The story of Damon and Pythias is a legend in Greek historic writings illustrating the Pythagorean ideal of friendship. Pythias is accused of and charged with plotting against the tyrannical Dionysius I of Syracuse. Pythias requests of Dionysius to be allowed to settle his affairs. Dionysius agrees, on the condition that Pythias' friend, Damon, be held hostage and, should Pythias not return, be executed in his stead. When Pythias returns, Dionysius, amazed by the love and trust in their friendship, frees them both.

Dionysius I or Dionysius the Elder was a Greek tyrant of Syracuse, Sicily. He conquered several cities in Sicily and southern Italy, opposed Carthage's influence in Sicily and made Syracuse the most powerful of the Western Greek colonies. He was regarded by the ancients as an example of the worst kind of despot: cruel, suspicious, and vindictive.