Seeing a large number of enemy sails in ports on the northern seaboard of Sicily, Octavian correctly judged that Sextus must be present, and that the moment was ripe for the army at Scolacium to embark for Tauromenium. He handed over command of the fleet to Agrippa and sailed to Italy to join his legions.
The following day, Agrippa engaged the enemy fleet off the northern port of Mylae and gained the upper hand. However, the Pompeians withdrew in good order and, with evening coming on, Agrippa decided it was too risky to give chase. Sextus cleverly guessed that Agrippa’s activities were a blind. Immediately after supper, he set off for Messana with his main fleet, leaving a detachment of ships to deceive Agrippa into thinking he was staying where he was. Hiding in port, he would await the triumvir’s arrival and catch him unawares.
Octavian, having climbed to a high point to survey the sea and finding no sign of the enemy, loaded as many legionaries as he could onto troopships and sailed from Scolacium to Italy’s toe, the cape of Leucopatra. Vulnerable to attack because of the troopships, he had thought of crossing the straits under cover of night, a dangerous stratagem in the days before radar, but safer than risking interception by Sextus. However, when he received news of Agrippa’s success at Mylae, Octavian decided, in Appian’s words, not “to steal over like a thief in the night but to cross in daylight with a confident army.” The war was drawing to a triumphant close, Sicily would soon be in his hands, and Sextus’ days as the last republican in arms were numbered.
Octavian made landfall on Sicily south of Tauromenium and disembarked his troops. Suddenly, before the army had even finished making camp, Pompeius appeared over the northern horizon with a large fleet. Riding in parallel on the shore was his cavalry. Then up from the south marched Sextus’ infantry. The surprise was total. The cavalry harried the soldiers still at work on the fortifications, but both Sextus’ fleet and infantry held back. This was a serious error, for they missed the opportunity not only to win a decisive victory but also to capture the triumvir.
Nightfall should have afforded some rest, but Octavian’s soldiers had to complete their defenses; when dawn came they were sleepless, exhausted, and unfit for battle. It was a desperate situation. Octavian knew he had to save the fleet; if it was not to be picked off at will on the beaches or at anchor, it must sail away as soon as possible, even if doing so meant risking battle with Sextus. So he handed command of the legions to Lucius Cornificius, an early follower of his who had prosecuted Brutus in 43 B.C. for Julius Caesar’s murder and was one of the new breed of politicians from outside the magic circle of great families.
Octavian himself put out to sea with his fleet, making the rounds of the ships in a fast, light trireme, called a liburnian, to encourage his sailors and raise their morale. Once he had done this, he stowed his admiral’s standard, presumably because he believed himself to be in extreme danger and anonymity would increase his chance of survival. Evidently he did not expect to win any encounter.
Sextus sailed out of Messana on the attack. There were two fiercely fought engagements, in which the triumvir’s ships came off worse. Numerous galleys were captured or set alight; some made off without orders to the Italian mainland. Other crew members swam to the Sicilian shore and were either caught and killed by Sextus’ cavalry or scrambled up to Cornificius’ camp and safety. Eventually darkness drew a veil over the catastrophe.
Octavian did not know what to do. He spent most of the night among his fleet’s small auxiliary craft, wondering whether to risk sailing back to Sicily through all the wreckage to find Cornificius, or to seek out his troops on the mainland. He decided on the latter course. Setting off in a single ship, he was hotly chased; it was probably now that, believing he was about to be captured, he asked a loyal aide, the eques Gaius Proculeius, to be ready to kill him.
However, Octavian just managed to elude his pursuers and reach the shore, where he disembarked. He was out of immediate physical danger, but found himself completely alone except for his armor bearer. Apparently he hid for a time in a cave. When he thought of his army isolated and under siege on the Sicilian coast, he was, according to Dio, “terribly distressed.” The war was about to be lost and his glittering career was in ruins.
His travails were not over. Octavian was walking on the coast road in the direction of Rhegium when he saw a flotilla of biremes heading for the shore. He went down onto the beach to greet them, only realizing in the nick of time that they were Pompeians. As he made his lucky escape by narrow, winding paths, he encountered a new and completely unexpected danger: an attack by the slave of an officer on his staff whose father he had proscribed. No more details of the attempt on his life are known, except that he survived.
Some people from the mountains came down to see what was going on and found Octavian nearing the limits of mental and physical endurance. They transferred him from one small boat to another to evade detection and at last brought him to his waiting legions.
Octavian gave another immediate and characteristic display of sangfroid. Food and sleep could wait; first, he dispatched a liburnian to Cornificius in Sicily to brief him on what had happened, and sent messengers around the mountains to let everyone know he was safe. Thorough-minded as always, he was not going to allow any administrative slipup or communication failure to nullify this new opportunity for a comeback.
The situation looked more difficult than it really was. Two immediate things had to be achieved if momentum was to be regained. First, somehow or other Octavian’s legions had to get themselves to Sicily. This seems to have presented few difficulties now that Agrippa, profiting from his sea victory, had occupied some ports on the island’s northern coast. A successful transfer was soon effected.
Second, Cornificius, pinned down by Pompeius’ troops near Tauromenium, had to extricate himself and join Agrippa. This was accomplished too, although it entailed a painful march across an arid expanse of old, cooled lava near Mount Etna.
Only a few days had passed since Octavian’s debacle, but the tables were turned. He was master in Sicily of twenty-three legions, twenty thousand cavalry, and more than five thousand light-armed troops. His forces were overrunning the island, and Sextus recalled his army in the west to the northeastern enclave, which was all that was safely left to him of his island realm.
Sextus realized that the only way he could retrieve a rapidly deteriorating situation was to provoke a confrontation at sea. On September 3, his fleet sailed north out of Messana, rounded the cape of Pelorum (today’s Cape Faro), and met Agrippa’s fleet in the sea between the ports of Mylae and Naulochus.
Octavian appears to have played little part in the battle. If we are to believe Suetonius, he was suffering some sort of psychological crisis—a relapse to his state of mind at Philippi.
On the eve of the battle he fell so fast asleep that his staff had to wake him and ask for the signal to begin hostilities. This must have been the occasion of Antony’s taunt: “He could not face his ships to review them when they were already at their fighting stations; but lay on his back in a stupor and gazed up at the sky, never rising to show that he was alive until his admiral Marcus Agrippa had routed the enemy.”
The surviving descriptions of the encounter say little about the opposing fleets’ tactics; maybe this grand mêlée of about six hundred warships was little more than a multitude of individual encounters, trireme against trireme, while from the land the infantry of both sides looked on apprehensively.
As time passed it began to appear that Sextus was losing more ships than his adversary (thanks in good part to Agrippa’s harpax). Some of his galleys began to surrender, and Agrippa’s men raised the paean, or victory shout, which was picked up and echoed by the soldiers onshore. A setback became a rout. One of Sextus’ admirals killed himself, the other surrendered to Agrippa. Only seventeen warships survived.