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Socrates and Diogenes at Thebes.

There is a story (or possibly; the truth) that whilst marching with Alcibiades and the army of Athens to take Syracuse (Scilly) and so start an empire; that the Athenian host passed the gates of Thebes.
Yes, Socrates, despite his fame, considered himself a humble soldier.

There Socrates met Diogenes (the father of the "cynic" movement) who, legend states, lived in a large pot outside the gates. The myth suggests that they talked all night but neither of them mentioned what was discussed thereafter.

I should say here that this meeting is almost certainly a myth.

However, Socrates later states that 'He is richest who is content with the least, for content is the wealth of nature.' (I had forgotten that quote until Olivia Rytwinski, ((Author)) offered it up in one of her posts)
That quote would suggest that they did meet and have a discussion. Fascinating. Can you imagine the father of democracy and the father of cynicism meeting and what they may have discussed?
It bogles the mind.

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