This is the story of a legendary conversation.
The exchange occurs between two men: Diogenes, an ascetic philosopher, and Alexander, the great military hero of Greece. It is a dialogue that enchanted the minds of many later thinkers. But first, the story:
One day, Diogenes was doing what he did best: sitting in his tub by the side of the street, naked or half-naked, castigating passing pedestrians for their foolish ambitions for money, fame, and leisure. ‘You are pathetic puppets of your society!’ he might have shouted. ‘You live for nothing more than your stomachs and pocketbooks!’
Diogenes is belligerent and crass. He berates everyone who walks by for wasting their lives in mindless pursuits. His nudity and overt poverty were intended to reinforce his creed: humans do not need anything but to be free — to speak their minds and enjoy the sunshine. Diogenes’ brazen critique of society earned him a reputation; he personified the philosopher who lived what he preached.
Alexander the Great, the great military conqueror of the known world, was curious to meet the legendary cynic, so he sought him out. Details vary as to the exact flow of their conversation, but most accounts converge on a particular point in their exchange: the great Alexander asked the humble Diogenes if there was anything he could do for him, and Diogenes replied: ‘Could you move over a bit? You’re blocking my sun.’
For many writers, this moment epitomized the ultimate juxtaposition in human status: Alexander, the most celebrated, famous, and ‘successful’ man in the world; Diogenes, the most disinterested, honest, and poor man in the world.
According to Plutarch (46-120 CE), Alexander was astounded by the wisdom of Diogenes. In Plutarch’s retelling, Alexander later says, ‘If I were not Alexander, I would be Diogenes’ — implying that he inwardly endorsed the philosopher’s rejection of social convention, even though Alexander himself carried the burden of disseminating Greek culture to the world.
Plutarch intentionally frames the story to highlight the dichotomy between Alexander the military imperialist and Diogenes the philosophical rationalist.
Laërtius, the third century CE historian, highlights the social class and value distinction. When he approached Diogenes, Alexander introduced himself, ‘I am Alexander, the Great.’ In response, Diogenes said, ‘I am Diogenes, the Dog.' The Dog proves to more satisfied and confident that the Great. Better to be content and happy and have nothing, than to be king of the world and be miserable.
Seneca (4 BCE-65 CE) had another theory: it was Diogenes’ security in his lowly position that gave him greater confidence than a man who directed armies. Because Diogenes had nothing to lose, he had nothing to fear, even when approached by an entourage of the ultimate power in the world. For all his pride and accomplishment, the ‘great’ Alexander was ‘beaten as soon as he met a man to whom he could give nothing, and from whom he could take nothing away.'
Cicero (106-43 BCE) drew a similar lesson from the encounter: Diogenes had nothing and was content; Alexander had everything and could not have enough. It was Diogenes’ disregard for earthly pleasures that granted him satisfaction with life, whereas royalty can never find contentment.
Juvenal, the early second century CE Roman poet, agreed with Cicero’s analysis:
The nude Cynic fears no fire for his tub; if broken, he will make himself a new house to-morrow, or repair it with clamps of lead. When Alexander beheld in that tub its mighty occupant, he felt how much happier was the man who had no desires than he who claimed for himself the entire world, with perils before him as great as his achievements.
The story of Alexander and Diogenes leaves us with a proposition to consider: the greatest strength, confidence, and courage does not come from accomplishment and reputation, but from having nothing at all to lose. We might frame the hypothesis in the following equation: the more we have to protect — whether our names or our treasures — the less free we truly are.
 Plutarch, On the Fortune or Virtue of Alexander 331f-332c
 Diogenes Laërtius, *Lives* 6.60
 Seneca, De beneficiis 5.6.1 (Trans. Dobbin, Robin. (2012). The Cynic Philosophers from Diogenes to Julian. Penguin Classics. p. 32)
 Cicero, Tusculan Disputations 5.92.
 Juvenal, Satire 14.308-12, Trans. G.G. Ramsay 1918