Plutarch, a Greek from Chaeronea in central Greece, wrote Parallel Lives around the year 100: paired biographies of famous Greeks and Romans, set side by side to show character. This life is Dion of Syracuse, a city on the east coast of Sicily. Plutarch pairs him with Brutus, another student of philosophy who took up a sword against a ruler.

Dion studied with Plato and lived at the court of Dionysius, the tyrant who ruled Syracuse as one man. He tried to turn that despot into a philosopher-king. Exile was the answer. He came back with a few hired soldiers and the city opened its gates. Dionysius fled. The democracy that followed proved as bloody as the palace. Callippus, a friend from Plato's Academy in Athens, had Dion murdered in his house. Killing a tyrant was easier than founding a free city.