The Tyrant Who Sold the Philosopher Plato Into Slavery

A few years back I wrote a series of brief biographical sketches collected in a volume entitled The Book of Ancient Bastards: 101 of the Worst Miscreants and Misdeeds from Ancinet Sumer to the Enlightenment. Now out of print (it is, in fact, the only one of my books not still in print), It remains one of my favorites from among my own work. This week I've decided to share the story from this book, of how an early poet–admittedly an incredibly powerful one–dealt with harsh criticism of his work.

Plato: you expect this guy to be fun at parties?

So here he is, Dionysius I, tyrant of Syracuse!

When Philosophers and Tyrants Don’t Mix (ca. 432–367 B.C.) 

[Dionysius], taking offence at something [Plato] said to him . . . ordered him to be brought into the common market-place, and there sold as a slave for five minas: but the philosophers (who consulted together on the matter) afterwards redeemed him, and sent him back to Greece, with this friendly advice. . . . That a philosopher should very rarely converse with tyrants.

—Diodorus Siculus, ancient Sicilian Greek geographer and historian 

If ever there was a piece of work who could prove single-handedly that one man holding all the levers of power is usually a lousy idea, it was that real piece of work, Dionysius I, tyrant of the Greek city-state of Syracuse in Sicily. Originally a government clerk, Dionysius rose through the ranks to ultimate power based on his ability as a political, diplomatic, and military strategist. To balance this out, he was also arbitrary, capricious, cruel, and (perhaps worst of all) harbored literary pretensions. 

Bear in mind that Dionysius was a tyrant in the ancient sense of the word (Note: in the ancient Greek world the word 'tyrant' didn't necessarily carry the negative connotation it does today. It simply referred to someone who control of a city by military force and used his troops to enforce his rule.). As such he was a military man, and particularly fearsome in battle. He’d lost an eye early in life, and as a result presented a ferocious image that struck terror in the hearts of his enemies. That terror was justified, as even in victory he could be a particularly ruthless bastard: In 386 B.C., Dionysius led his mercenary army in an attack on the Greek city of Rhegium (now Reggio, in southern Italy). After a protracted and bloody siege, the tyrant, who fancied himself a cultured and enlightened man, sold the entire population of the city into slavery. 

So this was the fearsome antagonist, ruthless conqueror and all-around rough guy, who also fancied himself both a poet and a philosopher, boasting “far more of his poems than of his successes in war,” according to Diodorus. Poetry being a big deal in the ancient world, and Dionysius being the big man on campus in Syracuse, he surrounded himself with other literary and intellectual types, including Plato, who, as described in the quote opening this chapter, got sold as a slave in the public market for speaking his mind in the presence of the philosopher-tyrant. 

In another example of why it’s a bad idea for a creative type to be bluntly open and honest with a benefactor possessing no discernable sense of humor, Dionysius asked the poet Philoxenus what he thought of Dionysius’s poetry. When Philoxenus answered candidly, Dionysius had him dragged off to work in the quarries. 

Dionysius regretted the action once he’d sobered up, freed Philoxenus the next day, then invited him to dinner again. The wine flowed (again) and Dionysius asked (again) what Philoxenus thought of his poetry. In response, Philoxenus told Dionysius’s servants to drag him off to the quarries. This time the tyrant laughed. 

From then on, and for the remainder of his time at Dionysius’s court, Philoxenus promised that he would give truthful criticism of the tyrant’s work while also never again offending him. He accomplished this by basically inventing the double entendre. Dionysius’s poetry, according to Diodorus, was “wretched,” and he had a taste for tragedy, so when Dionysius would declaim a poem with a sad subject, then ask Philoxenus what he thought about it, the poet would reply, “Pitiful!” 

Dionysius is reputed to have either been murdered by his doctors to make way for his son to succeed him or to have died of alcohol poisoning from having drunk too much celebrating a win by some of his poetry at a festival in Greece. Either way, neither Dionysius, nor his poetry, proved "deathless."

And Philoxenus? He eventually left Syracuse and went on to write his most famous and successful poem, a comic piece called Cyclops, about the ridiculous passion of the mythical one-eyed monster for a beautiful goddess. Most people assumed that he was making fun of his one-eyed former benefactor. 

If Dionysius wrote a poem about his feelings on the matter, it hasn’t survived.