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Emerging from exile after his brother’s murder, the Corinthian general sought and found redemption in Sicily. 

The tale should serve as inspiration for geezers everywhere: A general in his 60s leads a scratch force of low-quality mercenaries and wins a series of victories over domestic despots and foreign aggressors. Such is the story of Timoleon, a Greek general from the city-state of Corinth who crossed over into the Greek-populated portion of Sicily. Between 344 bc, when he arrived on the island, and his retirement in 337/36 bc he cast down tyrants and defeated an attempt by the Carthaginians to overrun the entire island.

Or did he?

Any historian seeking to appraise Timoleon’s military accomplishments immediately runs into difficulties, the first of which might be called the “too good to be true” conundrum.

The principal historical source for details on the Greek general’s exploits is the 1st century Greek historian Plutarch, who in his Parallel Lives presents Timoleon as a flawless hero who rarely, if ever, got anything wrong. As modern historian R.J.A. Talbert puts it, Plutarch’s Timoleon is a man “who always takes the most correct and honorable course of action in any situation.” In so doing, Plutarch does his subject no favor but only makes Timoleon’s exploits harder to believe.

A related problem arises from Plutarch’s belief the general received a helping hand from supernatural forces—that the Greek gods were apparently Timoleon’s greatest boosters. Plutarch records that Timoleon, before sailing for Sicily, went to the shrine at Delphi to make a sacrifice to Apollo. As he did so, a wreath fell from the altar and landed on his head—an omen of victory. Later, as Timoleon’s fleet set sail for Sicily, a divine fire shone torchlike from the night sky to illuminate its course. Such tales help clarify Plutarch’s mind-set, but they are of little value to someone seeking to learn how Timoleon managed to accomplish so much with so little.

Fortunately, there is an earlier, alternate source for Timoleon’s career, within Book 16 of Bibliotheca Historica, the multivolume history written by Greek historian Diodorus Siculus in the 1st century bc. While Diodorus, too, takes a generally favorable view of Timoleon, he also describes instances when the Corinthian general was willing to play dirty. Diodorus thus supplements Plutarch, who, in Talbert’s words, “tends to omit information that does not reflect well on Timoleon.”

One of Timoleon’s less savory chapters occurred in the 360s bc when he allowed assassins to slay his brother Timophanes. Entrusted by the Corinthians with a defensive force of 400 mercenaries, Timophanes instead used them to summarily execute leading citizens and seize control of the city-state. Timoleon—who had earlier saved Timophanes’ life in battle—was horrified by his brother’s misdeeds and beseeched him to back down and make amends. After one last appeal to reason failed, Timoleon stepped aside and, as previously agreed, allowed two companions to draw their swords and kill Timophanes. As Plutarch puts it, Timoleon had “set his country before his family.” But Timoleon was tormented by the death of his brother, and when his mother condemned him, he sank into depression and withdrew from public life for nearly two decades, emerging from his self-exile around 346 bc.

Sicily—the scene of Timoleon’s comeback—was a battleground in the mid-4th century bc. The Greeks had settled largely in coastal colonies, except in western Sicily, which remained in the hands of Carthage, the powerful Phoenician city-state in North Africa best known for its titanic conflicts with Rome (the Punic Wars, from the Latin term for Phoenicians) that broke out the next century. The island’s Carthaginians and Greeks had already fought several wars. Tyrants at the head of mercenary armies ruled most of the Greek cities, a reality historians often pin on the Carthaginians—the argument going that Greek rulers needed to exercise firm control in order to guard against the Punic threat.

By the 4th century bc, however, many of the mercenaries had broken free of their employers and thrown Sicily into chaos. Many of the island’s cities fell under the control of mercenary leaders, the most powerful of whom was Hicetas, the tyrant of Leontini, to the north of Syracuse.

A scarcity of sources makes a detailed history of Carthage difficult to reconstruct. But the sources provide a rough idea of what transpired there in the mid-4th century bc. Around 350 bc—while Timoleon remained mired in depression—political opponents of Hanno, one of the city-state’s leading officials, accused him of treason, tortured him to death and exiled his son Gisco. Once in power, Hanno’s opponents needed a military victory to legitimize their rule and looked to Sicily to provide one. Seeking first to expand their influence on the island, they forged alliances with some Greek mercenary leaders. Among those who allied with the Carthaginians was Hicetas, who sought Punic aid in his war against Dionysius the Younger, tyrant of Syracuse, the most powerful Greek city on the island.

Accordingly, a fleet of Carthaginian triremes arrived off the east coast of Sicily and blockaded the Great Harbor of Syracuse. Terrified Syracusans promptly sent a delegation to Corinth, Syracuse’s mother city, to ask for help (colonists from Corinth had first settled Syracuse in the 8th century bc).

That’s when Timoleon re-enters the story. In response to the Syracusan appeal, the Corinthian assembly approved an expedition to Sicily and appointed Timoleon to lead it. That in itself suggests they hadn’t taken the threat very seriously—after all, they put an elderly recluse in charge of a token force. Furthermore, the assembly apparently gave Timoleon little or no money to recruit mercenaries, thus he was forced to accept men no one else was willing to hire. In an earlier war some of these same men had plundered the sacred treasures at Delphi—an act of sacrilege that prompted most potential employers to shun them. Talbert suggests Timoleon was reduced to offering his men only rations or money enough to buy them. His men would have to earn their wages by seizing it as booty. At any rate, in 344 bc Timoleon sailed for Sicily with a force of fewer than 1,000 men.

En route Timoleon learned Hicetas had defeated Dionysius and driven him into the offshore fortress of Ortygia, among the initial sites of Greek settlement in Syracuse. In the 6th century bc the Greeks had built a causeway to the island. Behind the jetty formed by Ortygia and the causeway lay the Great Harbor of Syracuse, across which the Carthaginian fleet lay at anchor.

Timoleon’s first task was to defeat Hicetas.

The first clash between Timoleon and the tyrant of Leontini came at the Sicilian town of Adranum, southwest of Mount Etna. Loyalties there were divided: Some welcomed Hicetas and the Carthaginians, while others issued an invitation to Timoleon. The respective armies—Hicetas with 5,000 men, and Timoleon fielding perhaps 1,200 (Plutarch’s figure, suggesting Timoleon had recruited reinforcements after landing in Sicily)—converged on Adranum at the same time.

Late on the second day of Timoleon’s march his officers had halted the column for rest and food when their commander came up. Having received word Hicetas’ army had reached Adranum and was making camp, the Corinthian general urged his men to press on. If they struck quickly, he explained, they could take their preoccupied enemy by surprise. Timoleon then snatched up his shield and marched to the head of the column, inspiring his weary men to their feet. From that glorious moment the scales tilted in Timoleon’s favor, remaining there for the rest of his Sicilian campaign.

The column did achieve complete surprise, catching Hicetas’ men as they set up tents and prepared food. While most—including Hicetas himself—managed to escape, Timoleon’s men killed some 300 of the enemy and captured twice as many. With swift and decisive action the aging general had won his critical first victory.

Timoleon next had to deal with Syracuse, where Dionysius remained holed up in Ortygia. The besieged tyrant sent envoys to Timoleon, offering to surrender Ortygia (likely assuming he could get better terms from the Corinthian than from Hicetas), and Timoleon jumped at his offer. He infiltrated 400 men into Ortygia—in batches, possibly aboard boats small enough to slip between the triremes of the blockading Carthaginian fleet. These men took control of the fortress and military supplies, and Dionysius turned over to Timoleon 2,000 of his own soldiers. Finally, Dionysius left Ortygia by boat and surrendered to Timoleon, who sent him to live in exile in Corinth.

Timoleon tacitly allowed assassins to murder his brother, Timophanes, after the latter seized control of Corinth with a mercenary army and presumed to rule the city-state as a tyrant. (RMN/Martine Beckcopola)

According to Plutarch, fewer than 50 days had elapsed between Timoleon’s landing in Sicily and Dionysius’ surrender. In the spring of 343 bc, having learned of the victory, Corinth dispatched 2,000 infantrymen and 200 cavalry to Sicily as reinforcements. They were necessary, as Hicetas still held the mainland districts of Syracuse. Earlier in the campaign he had not advertised his alliance with the Carthaginians. But after a failed attempt at engineering Timoleon’s assassination, Hicetas dropped the mask and openly acted in association with them. At his invitation the Carthaginian commander Mago sent 150 ships into the Great Harbor and landed some 60,000 infantrymen to reinforce Hicetas’ men—the first and last time Carthaginian troops set foot in Syracuse.

Yet the alliance between Hicetas and Mago was a shaky one and achieved nothing. They moved to attack Timoleon’s supply base at Catana, up the coast from Syracuse, but on their departure Neon, Timoleon’s commander in Ortygia, noted that Hicetas’ remaining men in Syracuse had let down their guard. He, in turn, led a sortie from the fortress and captured the mainland district of Achradina. When Hicetas and Mago got word and rushed back to Syracuse, they discovered Neon had fortified the perimeter of Achradina, and they were unable to retake it.

At that critical juncture the Greek mercenaries in the Carthaginian army started fraternizing with Timoleon’s mercenaries, and Mago—suspecting treachery—panicked. According to Plutarch, the Carthaginian general had been unenthusiastic from the outset about the campaign in Sicily. Now, despite Hicetas’ entreaties, Mago abruptly withdrew his troops and sailed back to Carthage. Some historians have speculated Mago may have had additional reasons for his withdrawal, possibly related to the political situation back home. But Talbert, for one, considers it sensible to “abandon the presumption that Mago’s reasons for leaving Syracuse were logical.”

Whatever the impetus, Hicetas was on his own, and Timoleon soon took the rest of Syracuse away from him, probably in the latter half of 343 bc. Plutarch’s account of the event seems dubious. He claims Timoleon immediately launched a three-pronged attack on the city and took it without sustaining a single casualty, killed or wounded. Plutarch credits the outcome to Timoleon’s astonishingly good luck, making an over-the-top statement to that effect: “Those who hear his story may wonder at his happy successes more than at his laudable efforts.”

Finding such a scenario improbable, Talbert proposes Hicetas may have made a secret deal with Timoleon to hand over Syracuse, but only after a token fight. This would have saved face on both sides—Hicetas would come off well for not having seemed to surrender Syracuse without a fight, and Timoleon would record a victory and not have to explain why he cut a deal with a tyrant.

However it happened, Timoleon had wrested control of Syracuse. He found it a wreck, devastated and depopulated by years of warfare. His first action was to demolish Dionysius’ citadel as the symbol of tyranny. He invited the remaining citizens to join him; Plutarch writes the Syracusans “demolished not only the citadel but also the palaces and the tombs of the tyrants.”

Timoleon then issued a call to the Greek mainland, inviting exiles and colonists to repopulate Syracuse and its environs. That would eventually happen, but in the short term the impoverished city-state was unable to contribute much to Timoleon’s efforts to pay his mercenaries. Appreciating the danger posed by idle troops, he sent some of them west into Carthaginian territory to pillage and plunder. Diodorus notes the Corinthian general sold off the collected loot and was thus able to pay off his “contractors.”

Diodorus also relates an incident that casts Timoleon in a less than noble light. After the general and his troops took the strategically placed town of Entella from the Carthaginians, he ordered the execution of “the 15 persons who were the strongest supporters of the Carthaginians.” Far from a kindly old gent, Timoleon was willing to act ruthlessly when necessary. Diodorus also mentions another somewhat embarrassing event omitted by Plutarch—a failed siege by Timoleon of Hicetas’ home base at Leontini.

When Mago returned home in disgrace from Syracuse, the Carthaginians were furious to learn he had retreated without a fight—so furious, in fact, Mago was compelled to commit suicide. On news that Timoleon’s mercenaries were raiding Punic territory in Sicily, the Carthaginians—having so abruptly “terminated” their commander—simply organized a new expeditionary force. According to Plutarch, their aim was “to drive the Greeks out of all Sicily.”

The Carthaginians enlisted soldiers from all levels of society (including members of their noble class) and drew conscripts from among their Libyan subjects. By lavishing money on mercenaries, they were able to further boost the size of their army—Plutarch reports a total force of 70,000. By the spring of 341 bc—less than two years after Timoleon’s capture of Syracuse—their army was ready to cross over to Sicily.

In the face of the Carthaginian invasion Hicetas agreed to a truce with Timoleon and lent him troops. Talbert suggests Hicetas may have finally recognized the gravity of the Punic threat and realized Timoleon was the only one in a position to defeat it. Plutarch doesn’t mention the truce, perhaps out of his intent on making Hicetas the arch villain of the piece, a figure utterly void of redeeming qualities.

With the addition of Hicetas’ men and others recruited from among the Greek cities of Sicily, Timoleon amassed an army of 11,000 (Diodorus’ more likely figure). Displaying audacity once again, he chose to meet the Carthaginians on their home turf and led his army west from Syracuse. After eight days of marching, he met the Carthaginians at the River Crimisus (present-day River Freddo), which flows into the Tyrrhenian Sea on the north coast of Sicily. Some of the Corinthian general’s mercenaries lost their nerve at the thought of facing a vastly larger Carthaginian force in the open. Timoleon dismissed 1,000 of them; Diodorus praises Timoleon for retaining the others’ loyalty through “tactful handling.”

Plutarch’s description of the ensuing battle is so vivid that it must have been derived from an eyewitness account. It was the early summer of 341 bc, and Timoleon and his men climbed a hill overlooking the river. At first a thick mist impeded their view. As the sun rose and dispersed the mist, the Corinthians looked down and saw the Carthaginian army crossing the Crimisus.

War chariots led the way, followed by the Punic elite—10,000 foot soldiers bearing white shields. These were the Carthaginian citizen infantry; 2,500 of them formed the Sacred Band, recruited from among the wealthy aristocrats. After the Carthaginian citizens came contingents of their subject peoples, straggling along (according to Plutarch) “in tumultuous confusion.”

At the moment of crossing Timoleon noted the river had divided the Carthaginian army into vulnerable segments. He therefore ordered his cavalry to immediately attack the citizen-soldiers before they could deploy into battle array. Descending to the plain, he arrayed his own army for battle—the Syracusans and best mercenaries in the center, the Sicilian Greeks and remaining mercenaries on the wings. Watching the action on the river, Timoleon saw that the enemy chariots had stymied his cavalry by driving back and forth across the Carthaginian front, making a mass charge impossible. After redirecting his horsemen to attack the enemy flanks, the Corinthian general ordered his infantry to lock shields, and he personally led the charge against the enemy line.

The Carthaginians resisted stubbornly for a time, the outcome remaining in doubt. But then—as if on cue to prove the gods truly were on Timoleon’s side—a fearsome thunderstorm broke out, bringing torrential rain, hail and wind that blew directly into the Carthaginians’ faces. As the ground turned to mud, the Punic soldiers slipped and fell, their heavy armor making it all but impossible for them to rise. The Greeks soon broke their ranks, sending the Carthaginians fleeing back toward the river. They in turn crashed into the contingents of their army still fording the Crimisus, and predictable chaos ensued. The Carthaginian army disintegrated into a melee of frightened, fleeing individuals whom the pursuing Greeks easily cut down. According to Plutarch, 10,000 of the enemy—including virtually all of the citizen-soldiers—were killed.

Historian G.T. Griffith renders a concise verdict on the battle: “Crimisus proved conclusively that a horde of barbarians with a few picked troops from Carthage was no match for a much smaller army of trained and experienced Greek soldiers.” The Greeks stripped the Carthaginian dead of their beautiful armor and plundered the enemy camp. Plutarch notes that Timoleon’s tent was “heaped about with all sorts of spoils.”

Word soon reached Carthage about the devastating defeat at Crimisus. Fearing Timoleon might strike them at home, the rulers took a drastic step, recalling Gisco, son of Hanno, the statesman they had overthrown and tortured to death. Diodorus suggests Gisco’s military skill made him indispensable. In answering the call, Gisco took only symbolic revenge against his father’s killers, briefly placing his foot on their necks as they prostrated themselves before him.

Gisco promptly sailed to Sicily and on arrival found local allies. Though Hicetas had earlier furnished Timoleon with troops, the seeming turnaround prompted Hicetas and a fellow tyrant named Mamercus to again join forces with the Carthaginians. They won a few fights but in the long run could not prevail over Timoleon’s enthusiastic troops. Timoleon captured Hicetas and his son and had them executed as traitors. Mamercus later surrendered and, after a failed suicide attempt, was crucified. For his part, Gisco managed to salvage Carthage’s interests in Sicily by negotiating a status quo treaty with Timoleon.

With the fighting at an end, Timoleon was able to turn to the reconstruction of Greek Sicily. It was a resounding success—Diodorus and Plutarch agree the Greek cities prospered as never before, and archaeological evidence affirms their claim. The Corinthian general finally retired around 337/36 bc when his eyesight began to fail, but he continued to receive honors from the Syracusans—Plutarch states that whenever important business came before the assembly, the delegates would consult Timoleon before making a decision. To all appearances Timoleon was indeed a great leader, if not quite the plaster saint depicted by Plutarch.

With that in mind, there’s one last incident to consider. Before Timoleon forged his treaty with the Carthaginians, he did something that casts a pall on his career. Plutarch, to his credit, mentions it. The vengeful Syracusans had seized Hicetas’ wives, daughters and close friends and brought them to trial before the assembly. It was almost certainly the sort of “trial” in which the verdict is predetermined, for they were all put to death. “This would seem to have been the most displeasing thing in Timoleon’s career,” writes Plutarch, “for if he had opposed it, the women would not have been thus put to death.” Apparently in this instance Timoleon lacked moral courage and instead became complicit in mass murder.

Early in life Timoleon had allowed his brother to die because he was guilty. Late in life he allowed a group of women to die though they were innocent. While he basked in the praise of the Syracusans, one wonders whether he considered they had led him to betray his own principles. 

Richard Tada has a doctorate in history from the University of Washington and is a frequent contributor to Military History and Military History Quarterly. For further reading he recommends The Age of Alexander, translated by Ian Scott-Kilvert and Timothy E. Duff; The Carthaginians, by Dexter Hoyos; and Syracuse, City of Legends: A Glory of Sicily, by Jeremy Dummett.