Dear Classical Wisdom Reader,
What sort of leaders do we admire?
Are we drawn to discipline or charisma?
To patience or passion?
Do we forgive flaws if they come wrapped in brilliance?
And what happens when emotion begins to outweigh judgment in public life?
These questions emerge with every election cycle, every political movement, every public figure who rises more on personality than on principle. We argue again and again whether strength means control or conviction… restraint or fire.
Regular readers, of course, will not be surprised to discover that this same predicament afflicted the ancient Romans and indeed no two figures encapsulate it better than Octavian and Mark Antony.
In fact, as today is traditionally remembered as Mark Antony’s birthday, it is a fitting moment to revisit his story... But the Antony you think you know, the drunken lover ruined by Cleopatra, is mostly a creation of propaganda and poetry.
Before the legend, there was a man who nearly outplayed Octavian, who used spectacle better than any Roman alive, and who may have understood the future of power more clearly than his famous rival.
Mark Antony almost became emperor. He almost had the world at his feet. His charm and insights almost shaped history itself...
But he failed and the reasons for that are far more surprising than the story we usually tell.
Classical Wisdom Members, please enjoy today’s deep dive on Mark Antony on the anniversary of his birthday...
Was he the party boy he was made out to be? Was Cleopatra a liability or a weapon? And how was his legend preserved?
Find out below!
Also included is our Battle of Actium discussion which explains what really happened during that fateful war that made an empire. Featuring Barry Strauss, William Murray and Kara Cooney, Members you can enjoy the video and full transcript below.
If you aren’t a member yet, there is no time like the present! Subscribe today to enjoy our in-depth articles, Classical Wisdom Litterae Magazine, and podcasts with professors. Let the ancients guide you:
All the best,
Anya Leonard
Founder and Director
Classical Wisdom
The Man Who Could Have Been Emperor
On this day, traditionally given as January 14, 83 BC, Marcus Antonius was born into a crumbling Roman Republic. History remembers him as Mark Antony: lover of Cleopatra, rival of Octavian, and tragic figure at Actium.
But that familiar story hides a deeper and more interesting question.
What kind of man was Antony really...and how close did he come to becoming Rome’s first true emperor?
Antony’s life is often told as a fall: from Caesar’s loyal lieutenant to Cleopatra’s doomed consort.
Yet another way to see him is as a man who nearly mastered the new world that Caesar had created, and he failed not from lack of talent, but from a fatal mismatch between his nature and the age he lived in.
Before Caesar: The Making of a Roman Rogue
Mark Antony did not begin life as a polished aristocrat. His father died young, leaving him under the influence of a stepfather widely mocked for corruption and weakness. Ancient sources describe Antony’s youth as wild: gambling, drinking, debt, and scandal. Cicero later painted him as a drunken wastrel...but even his enemies admitted his charm, generosity, and magnetism.
When his debts became unbearable, Antony fled to Greece, where he studied rhetoric and philosophy, but books never defined him. He was built for action. He joined the army in the East, serving under Aulus Gabinius in Syria and Egypt, and quickly proved himself a gifted cavalry commander: bold, charismatic, and fearless in battle.
This mattered because in Rome, politics and war were inseparable. Military glory was the ladder to power, and Antony climbed it fast.
By the time he met Julius Caesar, he was already known as a daring soldier with a gift for winning men’s loyalty. He joked with soldiers, ate their food, shared their hardships, and spoke to them as equals rather than tools. He remembered names, praised bravery loudly, and rewarded loyalty generously. His potential at this moment was boundless.
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