Alexander’s great contributions on a cultural, political, economic, and educational level for the people of every part and region of his vast empire, which separate him from the majority of other conquerors in history, they add new meaning and understanding to this version of the conversation, even though we can’t be sure of its authenticity.

The only thing we learn from this story with any certainty, however, is that Alexander’s arrogance, the product of his power and youth, was tamed by one of the greatest philosophers in an unarmed and bloodless battle where Alexander was defeated for the first and only time in his life, albeit unofficially. A “defeat” that contributed the most to Alexander’s later greatness and undefeated status.

Top image: Reliefs based on the Pinelli engraving (1928). It depicts a scene from the everyday life and the campaign of Alexander the Great. Reliefs by the sculptor Pr. Tzanoulinos (bronze). Hellenic War Museum (Athens, Greece). CC by 2.0 / Tilemahos Efthimiadis

By Theodoros II

Theodoros Karasavvas's picture


Theodoros Karasavvas, J.D.-M.A. has a cum laude degree in Law from the University of Athens, a Masters Degree in Legal History from the University of Pisa, and a First Certificate in English from Cambridge University. When called upon to do... Read More

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