Mark Antony: Forever Frustrated
The entire life of Roman statesman Mark Antony was one of bedroom scandals, back-stabs, power grabs, and history-altering sliding doors moments. Starting his career as Julius Caesar’s right-hand man, Antony would rise to be a co-ruler of Rome. He even nearly became its first Emperor—alongside no less than Cleopatra—until it all went down in infamous flames.
Lusty, ambitious, and forever biting off more than he could chew, Mark Antony’s story rivals any ancient tragedy.
1. He Was Related To Julius Caesar
Even Antony’s early life was one of great privilege and great folly. Born in Rome in 83 BCE, Antony’s father was a military commander, and his mother was Julius Caesar’s third cousin. Yet for all that, the family had issues: His father was a deadly combination of both useless and corrupt, with one contemporary snidely claiming he only held power because he could neither use nor misuse it properly.
As Antony grew up, he began to take after the wrong side of the family.
2. He Was A Rake
Mark Antony liked too much of a good time. According to the historian Plutarch, he spent most of his youth bedding women, gambling away his money, and drinking himself into oblivion with his brothers. While some Romans were attracted to this extravagance, one in particular was appalled.
3. He Paraded Around Courtesans
The famed orator Cicero was a contemporary of Antony’s, and he had no love lost for the party boy. In his letters, Cicero complained of how Antony would brazenly put his courtesan mistress, Volumina Cytheris, in a place of pride on his litter, all while his own mother, “utterly neglected, followed the mistress of her profligate son, as if she had been her daughter-in-law”.
But this kind of lifestyle caught up to Antony.
4. He Had To Flee The Country
Whatever Mark Antony did, he did hard, and by the tender age of 20 he was in such debt from all his amusements that he had to flee town. He landed in Greece, where he took the ancient equivalent of a gap year, studying philosophy in Athens.
But like so many well-connected playboys, it didn’t take long for Antony to find his way back into the Roman fold.
5. He Turned To Violence
In 57 BCE, Antony became a commander of cavalry under the Proconsul of Syria, Aulus Gabinius. During this time, he fought with Gabinius’s army in Egypt as they sought to restore Pharaoh Ptolemy XII to his throne and consolidate Roman influence in the area.
Antony distinguished himself as an able commander and fierce warrior in these battles—but this chapter was fateful for him in another way.
6. He Met A Famous Queen
Ptolemy XII’s daughter was Cleopatra, the future Queen of the Nile. Years later, Mark Antony would claim that it was during these adventures in Egypt that he met the Egyptian royal, although she was only 14 years old at the time and more than a decade younger than the strapping Antony.
At that point though, Antony may have been a little preoccupied.
7. His Mentor Rose In The World
While Antony was making a name for himself in the military, his relative Julius Caesar was climbing closer to absolute power in Rome, and had just formed the top-secret “First Triumvirate” with two other men. And it had to be secret: Since Rome proudly considered itself a Republic, any official agreement between so few “rulers” would be dangerously unpopular.
Even so, Antony had no problem jumping on Caesar’s coattails.
Angel M. Felicisimo from Merida, Espana, Wikimedia Commons
8. He Became Caesar’s Lieutenant
Over the next years, Mark Antony turned himself into Caesar’s right-hand man, winning important battles in Gaul that gave Caesar control of even more lands. Even when the Triumvirate collapsed under the weight of its Roman egos, Antony stayed fiercely by his benefactor’s side, acting as Caesar’s de facto body guard. Caesar would need it.
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9. His City Fell Into Chaos
The concentrated power of Caesar’s First Triumvirate might have been secret, but everyone could feel that the Republic was undergoing a huge transformation all the same. By this time, the city streets were so rife with tension from every conceivable faction that in 52 BCE, gang violence forced Rome to cancel elections.
Which is about when Caesar came up with a brilliant idea for his lieutenant.
Andrea Ferrucci, Wikimedia Commons
10. He Could Tell The Future
Around this time, Caesar helped appoint Mark Antony to the College of Augurs, a priestly office that interpreted the will of the gods through birds’ flight patterns. This was anything but a make-work role: Since all public actions needed good omens to go ahead, Antony could simply declare any act he didn’t like as inauspicious.
And again, Caesar would need every ounce of influence he could get.
Andrea Ferrucci, Wikimedia Commons
11. He Followed Caesar To The Top
In 49 BCE, Antony’s world cracked. Caesar’s enemies, who had been watching his rise to power and were certain he was after solo rule, kicked off a civil war. Antony was right by Caesar’s side, and it was all worth it: After months of battles, with Antony acting as the second in command, Caesar subdued all his opponents. His next move was very telling.
12. He Reaped The Rewards
As Caesar racked up victories, he only proved his naysayers right. In 49 BCE, after crossing the Rubicon, he turned himself into a temporary dictator for 11 days, and another victory extended his stint to a year. It seemed Caesar did want to be Emperor, but Mark Antony had no problem with the kickbacks of this power.
After the conflict, Caesar traveled to Egypt and made Antony lieutenant governor of Italy, hoping his right-hand man would sort out the mess they’d left. It didn’t go well.
13. He Chased Women
If Antony had an Achilles’ heel, it was a beautiful woman. It’s even possible he had a very early marriage to a woman named Fadia, but it is certain that sometime during his service alongside Caesar, he married his first cousin Antonia Hybrida Minor, and in the next few years the pair had a daughter together, also named Antonia.
But like so many of Antony’s love affairs, this one went wrong—and in spectacular fashion.
14. His Wife Betrayed Him
While in Egypt, Caesar struck up an affair with none other than Cleopatra, eventually having a son, Caesarion, with her. Meanwhile, Antony’s love life was circling the drain: According to Plutarch, in 47 BCE Antony discovered that his wife was sleeping with his friend, the tribune Publius Cornelius Dolabella.
Despite often indulging in his own wandering eye, the enraged Antony kicked Antonia out of the house and quickly divorced her. But he still couldn’t let it go.
15. He Made Things Personal
The same year that Mark Antony threw his wife out, the cuckolding Dolabella proposed a debt-relief law in the Senate. Obviously, Antony wasted no time opposing it. He told himself it was because Caesar would never support such a thing, but most historians think Antony was leading with his bitter heart here, not his head.
His next move definitely wasn’t thought out.
16. He Triggered A Massacre
Dolabella didn’t give up so easily, and one day he and his followers seized the Forum and tried to push the law through by force. In response, a furious Antony sent in soldiers, massacring hundreds. The violence rocked Rome, and Caesar—who had appointed Antony to soothe the city—had to return from Egypt and fix his friend’s mess.
This one moment may have changed the history of the Roman Empire.
17. He Lost Caesar’s Trust
Suddenly, Caesar and Antony were no longer joined at the hip. Instead, after stripping Antony of his titles, Caesar spent his time quelling conflicts without his lieutenant—turning himself into a dictator for ten more years in the process—and loving up Cleopatra, who he brought to Rome along with their son.
Antony, meanwhile, moved on in his own way: With women.
18. He Married His Long-Time Mistress
In 47 BCE, directly after divorcing the unfaithful Antonia, Antony married Fulvia…who had likely been his mistress for over a decade. They would go on to have two sons together, Marcus and Iullus, and Antony began rebuilding his life from the ground up as a mere private citizen of Rome.
Only, Antony had a way of never staying in the dog house for long.
19. He Had A Powerful Reconciliation
By 44 BCE, Caesar and Antony officially reconciled—and the timing couldn’t have been better. That January, Caesar had finally consolidated enough power to name himself dictator perpetuo, no longer putting any time limit on his autocratic powers. He was, for all intents and purposes, the sole ruler of Rome, and Antony was once more beside him.
This only meant he had a front seat to Caesar’s downfall.
Rome,HBO
20. He Watched Caesar Perish
Fearing that Caesar was going to turn Rome into a monarchy, a group of men led by Marcus Junius Brutus and Gaius Cassius Longinus plotted against their eternal dictator. After distracting Antony at a senate meeting on the Ides of March in 44 BCE, the men swarmed Caesar and stabbed him to death.
Antony must have thought he’d lost everything. Except there was more to lose.
21. He Stepped Up His Game
After Caesar’s fatal stabbing, Rome turned into pandemonium—but this time, Antony was determined to control the chaos properly. Within days, he had woven together a compromise that appeased Caesar’s killers, Caesar’s veteran men, and the Senate majority by clearing the assassins of wrongdoing but also ratifying Caesar’s pending actions.
It was an impressive high-wire act that many likely thought Antony could never have pulled off. Then again, he had a big motivation to succeed.
22. He Called Himself Caesar’s Heir
In the days following Caesar’s end, the dictator’s widow gave Antony all Caesar’s papers and custody of his property. It was a clear sign that, despite their temporary falling out, Antony was destined to be Caesar’s political successor.
It must have been everything Antony dreamed of, but he was in for a rude awakening.
H. E. von Berlepsh, Wikimedia Commons
23. He Got A Nasty Surprise
On March 19, attendants opened and read Caesar’s will, and its contents were chilling. Although Antony received bequests here and there, Caesar had named his great-nephew Octavian as his principal heir, not Antony. Caesar even posthumously adopted Octavian as his son.
Would things have turned out different if Antony and Caesar never had a falling out? We’ll never know—but in any case, Antony wasn’t willing to accept it.
Getty Images24. He Fought For His Due
Following the reading of the will, Antony did the opposite of fading into the background. He now put on rousing orations about Caesar, displaying the dictator’s bloody toga during his public funeral. He also continued to present himself as the leader of the Caesarion faction no matter what Caesar’s final wishes said, even denying Octavian part of his inheritance.
It was only ever going to one way: Another civil war.
25. His Rival Was Formidable
Unfortunately for Antony, Octavian was no dummy, and he soon began amassing his own followers. Octavian made use of his position as Caesar’s heir to endear the people to him, and then further used his own cunning to get soldiers and money on his side.
Antony—never that good in a political crisis—soon made a fatal error.
S. I. Sosnovsky, Wikimedia Commons
26. He Reacted Badly
In 44 BCE, an embattled Antony decided to take the province of Cisalpine Gaul, which was already controlled by another Roman higher-up, for himself, marching an army there. It was a panicked move no doubt designed to announce his power to Octavian, but it backfired.
The Senate, incensed at Antony’s rashness, named him an “enemy of the state” before enlisting none other than Octavian and his considerable personal army to go quash Antony’s forces…which they did, extremely easily. But don’t forget: Mark Antony had nine lives.
27. He Became Co-Ruler Of Rome
Octavian may have gained the upper hand when it came to Cisalpine Gaul, but Antony’s connections to Caesar and the Senate ran deep, and his continued power couldn’t be denied. So eventually, instead of fighting each other, Octavian and Antony took a page from Caesar’s book and joined forces, creating the “Second Triumvirate” in 43 BCE along with Marcus Aemillius Lepidus.
Then they sealed it with a wedding.
28. He Turned His Enemy Into Family
Octavian and Mark Antony had no reason to trust each other, so Antony offered Octavian his stepdaughter Claudia—the daughter of his wife Fulvia from her first marriage—as a bride and a peace offering. With this, Antony, Octavian, and Lepidus’s co-rule of Rome could begin.
But while Caesar’s First Triumvirate had been under-handed, the Second was a bloodbath.
29. He Set Off A Bloody Purge
On the surface, Antony and his two co-rulers nobly set out to avenge Caesar after years of appeasing the assassins—and to be fair, they did run down Brutus and Cassius in 42 BC. Except in reality, this was all only a pretense to purge all their enemies.
The Second Triumvirate created lists of “proscribed” people, whose identities were announced to the public before the poor souls were stripped of their citizenship, wealth, and property and then outlawed. Antony also found a way to make this revenge personal.
30. He Destroyed His Rival
By the end of the purges, two thousand people from Rome’s property-holding class had been executed, not to mention a full third of the Senate. But for Mark Antony, the sweetest victim of the purges was an old rival: He successfully pressured Octavian to give up and execute Cicero, despite the fact that Cicero and Octavian were friends.
With this job done, Antony leant fully into the high life.
31. He Became The Ruler Of The East
The Second Triumvirate divided Roman territories between their rulers, with Mark Antony receiving the majority of the lands, most of them concentrated in the East. This suited Antony just fine: He returned to Athens in 42 BCE, where he quickly sank right into Hellenic culture, even eventually being worshipped in Ephesus as the god of wine, Dionysus, reborn.
And, as always, there were women.
32. His Mistress Turned Herself Into A Queen Mother
While in the Roman East, Mark Antony met with the beautiful and seductive courtesan Glaphyra. Antony fell hard into lust, and with such abandon that Glaphyra somehow convinced him to depose the current king and put her own son on the throne. Their tit-for-tat affair was so widespread, Octavian reportedly even wrote a dirty, snide poem about it.
But then there was the woman.
33. He Reconnected With A Woman
Soon after arriving in the East, Mark Antony requested the presence of Rome’s primary eastern ruler—his old acquaintance, and Egypt’s current woman pharaoh, Cleopatra. After Caesar’s assassination, Cleopatra had fled back home and then ascended to the crown, but she was immediately interested in reforming an alliance with Antony. It wasn’t all they formed.
34. He Fell Into An All-Consuming Passion
Mark Antony had always idolized Julius Caesar, and he now stepped into the late dictator’s shoes in a new way: He and Cleopatra struck up their own passionate affair. Cleopatra even bore Antony not one but three children, twins Alexander Helios and Cleopatra Selene, and Ptolemy Philadelphus.
But before Antony could settle down into this bliss, another woman went and ruined everything.
35. His Co-Ruler Offended His Family
Back in Rome, Antony’s wife Fulvia (yes, he was still married) had been clashing with Octavian in an effort to maintain Antony’s influence in the West. So when Octavian informed Fulvia that he was divorcing Claudia, the daughter given to him as a peace offering for the Second Triumvirate, it was the last straw.
With Antony away, it was his wife’s turn to make a political disaster.
36. His Wife Lashed Out
Livid, Fulvia and Antony’s brother Lucius marched on Octavian’s men and began yet another civil war, this time within the Second Triumvirate. Indeed, Fulvia loudly proclaimed to anyone who would listen that they would destroy the Triumvirate and turn Antony into the sole ruler.
But…Fulvia maybe should have asked Antony.
37. He Hung Her Out To Dry
Some historians believe that Fulvia’s attack on Octavian was at least partially an attempt to draw Mark Antony away from his new lover Cleopatra and back to Rome. But if so, it didn’t work. Antony was mortified by Fulvia’s actions and, in a show of his disapproval, gave his legions no instructions to relieve his wife’s forces.
In fact, he all but abandoned her—and to an incredibly dark fate.
38. He Was Cruel To The End
With no help from Antony, Fulvia and Lucius’s men were doomed in the face of Octavian’s formidable army. They surrendered in 40 BCE, and although Lucius earned a pardon from Octavian, Fulvia had to flee with her children to Greece, only to perish from a sudden illness soon after. Not that this prevented Antony from giving his wife one final insult.
39. He Gave His Wife A Cruel Parting Gift
Eventually, Mark Antony decided the turmoil back in Rome with his rival Octavian meant he needed to leave his Egyptian love nest. Then, he finally made time for his wife: On his way back to Italy, he met up with Fulvia in Athens, where he proceeded to rebuke her for her choices before sailing away.
He would never see her again, but he got over her quickly enough.
40. He Remarried Again
Tensions again simmered between Octavian and Antony, but instead of choosing war (for now), the two big men made another marriage alliance. Antony used his newly single status to marry Octavian’s sister Octavia in 40 BCE. If you’re keeping count, though, these marital alliances had literally never worked out for them.
Neither would this one…and it would also precipitate Antony’s downfall.
41. He Lost His Luck
For one, Antony’s marriage to Octavia coincided with a dip in his military fortunes, and starting in 38 BCE, he led a disastrous invasion of Parthia. More than that, he was unwilling to let his new wife share in his sorrows. Octavia tried to help by sending on fresh men, money, and provisions to Athens, only to be handed a letter from her husband when she arrived telling her she should go no further.
Instead, Antony went right back to his old habits.
42. Love Blinded Him
Mark Antony was now head over heels for Cleopatra, and he spent an increasing amount of time in Egypt…which was a very bad idea, considering Octavian was looking for ways to shore up his own power, diminish Antony’s, and become sole ruler of Rome. With Antony on a losing streak and away in Egypt instead of with his faithful wife, Octavian easily turned Romans against Antony, painting him once more as an enemy of the state.
But Antony didn’t back down. Not even close.
43. He Had A Bitter Breakup
Over in Egypt, Mark Antony lashed out at Octavian in his own way, officially declaring his breakup with Octavian and the Triumvirate to the Egyptians and distributing his lands among his children with Cleopatra. Even more upsetting for Octavian, if he ever found out, was Antony’s recognition of Cleopatra’s son Caesarion as Julius Caesar’s child, making him a direct rival to Octavian’s position as Caesar’s heir.
Antony was making sure there could only be one.
44. He Trash Talked Octavian
After the Second Triumvirate officially expired in 33 BCE, Antony and Octavian threw themselves into a propaganda war in preparation for real conflict. On Antony’s end, he divorced Octavia, then called Octavian an upstart and a usurper who had forged Caesar’s will.
Unfortunately, compared to what Octavian produced, these accusations were dust in the wind.
Louvre Museum, CC0, Wikimedia Commons
45. The Contents Of His Will Shocked Rome
On a tip from some of Antony’s defectors, Octavian raided the sacred Temple of Vesta, where Antony kept his will. He then showed it—and all its anti-Roman provisions for Cleopatra and their children—to the public. Aghast, the Senate stripped Antony of his titles and declared war on Cleopatra, with a third of the Senate leaving Rome to go fight.
Antony didn’t stand a chance.
Carole Raddato from FRANKFURT, Germany, Wikimedia Commons
46. His Men Broke
Octavian could feel how close he was to truly stepping into Julius Caesar’s shoes; how close he was to absolute power. By now, his army was awe-inspiring, and he pummeled Antony’s forces, creeping further and further into his eastern lands. In 30 BCE, Octavian managed to invade Egypt itself.
Antony and Cleopatra had nowhere to run: their tragedy was coming to a climax.
47. He Ended It All
With chaos all around and only chains to look forward to, Antony stabbed himself with his sword. To make it even more tragic, he had done it mistakenly thinking Cleopatra had already taken her own life. While bleeding out, he was carried to where she was hiding and perished in her arms just before Octavian’s forces broke in.
After days in captivity, Cleopatra also managed to take her own life, though likely not with an asp, as myth often reports, but rather with a toxic ointment or a poisoned hairpin. Thus passed two of the ancient world’s most dramatic characters—and thus passed the Roman Republic.
Silver Screen Collection/Getty Images
48. His Enemy Became Emperor
With Mark Antony and Cleopatra out of the way, Octavian now had a clear path to power. He walked down it immediately. After returning from his triumph in Egypt—and killing his final rival, Caesar’s son Caesarian—Octavian took on the title of “Augustus,” becoming the first Emperor of Rome. Indeed, every emperor after him would carry the title “Augustus.”
To think, it could have been Mark Antony. But then again, he did get his day.
Gautier Poupeau from Paris, France, CC BY 2.0, Wikimedia Commons
49. He Got The Last Laugh
In a twist of fate worthy of Macbeth, Antony may not have been emperor, but he became the ancestor of emperors—and with his neglected wife Octavia at that. During their miserable marriage, they managed to have two daughters together, and through these children Antony was the grandfather of Emperor Claudius, the great grandfather of Caligula, and the great-great grandfather of Nero.
Carole Raddato from FRANKFURT, Germany, Wikimedia Commons
50. He Could Have Been A Contender
If just a few things had gone differently in Mark Antony’s life—if he’d never had a falling out with Julius Caesar, if he’d never met Cleopatra—Roman history might have been completely different. Perhaps Antony would have been the First Emperor of Rome; perhaps Rome never would have turned into an Empire. Instead, fate dealt Antony a hand full of potential, but marred by tragedy.
Justin Benttinen, Wikimedia Commons
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