Around the 4th century BC, Pythias and his friend Damon, both followers of the philosopher Pythagoras, travelled to Syracuse. Pythias was accused of plotting against the tyrant of Syracuse, Dionysius I. As punishment for this crime, Pythias was sentenced to death.

Accepting his sentence, Pythias asked to be allowed to return home one last time, to settle his affairs and bid his family farewell. Not wanting to be taken for a fool, Dionysius refused, believing that once released, Pythias would flee and never return.

Risking his own freedom for his best friend, Damon proposed that Dionysius hold him hostage until Pythias returned. Dionysius agreed, on the condition that, should Pythias not return when promised, Damon would be put to death in his place. Damon agreed, and Pythias was released.

Dionysius was convinced that Pythias would never return, and as the day Pythias promised to return came and went, Dionysius prepared to execute Damon. But just as the executioner was about to kill Damon, Pythias returned.

Apologizing to his friend for his delay, Pythias told of how pirates had captured his ship on the passage back to Syracuse and thrown him overboard. Dionysius listened to Pythias as he described how he swam to shore and made his way back to Syracuse as quickly as possible, arriving just in the nick of time to save his friend.

Dionysius was so taken with the friends' trust and loyalty, that he freed both Damon and Pythias, and kept them on as counsel to his court.