After the death of Julius Caesar, Rome was plunged into a civil war. Another one. If the previous had been due to the power struggle between the deceased and Pompey the Great, this time it was between the heirs of Caesar’s legacy and the assassins. The former, Octavian and Mark Antony, agreed to an alliance against the latter, who were led by Cassius and Brutus, whom they defeated in the Battle of Philippi (Greece) to share power and form what is known as the Second Triumvirate, with Marcus Aemilius Lepidus as the third member. They were on the verge of facing each other, but first they had to resolve one last problem: the outlaw who threatened to cut off the wheat supply to Rome thanks to the powerful fleet he commanded… and who suffered a decisive defeat in the naval battle of Naulochus.

Sextus Pompey was the youngest son Pompey the Great had with his third wife, Mucia Tertia, around 75 BC. Due to his youth, he did not participate in the civil war and remained in Rome with his stepmother, Cornelia. Despite this, when his father was defeated in the Battle of Pharsalus, he had to flee to Lesbos, where the family gathered to move to Egypt. He never set foot on Egyptian soil; from the ship, he witnessed how his father was beheaded to prevent Roman intervention in the country and then went to Cyprus to join his brother Gnaeus.

Both fought alongside several senators opposed to Caesar from Hispania and the African provinces. But one by one they fell: Metellus Scipio and Cato the Younger took their own lives after losing the Battle of Thapsus; and Titus Labienus was slain in the Battle of Munda, the same battle from which Gnaeus initially escaped before being captured and executed. Only Sextus Pompey remained, who took refuge among the Lusitanians (an Iberian tribe from northeastern Hispania) dedicated to piracy. He managed to gather a considerable number of supporters that allowed him to seize Baetica, being proclaimed imperator by the locals.

Aureus minted in Sicily with the effigy of Sextus Pompey
Aureus minted in Sicily with the effigy of Sextus Pompey. Credit: Siren-Com / Wikimedia Commons

Caesar’s death seemed to promise him a respite and a return to legality, to the point that he had the support of Lepidus, and the Senate even appointed him praefectus classis, that is, admiral of the fleet. But Caesar’s supporters demanded vengeance, and he was dragged into the subsequent events, as we mentioned at the beginning, Octavian and Mark Antony unleashed a political persecution. Sextus Pompey’s great mistake was to trust the Senate’s animosity towards the latter and not to come to reinforce him at the siege of Mutina (Modena), in Gaul, against the rebel praetor Decimus Junius Brutus Albinus.

With the signing of the Second Triumvirate, Mark Antony imposed the inclusion of Sextus Pompey on the list of proscribed persons by the Lex Pedia (promulgated by Quintus Pedius – hence the name – Octavian’s consular colleague) against the assassins of Caesar, even though he had not taken part in the assassination. Approximately two hundred senators and two thousand knights were accused, their properties and wealth were confiscated, and cash rewards were offered for their heads. For the time being, he remained safe thanks to his control of the sea with his ships, although he had the drawback of not controlling any port except those of Sicily, to which he added the alliance of Quintus Cornificius, governor of the province of Africa.

Strategically located enclaves, otherwise, as they were essential to block the grain supply to Rome, and indeed, the interruption of that supply would cause a severe famine in 39 BC, forcing the Second Triumvirate to negotiate with Pompey. In what is known as the Pact of Misenum, he agreed to allow the arrival of grain in exchange for being recognized dominion over Sicily, Sardinia, Corsica, and the Peloponnese for a period of five years, which was the established duration of the government. As expected, neither side was willing to honor its commitment, and the suspicion that they would not ultimately respect the pact led the praefectus classis to interrupt that provision again.

Distribution of Roman provinces in the Treaty of Miseno: in pink, Octavian; in green, Marcus Antonius; in brown, Lepidus; in purple, Sextus Pompey
Distribution of Roman provinces in the Treaty of Miseno: in pink, Octavian; in green, Marcus Antonius; in brown, Lepidus; in purple, Sextus Pompey. Credit: Borsanova / Wikimedia Commons

Everyone surrendered to the evidence, and there was no other way but war. The immediate enemy was to be Octavian since he had been assigned the Italian peninsula in the distribution, in addition to Gaul and Hispania (Mark Antony kept the rich provinces of the East, and Lepidus the African ones). He was not in an easy position due to the discontent against him for two reasons: being forced to expropriate lands and entire populations to fulfill the promise of settling the tens of thousands of veterans from the civil war discharged and having executed hundreds of senators loyal to Lucius Antony, Mark Antony’s younger brother, whom he had to militarily confront as a rebel.

The irony of the situation was that it was Octavian who managed to strike a deal with Sextus Pompey by divorcing his first wife, Claudia (whose mother, Fulvia, Mark Antony’s third wife, felt insulted and joined the aforementioned rebellion of Lucius Antony), to marry Scribonia, daughter of Lucius Scribonius Libo, father-in-law and supporter of Pompey, although a year later he would also divorce her, the same day she gave birth to his only natural daughter, Julia Major, to marry for the third time with Livia Drusilla. Likewise, Octavian had promised Sextus Pompey the consulate for 35 BC.

However, two events occurred that were to ruin that precarious agreement: on the one hand, Scribonia’s divorce in 38 BC outraged Pompey’s family; on the other hand, the praefectus classis was betrayed by one of his naval commanders, Menodorus, who handed over control of Corsica and Sardinia to Octavian. And this, given that Fulvia’s death left Mark Antony widowed (which he did not feel much because by then he was already living with Cleopatra), offered his sister Octavia as a new wife, obtaining her help to confront Pompey’s fleet and agreeing both to extend their mandate until 37 BC.

View of Cumae Bay
View of Cumae Bay. Credit: Saverio.G / Wikimedia Commons

In this way, Octavian received one hundred twenty ships, and in return, promised to send his partner twenty thousand legionnaires for his campaign in Parthia. In the end, many fewer soldiers traveled to the East, which angered Mark Antony. But Octavian could now count on a naval force according to his needs, and in 38 BC, helped by Lepidus, he organized the invasion of Sicily… which was on the verge of being a catastrophe. Gaius Calvisius Sabinus, the admiral of his squadron, was decisively defeated when the enemy ships, commanded by Menecrates, cornered him against the cliffs of the bay of Cumae. However, Menecrates died in combat, and Sabinus managed to escape.

However, Octavian came to the aid of his admiral and also suffered a setback by not taking advantage of a moment of numerical inferiority of the adversary and allowing reinforcements to arrive. As Goldsworthy says, the invasion plans were full of complacency and lack of respect for the unpredictability and power of the sea. Everything had to be postponed while waiting to receive the ships that Mark Antony would send him, but above all, to go to what had until then been his unconditional and tireless support, a childhood friend without whom he could not have reached the position he occupied, and who was also a military genius: Marcus Vipsanius Agrippa.

Agrippa was born into a wealthy equestrian family in 63 BC, the same year as Octavian. Both were raised together, sponsored by Julius Caesar, along with a third, six years older friend, Gaius Maecenas (who would become famous for giving his name to the patronage of artists and writers), establishing such a close relationship that they considered each other almost brothers. Agrippa did not have Octavian’s political cunning, but instead, he was a very complete man, with training as an architect (he was responsible for turning Rome into a monumental city), literary passion, and an extraordinary administrative capacity that were sublimated with what was most needed of him at that time: military genius.

Bust of Agrippa
Bust of Agrippa. Credit: Shakko / Wikimedia Commons

Trained, like his friend, in the legions of Illyria, he participated in the civil war in favor of Caesar, demonstrating leadership and command skills; in fact, after Caesar’s death, it was thanks to his charisma that the Macedonian legions sided with Octavian, and it was he who recruited new ones in Campania to gain a position of strength against Mark Antony. He played a role in the Battle of Philippi against Caesar’s assassins, suppressed the uprising of Lucius Antony, and thwarted Sextus Pompey’s attempts to invade Italy in 40 BC.

All this made him Octavian’s trusted general the following year, taking over from the deceased Quintus Salvidienus Rufus, another member of that circle of friendship who, however, had tried to switch sides to Mark Antony and therefore lost his life (it is not known if executed or forced to do so). Agrippa could not help Octavian in his failed Sicilian adventure because he was governor in Transalpine Gaul fighting Aquitanians and Germans, but now the situation had become tight, and he was appointed consul – despite not having the usual minimum age of forty-three – to take care of Sextus Pompey.

It was not going to be easy. We saw earlier that Sextus Pompey not only had experienced commanders like Menodorus – until his desertion – Menecrates, and Democares but also initially attracted the support of the optimates, eager to restore the true republic, and even many slaves who fled from patrician villas to his side in hopes of earning freedom; a real social subversion that led the Vestals of Rome to publicly pray to end it. Through the Pact of Misenum he signed with Octavian, he agreed to give it up, but it was a show of destabilizing power that, along with the grain blockade, had come to achieve.

Denarius issued by Sextus Pompey to celebrate his victory over Octavian
Denarius issued by Sextus Pompey to celebrate his victory over Octavian. Credit: CNG / Wikimedia Commons

In fact, that pact was determined by another victory previously obtained against the Octavian squadron of legate Quintus Salvidienus Rufus, disrupted by bad weather and finished off by Pompey’s galleys, something that earned Pompey the nickname Neptuno filius (Son of Neptune) and even allowed him the luxury of minting a silver coin praising his triumph. His father-in-law, Lucius Scribonius Libo, mediated with Octavian on that occasion, obtaining not only Sicily but also the promise of payment of a fortune and the promise of a wedding between his daughter and Marcus Marcellus, Octavia’s offspring.

Sextus Pompey could have changed history if, from that position of strength, he had landed in an Italy exhausted by hunger and war fatigue, but he did not, thus giving Agrippa time to seize the bull by the horns. That summer of 36 BC, the triumvirs had three fleets: the eastern one of Antony, which was in Tarentum; Lepidus’s in Africa; and Octavian’s anchored in Portus Iulius, an artificial port built ad hoc by Agrippa in a suburb of Puteoli (today Pozzuoli) after digging a canal that connected it with the Lucrine and Avernus lakes cutting part of the Via Herculea.

That infrastructure allowed the installation of a shipyard where more ships could be built and thus properly train the new crews, formed with about twenty thousand slaves liberated for this purpose. They were larger ships than usual, designed to facilitate combat on their decks for a significant number of soldiers. It was one of Agrippa’s imaginative initiatives for the occasion, the other being the design of the harpax (or grappling hook), a kind of catapult that fired multi-armed hooks to hold enemy galleys and prevent them from maneuvering and being boarded; an updated and much lighter version of the corvus, so to speak.

Parts making up a harpax
Parts making up a harpax. Credit: Ramnavot / Wikimedia Commons

One hundred twenty ships sent by Antony also arrived, whose command was handed over to Titus Statilius Taurus (who would later play a fundamental role against his former boss by defeating his land troops while he fell at Actium and, later, would lead the war against Cantabrians and Asturians in Hispania). However, Taurus saw how his fleet was scattered near Tarentum – losing half a hundred units – by a storm that also affected Octavian’s fleet near Palinurus. Consequently, the plan for a triple invasion of Sicily was reduced to Lepidus’s landing in Lilybaeum.

Lepidus was isolated in that position and could only receive half of the reinforcements he expected – two legions out of four – because the rest were intercepted at sea by Pompey’s squadron. It seemed that the war was turning in his favor, but he also suffered an unexpected setback: Menodorus’ aforementioned desertion, who joined Octavian during a patrol when he was sailing near the island of Strongyle (modern Stromboli). Meanwhile, Agrippa finally went into action and forced a confrontation with Democares to test him. Since his commander had only forty ships, Pompey sent Apollodorus to his aid with another forty, and he himself joined with seventy more.

The battle of Mylae (modern Milazzo) tilted towards Agrippa, who knew how to take excellent advantage of the spurs and the harpax to board the enemy and minimize the fact that the latter’s ships were lighter and more maneuverable. In the heat of the battle, having already lost thirty ships, Pompey realized that his rival was prevailing and ordered a retreat. According to Dion Cassius, Agrippa gave up pursuing him to prevent his victory from being too resonant and diminishing his friend Octavian.

Plan of Octavian and Agrippa against Sextus Pompeius in 36 BC
Plan of Octavian and Agrippa against Sextus Pompeius in 36 BC. Credit: ColdEel / Wikimedia Commons

When he received the news, Octavian believed that the campaign was won and, having sailed from Messina, sailed to the city of Tauromenium (Taormina) with the idea of occupying it. As he could not, he advanced a little further, landed in Argegnum, and prepared to camp… and suddenly he was surprised by the appearance of Pompey’s fleet. Fortunately for the triumvir, his rival only sent the cavalry, whose attack had a very limited effect, so he was able to quickly dismantle the camp and form up for battle. Leaving Quintus Cornificius in command of the ground troops, Octavian embarked to face the enemy at sea.

Cornificius was surrounded in his camp, defending it desperately, but the naval confrontation was no better. Pompey proved to be superior tactically and destroyed much of Octavian’s fleet; his own leader received a leg wound and narrowly escaped, seeking refuge in Abala aided only by a bodyguard. From there he sent messages to Gaius Carrinas, requesting the assistance of his three legions for Cornificius.

In the end, he was able to withdraw, but closely pursued by Pompey’s horsemen, who were about to exterminate his men when Quintus Laronius’s relief troops, sent by Agrippa, arrived.

Naulochus was located near the modern Spadafora
Naulochus was located near the modern Spadafora. Credit: Scienziatone / Dominio público / Wikimedia Commons

Everything seemed to lead to a last and definitive clash, possibly agreed upon by the contenders, which took place between the promontory of Mylae and the city of Naulochus. The forces were evenly matched, with about three hundred ships on each side; as in previous cases, Pompey’s were lighter and faster than Agrippa’s, heavier because they were equipped with the aforementioned harpax, which had an iron-covered shaft so that enemy sailors could not cut it. This weapon proved to be tremendously effective, allowing Agrippa’s soldiers to immobilize enemy ships and board them.

The Pompeians gradually yielded, and Agrippa decided to deliver a final blow by cutting off the attempted withdrawal of some. Seventeen managed to escape, but twenty-eight sank to the bottom by spurring and one hundred fifty-five were captured, clearly showing who was going to win the battle; in fact, Agrippa did not lose more than three ships. Since Sextus Pompey was among those who fled, those who remained, without a leader to follow, accepted surrender.

Thus, the good omens Octavian had had the day before, when he was walking on the beach and a fish jumped from the water at his feet, were fulfilled. Suetonius tells it this way, although he later reproaches him for having fallen deeply asleep during the battle – out of exhaustion -, delegating responsibility to Agrippa.

The decisive campaign in 36 BC
The decisive campaign in 36 BC. Credit: Homoatrox / Wikimedia Commons

Sextus Pompey managed to reach Messina to discover that, faced with the disaster suffered, the bulk of his land troops also surrendered; he only had the eight legions stationed in Lilybaeum under Lucius Plinius, who entrenched themselves in Messina and were surrounded by Lepidus, who had meanwhile conquered Sicily. With everything lost, Pompey chose to flee to the East and negotiate with Thracians and Parthians to crush the weakened Mark Antony, ignoring those who recommended trying to negotiate with him. He could do neither one nor the other because Antony confronted him, and as his fleet was much superior, he forced him to continue his escape.

He ended up capturing him in Armenia. From there, he transferred him to Miletus, where he ordered his execution, violating the integrity conferred on him by Roman citizenship; an irregularity that Octavian would later exploit for propaganda purposes when his relationship with Mark Antony broke definitively. Before that, he had already got rid of Lepidus, after Lepidus expelled him from his camp upon seeing that his army acclaimed him as Julius Caesar’s heir and the legionaries reacted by overwhelmingly siding with him. Lepidus was eventually deposed, retaining only the dignity of pontifex maximus… in exile.

Meanwhile, Octavian was received in Rome with triumph, and Agrippa was granted the naval crown, a new gold decoration shaped like ship prows; no one had received it until then, and it would not be given again. The Second Triumvirate had come to an end to make way for the duel between the two remaining leaders, Octavian and Mark Antony, in what would be the fourth Roman civil war.

This article was first published on our Spanish Edition on April 8, 2024. Puedes leer la versión en español en Nauloco, la gran victoria naval de Agripa sobre Sexto Pompeyo que encumbró a Octavio


Suetonio, Vidas de los doce césares | Apiano, Historia romana | Veleyo Patérculo, Historia romana | Plutarco, Vidas paralelas | Dion Casio, Historia romana | Adrian Goldsworthy, Augusto. De revolucionario a emperador | Pat Southern, Augusto | Sergei I. Kovaliov, Historia de Roma | Pedro López Barja de Quiroga y Francisco Javier Lomas Salmonte, Historia de Roma | Wikipedia

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