The "sword of Damocles" is a modern expression, which to us means a sense of impending doom, the feeling that there is some catastrophic threat looming over you. That's not exactly its original meaning, however.

The expression comes to us from the writings of the Roman politician, orator, and philosopher Cicero (106-43 BC). Cicero's point was that death looms over each of us, and we ought to try to be happy in spite of that. Others have interpreted his meaning to be similar to "don't judge people until you've walked in their shoes". Others, such as Verbaal (2006) argue that the story was part of a subtle suggestion to Julius Caesar that he needed to avoid the pitfalls of tyranny: the denial of spiritual life and the lack of friends.

The Story of Damocles

The way Cicero tells it, Damocles was the name of a sycophant (adsentator in Latin), one of the several yes-men in the court of Dionysius, a 4th century BC tyrant. Dionysius ruled Syracuse, a city in Magna Graecia, the Greek area of southern Italy. To his subjects, Dionysius appeared to be very rich and comfortable, with all the luxuries money could buy, tasteful clothing and jewelry, and access to delectable food in lavish feasts.

Damocles was prone to compliment the king on his army, his resources, the majesty of his rule, the abundance of his storehouses, and the greatness of his royal palace: surely, said Damocles to the king, there had never been a happier man. Dionysius turned to him and asked Damocles if he would like to try living Dionysius's life. Damocles readily agreed.

A Tasty Repast: Not So Much

Dionysius had Damocles seated on a golden couch, in a room decorated with beautiful woven tapestries embroidered with magnificent designs and furnished with sideboards chased in gold and silver. He arranged for a feast for him, to be served by waiters hand-picked for their beauty. There were all kinds of exquisite food and ointments, and even incense was burned.

Then Dionysius had a glittering sword hung from the ceiling by a single horsehair, directly over Damocles' head. Damocles lost his appetite for the rich life and begged Dionysius to let him go back to his poor life, for, he said, he no longer wanted to be happy.

Dionysius Who?

According to Cicero, for 38 years Dionysius was the ruler of the city of Syracuse, about 300 years before Cicero told the tale. Dionysius' name is reminiscent of Dionysus, the Greek God of wine and drunken revelry, and he (or perhaps his son Dionysius the Younger) lived up to the name. There are several stories in the Greek historian Plutarch's writings about the two tyrants of Syracuse, father, and son, but Cicero didn't differentiate. Together the Dionysius family were the best historical example Cicero knew of cruel despotism: a combination of cruelty and refined education.​

The Elder invited two young men to dinner who were known to abuse the king when drunk. He noticed that one became more talkative as he drank while the other kept his wits about him. Dionysius let the talker go—his treason was only wine-deep—but had the latter put to death as a true traitor. (in Plutarch 's Apophthegms of Kings and Great Commanders)

The Younger is often portrayed as spending much of his life in drunken revelry and for having a superb collection of wine cups. Plutarch reports that he was known to have led a licentious life in Syracuse with lots of drinking parties, and when he was exiled to Corinth, he frequented the taverns there and earned his living by teaching girls how to be useful at drinking parties. He blamed his misspent ways on being "the son of a tyrant". (in Plutarch's, Life of Timoleon)

McKinlay (1939) argued that Cicero could have meant either one: the elder who used the Damocles story as a lesson in virtue directed (in part) to his son, or the younger who staged a party for Damocles as a joke.

A Bit of Context: The Tusuclan Disputations

The sword of Damocles is from Book V of Cicero's Tusuclan Disputations, a set of rhetorical exercises on philosophical topics and one of the several works of moral philosophy that Cicero wrote in the years 44-45 BC after he had been forced out of the Senate.

The five volumes of the Tusuclan Disputations are each devoted to the things that Cicero argued were essential to a happy life: indifference to death, enduring pain, alleviating sorrow, resisting other spiritual disturbances, and choosing virtue. The books were part of a vibrant period of Cicero's intellectual life, written six months after the death of his daughter Tullia, and, say, modern philosophers, they were how he found his own path to happiness: the blissful life of a sage.

Book V: A Virtuous Life

The Sword of Damocles story appears in the fifth book, which argues that virtue is sufficient for living a happy life, and in Book V Cicero describes in detail what an utterly miserable man Dionysius was. He was said to have been "temperate in his mode of living, alert, and diligent in business, but naturally malicious and unjust" to his subjects and family. Born of good parents and with a wonderful education and huge family, he trusted none of them, certain that they would blame him for his unrighteous lust for power.

Ultimately, Cicero compares Dionysius to Plato and Archimedes, who spent happy lives in the pursuit of intellectual inquiry. In Book V, Cicero says he found the long lost tomb of Archimedes, and it inspired him. Fear of death and retribution is what made Dionysius wretched, says Cicero: Archimedes was happy because he led a good life and was unworried about death which (after all) looms over all of us.

Sources:

Cicero MT, and Younge CD (translator). 46 BC (1877). Cicero's Tusculan Disputations. Project Gutenberg

Jaeger M. 2002. Cicero and Archimedes' Tomb. The Journal of Roman Studies 92:49-61.

Mader G. 2002. Thyestes' Slipping Garland (Seneca, "Thy." 947). Acta Classica 45:129-132.

McKinlay AP. 1939. The "Indulgent" Dionysius. Transactions and Proceedings of the American Philological Association 70:51-61.