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On this occasion, his hopes were frustrated:

Here, like an utter fool, I stayed awake till midnight

Waiting for a girl who broke her promise. Sleep in the end

Overtook me, still keyed up for sex. Then scenes from a dirty

Dream spattered my nightshirt and stomach as I lay on my back.

Three more days rolling along in wagons were made exceptionally uncomfortable and exhausting because the roads had been damaged by heavy rain, still bucketing down. The weather improved as Horace and his friends approached Brundisium, before making their way to the elegant Greek city of Tarentum and the world of great affairs.

The principals—Mark Antony and Octavian—eventually met at the little river Taras, which flowed into the sea at a point between Tarentum and Metapontum, another city founded by mainland Greeks. It was a splendid sight: an army peacefully encamped on land and a great fleet lying quietly offshore. The idea was that the stream should separate the two mutually distrustful parties. Without planning to do so, the triumvirs arrived at the same time. Antony, who was staying at Tarentum, leaped down impulsively from his carriage, jumped unaccompanied into one of the small boats moored at the riverbank, and started to cross over to Octavian.

Realizing that he would lose face if he did not immediately return this demonstration of trust, Octavian, too, boarded a boat himself. The triumvirs met in midstream, and immediately fell into an argument, because each politely wanted to disembark on the other’s bank. Octavian won, on the grounds that Octavia was at Tarentum and he would not see her if Antony and he met on his side of the river. He sat beside Antony in his carriage and arrived unescorted at his colleague’s quarters in the city. He slept there that night, without any of his guards.

This little incident is of no great importance in itself, but it does illustrate a difference between the two men. When they disagreed, it was always Octavian who got his way. When he wanted something, he tended to pursue it with single-minded intensity, whereas Antony, seeing himself as the senior partner in government, had the careless self-confidence to give way.

Antony was eventually persuaded to back Octavian and abandon any thought of going over to Sextus. It was agreed that the Triumvirate, the term of which had expired on December 31 of the previous year, 38 B.C., be renewed for a further five years. The triumvirs also rescinded all the concessions to Sextus and promised mutual assistance. Antony offered 120 ships from his fleet (which was expensive to keep up and not very useful for a general intent on conquering the Asian landmass), and in return was promised four legions.

Once more the colleagues parted. Everyone was becoming accustomed to treaties signed with great solemnity that almost instantly became obsolete, so there were no celebrations of the kind that had marked the accord at Brundisium. However, a coin of Antony’s, issued at Tarentum, shows Antony’s and Octavia’s heads facing each other: unusual in Roman coinage, although common enough among Hellenistic kings who wished to emphasize harmony between husband and wife.

Octavian now prepared for a showdown with Sextus. He was pleased to receive his colleague’s ships, but had no serious intention of finding him his legions. This raises the question of his good faith. It was clear that Antony took their entente seriously, but Octavian’s behavior betrays a patient and undeviating pursuit of power. A sharp-eyed opportunist, he seized every gain that came his way, giving as little as possible in return.

During 37 B.C. and the spring of 36, Agrippa continued with his preparations in the lake of Avernus and the Lucrine lake. At last, the armada was ready. The plan of campaign was complex but potentially devastating. Three fleets were to set sail simultaneously for Sicily. Lepidus had been roused from his torpor in Africa; he would come with a thousand transport ships, seventy warships, sixteen legions, and a large force of Numidian cavalry, make landfall on the south of the island, and capture as much territory as he could. Another fleet, including Antony’s donated ships, would sail from Tarentum, and Octavian himself from Puteoli.

To counter this formidable convergence of military and naval power, Sextus could muster no more than three hundred ships and ten legions. Unlike his opponents, he did not have an inexhaustible supply of manpower. Nevertheless, his successes to date gave him every reason to suppose he could maintain his mastery of the seas.

To begin with, fortune favored Octavian. Lepidus succeeded in landing twelve legions—a large part of his army—on Sicily and immediately invested the port of Lilybaeum on the island’s western tip. If there was one way in which he could be depended on, though, it was that his loyalties were undependable. He seems immediately to have opened a line of friendly communication with Sextus, so that he would be ready to profit from any eventuality.

On July 3, disaster struck. The skies opened and the fleets were all overwhelmed by another terrible storm. The ships from Tarentum returned to port as soon as the wind began to rise. Octavian took refuge in a well-protected bay on the west coast of Italy, but then the wind veered to the southwest and blew straight onto the shore. It was now impossible to sail out of the bay, and neither oars nor anchors could hold the ships in position. They smashed against one another or the rocks. The tempest lasted into the night. Many ships were lost. It would take a month to rebuild the fleet.

It was probably now that, in a combination of defiance and despair, Octavian cried out, according to Suetonius, “I will win this war even if Neptune does not wish me to!”

Unfortunately, the end of summer was already in sight. A wise commander would call it a day until the following spring, especially after such a mauling. At Rome the popular mood was swinging against the triumviral regime and in favor of Sextus. A current lampoon demonstrated the scorn with which the people now regarded Octavian:

He took a beating twice at sea

And threw two fleets away.

So now to achieve one victory

He tosses dice all day.

The criticism was unfair; Octavian did indeed like to gamble in his leisure hours, but he was not idling now. He sent Maecenas to Rome to try to quiet his critics, while he himself rushed around Italy talking to settler veterans and reassuring them. Strenuous efforts were made to refurbish the damaged ships and lay new keels.

For Octavian was going to take a gamble, one of the riskiest of his life. He could not afford a long winter of discontent at Rome, so he would stake everything on one last throw of the dice. The war against Sextus was to resume.

Now that Lepidus was safely established on Sicily, Octavian and Agrippa saw that their best tactic was to find a way of landing more troops on the island so that they could bottle up Sextus in Messana. With massively superior land forces, it would then be a relatively simple matter to crush him or drive him into the sea. To attain this objective, they would have to draw most of Sextus’ navy into an engagement in the seas off northern Sicily. While he was so distracted, the legions in the toe of Italy would have an opportunity to slip across to Tauromenium (Taormina), south of the straits of Messana, unchallenged, perhaps even unnoticed.

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.