Augustus

That was the idea. It did not work. Lepidus ferried his remaining four legions from Africa, but unfortunately one of Sextus’ squadrons came upon them. In the misapprehension that the flotilla was friendly, the transports sailed up to it and many were destroyed. Two legions drowned.

While Octavian sailed down the western coast of Italy, the fleet at Tarentum set out for the port of Scolacium (today’s Squillace), on the “sole” of the Italian boot. It was accompanied by an army marching along the coast beside the ships.

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.