Timoleon – Finally Freeing Sicily

Important People

Timophanes – Timoleon’s brother and the first tyrant we meet in this story. His name, rather fittingly, means “seems honorable.”

Dionysius II – The tyrant whom Dion overthrew, but did not execute. He returns to power after Dion’s death only to be replaced by Hicetas. His story grows more complex than it had been in Dion’s life. He becomes the tyrant we pity the most, while the other tyrants in this Life receive ends they deserve. Dionysius comes closest to redemption.

Hicetas – The tyrant who replaces Dionysius II, who had allied with the Carthaginians to gain power. Starting out allied with the Corinthians, he becomes Timoleon’s main enemy in the fight to free Syracuse.

Mago – Carthaginian general allied with Hicetas and leading a formidable navy. He’s the first Carthaginian general to “capture” Syracuse, though it’s Hicetas who hands the city over. Though he acts like a mercenary and cuts when times grow difficult, the Carthaginians don’t respond well to his cowardice and redouble their efforts against Syracuse. A life-within-a-life perspective that tells us a lot not just about the man, but about why Plutarch may still consider the Carthaginians barbarians.

Mamercus – Tyrant of Catana and ally of Hicetas. Allied with Carthage but losing to Timoleon, his end is also telling about the nature of a tyrant when pitted against a democracy to beg for his life.

Plato – Though dead by the time Timoleon comes to power, he haunts this dialogue both in its analysis of tyranny and its understanding of justice.

Important Places

On Sicily

Syracuse – The most powerful polis on the western side of the island. It had grown significantly in the last century and now had five sections, the most important for this life are the Achradina and the Epipolae. See the map below:

Leontini – A polis founded by Naxos in the 8th-century just twenty miles north of Syracuse. Often dominated by Syracuse in this period, they had acted as a reliable ally against the Syracusans for anyone wanting a home base from which to attack the tyrants (cf. Life of Dion).

Tauromenium – Another small polis at the foot of Mt. Aetna on the western coast of Sicily, but further north than Catana, Tauromenium gives immediate aid to Timoleon and, after he sneaks past the Carthaginian fleet, becomes his main base of operations in his early Sicilian campaign.

Catana – On the slopes of Mt. Aetna, Catana was also a colony of Naxos. Their rich volcanic soil made them a prime target for the more powerful poleis around them, like Syracuse. Conquered by Dionysius I, the polis remains under Syracusan sway until it switches to Roman rule in the 3rd century BC. Though greatly damaged by earthquakes, its Roman amphitheater is still used by the modern city.

Messana – Situated on the straits between Sicily and Italy (the straits of Messina, its modern name), it was originally founded under the name Zancle (meaning sharp corner), emphasizing its position at the corner of the island. Strategically important but not politically dominant, its neighbor city across the straits, Rhegium, was usually the politically dominant power. This site would later also be the spark that ignited the First Punic War between Carthage and Rome.

On Mainland Greece

Peloponnesus – The main body of the Greek mainland west and south of the Isthmus of Corinth. Generally, Sparta considers it her back yard, but Argos and Corinth are the next most powerful cities with a claim to this space.

Corinth – The prosperous mother-city (μητροπολις – metropolis) of Syracuse with a vast trading network all over the Mediterranean. Keeping Syracuse safe and prosperous remained in Corinth’s best interests and so her people send Timoleon to lead that mission against tyrants and Carthaginians.

Delphi – The pan-Hellenic oracle and most important site for advice and perspective from the gods. Plutarch served at this temple for the majority of his adult life. It plays a small role in that some men whom Timoleon ends up losing likely deserved their fate since they had captured and sacked the sanctuary at Delphi earlier in their military careers. Plutarch sees such sacrilege repaid by Divine Justice.

Elsewhere in the Aegean

Italy – Too close to Sicily to be ignored, Italy contained many cities that would either be sympathetic to democracies or willing to house tyrants, at least temporarily.

Rhegium – Right across the straits from Sicily, Rhegium acts as a neutral meeting ground for negotiations. A cross-roads city that always has representatives milling about from Corinth, Carthage, and Syracuse.

Bruttium – The region around Rhegium, loosely corresponding to modern Calabria.

Key Virtues and Vices

Justice (δίκη – dikē) – Plutarch argues (30.9) that Justice preserved Timoleon’s good fortune. With this in mind, it’s helpful to remember that Dion didn’t have the same good fortune, though he seems to have deserved it. Perhaps he stepped off the road of Justice and Plutarch allows us to decide where and when. Timoleon also puts justice and honor over convenience (5.1), his brother acts without justice (4.5) when he becomes tyrant, and Timoleon not only acts justly (5.1; 10.7; 29.6), but physically restores the courts of justice (22.3) to the democracy of Syracuse that before had to rely on the whims of the tyrant. 

Gentleness (πραότης – praotēs) – Though not mentioned often, it’s important for us to remember that this is a virtue listed explicitly in Aristotle’s Ethics and one that Plutarch takes great interest in for his characters. Timoleon is introduced to us as gentle (3.4), but not with tyrants and base men. We’re also told at the end that he dealt gently and justly with friends (37.5), but boldly and powerfully against barbarians (i.e. Carthaginians in this case). See Plutarch’s “On the Moderation of Anger” or Aristotle’s Ethics Book 4, Ch. 5 (1125b35) for a more thorough discussion of this virtue and its most obvious excess: anger.

Fortitude (ἀνδρεία – andreia) – Several times it seems like Timoleon should give up after a major setback, but he doesn’t. This virtue isn’t just for tyrants, as Dionysius I had argued with Plato in the Life of Dion.

Wisdom (φρονήσις – phronēsis) – Especially on the heels of Dion’s life, Timoleon just strikes us as lucky. Yet, Plutarch primes us in the preface (0.8) to read with an eye for his wise choices and not to judge every decision by its (usually positive) outcome. Plato’s wisdom even helps men like Dionysius (15.4)

Thoughtful Questions and Reflections

Should we prioritize our homeland over our family? If so, is it virtuous to go as far as Timoleon does: consenting to and helping plan the assassination of a brother?

What is the attraction of being a tyrant? How does Plutarch agree with Plato that a tyrant’s life is the worst kind?

C. 0 – (Sometimes placed as preface for Aemilius Paulus)

1. Preface on why Plutarch wrote the lives (for others) and why he continues to do so: “using history as a mirror and striving to mold and adorn my life in conformity with the virtues therein depicted”
2. Because this research is like having these characters as guests, admiring, observing, and selecting what is best and most important about them.
3. And what is better than moral improvement? (Sophocles quotation)
4. Democritus advises us to pray that only good spirits influence us, but in doing this he ruins good philosophy by injecting superstition.
5. Rather than seeking spirits from the air, I look to the men of the past to help me cherish what is noblest and most worthy of their characters and reject anything base, malicious, or ignoble.
6. Timoleon and Aemilius Paulus were two such men who are a delight and profit to study.
7. Alike in their sound principles but also the good fortune they enjoyed in their conduct.
8. Thus it will be hard for the reader to decide which was the root cause of their successes: fortune or wisdom.

C. 1 – Meanwhile in Syracuse

1. Let’s get some context on Syracuse before Timoleon was there.
2. Dion killed not long after taking power, and a succession of short-lived tyrants follows. (354 BC)
3. The whole island depopulated of Greeks from recent wars and many opportunistic retired mercenaries made tyranny tempting for many.
4. (346 BC) Dionysius returns, and regains his former power.
5. Dionysius still unreasonable (see Life of Dion), but now also savage because of recent misfortunes.
6. Those resisting Dionysius choose a tyrant from Leontini as their general not because they like him, but because he likely has the forces necessary to beat Dionysius AND he’s at least a native-born Syracusan.

C. 2 – Enter Carthage

1. Carthaginians begin to invade Sicily, and the Sicilians ask Corinth for help.
2. Syracuse a colony of Corinth’s from 735 BC and most of Corinth’s wars had been for liberty not for love of tyrants.
3. Hicetas (tyrant from Leontini) was already secretly meeting with the Carthaginians but openly praised the plan of seeking help from Corinth.
4. Hicetas expected the Corinthians to be too busy with their affairs in Greece, so he fully expected to bring the Carthaginians in as allies.

C. 3 – Enter Corinth (and Timoleon)

1. Corinthians agree to help Syracuse.
2. While looking for a commander to put to a vote, some commoner recommends Timoleon, perhaps inspired by a god.
3. An example of fortune smiling kindly upon him (Timoleon held no political position and wasn’t even nearby for this preparation).
4. Noble parents, lover of his country, exceptionally gentle except with tyrants and base men.
5. His calm temperament meant he made wise decisions in his youth but could still be brave in old age.
6. His brother was not much like him, passionate for power and impetuous.
7. His brother nonetheless rose in the ranks and Timoleon tried to help, while hiding his faults and embellishing his good natural qualities.

C. 4 – Backstory on Timoleon and Timophanes

1. (368 – 366 BC) Timophanes (Timoleon’s brother) overtaken in a perilous position when leading the cavalry.
2. His horse had been wounded and thrown him, and many of his comrades left him, so it was a few versus many of the enemy.
3. Timoleon protects his brother with his shield but ultimately pulls his brother from the danger while taking many wounds himself. (this parallels Socrates saving Alcibiades in the Battle of Potideia; cf. The Symposium)
4. Corinth puts in place a garrison of 400 mercenaries under the leadership of Timophanes.
5. Timophanes uses these mercenaries to make himself tyrant and tries to reason with him to renounce power and make amends for the way he had treated many citizens already.
6. When his brother rejects him solo, he grabs a brother-in-law and a seer to accompany him for a second attempt.
7. Timophanes rejects the second attempt as well, mocking them and becoming violent.
8. Timoleon withdraws a little, covering his head and the other two kill Timophanes. (Nepos’s account agrees, more or less; Diodorus Siculus says he killed his brother in the agora).

C. 5 – The Aftermath of Fratricide

1. Timoleon praised as news flies around the Greek world, since Timoleon set country above family and justice over expediency, saving his brother when it helped the polis and plotting against it when it didn’t.
2. Those sycophants who fanned at the courts of the powerful bothered? (With their words) Timoleon.
3. His own mother was angry with him and she refused to look at him when he came to her, closing her house against him. This affected him the most and he decided to starve himself to death.
4. His friends entreat him not to and he eventually gives in, but decides to give up public life and live apart from the world, wandering in the desolate parts of the country.

C. 6 – Philosophy Makes One Resolute

1. If men do not act from firmness of philosophy and strength of reason, we are easily unsettled and tossed between praise and blame, forced from our own clear view of things.
2. Not only should our actions be just, but our convictions should be abiding and unchangeable.
3. We cannot become disgusted with our former actions like the glutton does with the food he once gorged on.
4. The choice that springs from wise and understanding counsel does not change, even if the results are not success.
5. Thus Phocion had still been glad about the success of the Athenians against Antipater but stood by his advice not to engage in that battle.

6-7. Dionysius asks Aristides the Locrian for one of his daughters in marriage. Aristides (a friend of Plato’s) responds that he would rather see his daughter dead than married to a tyrant. Dionysius puts all his children to death and then asks Aristides if he’d changed his mind. He said he was afflicted/saddened by the deed but not repentant of what had been said.

C. 7 – Hicetas’s Perfidy

1. So great was the grief that Timoleon withdrew from public life for 20 years.
2. Once he is chosen, the greatest man in the city advises him to do well to be thought of as a tyrannicide instead of a fratricide.
3. As Timoleon prepares, Corinthians discover that Hicetas has gone over to the Carthaginian side.
4. Hicetas replaced Dionysius with himself.
5. Hicetas sends a letter to the Corinthians telling them their services are no longer needed and that they should spare themselves the expense.
6. Also, Hicetas adds, because it took you so long to get here I allied with the Carthaginians and they don’t want you to come… they’re watching out for you with their navy.
7. Now anger supplied the expedition with greater speed in getting ready.

C. 8 – Oracles and Persephone

1. A priestess of Persephone has a dream that Persephone and Demeter are getting ready to go to Sicily as well.
2. So, the Corinthians equip a sacred trireme, name it after both goddesses, and send it along with the fleet. Timoleon goes to Delphi to sacrifice and receives the following sign:
3. A crown slipped from the votive offerings and fell right on Timoleon’s head, as if the god himself were crowning him.
4. In 344 BC, he sets sail with a navy of ten ships.
5. He saw a heavenly sign of fire. Coming from the heavens
6. In which a torch seemed to lift itself above this fire and follow the ship on its course, landing in the precise part of Italy toward which they headed.
7. The soothsayers declared this to be favorable and in line with the priestess’s dream since Persephone was abducted from Sicily and it was later given to her as a wedding present.

C. 9 – Hicetas and the Carthaginians

1. They hastened to the coast of Italy.
2. The news from Sicily was less good than the omens.
3. Hicetas was besieging Dionysius in a small part of the acropolis.
4. Hicetas also commanded the Carthaginians to prevent Timoleon from landing in Sicily. He promised to divide Sicily between himself and the Carthaginians.
5. Lying envoys were sent inviting Timoleon to come as advisor and partner to Hicetas, who really had in play his demise the whole time.
6. Since the Corinthians could see what plan the Carthaginians had put in place, they saw through Hicetas’s lies and were further enraged by his treachery and Carthaginian tyrant-making.
7. And finally, the Corinthians are outnumbered at sea by the Carthaginian navy, and on land by Hicetas’s infantry.

C. 10 – Timoleon’s Trick to Get to Tauromenium

1. The envoys of Hicetas, Carthaginian commanders, and Timoleon meet with Timoleon requesting a third-part to serve as witness: Rhegium’s entire citizen body (in Italy) chosen as friendly to both sides.
2. This move kept him safe from treachery and make their oaths more binding because more public.
3. Rhegians also set up an escape route for Timoleon and are more on the side of the Greeks and Sicilians than the Carthaginians, because they fear the barbarians as neighbors.
4. The gates of the city are closed, the assembly is called, and the long speeches begin, buying time for the Corinthian navy to move in to Sicily.
5. Timoleon looks as if he’ll speak soon, but manages to get away with some help from the Regions (because he’s near the bema and can probably be easily seen).
6. They land and are welcomed at Tauromenium by their ally, Andromachus.
7. This man was the father of the historian Timaeus (source for Life of Nicias) and led the Tauromenians well in “law and justice” hating tyrants.
8. Thus, Tauromenium becomes the base of Timoleon’s operations.

C. 11 – Timoleon’s Chances

1. When the Phoenicians/Carthaginians discover the deceit, they’re not happy with it, which gives even more pleasure to the Rhegians because Carthaginians are known for being crafty… and now the craftiness had been used against them.
2. Carthaginian envoy threatens to utterly overturn (with a palm face-up to face-down, for emphasis) Tauromenium for helping the Corinthians.
3. Andromachus threatens the envoys ship with the same gesture.
4. Hicetas, in fear, orders a huge Carthaginian fleet.
5. At this point, the Syracusans thought they’d never be free of Hicetas, seeing harbor full of Carths., city in hands of Hicetas, and citadel in power of Dionysius when compared to Timoleon who had a small scrap of Sicily and 1000 soldiers.
6. The other cities of Sicily also had little reason to hope, particularly in light of Callipus and Pharax recent behavior (cf. Dion 54-57 and 48.3 and 49.1) foreigners who came at first to free cities from tyranny but made the current tyrants seem like gold in comparison, making many wish to be dead or enslaved than to live to see this “independence” (autonomia: is there a difference in the way Plutarch uses autonomia and eleutheria?)

C. 12 – Opportunity Knocks

1. Thus, the other cities on Sicily assume this “Corinthian commander” will be just like the others: luring them with false hopes and fair promises to receive a new master in place of the old one. All the cities felt this way except Adranum.
2. This small city was sacred to Adranus, a god devoutly worshiped in Sicily and the two parties of the city were in communication with both men: Hicetas and Timoleon.
3. Both men arrived in person at the same time to the summons.
4. Hicetas with 5000 soldiers; Timoleon with 1200.
5. In two days of marching, Timoleon had made it to the outskirts of Adranum and there heard that Hicetas was pitching tent outside the city that night as well.
6. Timoleon’s lower officers want the men to eat to prepare for battle the next day. Timoleon wants to attack right away, while the enemy is tired and dealing with tents and dinner.
7. As he made the plan, he enacted it, taking his shield and leading the men as if to victory (still 30 furlongs from the enemy).
8. They closed the gap and put the enemy to flight, killing only 300 because so many fled, but 600 were taken alive and their camp, with all its supplies, was captured (remember, Timoleon was “poorly supplied” and people were worried about it).
9. Sacred signs: The people of Adranum open their gates to Timoleon and report to him an omen they saw while he fought the battle: the cult statue of the god was seen to sweat while the tip of the spear it was holding visibly quivered.

C. 13 – Dionysius Joins Timoleon

1. This battle offered a propitious beginning that things would go well for Timoleon, which they start to do.
2. Mamercus, the tyrant of Catana, presents himself as an ally after this battle.
3. Dionysius, holed up in the citadel, communicates with Timoleon and offers to surrender himself to Timoleon rather than Hicetas.
4. Timoleon accepts and secretly builds up a contingent of 400 soldiers inside the acropolis.
5. These soldiers eventually control everything Dionysius still had:
6. Horses, missiles, and armor for 70,000 troops
7. Dionysius had 2000 soldiers with himself, and hands these over to Timoleon, while he sails off with a few friends (as a private citizen?)
8. He comes to the camp of Timoleon and is seen for the first time dressed as a regular citizen.
9. He is sent to Corinth with one ship and a bit of treasure, and Plutarch reflects that he had been “born and raised in a tyranny” and then held the most illustrious tyranny for ten years before becoming involved in struggle and war so that his suffering eventually matches and surpasses all his acts of tyranny.
10. The sorrows of Dionysius: He lived to see the violent death of his grown-up sons and violation of his unmarried daughters, shameful abuse of his wife (and sister), abused murdered, and cast into the sea with he children. These things are described in the Life of Dion (the Locrians do this to him because of his tyrannical acts; cf. Athenaeus 541 c-e, but unsure of what parts of Dion to look in for this story).

C. 14 – The Character of Dionysius

1. Everyone flocks to see Dionysius
2. Some, however, wanted to abuse him even after (especially because?) Fortune had laid him low. Those who pitied him saw him as proof of divine justice being visited in one’s lifetime.
3. Nothing was as important as Fortune’s ability to bring this tyrant of all Sicily to Corinth where he fought with prostitutes, corrected flute-girls in their singing, and wasting time in taverns drinking diluted wine.
4. Some thought he was naturally licentious, but others thought he was choosing to be held in contempt rather than fear.

C. 15 – Dionysius in Exile

1. Some saying remain that show that he had some noble responses to his reversal of fortune.
2. He said, when visiting another colony of Corinth’s (Leucadia), that he’d rather live there because:
3. Brothers who commit misdeeds more easily spend time again with their fellow brother than they do with their fathers, who hold them accountable. Thus, he was uncomfortable going back to his “father” Corinth in light of all his misdeeds as a tyrant.
4. Some mocked Dionysius for his love of philosophy while he was ruling (see Life of Dion) and if Plato’s philosophy is helping him now. Dionysius responds, “Do you not think that I have had no help from Plato, when I bear my change of fortune as I do?”
5. When someone asks him about what happened with Plato he says that the greatest downside to tyranny is that no one speaks frankly to the tyrant as a friend, and so these deceivers had denied him the good will of Plato.
6. Someone else, wishing to mock Dionysius, shook out his robes to prove he had no weapon, a necessary thing when coming into the presence of a tyrant. Dionysius joked back that he should also shake it out upon leaving to prove that the had not stolen anything form the house.

C. 16 – Timoleon’s Luck

1. Timoleon’s fortune as extraordinary as Dionysus’ misfortune.
2. Dionsyus surrenders Syracuse (for a second time) and sails away.
3. The Corinthians send 2200 reinforcements, who are prevented from landing in Syracuse by the Carthaginian navy. They instead go to Thurii (southern Italy).
4. The Corinthian reinforcements faithfully guard the city of Thurii so that the Thurians can attack their neighbors the Bruttians.
5. Hicetas, however, still besieges the acropolis of Syracuse, and now they’ve gone from fighting two tyrants to one. Hicetas comes up with the plan to assassinate Timoleon where he is in Adranum (map). Timoleon kept no bodyguard.
6. The assassins enter a sacred area just as Timoleon is about to offer a sacrifice.
7. Just before they signaled to each other to kill Timoleon, one of them is struck on the head with a sword. The man dies, his companion grabs the altar and begs for mercy, and the killer jumps up on a high rock to prevent immediate retaliation from the mob for committing murder in a sacred area.
8. The remaining assassin confesses to the crime he and his accomplice were going to commit.
9. The man on the rock was now claiming that he avenged the murder of his father, who had been killed in Leontini.
10. Many of the bystanders act as witnesses and affirm both men’s testimony as to what happened. Everyone marvels at the Fortune that guided the guilty to punishment while sparing the innocent Timoleon.
11. Corinthians reward the man on the rock with ten minas, because he had put his revenge at the service of the gods who were obviously guarding Timoelon.
12. Timoleon now respected even more by his men, since his person is now seen as sacrosanct, protected by the gods.

C. 17 – Carthaginians in Syracuse

1. As support for Timoleon grows throughout western Sicily, Hicetas regrets having used his Carthaginian mercenaries/allies in guerilla tactics. Now he wants to use their full force and call Mago, their general, closer to Syracuse with the whole army and navy.
2. Mago arrives with 150 ships and 60,000 infantry encamping around Syracuse, essentially making it have more Carthaginians than Greeks.
3. The Carthaginians had never succeeded before this in taking Syracuse, but now it was handed to them by Hicetas.
4. The Corinthians on the acropolis had no access to the harbors, and thus lacked food and were constantly defending all sides of the steep walls from skirmishes and siege warfare.

C. 18 – The Achradina

1. Timoleon ships them grain from Catana in small boats that don’t need a harbor to land. They’re also small enough to run the Carthaginian blockade.
2. Mago and Hicetas thus try to take Catana.
3. Neon, watching from the acropolis of Syracuse, sees that the enemy left behind now grew careless, sallies forth suddenly upon them.
4. In his risk, he manages to capture teh Achradina, (giving the besieged direct access to the sea even if not to a port ). Here Syracuse called a unification of several cities, and the Achradina considered the strongest part, easiest to defend.
5. Neon unites his acropolis fortifications to the Achradina fortifications and thus solidifies his gains.
6. Mago and Hicetas learn of this as they approach Catana.
7. They return quickly, having achieved nor attempted anything.

C. 19 – Foresight v. Fortune

1. Thus far, it seems equally that foresight and fortune have worked together, vying for supremacy. From here on in the story, Plutarch thinks Fortune wins.
2. The Carthaginian reinforcements are waiting for a break in the storm and the Carthaginian navy to leave Thurii. When one doesn’t present itself quickly, they walk to Bruttium.
3. They walk down to Rhegium on the tip of the boot, more persuasive than a normal group because they’re armed.
4. The Carthaginian admiral (Hanno?) grew tired of guarding the Corinthians whom he didn’t expect to leave Thurii, and so he crowned himself with victory and sailed for Syracuse.
5. As he passed the acropolis and Achradina, he made it clear that he was celebrating victory over the Carthaginian reinforcements.
6. Meanwhile, at Rhegium, the undefeated Carthaginian reinforcements arrive to see that the Carthaginian navy is now nowhere in sight and the straits are calm. Thus they commandeer any vessel they can to carry them all across. The waters were so calm the horses could swim a

C. 20 – Mercenary Mutterings

1. After taking Messana, the newly-combined forces march on Syracuse, numbering about 4000.
2. Mago grows suspicious:
3. Normally, eels are easy to catch in the shallow, brackish water at the coast.
4. The mercenaries from both sides would hunt these eels on their free time, since they were both Greek.
5. In time of truce, this brought them all closer together.
6. As they converse, they admire the land and sea around them.
7. One Corinthian mercenary challenged one of the Carthaginian mercenaries as to whether or not he saw that he was barbarizing all of Sicily, especially by handing it over to the basest and bloodiest of men, Carthaginians.
8. Or did he think the Carthaginians would hand the tyranny back to Hicetas and be done with Syracuse?
9. Hicetas himself isn’t worth fighting for since he banishes relatives and brings armies against his own people.
10. Mago thus suspected treachery as these speeches spread through his camp.
11. So, Mago abandons Syracuse, in spite of Hicetas’s pleas for him to stay and his own superior numbers.

C. 21 – Timoleon Takes Syracuse

1. Timoleon arrives the next day, arrayed for battle, but laughing at Mago’s cowardly retreat.
2. Hicetas still joins battle to defend what he still controls of the city. Timoleon splits his troops and leads near the River Anapus.
3. The other group, led by Isias, attempt their attack from the Achradina (N). The third group attack the Epipolae.
4. The attack falls in all three places at the same time. The city falls quickly to the onslaught of the soldiers.
5. Amazingly, not a single Corinthian was even wounded.
6. Thus Timoleon’s fame not only fills Sicily and Italy, but within a few days spreads through Greece itself. The Corinthians find out about his success within days of finding out about his arrival.

C. 22 – Restoration and Rebuilding

1. Timoleon learns from Dion’s mistakes (cf. Dion 53.1) and immediately orders the destruction of the fortified tyrant’s palace.
2. The people demolished the citadel, the palaces, and the tombs of the tyrants, stamping out the physical footprints of tyranny.
3. Timoleon builds the courts of justice in the spot where the tyrants used to rule, “making their democracy triumphant over tyranny.”
4. The citizen-body of Syracuse has been greatly reduced in the past generation: war, sedition, exile. The marketplace had grown grass thick enough to allow horses to pasture.
5. Wild animals had moved back into other parts of the city and men could hunt inside the city.
6. Public business had ceased for those in the city, even when called to the market place or public speaking, because the tyrants had snuffed out public life.
7. Timoleon and the Syracusans request more settlers from the Corinthians to repopulate Syracuse.
8. Timoleon knew this wasn’t the last they’d heard from the Carthaginians. Mago committed suicide, but the Carthaginians impaled his body as a public explanation of their rage at his cowardice. They’d be back.

C. 23 – Repopulating Syracuse

1. The Corinthians respond well to Timoleon’s request for settlers.
2. They visited the PanHellenic Games and festivals and invited not just exiled Syracusans but any interested SIcilian Greeks to become free and independent citizens of a polis whose land would be redistributed.
3. They sent messengers to Asia and the islands, to gather as many exiles as they could, and send them at Corinthian expense and under Corinthian protection back to Syracuse.
4. Corinth justly earns glory and praise for freeing Syracuse from tyrants, protecting it from barbarians, and now restoring it to its rightful citizens.
5. Even with the Sicilians and exiles returned, they beg for fresh colonists from anywhere in Greece because their numbers are still small.
6. Once Timoleon reaches about 60,000 men he divides the land among them and sells the houses for 1000 talents.
7. This gives the ability for some to buy their property back and raises money for Syracuse, which has none and resorted even to selling their public statues to raise funds.
8. Among the statues, only one tyrant remains, Gelon, because, on the same day as the Battle of Salamis, Gelon had repulsed the Carthaginians at Himera.

C. 24 – From Tyrants to Private Citizens

1. Timoleon sees Syracuse filling with free peoples, and sets out to free the rest of Sicily from tyranny. Hicetas forced to live as a private person in Leontini.
2. Leptines, tyrant of Apollonia, surrendered himself and was sent back to Corinth as a private citizen and exile.
3. This attack on tyranny also allowed his mercenaries to gain more plunder. He then returns to Corinth to join two other lawgivers in crafting good laws for Syracuse.
4. He sends forth his troops under his lower commanders to the part of the island the Carthaginians control, encouraging as many Greek cities to revolt.

C. 25 – Carthage Returns in Force

1. Carthaginians land at Lilybaeum with 70K troops, 200 triremes, and everything else necessary both for sieges and cavalry warfare.
2. The force was sufficient to capture the whole island in one maneuver.
3. Under the command of Hasdrubal and Hamilcar, they march against the invading Corinthians immediately.
4. The Syracusans so paralyzed with fear that Timoleon only marches forth from Syracuse with 3000 volunteers to meet the Carthaginians.
5. Of the 4000 mercenaries, 1000 back out due to fear at taking on so superior a force. Timoleon now called crazy for taking 5K foot and 1K horse against 70K men 8 days’ march away from Syracuse. Those who fled would have no safety and those who fell no burial.
6. Timoleon considers the loss of men a gain, better to be a coward before battle begins. Then he marches to the River Crimesus to engage the Carthaginians.

C. 26 – Turning Omens

1. Marching up a hill, the soldiers pass some mules laden with parsley.
2. The soldiers receive this as a bad omen since parsley is often used to decorate graves. There’s even a old Greek proverb that the man who is hopelessly sick “needs only parsley.”
3. Timoleon here stops them and, in the middle of giving a speech of encouragements, reinterprets the omen as a sign of victory, since the Corinthians crown their victors at the Isthmian games with parsley.
4. At the time, parsley was used at the Isthmian, even though not the Isthmian games crown with pine and the Nemean games crown with parsley.
5. Timoleon takes the parsley and crowns himself, with his captains adn then his soldiers doing likewise.
6. Finally, soothsayers spot two eagles, one having killed a snake and the other giving forth an inspiring cry.

C. 27 – Battle Begins at the River Crimesus

1. Early June 339 (Thargelion in Attic calendar)
2. The river’s mist was so thick, Timoleon and his men could only hear the large enemy camp stirring.
3. The mist rose as the day continued and eventually came up to the summit where the Corinthians were resting.
4. As the River Crimesus came into view, the Carthaginians are seen crossing it with their four-horse chariots and then 10K men armed with white shields.
5. They were recognized as Carthaginians because of their resplendent armor and good order of their march.
6. The Carthaginian allies crossed in much more confusion and tumult. Noticing that the river essentially cut the enemy in half, Timoleon orders his horse to bear down on them and increase the disarray.
7. Timoleon then arranges his phalanx, leading the Syracusans in the center.
8. His cavalry rebuffed by the four-horse chariots in the front, so Timoleon shouts and charges to bring them aid.
9. His voice seemed more than human (cf. Achilles’s shout in Book 18/19) and some deity may have joined his hsout.
10. Timoleon signals to his cavalry to attack the flanks while he attacks the center.

C. 28 – The Storm in the Battle

1. The Carthaginians, well-armed and well-trained, stand firm through the first onslaught.
2. As the struggle moved from spears to swords, thunder and lightning crashed and flashed overhead.
3. Then the darkness grew intense and brought with it rain, wind, and hail. The Greeks were mostly hit from behind, but the Carthaginians received the hail, rain, wind, and lightning in their faces.
4. Between the thunder and the clatter of hail on the armor, it was difficult even to hear the commands being given, so confusion reigned.
5. Since the Carthaginians were more heavily armed, their armor grew more cumbersome as parts filled with water or mud.
6. Being unwieldy, the Carthaginians were easily knocked down but also struggled to rise once they fell in the mud.
7. As the rain continued, the river began to rise and take in more and more of the Carthaginian army that had already “crossed.”
8. Finally, the whole army is put to flight.
9. Some overtaken in their flight, many taken away by the river.
10. 3000 of the 10K dead were Carthaginian citizens, a huge loss.
11. Never before had so many native Carthaginians died in a single battle, since they used so many mercenaries they often “sustained their defeats at the cost of other nations.”

C. 29 – The Spoils of Victory

1. Many high-ranking Carthaginians had fallen, as evidence by the amount of gold and silver among the plunder, causing most men to ignore the bronze and iron. The Corinthians seized not only the baggage trains but the camp itself.
2. 5000 prisoners sold into slavery, 200 four-horse chariots captured.
3. Timoleon’s tent heaped with all sorts of plunder, breastplates and ten-thousand shields.
4. It took the men three days to collect and organize the plunder before setting up the trophy.
5. Timoleon sent the best specimens of captured armor back to Corinth.
6. So that finally, the Greek might see the Corinthian temples decorated not with the armor of their fellow Greeks, but the barbarians who had attacked justice.

C. 30 – Mercenaries and Timoleon’s Luck

1. Timoleon leaves his mercenaries again plundering the Carthaginian land.
2. He returns to the mercenaries who deserted and order them to leave Syracuse before nightfall.
3. After they crossed into Italy, they were slain by the citizens of Brutti, which Plutarch sees as divin vengeance for their treachery.
4. Mamercus, tyrant of Catana, and Hicetas try to lure the Carthaginians back into war with Timoleon.
5. Early 338 BC (spring), Gisco sails with 70 ships and uses Greek mercenaries for the first time (as they now admire them as soldiers).
6. Converging near Messana, they overpower Timoleon’s auxiliaries killing 400 in an ambush.
7. Even these mercenaries seemed to have brought divine vengeance upon them as they had been involved in the spoliation of Delphi in 356 BC.
8. Since they were rejected by the Greeks, these men had wandered around the Peloponnese, where Timoleon finally included them in his army.
9. They were victorious with Timoleon and then finally died only after they had been separated from the main group, and they all died together, just showing how divine justice was looking to preserve the good Timoleon had done and punish their evil.
10. Even Timoleon’s reverses showed the good will of the gods.

C. 31 – Tyrants Still Harassing

1. The tyrants still harass Syracuse, Mamercus with poetic descriptions of the earlier defeat.
2. And Hicetas by invading Syracuse at opportune times when Timoleon’s (still rather small) army was far enough away.
3. Timoleon pursues Hicetas out of Syracusan territory, and Hicetas turns to face him at the river Damurias.
4. Timoleon’s cavalry officers compete
5. because they all want to cross the river first and engage with Hicetas.
6. Timoleon takes a signet ring from each captain and mixes them up in his cloak, the one marked with a victory trophy falls out.
7. Such a good omen, they all dash into the river to take on the enemy.
8. The onslaught was so sudden and forceful, Hicetas’s army flees and 1000 of his troops are left dead on the field.

C. 32 – Hicetas Captured and Killed

1. Finally, Timoleon captures HIcetas in Leontini, with his son and master of horse.
2. All three put to death before Timoleon’s soldiers, Hicetas and his son for tyranny and treachery. Euthymus, the master of horse, found no pity in spite of his boldness and bravery and was kliled for insulting the Corinthians publicly.
3. Euthymus had encouraged his own troops against the Corinthians by calling them all women.
4. So, Plutarch concludes, hostile words are so often more offensive than hostile acts, as words in particular always seem to spring from an excess of hatred, but actions are often in defense of oneself.

C. 33 – Vengeance for Dion

1. Wives and daughters of Hicetas put on trial and also condemned to death.
2. If Timoleon had opposed it, the women would not have been put to death. He left them to the wrath of the people, something Plutarch judges him for as his worst moment.
3. The people were bent on taking vengeance for Dion (cf. Dion 58.4).
4. For Hicetas arranged for the death of Dion’s surviving family, who had turned to him for protection after Dion’s death.

C. 34 – Two More Tyrants Toppled (Mamercus and Hippo)

1. Now Timoleon turns to face Mamercus in Catana, beating him in a pitched battle killing many of the Carthaginian mercenaries Gisco had sent.
2. Now the Carthaginians want to conclude peace directly with Timoleon, asking for all their land back beyond the River Lycus and the restoration of property to all those Carthaginians who wanted to leave Syracuse.
3. So, Mamercus, seeing his final allies abandon him, turns to Italy (Lucanians?) to gather more troops to attack Syracuse. His friends turn the boat around, hand Catana over to Timoleon, and Mamercus is forced to flee to Hippo, tyrant of Messana.
4. Timoleon now besieges Messana, and Hippo tries to escape but is caught. The Messanians gathered in the theater, bringing their children with them from school to behold the torture and death of a tyrant.
5. Mamercus gives himself up for trial at Syracuse.
6. Mamercus attempts to recite a speech he’d memorized but no one in Syracuse listens. He runs across the theater at full speed and attempts to bash his head in on the stone steps.
7. He did not die, but was taken by the Syracuans and “crucified like a thief.”

C. 35 – Sicily Returns

1. Timoleon restored Sicily to peace and political stability, making it a desirable place to live again.
2. Agrigentum and Gela, which had been depopulated after the “Attic War” were resettled.
3. Timoleon revered as a founder because of the help he gave these cities in their refounding.
4. Timoleon was like the master builder, consulted for every war, law, territory settlement, so that he could put the finishing touches and bring the parts into a harmonious whole.

C. 36 – Timoleon the Syracusan

1. In his own time, Greece produced many great men: Timotheus, Agesilaus, Pelopidas, and Epaminondas (whom Timoleon emulated most), their achievements required more violence and effort or they made mistakes they later regretted.
2. Other than his treatment of his brother, Love seemed to adorn all of Timoleon’s actions.
3. In painting and poetry, too, we praise not just the beautiful lines, but the ones that seem to us to have been crafted readily and easily (Homer).
4. Compare Timoleon to Pelopidas or Epaminondas or Agesilaus and see with how much more ease the first reached glory through “fortunate virtue.”
5. Timoleon often thanked God in his public speeches and private letters, claiming God chose to save Syracuse and in so doing gave Timoleon the title and role of savior.
6. He built a shrine to Chance in his house, but consecrated the whole house to daimon.
7. The Syracusans selected his house as a prize for his achievements, giving him also the most beautiful country estate. He brought over his wife and children and spent much of his leisure time there.
8. He did not return to Corinth or take part in the disturbance of the Greek mainland or expose himself to jealousy of fellow Corinthians. These rocks many other generals have foundered on in their insatiable greed for honor and power.
9. He enjoyed his greatest blessing by remaining in Sicily, and seeing every day the cities and countless citizens whose happiness were due in large part to him.

C. 37 – Timoleon’s Trophies

1. Timoleon was not completely immune to political intrigue; two populists denounce him: Laphystius and Demaenatus.
2. Laphystius once tried to subpoena Timoleon for a certain trial, which the citizens found an offsneive way to treat the man. Timoleon does not allow their angry defense of him, saying that he fought for all to have access to the laws.
3. The other, Demaenatus, openly denounced him in court and Timoleon only thanked the gods that he might see such a day when the Syracusans once again used their exercise of free speech.
4. Everyone now agreed he’d performed the most glorious deeds of any Greek of his time, succeeding at what the orators of this era were constantly yelling at the Greek about.
5. He had been removed by Fortune from the Greek mainland’s squabbles, shown virtue in his dealings with barbarians, and justice and gentleness with his Greeks and friends
6. His victories had not cost the lives of many citizens and in 8 years he had purged Sicily of tyranny.
7. As he aged, he lost his sight,
8. for some genetic reason.
9. Athanis says that while waging war against Mamercus and Hippo he was already being blinded by a cataract in his eye but he didn’t let that interrupt his siege.
10. YET, when he returned to Syracuse he put down his sole command and asked the citizens to be excused from it.

C. 38 – The Gratitude of Syracuse

1. We shouldn’t be surprised that he handled the misfortune of blindness so well.
2. The Syracusans, however, did not reject him as he grew weak and blind. Rather, they admirably continued to honor him with visits to his house,
3. proud that he chose to end his days among the people he’d helped.
4. Syracuse then voted that in the future, whenever they went to war against any foreign power, they would employ a Corinthian as their general.
5. For important deliberations, they would still summon him to their council.
6. He would be brought in honor to the theater, greeted with praise and thanks, and then listen to their debates and pronounce his opinion.
7. Once the citizens enacted his opinion, he would return by mule-car to his own house and the citizens would ifnish the less important business for the day.

C. 39 – Timoleon’s Public Funeral

1. He died in 337/6 BC
2. His body solemnly processed through the spot where Dionysius’ palace had been built.
3. Thousands attended the funeral, but it didn’t feel like a tyrant’s funeral (thousands attending in obedience to public decree or because formal tributes of respect were called for). Rather, all those in attendance seemed motivated solely by sorrow and gratitude arising from their good will to Timoleon.
4. Demetrius, the loudest herald of his day, read the following about Timoleon:
5. Timoleon here buried at public cost, honored for all time with contests because he overthrew tyrants, repulsed barbarians, repeopled devastated cities, and restored the laws to the Greeks of Sicily.
6. His ashes were buried in the marketplace and eventually a gymnasium was built up around his shrine named for him: The Timoleonteum.
7. And they lived happily and prosperously for a long time.

External Links

• Ambleside Online’s Study Guide for Timoleon
• Herman Melville’s Poem Timoleon, of which I read the eighth and final stanza in the podcast
• English Translation of Plutarch’s Life of Timoleon
• Greek and English of Plutarch’s Life of Timoleon (Perseus)
• Art of Manliness Podcast about Plato Trying to Convince Glaucon not to Grow into a Tyrant in the Republic