Diogenes the Cynic (412 BCE – 323 BCE) was a piece of work.

You have to think the man knew a few things about discontent early on in life. Banished from his home, Sinope (modern day Sinop, in Turkey), for debasing the currency his father minted, Diogenes fled to Athens. He attached himself to the philosopher Antisthenes, a pupil of Socrates and founder of the school of the Cynics.

Cynicism then did not mean what it does today, though Diogenes’ acerbic wit might have had some role in shaping our modern understanding of the term. The word cynic actually derives from the Ancient Greek words for dog and dog-like. Antisthenes tried to beat him off with a stick; he wasn’t taking any pupils. But Diogenes the Dog refused to leave.

Cynics rejected the conventional pursuit of wealth, power, sex and fame. Such things had no real value.

They sought to lead instead a simple life free from possessions. How different this was from the aristocratic Plato, who promoted the idea of the Philosopher King, necessary to the ideal city-state; or Aristotle, well-paid tutor to Alexander the Great, who was being groomed to be such a king.

Although Diogenes reportedly authored over ten books, seven tragedies, and a volume of letters, no writings of his survive. Cynics practiced what they preached, however. The stories about Diogenes’ life and the sayings attributed to him in various classical sources are a good reflection of his philosophy – even if they contain contradictory details, and a judicious dose of the legendary.

Many stories about Diogenes come from another Diogenes, Diogenes Laërtius, who wrote the Lives and Opinions of Eminent Philosophers.  

Here the sharp tongue of Diogenes the Cynic is at its most cutting and precise.

A man once reproached him with his banishment, and his answer was, “You wretched man, that is what made me a philosopher.” And when, on another occasion, some one said to him, “The people of Sinope condemned you to banishment,” he replied, “And I condemned them to remain where they were.”

On one occasion a man was reading some long passages, and when he came to the end of the book and showed that there was nothing more written, “Be of good cheer, my friends,” exclaimed Diogenes, “I see land.”

A man once asked him what was the proper time for supper, and he made answer, “If you are a rich man, whenever you please; and if you are a poor man, whenever you can.”

Plato once described Diogenes as “a Socrates gone mad.”

Diogenes was essentially homeless, taking shelter in a wine barrel, begging on the streets of Athens. He doubled up his cloak and used it as a sleeping bag, something considered a remarkable innovation at the time. He owned a bowl – till he saw a child cup his hands to drink from the river, and gave that up too. “Fool that I am, to have been carrying superfluous baggage all this time!”

He was notorious for what I’ll call enlightenment stunts: begging alms from a statue “to get used to rejection,” carrying around a lantern in the daytime “in search of an honest man.” If he were living on the streets of New York today, we might call him a performance artist.

Diogenes ate where he wanted to, slept where he wanted to, relieved himself where he wanted to. Like dogs, cynics had no shame. They used this shamelessness and disdain for social convention to wake people up. Diogenes was exceptionally good at the rude awakening. In response to being criticized for masturbating in public, he retorted that he wished rubbing his belly relieved hunger so well.

To philosophers not of his school, Diogenes could be downright disagreeable.

As Diogenes Laërtius notes:

He was very violent in expressing his haughty disdain of others. He said that the scholê (school) of Euclides was cholê (gall). And he used to call Plato’s diatribê (discussions) katatribê (disguise).

To his mind, Antisthenes was the true heir to Socrates. He told Plato his interpretations of Socrates were wrong, undermined his lectures, called him longwinded, and delighted in embarrassing him in public.

Plato defined man thus: “Man is a two-footed, featherless animal;” and was much praised for the definition; so Diogenes plucked a cock and brought it into his school, and said, “This is Plato’s man.” On which account this addition was made to the definition, “With broad flat nails.”

Even Diogenes Laërtius must be snickering into his broad, flat-nailed hand as he writes.

Eventually our dog Diogenes was captured by pirates (perhaps to Plato’s relief) and sold into slavery in Corinth. When the slave auctioneer asked what he was good at, Diogenes said “Ruling men.” Then he pointed to a man in the crowd with purple-trimmed garments and said “Sell me to him, he needs a master.” Which apparently Xeniades did.

The story most often told about Diogenes – and most often portrayed in art – involves his encounter with that most famous pupil of Aristotle’s, Alexander the Great. 

There are many versions of the story, some of which take place in Athens when Alexander was a young boy, others in Corinth after he has become the great conquerer, others as far away as India. These seem to be conflated with other stories of Alexander meeting the ascetic philosophers of that country who, like Diogenes, lived simple, naked, ascetic lives. I will relate two.

When Alexander the Great visited Corinth, Diogenes ignored him, preferring to sunbathe by the river. The conqueror, so taken with the philosopher, offered to grant him any favor. Diogenes told him to stop blocking his sun.

The great Alexander moved aside.

“If I were to live again,” Alexander said, still eager to express his admiration, “I would like to be reborn as Diogenes.”

According to one account, Diogenes opened one eye, cleared his throat, and replied “If I were to live again, I too would like to be reborn as Diogenes.”

There is another version of this story in which Diogenes tries to give Alexander some advice.

He asks Alexander what he plans on doing after he conquers Greece. Alexander says he intends to conquer Asia Minor.

And after that? Diogenes asks.

Then he intends to conquer the world.

And then? Diogenes persists.

Well, then he plans to relax.

To which Diogenes responds that this is a whole lot of needless effort, as he himself is already doing this without conquering anything.

Which is not entirely true. Diogenes has in fact conquered a great deal, but it’s all internal territory.

Plutarch and Diogenes Laertius both report that Alexander and Diogenes died on the same day.

A coincidence that has a great deal of the legendary to it. The Indian version of the story I read has Diogenes trying to get through to helmet-headed Alexander even beyond the grave. But while Alexander is a willing pupil, he remains deluded, like his father Philip of Macedon, by insatiable desire.

It is difficult to know the historical truth about a man whose life rises to the level of legend. Archaeologists have found debased coins from Sinope during the period Diogenes was said to live there. That’s something. But whether the Oracle at Delphi told him to debase the currency and really meant Question Authority – well, that we’ll never know.

Still, when a man like Diogenes says

He has the most, who is most content with the least.

I think we can agree that he knows whereof he speaks.