Plutarch's Lives, Vol. 1

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.

Timoleon is praised by many Greeks for putting the needs of the city-state above his own family. However, Timoleon is very hurt when his mother casts him out of her house, resolving to abandon public life.

After a digression in which he discusses the importance of being resolute, Plutarch turns back to the situation in Sicily. Timoleon agrees to lead Corinth against the Carthaginians in Sicily. Meanwhile, Hicetas besieges Dionysius and openly goes over to the Carthaginian side. He tries to tell the Corinthians not to come, but a series of omens persuades Timoleon to sail anyway. In Sicily, the Corinthians find Syracuse besieged by Hicetas. The Corinthians are also outnumbered by Hicetas and the Carthaginians. Timoleon is able to outmaneuver the treacherous Hicetas and reaches the allied city of Tauromenium. This becomes Timoleon’s base of operations.

Though many Sicilians are skeptical about the motives of the Corinthians, Timoleon’s boldness and skill win him some important victories and he starts to get more allies, including Syracuse, which Dionysius surrenders to Timoleon. Dionysius is sent back to Corinth. Hicetas tries to have Timoleon assassinated, but the plot is botched, and Timoleon’s support in Sicily grows even more.

Hicetas and the Carthaginians’ position becomes weaker, and they have a hard time supplying their forces. Eventually, the Carthaginians begin to suspect Hicetas of treachery and abandon Sicily. With the Carthaginians gone, Timoleon easily beats Hicetas in a battle near Syracuse.

Timoleon sets out on a program of restoration and rebuilding, destroying the citadel and palaces of the tyrants and erecting new lawcourts. He has the Greeks send more settlers to repopulate Syracuse. Soon, however, the Carthaginians return with a massive army, and Timoleon sets out with a tiny force to meet them. Despite being heavily outnumbered, Timoleon defeats the Carthaginians at the Crimesus River. Hicetas and other Sicilian tyrants, however, continue to harass Syracuse until Timoleon at last captures Hicetas in Leontini and puts him to death. He then beats two more tyrants, Mamercus of Catana and Hippo of Messana.

Having restored peace to Sicily, Timoleon chooses to remain there rather than return to Corinth. Though some populist leaders try to discredit him, Timoleon generally retains the love, esteem, and gratitude of the Sicilians. He goes blind in his old age and finally dies in Syracuse. He is given a lavish public funeral.