The Rise of History’s Greatest Emperor: An Untold Story - Alex Petkas - #1085

Why should anyone in the modern world care about Roman history?

History can drain you or light you up. Nietzsche warned about the first, but praised the second through Plutarch’s 'monumental' reading, where you hunt for living examples of greatness that wake you up. I use the past to find models that resonate with my own best path, the way Caesar staring at Alexander’s statue sparked a painful, clarifying jolt about what his life should be.

It’s wild that history had its own historians even back then, like Egypt studying ancient Egypt.

Exactly. Late antiquity already felt old to them. Plutarch, writing under Roman rule, was looking back centuries and still treating the past as a living guide, which isn’t how we often approach it today.

What can Caesar teach us about living well?

That moment in Spain when he wept before Alexander’s image says it all. He realized he’d been playing small and felt the sting of falling short of what he could be. You want history to crack you open like that, then use emulation wisely—find the specific figure who calls you to your best work, even if you’re not copying their path.

And what does that reveal about his ambition?

It was enormous and visible early. He came from ancient lineage but grew up around Rome’s gritty underbelly, tied to the popular side through Marius. When Sulla won the civil war and demanded Caesar divorce Cornelia, he refused, fled, was hunted, bribed his captors, and was spared only after allies begged. Sulla’s warning—'there are many a Marius in that boy'—captured Caesar’s defiance, loyalty to his own, and a clear bet on a populist, outsider future.

What’s the pirates story from his youth?

Captured off Asia Minor, he mocked the ransom as too low and talked them into asking for more, then entertained and taunted them, promising he’d return to execute them. Freed, he quickly raised ships, seized the pirates, and had them crucified, granting a swift death out of a cold courtesy. It was swagger, an instinct for reputation, and ruthless follow-through.

Before command, he built popularity with style and theater. He dressed with flair, prosecuted corrupt governors to signal what he stood for, and positioned himself against a cozy oligarchy. As a general, he led from the front, gave generously, lived like his men, and turned wealth into loyalty rather than hoarding it.

How deep did that loyalty run?

One officer, offered freedom by the enemy, chose to die rather than accept mercy not given to his men. In Greece, when Pompey’s forces mocked their hunger, Caesar’s troops slung over their coarse weed-bread to show what they’d endure. He knew centurions by name, ate the bad rations, slept on the ground, and spent winnings on people. That’s how you bind hearts.

Walk me through his relationship with Pompey and the arc of his rivals.

Pompey was a brilliant organizer who loved command more than politics and styled himself like Alexander. Caesar’s real bond early on was with Crassus, who financed him. Caesar then brokered the first triumvirate—solving Pompey’s soldier settlements and treaty ratifications and getting Crassus his tax relief—in exchange for their backing. He married his beloved daughter Julia to Pompey, turning rivals into family for a time.

So how did they end up at war?

Caesar went to Gaul and forged elite legions through years of hard fighting. While he was away, Crassus died, the establishment courted Pompey, and Julia’s death cut the last personal tie. Caesar’s enemies threatened prosecution if he returned without surrendering. The ground shifted until conflict became inevitable.

What does 'crossing the Rubicon' really mean?

Italy’s legal boundary barred generals from bringing legions in. After a standoff, the Senate branded him a public enemy. At Ravenna with one legion, he quietly made his move, stepped over that small river, and chose war. His advantage was speed and surprise. He swept into Italy, forcing Pompey and the Senate to evacuate to Greece to regroup and try to starve Rome. Lacking ships, Caesar first crushed enemies in Spain, then chased the war across the Mediterranean.

And Egypt—what happened with Cleopatra?

After Farsalus, Pompey fled to Egypt and was murdered by courtiers eager to please Caesar. Caesar mourned a former friend and punished the plotters. Egypt was fabulously rich and mid–civil war between Ptolemy XIII and Cleopatra. Cleopatra famously slipped into the palace rolled in a bundle, charmed Caesar, and won his support. He installed her, beat her rivals, and they became lovers. Their son, Caesarion, symbolized a fusion of Greek and Egyptian power in a city where marble, learning, and old gods mixed.

What do we know about Caesar’s final night?

He knew of threats but refused a bodyguard because it looked tyrannical and chilled free speech. Friends begged him to tighten security; he waved them off and focused on a planned Parthian campaign and an overflowing docket. He preferred risk to ruling by fear.

Those Roman banquets were set on couches in a circle, which forced one shared conversation. I loved the story of the trick cup that drains when you overfill it, a built-in lesson in moderation.

At Lepidus’s place on Caesar’s final evening, he was literally clearing his correspondence between toasts while the table debated a single theme. When it was his turn, he called the best death swift and unforeseen, with Decimus Brutus, a trusted lieutenant even named in his will, listening a few feet away.

The night was riddled with bad signs and Calpurnia’s nightmare shook him; for once, the man who usually mocked omens felt off and thought about skipping the Senate. A sacrifice that morning came up ugly, and he stayed home.

Then Decimus arrived to needle his confidence, remind him of past courage, and insist Rome needed to see him show up.

He let himself be persuaded, despite another warning on the street from a young acquaintance tied to Marcus Brutus who slipped him a note he never read. They met not in the old chamber but at Pompey’s theater complex, beneath a statue of Pompey himself.

So the coaxing worked, and he walked straight into the trap.

Inside, petitioners closed around him with a staged plea, hands grabbed his robe, and knives flashed; former allies and beneficiaries were among them, including both Brutuses and Cassius. Panic emptied the chamber, and in the rain a few attendants struggled to carry his body home to Calpurnia.

For all his flaws, he had fused his own success to Rome’s stability, which is why Cicero had begged him to keep a guard. That mercy he showed in sparing opponents after the civil war only widened the pool of men close enough to strike.

Why did they choose that path, knowing history would stamp them as assassins?

They believed he was turning a citizen republic into a one-man dispensary of honors and offices, and that robbed them of the very game they were raised to play. In a culture where the highest external good was honor granted by the state, living as a permanent client of Caesar felt like a collapse of meaning.

So they picked agency over comfort, even if that meant treachery.

Exactly; they saw more dignity in that risk, though Dante later drops them in the lowest pit.

Before we wrap, I brought you a small relic to lure you deeper into the Empire: a Hadrian coin from a dealer I like. You can make out Hadrian’s title and a figure of Roma on the reverse, a nod to the emperor under whom Plutarch’s life overlapped and a famous patron of Greek culture.

This is fantastic, thank you. Where can listeners find more of your work?

Cost of Glory is on every podcast app and on YouTube, with more at costofglory dot com. We also run immersive retreats in Greece and Rome for people who can’t stop thinking about the Empire and want to think about it even more.

Loved this; can’t wait to do it again. If you want book ideas, grab my Modern Wisdom reading list for free at chriswillx dot com slash books.