After Philippi, Antony had set about securing the East. The region had been under the control of the assassins. There had been some resistance and some support for their cause. The Parthians were active on the frontiers. They were supported by Labienus, a Roman general who had defected to the Parthians when news of the defeat of Brutus and Cassius came through.
Antony Meets Cleopatra
His first major political engagement in the East, though, was meeting Cleopatra, a meeting lavishly described by Plutarch and one which has caused various re-imaginings.

Fom Georg Ebers, Egypt: Descriptive, Historical, and Picturesque, Volume 1. (New York, 1878), 20 (from Travellers in the Middle East Archive)
The result of the meeting was manifested, after the due course of time, in the births of Alexander Helios and Cleopatra Selene. Cleopatra had been loyal to Caesar and the triumviral alliance. She was now to sit at the centre of Antony’s political arrangements for the East, as well as becoming his lover.
What she brought to the relationship was the power and prestige of the Ptolemaic throne and the wealth of Egypt. Her money could be used to support Antony’s campaigns. Egypt could provide the material needed for a major campaign. Probably, she also provided knowledge of the East and its complex political arrangements.
Prestige came from three centuries of Ptolemaic rule in Egypt. We tend to think in terms of national territories, but we could and perhaps should think about politics in the East more personally, in terms of dynasties. In the past, Ptolemaic rule had not been confined to Egypt, but had encompassed territories across the Eastern Mediterranean. Ptolemaic cultural and economic influences were widely felt. A Ptolemaic queen could wield influence and help support Roman hegemony in the East.
For Antony, securing Cleopatra’s affections meant securing Egypt. Although there was considerable later criticism of the relationship from his Roman enemies, a regal lover had boosted the prestige of Caesar and one might expect that it did the same for Antony. The relationship was useful and productive. It was good geo-politics, whatever the personal side.
Against Parthia
The Parthians took the initiative in the war, invading northern Syria, perhaps intending to keep the Romans west of the mountain ranges that today mark the borderlands between Syria and Turkey.
Parthian forces, led by Labienus, managed to secure much of the Syria-Palestine-Judaea region. Syria was a Roman province, but Pompey had left much of the rest of the region under what we refer to, though the Romans did not, as client kings.
Provinces tended to be expensive. they required administration and often armies. Pompey preferred to appoint, or reappoint kings. They were cheap. They still provided Rome with money and with men to fight in her armies. For Pompey himself, the great advantage was that such men would have been personally loyal to him.
But with Pompey dead, loyalties were fragile. Most of the kings made their peace with Caesar. With Caesar dead, many of the powers of the region supported Brutus and Cassius. With Brutus and Cassius dead, would they support Antony? In retrospect, not supporting Antony looks foolish, but the Romans had been a presence in the region for little over two decades. They seemed hopelessly divided and Parthia looked like the great power, its territory stretching far to the West (map). In their most recent engagement with Rome, at Carrhae, the Parthians had decisively defeated Roman legions under Crassus. In any case, what would Antony do to supporters of Brutus and Cassius?
Rome’s allies in the region defected to Parthia. Antony was also distracted by events in Italy, allowing the Parthians scope to expand and consolidate their control in 40 BC. But he was able to resume the war in earnest in 39 with a lightning campaign led by Ventidius.
The strength of the Romans lay in their heavy infantry, their legions, which although relatively slow, were very difficult to stop. The strength of the Parthians lay in their heavy cavalry, from which they used bows. The cavalry were very fast and very difficult to catch. The Parthians wanted to catch the Romans in battle. Their cavalry would be able to approach, attack and retreat without being attacked themselves. Even better would be to catch the Romans on the march in open ground. Every time the cavalry approached, the Romans would be forced to stop, draw up their lines, and defend themselves, making any march painfully slow. The Romans needed to push slowly into their territory, progressing without being caught in the open, fortifying positions, and moving slowly.
Rome’s other advantage was that their soldiers were in the field all the time. The Parthian cavalry needed to go back to their estates from time to time.
Wars between Rome Parthian tended to be drawn out and inconclusive, though it seems that the military balance was in Rome’s failure. The Parthians had more to lose from conflict with Rome and when convinced that the Romans were coming seriously, tended to seek peace, as in Augustus’ campaign in 20 BC.
After the crises of 40 BC, the Antonians moved fast. Ventidius attacked Labienus who had legionaries, but had limited cavalry support. Labienus was deafeated and killed and the Parthian retreated, allowing Antony and his forces back into the Levant.
Antony took revenge on some of the treacherous kings, notably Antigonus of Judaea. Antony then established the Herodian dynasty in Judaea. Securing his base was essential before pursuing the Parthians.
The war resumed in 38, but both sides were distracted by problems at home. Antony, however, took the offensive. His strategy was to break up the coalition of Parthian allies. This led him into wars in Media and Armenia, which was to be a contended territory between Rome and Parthia for a further century.
The campaign initially had mixed success, with Antony being forced to rapidly retreat in 36 and request reinforcements from Octavian (which were delivered by Antony’s wife, Octavia). From the account of the campaign in Dio (49.19-33), it looks a sequence of disasters. But in 35 and 34, the Medians made peace. The Armenians followed them into the Roman camp after Antony’s offensive drove the king from Armenia. The balance of power in the region was shifted: the Parthians had seen their dependent kingdoms taken away by the Romans, Syria had been secured, the Parthian dynasty had been weakened. They had little alternative other than to make peace (Dio, 49.39-40).
Dio takes a hostile position on Antony’s victories in the East. As in the accounts of the campaign against the assassins, the results seem to undermine the narrative. Antony seems like a terrible general, but he wins. The hostility between Octavian and Antony casts a long shadow over these events.
One can imagine how these wars would have been received had Antony won the war at Actium. Rome had revenged its catastrophic defeat at the battle of Carrhae in 53 BC and Antony had established Roman hegemony. He declared victory and went to Alexandria to celebrate.