The son of Cleopatra and Julius Caesar was born with perfect timing: just as the Nile was beginning its summer inundation, signalling the start of Egypt’s annual natural renewal. It was an auspicious symbol of the political renewal that Cleopatra devoutly wished herself and Caesarion to embody for their people. She embraced her pharaonic identity with more vigor than ever. In the iconography of Egypt, she was the earth mother — the goddess Isis, the Lady of Abundance, whose spirit nourished her people as the milk of her breasts fed her baby. Her supposed co-monarch Ptolemy XIV couldn’t hope to compete; the boy became an irrelevancy in the face of her all-consuming splendor. Watching her hold court bedecked in her gold and jewels, one could easily forget how precarious her country’s position still was, could forget that she still owed whatever power she possessed to Rome’s sufferance and Caesar’s largess.

She visited her paramour and benefactor regularly in his capital, which had now overtaken her own to become the biggest city in the world. For, not being constrained by sea and lake as Alexandria was, Rome had room to grow which the latter did not. Its chaotic warrens of muddy streets and wooden buildings — so different from the stately limestone and marble of Alexandria — were already home to almost 1 million people. Caesar put Cleopatra up in a villa of her own, and the two of them scandalized the city’s polite society by continuing their affair in a very public fashion, despite the ongoing existence of Caesar’s wife Calpurnia. Cleopatra’s exotic appearance made her all the rage among those less beholden to traditional mores; her Egyptian braids ignited a new hairstyle craze.

Meanwhile Caesar was cementing his position, securing for himself the title of dictator of Rome — a position of absolute power, which was supposed to be reserved for short terms during times of extreme emergency — and mopping up the last partisans of Pompey and of the Republic as it had previously been constituted. These activities still forced him to spend a great deal of time away from Rome. When he was away, he left in charge the ever-faithful Mark Antony, his best friend although seventeen years his junior. Stalwart in battle, Antony proved an erratic civilian administrator at best. His residency in Rome was marked by days-long drinking binges, a byzantine love life, and a willingness to flout any and all political conventions: he appeared at public functions so hungover that he vomited all over his nearest companions, and presided over Senate business with his feet on the rostrum and an unsheathed sword in his hands. There is no indication that he and Cleopatra had any personal relationship at this time.

This bust of Mark Antony was made about a century after his death. No depictions from life are known to exist; they were presumably destroyed after his final downfall, when even his name was outlawed as that of a traitor to Rome. (Public Domain)

It soon became clear that Caesar had no intention of ever giving up his extraordinary powers. In 46 BC, having forced the final exigency of suicide upon his most formidable remaining political opponent, the incorruptible statesman and orator Cato the Younger, he engineered a Senate declaration that guaranteed him the title of dictator for the next ten years; the following year, he had done with all pretense and made himself dictator for life. The Senate was nominally still in existence, but it had become a rubber-stamp assembly that fell in line with every whim of Caesar. The Roman Republic was dead in all but name; Caesar himself called it “nothing, merely a name without body or shape.” In later years, Romans would take to saying that the Republic had died with Cato.

But Caesar mistook the fawning of the ambitious men who surrounded him for love, and underestimated the resentment that he and his high-handed compatriot Antony were stirring up among the remnants of Rome’s political class. These whispered among themselves that, having seen the ritual decadence of Cleopatra’s court, he now wanted the same for himself. He wanted, they believed more and more, to be king of Rome; perhaps the lovers would even unite their empires and rule jointly as king and queen of most of the known world, with Caesarion as their anointed heir. (Caesar had no children with Calpurnia.) To this accusation, Caesar laconically but prophetically replied, “Not king, but Caesar.” Very soon now, his surname would become a synonym for a reigning monarch — but he would not live to see that day.

At the onset of 44 BC, Cleopatra was in Rome with Caesar yet again, enjoying what she knew would probably be their last tryst for quite some time. For, despite now being 55 years old and in less than glowing health, Caesar had made plans to lead an army all the way to the Far East; he was, in other words, still chasing the Alexander the Great obsession he shared with so many of his peers. But premonitions of disaster rather than dreams of glory haunted those around him. Calpurnia, whose love for her husband was unabated by his blatant unfaithfulness, woke up screaming in the night from visions of him bathed in blood, and a trusted soothsayer told him to “beware the Ides of March.”

The day in question — March 15, 44 BC — dawned gray and cool in Rome. Caesar was still in the city, much to his own frustration; raising an army is complicated work even when one is the most powerful man in the world. He was tired, having just spent a long, hazy, boozy evening with friends. At one point, they had discussed what sort of death was the most desirable; “A quick one” was Caesar’s simple verdict.

So, it was a bleary-eyed Caesar who left his home for the Senate that morning to continue making arrangements for his absence. He met his Cassandra of a soothsayer on the way, and gave him a good-natured wink. “The Ides of March have come,” he said.

“Yes, but they have not yet gone,” said the other man gravely. Caesar just shook his head and drove on. What could you do with such people? He was still in Rome, for the gods’ sake. What had he to beware of here?

When Caesar got out of his litter before the Senate chambers, a crush of men rushed up to greet him as usual. One of them pressed a written tablet into his hand, but he had no chance to read it amidst the tumult. The imposing figure of Mark Antony was initially among the men, hovering protectively over Caesar as was his wont. But as the group walked toward the door, one of the other senators drew Antony aside for a private word. Thus Caesar was without his best friend when, just after he had passed through the door, all of those around him pulled knives out of their belts and assaulted him so savagely that, in addition to stabbing their intended target 23 times, several of them accidentally stabbed each other. As Caesar slumped to the floor, the tablet in his hand clattered uselessly onto the tiles next to him; later examination would reveal it to contain an urgent warning about the attack that was about to take place.

A far-flung conspiracy lay behind the assassination, involving some 60 men in all with an equally far-flung range of motivations, from simple jealousy of Caesar to an earnest desire to restore the Roman Republic to what it once had been. Its leaders were Marcus Junius Brutus, the son-in-law of the dead Cato, and Gaius Cassius Longinus, Brutus’s brother-in-law. Both had been firmly in the camp of Pompey, but Caesar had treated them with generosity after their cause had failed, and had believed them to have gone from being his enemies to his staunch friends. Thus his plaintive last words on the floor of the Senate, as later immortalized by Shakespeare: “Et tu, Brute?” (“You too, Brutus?”)

The born survivor had met his match at last. Caesar’s assassination was a tragedy, notes Will Durant, “in the sense that probably both parties were right: the conspirators in thinking that Caesar meditated monarchy, Caesar in thinking that disorder and empire made monarchy inevitable.”

Antony, knowing that he could do nothing for Caesar now and fearing that he was likely to become the conspirators’ next target, slipped away from the scene disguised in robes he stole off the back of a slave and barricaded himself inside his house. Cleopatra did the same in her villa. History does not record the private grief both must have been suffering, but we can presume it to have been considerable. Certainly there is every indication that both had genuinely loved Caesar.

But it turned out that the conspirators themselves had little to no plan for life after Caesar. United only by their dislike of him, they failed completely to seize the moment after they had done away with him. Lacking any coherent, mutually agreed upon ideology to justify murder, they managed only to create a power vacuum. Nobody seemed to know for sure who had and hadn’t participated in the conspiracy, who should be considered friend and who should be considered foe. On March 17, realizing that he had overestimated the conspirators, Antony came out of his house to read Caesar’s will in public.

The document was shocking for the way it failed to confirm all of the conspirators’ worst accusations. Caesar left much of his estate to the ordinary people of Rome, bestowing a cash gift upon every adult male citizen. He made no provision for Cleopatra, no provision for Caesarion, and, most surprisingly of all, no provision even for Mark Antony. His heir was instead to be Gaius Octavius, his eighteen-year-old grandnephew, henceforward to be known as Gaius Julius Caesar; to avoid confusion with his granduncle, we’ll follow the lead of historians for time immemorial and call him Octavian. Although the boy would receive the balance of Caesar’s property, he would not receive any title — definitely not that of dictator or king.

This partially reconstructed statue of Octavian was probably sculpted from life around 30 BC. (Public Domain)

With monetary proof of Caesar’s solicitude for them clutched in their fists, the people of Rome were no longer on the fence about recent events. They sought vengeance for their slain leader, who had always been more popular among the ordinary citizens than among the councils of the elite. Now that he knew which way the winds were blowing, Antony felt free to pour oil on the flames, leading the mob on a march through the streets of the city. The conspirators in the assassination fled the chaos like the common criminals Antony was now declaring them to be.

Cleopatra wisely did the same. She would never set foot in Rome again.

Four months after her return to Alexandria, the brightest comet of recorded human history streaked across the heavens for a week, lighting up the night all around the Mediterranean. It was immediately assumed to be the soul of Julius Caesar, being taken up by the gods to join their ranks on Mount Olympus. Cleopatra was thus able to claim to be, if not quite a god on earth herself, the former consort of one, now the mother of his progeny. The hapless Ptolemy XIV died under mysterious circumstances shortly thereafter, probably at her instigation; his demise cleared the way for her to make the three-year-old Caesarion her official co-monarch.

In the meantime, yet another Roman civil war was getting underway. Mark Antony and Octavian formed an alliance to oppose the murderers of Caesar. They made for an odd couple indeed. While Antony was a muscular, virile warrior, Octavian was frail and sickly, allergic to just about everything, and by many accounts something of a physical coward to boot. In personality, he was fussy and often petulant, a thoroughly unprepossessing figure in all respects except one: he had immense reserves of sanguine self-confidence, an unshakeable faith that his familial heritage of greatness in the form of his granduncle Julius Caesar must inevitably lead to greatness for himself. It must have struck those around the awkward boy as deeply delusional in the beginning, but future events would prove it to be well-founded.

Antony, Octavian, and Marcus Lepidus — another faithful former lieutenant of Caesar — seized control of Rome itself, ruling it as a Second Triumvirate. On December 7, 43 BC, they killed hundreds if not thousands of citizens whose loyalties were deemed suspect in a vicious purge, among them the great Republican political theorist Cicero. Ten months later, their army met that of Brutus and Cassius near the Macedonian city of Philippi. It was one of the most titanic clashes of ancient history: two armies of about 100,000 soldiers each, evenly matched in almost all other respects as well, engaged in two days of furious fighting. In the end, the Second Triumvirate triumphed; Cassius ordered his own men to kill him, while Brutus threw himself onto his sword rather than be captured. With them died any last flickering hopes for a revival of the Republic. Rome, and thus the entirety of the classical world, had entered a new era.

Mark Antony personally led the final, decisive charge at Philippi, and emerged from the battle almost as hallowed as Caesar himself. Octavian, on the other hand, stayed in his tent complaining of a stomach ailment.

Although more personally sympathetic to the would-be avengers of Caesar than to his killers for very understandable reasons, Cleopatra was always better than most of her male peers at separating personal feelings from the affairs of state; she managed to avoid getting Egypt caught up in the war as she waited for a victor to emerge. The combatants themselves likewise had much other than Egypt to concern themselves with. But in 41 BC, with victory secured, Antony turned his gaze southward at last. At the time, he was tidying up affairs in Tarsus, the capital of what was then the Roman province of Cilicia, and a major port city in its own right in what is today southern Turkey. He felt the time was nigh to see Cleopatra in person, to assure himself of her loyalty to the new world order of the Second Triumvirate. He knew, after all, that conquering Egypt would present little challenge in contrast to the war he had just waged, if he should be left with any doubts about her fealty. Of course, it wouldn’t do to go to Alexandria himself; Cleopatra must be ordered to come to him, to emphasize the power dynamic at play.

He sent as messenger a feckless opportunist named Quintus Dellius, who had jumped from the conspirators’ camp to that of Antony and Octavian just in time to avoid the fates of Brutus and Cassius. Dellius came to Alexandria expecting to bully Cleopatra, but instead he was, according to Plutarch, awed by her: “He applied himself to paying his court to her, and he encouraged [her] to go to Cilicia bedecked in her best fashion, and not to be afraid of Antony.” She took his advice to heart: “She was going to visit Antony at an age in which women have their most brilliant beauty and their understanding has attained its perfection.” (She was now 28 years old.)

Her first method of asserting her independence was the time-honored one of keeping her suitor waiting. Antony sent several increasingly impatient letters, but she refused to be hurried. She had met Caesar seven years before as a bedraggled fugitive smuggled into his presence in a sack; now, she would meet Antony clothed in all the splendorous array of an Egyptian pharaoh of old. Plutarch describes her belated arrival in Tarsus, whose people she struck as a veritable goddess descending upon them:

She sailed up in a vessel with a gilded stern, with purple sails spread and rowers working silver oars to the sound of the flute in harmony with pipes and lutes. Cleopatra reclined under an awning spangled with gold, dressed as Aphrodite is painted, and youths like Eros stood on both sides fanning her. In like manner, the handsomest of her female slaves, in the dress of Nereids and Graces, were stationed some at the rudder and others at the ropes. And odors of wondrous kinds from much incense filled the banks. Some of the people accompanied her immediately from the entrance of the river on both sides, and others went down from the city to see the sight. As the crowd from the Agora also poured forth, Antony was finally left on the tribunal sitting alone. A rumor went abroad that Aphrodite was coming to revel with Dionysus for the good of Asia.

(Mark Antony, no stranger to public adulation himself after his performance at Philippi, was frequently compared to Dionysus, the Greek god of wine and revelry, for the lusty joy he found in life.)

Observing the usual diplomatic niceties, Antony sent a formal invitation to Cleopatra to join him for a welcoming banquet. Asserting her independence once again, she declined; he could come to her instead, she wrote. Intrigued by this exotic creature, Antony agreed in spite of himself. When he came to join her aboard her vessel, writes Plutarch, “he found a preparation greater than he expected, but he was most surprised at the number of the lights: for it is said that so many lights were hung down and shewn on all sides at once and arranged and put together in such inclinations and positions with respect to one another in the form of squares and circles, that of the few things that are beautiful and worthy of being seen this sight was one.” The only thing Antony appreciated more than spectacle was sensuous luxury, which Cleopatra could also offer him in abundance. The two quickly became lovers — if not on that first night, then very shortly thereafter.

Like Caesar before him, Antony had a wife in Rome when he met Cleopatra, but that mattered no more to him than it had to his predecessor in Cleopatra’s bedchamber. He soon returned to Alexandria with her on her pleasure yacht, his haughty conqueror’s pride forgotten. There they spent their days hunting, fishing, and riding, and spent their evenings attending lectures at the museum, plays in the royal theater, and dances in the royal ballroom, as Cleopatra endeavored to polish some of her lover’s rough edges. The legendary opulence of the Ptolemaic court was unabated; even the chamber pots were made of gold. Again like Caesar before him, Antony tarried far longer in Egypt than was reasonable. He was, writes the ancient historian Appian, “disarmed by Cleopatra, subdued by her spells, and persuaded to drop from his hands great undertakings and necessary campaigns, only to roam about and play with her on the seashore.”

Recognizing that her country stood alone and vulnerable in a rapidly changing world, Cleopatra had set out to secure a protector in the one way she knew how. And her gambit appeared to have succeeded magnificently. Antony promised her that Egypt would remain under Roman protection but at the same time politically independent, truly the best of both worlds. And he did another, uglier favor for her, a favor that even Caesar hadn’t been willing to grant her: he had her sister Arsinoe pulled out of the ranks of the priestesses at the Temple of Artemis at Ephesus and executed. Cleopatra was now the last of the five acknowledged children of Ptolemy XII who still lived. In the best tradition of her family, all of the others had died at the direct or indirect instigation of herself or her father.

In the spring of 40 BC, nine months after their first meeting, Antony finally moved on. But, yet one more time like Caesar before him, he left Cleopatra pregnant with his child — or, as it would turn out, his children. Later that year, she had twins: one male, one female. The former she named Alexander Helios, after Alexander the Great and the Greek god of the sun; the latter she named Cleopatra Selene, after herself and the goddess of the moon.

Antony and Cleopatra didn’t see one another again for three and a half years. Roman politics remained as lively as ever during that time. The Second Triumvirate continued to rule as a collective dictatorship, but its three members — particularly Antony and Octavian — were frequently at odds with one another. Wily as a snake, Octavian had a knack for outmaneuvering his beefy brethren whenever it really counted — not least because Antony and Lepidus persisted in disesteeming this young man who so comprehensively failed to live up to the warrior ideal against which they measured their own worth.

When his wife died the same year he left Alexandria, Antony agreed to marry Octavia Minor, the half-sister of Octavian, in a bid to prevent their burgeoning rivalry from turning into the third Roman civil war in the span of a decade. And, in combination with a lack of close proximity between the rivals, the union did indeed manage to secure the peace for a number of years. Octavian, who was anything but a soldier — he tended to collapse from sunstroke if he had to walk any distance at all — mostly stayed in Rome, while Antony hopscotched around the realm with Octavia in tow, doing a bit of conquering here, shoring up defenses there. He failed to recognize until it was too late how much Octavian was shoring up his own political base while he was away. By 37 BC, Antony had been all but frozen out of the power structure back home.

In response, he fell back on his own Alexander the Great fixation. He decided to do what Julius Caesar had been prevented from doing by assassins’ knives: to raise an army and retrace their mutual hero’s course into the semi-mythical East. Once he had reforged Alexander’s empire, Rome would have to make him its sole dictator at the expense of the weak boy Octavian. He sent Octavia back to Rome, and sent word to Cleopatra to join him in the bustling metropolis of Antioch; the third largest city in the known world after Rome and Alexandria, it lay near the eastern bank of the Mediterranean at the most southerly extremity of modern-day Turkey.

One can imagine that Cleopatra had mixed feelings as she sailed to Antioch with the twin children Antony had never met. For all that she had probably begun their affair as a practical expedient, she evinced every sign of falling in love with Antony during his stay in Alexandria, and she must have been excited to see him again and to introduce him to his children by her. Still, his current plan was a rash one that stood little chance of success, and it’s difficult to believe that a woman as shrewd as Cleopatra didn’t recognize this fact. Much of the Near East was under the control of a formidable rising force known as the Parthian Empire, which had taken advantage of the decline of the Seleucid Empire and the Romans’ internal power struggles to gobble up large chunks of territory. These Parthians didn’t look like the easy pickings which Alexander had once found the decrepit Persian Empire to be. Cleopatra brought no army of her own with her; in what might be read as evidence of her opinion of the venture’s chances, she left whatever remained of the 12,000 legionnaires Julius Caesar had once given her behind in Egypt. Instead she played the doting mistress while Antony assembled his own motley collection of legionnaires, mercenaries, and adventurers, who came to number 100,000 or more in all. With little support forthcoming from Rome, the army’s existence was mostly down to the gold she had brought with her in lieu of soldiers.

Whatever her misgivings, she was doubtless gratified that Antony’s passion for her hadn’t been cooled a whit by an absence of three and a half years, much less by the death of one wife and the acquisition of another. He showered his lover and his children with gifts, some of which took the form of territories, such as Cyrene and parts of Crete, that had previously belonged to Rome. Just like that, Ptolemaic Egypt became the Ptolemaic Empire again, at least on paper. (Whether these gifts were really Antony’s to bestow, and what Octavian’s opinion of the matter would be, were very much unsettled questions…) Cleopatra may have imagined that, if the day did come when Antony made a final break with Rome, the two of them might wind up ruling a new, potentially even larger empire together. More likely, though, she saw Antony’s grandiose fantasies for what they were, but indulged them through some combination of necessity and love.

In the spring of 36 BC, Antony set off on his campaign. Cleopatra accompanied him as far as the edge of Mesopotamia before turning for home. In what was now becoming something of a tradition, when she left him she was pregnant with her fourth child, a boy she would name Ptolemy.

While Cleopatra traveled west toward the safety and luxury of Alexandria, Antony traveled east into disaster. His ill-conceived, ill-planned campaign went predictably wrong. The Parthians were largely content to harry his army with cavalry, focusing particularly on the wagons carrying its precious food supplies, and to take refuge behind the walls of their cities as Antony overextended himself in rugged, unfamiliar terrain. The natives of these regions — the same ones who had helped or even joined up to fight with Alexander against the Persians when he passed through — proved less enthusiastic this time around. Caught friendless in a nowhere-land as winter approached, Antony had no choice but to order a long, humiliating retreat from the edge of the Caspian Sea back to the Mediterranean shoreline. It was at this point that the suffering really began. His men died in the thousands of exposure and thirst as they made their way over a landscape that alternated barren mountain ranges with equally murderous deserts.

When they reached the sea at last near the modern-day city of Beirut, they had marched 1800 miles (2900 kilometers) in nine months. Between a quarter and a half of them were dead, the rest of them on the verge of death. Antony sent a messenger to Cleopatra in Alexandria, and she swooped in like the beneficent goddess she loved to play, bringing food, medicine, and comfort. When she returned to her capital, Antony came with her. From this point forward, the two were almost inseparable; Antony would see neither his lawful wife Octavia nor his home city of Rome again. His lieutenants marveled at the hold which Cleopatra, now well into her thirties and possibly tending a bit toward pudginess after three pregnancies and many years of opulent living, continued to exert on a man who had never before been wont to look beneath the exterior of his lovers. It would certainly appear that, however their relationship had begun, it had by now blossomed into full-blown, earnest love on both sides.

When not frolicking with Cleopatra or playing with his own and Julius Caesar’s children in the royal palace, Antony did a bit more adventuring here and there, plucking such low-hanging fruit as the rather down-at-the-heels land of ancient Armenia. His relationship to Rome grew increasingly indeterminate, as he continued to bestow territories, many of which he hadn’t yet actually conquered, upon Cleopatra instead of claiming them in the name of his homeland. This period must have been the high point of Cleopatra’s life, as described by her modern biographer Stacy Schiff:

For the young woman who fourteen years earlier had smuggled herself into Alexandria to plead for her diminished kingdom, it was a sensational reversal. Cleopatra stood divine and indomitable, less queen than empress, the supreme Roman commander at her side. She was protected by Roman legions; with her children, she now reigned, at least nominally, over more land than had any Ptolemy in centuries.

But there was a flip side to that coin, as described by the historian Adrian Goldsworthy:

The sheer size of her territory should not conceal the essential weakness of her position. Land, wealth, and influence were all dependent on Antony’s favour. Cleopatra remained a client monarch, if one on a grand scale, and she should not be considered in any way ruler of an autonomous allied kingdom. The new territories were gifts, not conquests. Cleopatra had no significant military resources and could not have taken any of these lands. The royal army was tiny and barely adequate for internal control of Egypt itself. The only royal troops were mercenaries.

Still, on paper at least, Cleopatra now ruled over most of the empire which had belonged to Ptolemaic Egypt at its peak of two centuries earlier. The one notable exception was the Jewish homeland; this now belonged to Herod the Great, a native of that land and a close friend of Rome, whose support from that quarter made him too dangerous a target even for the ever-daring Antony.

It was a dangerous enough game Antony was playing as it was. Back in Rome, Octavian was continuing to bolster his own position. In 35 BC, he put down a rebellion by Sextus Pompey, the son of Julius Caesar’s erstwhile rival. He used that war to polish his less than stellar reputation as a military commander, albeit more through elaborate play-acting than actual battlefield feats; in an escapade that was almost certainly scripted and staged, he and his lieutenants made an extended show of him being wounded in battle. Nevertheless, he used his carefully scripted glory to force Marcus Lepidus to step down, ending the Second Triumvirate. The frail young man was methodically taking up each and every rein of power; his only nominal equal was now Mark Antony, but he had sidelined himself in Egypt. In effect, Octavian was already the sole ruler of Rome and all of its territory. He awaited only the right opportunity to eliminate Antony and become sole dictator in name as well as effect.

Over the course of several years, Octavian engineered a masterful whisper campaign in Rome against Antony. And the latter, as usual, played right into his hands. Antony was spending less and less time in the field, more and more in Alexandria. The excesses of the royal palace there became the stuff of gossip everywhere. One story told of a 2.5 million denarii feast — a staggering sum of money — that culminated in the ingestion of a real pearl dissolved in vinegar. Antony was said to be growing fat and slothful like his mistress, and to spend his days wallowing with her in a mutual haze of food, drink, drugs, and sex. The worst of these tales were undoubtedly exaggerations — all indications are that Cleopatra remained a fairly able administrator of her land despite all the distractions that surrounded her — but there was enough truth to them to suit Octavian’s purposes. Antony, he said, had lost his soul to an exotic harlot who quite possibly used witchcraft to control him, and had forgotten his loyalty to his homeland along with his duty to it.

In 32 BC, Antony formally announced his divorce from the long-suffering Octavia, who had been waiting for him patiently back in Rome for almost five years. It was very likely intended as an act of mercy on Antony’s part; he was, for all his vanity and impulsivity that got thousands killed unnecessarily, not generally a bitter or cruel man in his personal relations. And yet the divorce, combined with a concurrent revelation that his will stipulated that he wished to be buried with Cleopatra in Egypt rather than in Rome, provided Octavian with the ammunition he needed to begin the final stage of his power grab. Octavian’s Rome declared war on Antony and Cleopatra’s Egypt. This way, said Octavian, Antony could have the Egyptian burial he so desired sooner rather than later.

When word of the declaration of war reached Alexandria, Antony professed confidence in the outcome — claimed in fact to be pleased that matters had come to a head at last. He would soon eliminate Octavian and marry Cleopatra, and together they would rule over a combined Roman and Ptolemaic Empire.

The outcome of the war would be determined in Greece, a natural arena given its location between the opposing camps. In October of 32 BC, Antony sailed from Alexandria for Greece at the head of an armada of 500 ships laden with all the soldiers they could carry. In a telling sign of just how close he and Cleopatra had become, she sailed with him on this campaign instead of remaining behind. Meanwhile more Egyptian infantry and cavalry were massing for the long march overland to Greece; Antony’s complete force numbered at least 100,000 of the former and 12,000 of the latter. Octavian, for his part, was moving east from Rome with 400 ships, 80,000 infantry, and 12,000 cavalry, most of it under the direct day-to-day command of one Marcus Vipsanius Agrippa, a brilliant tactician who had been the true architect of the victory over Sextus Pompey.

Antony’s slight advantage in numbers was a delusion in terms of the two forces’ real effectiveness. While Octavian and Agrippa’s soldiers and sailors were disciplined and battle-hardened, Antony and Cleopatra’s ragtag assemblage of mercenaries, native recruits, and aging legionnaires proved less reliable. Antony attempted quite literally to whip them into shape, but that only exacerbated the problem. Desertion became a constant fact of life once they reached Greece; Antony watched his numerical superiority slowly slip through his fingers as time went on, as his forces dwindled and a steady stream of reinforcements arrived on the opposing side. Perhaps because he was aware of his army’s shortcomings, he was uncharacteristically timid, avoiding a decisive battle with the enemy at the cost of his strategic position. By the late summer of 31 BC, Antony, Cleopatra, and the bulk of their remaining forces found themselves hemmed in on the promontory of Actium, which stands between the Ionian Sea and the Ambracian Gulf on the west coast of Greece. They were now surrounded by enemy forces on both land and sea.

Antony and Cleopatra decided to attempt a breakout by sea with their remaining 300 ships, after which they would return to Alexandria and regroup. This meant leaving a substantial number of their land-bound soldiers behind to effect a breakout of their own — or, more likely, to perish or surrender. Such was not a very honorable course of action according to the ancient code of warfare, but it was only the beginning of the shame Antony was about to bring upon himself.

On the night of September 1, 31 BC, the ships put to sea. Antony commanded the majority of them, despite having never led a sea battle before. Cleopatra followed behind with her own squadron of about 40 ships.

Precisely what happened when the battle was joined the next morning is not well understood. The ancient historian Dio Cassius claims that it was a fairly even affair until Cleopatra, “being a woman and an Egyptian,” lost heart, raised her ship’s sails, and took advantage of a favorable wind to dash away from the battle to the open water beyond. Antony then did the same in his own ship, but the rest of his fleet did not. The reason may have been that their ships were not equipped with sails, or it may have been down to the confusion of battle. Or, most damningly of all for the lovers, a personal escape at the cost of their fleet may have been their premeditated plan from the beginning. Whatever the reason that events transpired as they did, their men paid a terrible price to secure their leaders’ safety. Agrippa’s fleet, which outnumbered the Egyptian ships by as much as two to one, hemmed them in and brought fire to bear against the now-leaderless wooden vessels. Dio describes an inferno on the water:

Some sailors perished by the smoke before the flames could reach them; others were cooked in their armor, which became red hot; others were roasted in their vessels as though in ovens. Many leaped into the sea; of these some were mangled by sea monsters, some were shot by arrows, some were drowned. The only ones to obtain an endurable death were those who killed one another.

As many as 10,000 men may have died in this Battle of Actium.

Honor meant everything in the ancient world, and Antony had conducted himself with patent dishonor. Plutarch describes how he “went forward alone to the prow [of his ship] and sat down by himself in silence, holding his head in both hands.” It seems he blamed Cleopatra for his shame; although he soon joined her aboard her own flagship, the two found little to say to one another as they sailed back to Alexandria to wait for the end. Very few would be willing to fight for Antony now; within a week, all of the forces he had left behind in Greece had surrendered.

But the end was tortuously long in coming. Well aware that they could afford to deal with the couple at their leisure, Octavian and Agrippa took their time securing the victory they had won at Actium; in fact, they moved so slowly that one can almost imagine that Octavian was deliberately toying with his prey. Antony lived alone in a shack at the edge of the harbor in Alexandria, nursing his despair, seeing no one. In his self-pity, he built a shrine there to Timon of Athens, a mythological figure who had lived a privileged life until his money ran out, whereupon he was rejected by his fair-weather friends and plunged into misanthropic misery. “Timon, hater of men, dwells here, so pass along,” ran the words on his tomb of legend, which Antony now copied for his shrine. “Heap many curses on me, if thou wilt, only pass along.”

Cleopatra was a bit more active: she used the enormous wealth that was still at her disposal to attempt to raise another army that might transport her and Antony away, that might perchance be able to carve out a small realm for them somewhere well away to the east. But her plans kept falling through; not even mercenaries were willing to follow them now. She succeeded in sending into exile only the teenage Caesarion, who as a son of Julius Caesar and thus a possible rival to Octavian’s own familial legacy must be an obvious target for elimination by him. She sent a string of letters to Octavian himself, attempting to bargain for her kingdom. But she had little left to bargain with. So, she began to study the properties of various types of poison, settling eventually on snake venom as the most foolproof and painless way to die.

In late July of 30 BC, word of the inevitable finally reached Alexandria: not one but two large Roman armies were converging upon the city, one from the east and one from the west. Cleopatra held a last lavish feast at the palace, at which Antony suddenly appeared in his full battle regalia, restored for one night to the proud warrior she had met eleven years before in Tarsus. He expected to lead what few ships and men remained into battle the next day, for a valiant last stand that would certainly fail but that might erase some of the stain from his name.

But Cleopatra had a different sort of final gambit in mind. The next morning, she countermanded Antony’s order to attack, hid herself away, and told her servants to inform him that she had killed herself. Upon receiving the news, he decided to do the same. He stabbed himself in the stomach, but botched the stroke, and bled out only slowly and painfully. He begged the courtiers and servants around him to end his suffering, but no one dared risk acquiring the tag of Mark Antony’s murderer.

When someone let it slip that Cleopatra was in fact still alive, Antony begged to be taken to her, and this a pair of servants agreed to do. Plutarch:

She rent her garments over him, and beating her breasts and scratching them with her hands, and wiping the blood off him with her face, she called him master and husband and Imperator; and she almost forgot her own misfortunes through pity for his. Antony, stopping her lamentations, asked for wine to drink, whether it was that he was thirsty or that he expected to be released more speedily. When he had drunk it, he advised her, if it could be done with decency, to look after the preservation of her own interests, and not to lament him for his last reverses, but to think him happy for the good things that he had obtained, having become the most illustrious of men and had the greatest power, and now not ignobly a Roman by a Roman vanquished.

Mark Antony died in Cleopatra’s arms on August 1, 30 BC, at the age of 53.

Despite the sincere grief she now felt, Cleopatra must have guessed beforehand that the news of her own death, piled atop the news that he would not be allowed the final battle he craved, would cause him to kill himself; he had, after all, discussed the idea of doing so often since the shame of Actium. She loved him, but she was also a pragmatist. Why should both of them die if one of them might live? She still had a sliver of hope that, by not fighting against the invasion force and by showing Octavian Antony’s body, she could save herself and perhaps even her throne. She must have known that it was a slim thread of hope indeed, but it was all she had left to cling to.

So, the Roman armies marched into Alexandria unopposed, with Octavian himself presiding. He promised leniency to the people of the city, but he ordered Cleopatra to be forcibly removed from her palace and brought before him as a prisoner. Plutarch describes another pathetic scene:

She fell at his feet with her head and face in the greatest disorder, her voice trembling and her eyes weakened by weeping. There were also many visible marks of the blows inflicted on her chest; and in fine her body seemed in no respect to be in better plight than her mind. Yet that charm and saucy confidence in her beauty were not completely extinguished, but, though she was in such a condition, shone forth from within and showed themselves in the expression of her countenance. When Octavian had bid her lie down and had seated himself near her, she began to touch upon a kind of justification, and endeavored to turn all that had happened upon necessity and fear of Antony; but as Octavian at each point met her with an answer, being confuted, she all at once changed her manner and moved him by pity and prayers.

Octavian agreed to spare her life, but declined to give her back her kingdom. Instead she would be taken back to Rome to be paraded as a captive, just as her sister Arsinoe had once been. She probably made her decision right there; she loved life, but she was far too proud to suffer a public humiliation of that sort. Octavian left the interview, says Plutarch, “thinking that he had deceived her. But he had deceived himself.”

His heart was sufficiently softened that he allowed her to occupy her royal bedchamber again for the time being, attended by her servants, albeit with guards also in attendance at the doors and windows. On August 10, she was allowed to see Antony’s corpse one last time before it was interred in her own royal mausoleum, in accordance with his last will. Plutarch again:

After making lamentation and crowning and embracing the coffin, she ordered a bath to be prepared for her. After bathing, she lay down and enjoyed a splendid banquet. And there came one from the country bringing a basket; and on the guards asking what he brought, the man opened it, and taking off the leaves showed the vessel full of figs. The soldiers admiring their beauty and size, the man smiled and told them to take some, whereon, without having any suspicion, they bade him carry them in.

An asp was brought with those figs and leaves, and was covered with them; for that Cleopatra had so ordered. Baring her arm, she offered it to the serpent to bite.

When his soldiers told him of the deception that had been perpetrated upon them and of its deadly result, a much vexed Octavian ordered that everything possible be done to revive the lifeless body of Cleopatra. He even sent for native snake handlers, who were reputed to be able to suck the venom out of wounds like hers. But it was all to no avail: Queen Cleopatra VII was dead at age 39. And with her died the Ptolemaic era of Alexandria and Egypt.

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(A full listing of print and online sources used will follow the final article in this series.)

8 Comments for "Chapter 11: Cleopatra and Antony"

  • Aula

    Is it “Caesarean” or “Caesarion”? I think both spellings are fine, but you should pick one and stick with it.

    • Jimmy Maher


  • Ilmari Jauhiainen

    Was Cicero really leaders of the assassination plot? The story I’ve usually heard is that he endorsed their cause after the killing of Caesar, but was not in the know before it. For instance, in a letter to Trebonius, one of the conspirators, Cicero says in his florid manner that he would have wished to be invited to the glorious banquet on the Ides of March, because he would have left no leavings (that is, Marc Antony alive).

    • Jimmy Maher

      You’re right. It seems that Cicero was not an active participant in the conspiracy, although the conspirators felt confident he would join their side once the deed was done — as he in fact did. Edits made. Thanks!

  • Epistaxis

    One should beware of falling into the trap, as many Western historians have done, of assuming that Greece and Rome were the axis of the entire world. A phrase like “Rome, and thus the world, had entered a new era” wouldn’t seem out of place for a classics-oriented historian of fifty or one hundred years ago. But the peoples of Asia, Africa, and the New World, many of whom were living in empires with monumental architecture at the time, wouldn’t have known about this political squabble in a far-off land and wouldn’t have cared if they did. In fact, Rome wasn’t even the greatest empire in the world at the time; the Chinese Han dynasty was both larger in extent and more populous.

    A slight emendation like “Rome, and thus the Western world, had entered a new era” would make it sound less Eurocentric.

    (Typo: “at odd” should be “at odds”)

    • Jimmy Maher

      When I write a phrase like that, I mean for there to be some implied sense that this was the classical world, or, perhaps better said, the world as the participants in these dramas themselves knew it. But perhaps that sense doesn’t come through clearly enough. Edit made on this occasion — and I’ll try to keep a better eye out for that sort of thing in the future, and when I go back over these chapters to polish them up for release as ebooks. Thanks! (China will be the subject of my next big series after this one, by the way…)

  • Alexey Romanov

    If Caesar said anything, it was “You too, child” (and that has been argued to be not plaintive but more “may the same happen to you”).

    • Jimmy Maher

      I think we can allow a slight poetic license in this case, given how resonant those (apocryphal) last words have become. History is our collective past, yes, but in another sense it’s the way we process that past.


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