One of the most interesting stories in early history is the relationship between Alexander and Diogenes. Unfortunately, most of its retellings — even ones told in the classroom — are misleading and largely inaccurate. So let me tell you here the truth behind one of my favorite Greek tales.

Alexander the Great, the son of the great king Philip II, really was pampered for most of his life. Part of his pampering was access to Greece’s greatest minds during what many saw as the late era of the Greek golden age. Aristotle, one of the big three Greek philosophers, was the boy’s head mentor and served him for much of his life.

But what made Alexander different as a young prince — and perhaps a sign of his greatness later — is that he actually embraced the teaching, rather than ignored it like most princes before and after. In fact, Alexander made it a mission of his as a young man to try and gather as much knowledge as possible, preferring to hear straight from the source rather than reading books or tablets.

And so, it was this drive that likely led Alexander towards Diogenes. The story of how exactly the two met is mostly apocryphal — funny speaking that its most famous anecdote is also part of this mostly mythological story.

As it goes, Alexander was chatting among the people in the slums of Athens (something his bodyguards really rather he’d not). Two harlots, who heard how he was searching for the wisest men in Greece, suggest that he talk to “the old man that lives in the barrel”. Instantly curious, Alexander roamed around until he found a man who fit the description — a seemingly homeless loaf laying among a pile of trash. With a great crowd now gathered around the prince, Alexander asked if he were the man — the fabled Diogenes.

“Yes,” the man reportedly responded. “and you can step out of my sunlight.”

The crowd standing around, who knew Diogenes mostly as a crazy old man, let out a laugh when they heard what he had said. Others, worried about what the prince might do (his father and mother both had rather sour reputations) stayed quiet and on the sidelines. But Alexander simply smiled, and — perhaps in an effort to lighten the situation, turned back around to the crowd and spoke:

“Well, were I not Alexander, I would wish to be Diogenes!”

This remark led to a much louder laughter from the crowd, and served to ease the situation. With no harm done, Alexander bid Diogenes farewell, and the prince went his separate way.

Diogenes, whose barrel served as his home, stayed there until it was night. When night finally came and the streets began to clear, however, he was met by someone else. This person wore disheveled rags, burlap cloth, and looked about as ragged as most of the others who passed by this time of night. Yet, as the man approached, Diogenes noticed something off — he looked familiar, but not as one of the many homeless he had seen before. This was in fact the young man he had seen earlier that very day — Alexander, in disguise, had come back to receive teaching from the old man!

At this point, Diogenes was rather amused, and so he agreed to teach the boy. At least, like I said, that’s the way the story goes — we do know that Diogenes was one of the people who taught Alexander (particularly in the values of life philosophy, mostly Stoicism) but we do not know if any of this meeting really was true or not. Of course, if you have heard this story, you likely have only heard the part about Diogenes’ sunlight comment. This is likely due in fact to the wide amount of anti-monarchal thought that came in the centuries later, and the idea of framing a poor old man as superior to a young prince hits at an underdog trope. But the historical fact was that the two were friends, and I do think the full story makes a rather more compelling and complex story of a young bright boy who would later become an ambitious general and then, at the end of his life, a twisted and paranoid recluse. It especially hits hard with some versions of the story, which says that the day Alexander left for Persia, he had one last meeting with Diogenes who warned him about his ambition — the thing that would eventually be his downfall.

Then again, as history gets older it becomes harder and harder to distinguish truth from myth. Much of what we know about Alexander’s princely days comes from tales told by Plutarch, a man notorious for adding flavorful narrative elements to his historical retellings. Of course, as a fiction author, I am no different — in fact, in the course of this article, I may have added some fiction of my own ;).