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Sextus was so stunned by what had taken place that he omitted to give any orders to his infantry, with the result that they, too, immediately surrendered. He rushed to Messana and changed out of his commander in chief’s uniform with its blue cloak into civilian clothes. He loaded everything of any use, including all the money he had, into the poor remainder of his fleet, embarked with his daughter and some of his entourage, and sailed eastward, intending to apply to Mark Antony for help. Yet again, unconsciously no doubt, he was following his father’s example, who, when shocked by his defeat at Pharsalus, fled to seek safety in the east.

The battle of Naulochus, as it was named, was over, and with it the Sicilian war.

Lepidus was feeling extremely pleased with himself. Sidelined by Antony and Octavian, he had found the last few years less than satisfactory; but now he was having an excellent war. As commander of a great army, he was the master of Sicily. The chance of a lifetime presented itself. It was time for him to flex his muscles. He laid claim to the island on the grounds that he had landed there first and received the largest number of surrenders by cities.

Octavian, enraged, took action typical of him, at once careful and bold. He sent out some agents, who discovered that Lepidus’ soldiers thought little of him, admired Octavian’s courage, and were exasperated by the prospect of another civil war.

Once the ground had been prepared, the moment came for a bravura display of personal heroism. Octavian rode up to Lepidus’ camp with some cavalry, which he left by the outer defenses. Then, unarmed and dressed in a traveling cloak, he walked with a handful of companions into the camp—as one contemporary commentator put it, “bringing with him nothing but his name.” It was a striking piece of political theater, repeating his earlier forays into potentially hostile crowds. As he walked through the lines, the soldiers he met saluted him.

As Naulochus had shown, Octavian still found it hard to cope with the experience of battle, but when stung by opposition to him personally he did not hesitate to place his life at risk. For him, bravery was not an assertion of collective defiance and solidarity among colleagues but a solitary, obstinate act of will.

Lepidus, alerted by the uproar that something was amiss, rushed out of his tent and ordered that the intruder be repelled by force. Suddenly Octavian was in mortal danger. According to Appian, Octavian “was hit on the breastplate but the weapon failed to penetrate to the skin and he escaped by running to his cavalry. The men in one of Lepidus’ outposts jeered at him as he ran.”

It was a painful humiliation. Yet in the next few hours Lepidus’ men began to desert him. He went out and pleaded with them to remain loyal. He caught hold of a standard, saying he would not release it. “You will when you’re dead!” one of the standard-bearers said. Now it was Lepidus’ turn to be humbled. Frightened, he let go: the game was up. Seeing that this was so, he changed out of uniform and made his way to Octavian at top speed, with spectators jogging along beside him as if at a public entertainment.

Octavian was well able to be ruthless and cruel when opponents fell into his hands; his performance to date had been an implicit criticism of his adoptive father’s policy of clemency. But now he made a decision that presaged a change of approach.

At this very moment, for the first time since leaving Apollonia eight years previously, he faced no visible threat to his position. He knew that what everyone wanted was peace and a return to the rule of law. As a demonstration that this was his desire, too, he stood when Lepidus came up to him, and prevented the suppliant from falling to his knees as he intended. He administered no punishment and sent Lepidus to Rome dressed as he was, as a private individual.

Most significantly of all, Octavian did not strip him of his highly prestigious position as pontifex maximus, where his predecessor had been Julius Caesar. He was, however, deposed as triumvir; he left public life and spent his remaining twenty years in comfortable retirement at Circeii, a seaside resort about fifty miles south of Rome.

The town was built on the side of a steep crag, crowned by a temple of the sun and a lighthouse; it was originally an island, and the malarial Pomptine Marshes lay on its landward side. According to legend, in one of the numerous caves on its slopes the witch Circe had once lived, she who changed visitors into swine. It was not an inappropriate spot for one of Rome’s least appealing politicians to end up in.

When he gathered together all the various armies, Octavian found that he had under his command a grand total of forty-five legions, twenty-five thousand cavalry, about thirty-seven thousand light-armed troops, and six hundred warships. It was impractical to demobilize them all at once, for to acquire land on which they could settle would take time and money. Instead he paid part of the promised donatives, distributed honors, and pardoned Sextus’ officers.

The soldiers, especially his own, mutinied, demanding full payment of everything owed and immediate discharge. In response, Octavian announced a campaign against the Illyrians (in today’s Albania), for which he would need legions, and increased the number of awards to officers and men. He also made some conciliatory gestures, discharging those who had fought at Mutina and Philippi and offering an additional donative of two thousand sesterces. Calm returned to the camp.

After Naulochus, Sextus Pompeius made good speed to the eastern Mediterranean and, in another uncanny echo of his father’s flight in 48 B.C., put in at Mytilene. Only sketchy accounts survive of his next moves. He seems to have been well provided with cash, for he crossed over to the province of Asia, where he managed to raise large numbers of troops. Soon he was in command of three legions.

Antony showed little interest in Sextus, but was irritated to find that he had offered his services to the Parthian king. The governor of Asia, Gaius Furnius, offended by Sextus’ incursion into his province, marched against him with a large force. A sensible man would have surrendered, and Sextus was promised honorable treatment if he did so. Unaccountably he dug his heels in, tried to escape, but was caught.

The son of Pompey the Great had wasted his last chance of survival. He no longer had the slightest political or military value and could not be trusted to behave intelligently. In 35 B.C., Sextus Pompeius was executed, presumably with Antony’s approval. He was about twenty-six when he died—an age at which most men are launching, not concluding, their lives and careers.

Why did Sextus not win his war? For a long time he went from victory to victory. If he had taken Menodorus’ advice and refused to discuss terms with the triumvirs he could have starved Italy into submission and this biography might well have had him instead of Octavian as its subject.

The later ancient literary sources depict Sextus as a pirate, but he and his contemporaries saw him as a great Roman nobleman in pursuit of his rights. Appian claims that Sextus had no discernible strategic purpose and a pronounced tendency to avoid following up successes. There is some merit in the charge that Sextus failed to prosecute a long-term aim with adequate vigor.

He also did not take into account the disproportion in the relatively limited resources over which he had control and those at the disposal of the triumvirs, even when taken singly. This meant that he could not afford to wait on events, for sooner or later he would be outnumbered.

The youthful challenger to the post-republican regime lost, not so much through lack of intelligence or military and naval ability, but because he failed to think things through.