Plutarch begins his Life of Timoleon with a reflection on why he writes biographies: To learn and teach lessons by examining the character of important figures from history. He hopes that his biographies can inspire moral improvement in himself and his readers.

Timoleon is born during a tumultuous period in the history of Sicily. Dion, the tyrant of Syracuse, is killed, and he is followed by a series of short-lived tyrants. Eventually, the tyrant Dionysius returns to power, having been banished before. His rule is even more savage now and soon sparks resistance.

Meanwhile, the Carthaginians invade Sicily, and the Sicilians enlist the help of Corinth. Hicetas, the tyrant of Leontini, is hoping to make an alliance with the Carthaginians. But Corinth disrupts his plan by sending forces to help Sicily under the command of Timoleon. Timoleon comes from a noble Corinthian family. He is gentle and calm by nature; he is also wise and brave. Timoleon’s brother is the more impetuous Timophanes, whom Timoleon had once saved when he fell in battle. The power-hungry Timophanes tries to make himself tyrant of Corinth, refusing Timoleon’s request that he surrender his power. He is finally assassinated while Timoleon covers his head and withdraws.