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LXXIII. Plutarch on What Made & Ruined Alexander the Great
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LXXIII. Plutarch on What Made & Ruined Alexander the Great

Today we'll learn from the Life of Alexander the Great, to integrate his virtues and avoid his vices, as analyzed by the moral biographer, Plutarch.

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Stoic Philosophy
Apr 03, 2025
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The Stoic Manual
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LXXIII. Plutarch on What Made & Ruined Alexander the Great
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Welcome! Note that the ‘Neuroscience-based Tools’, ‘Lead to Win’ & the Le Monde Élégant social skills sections are companions for The Stoic Manual to enhance your physical and psychological health, vitality, stress resilience, discipline, focus, motivation, and refine your people skills, relationships & leadership skills for a distinguished life—by Dr. Antonius Veritas


Michelangelo, Pietà, 1498 – 1499

“We can remove most sins if we have a witness standing by as we are about to go wrong. The soul should have someone it can respect, by whose example it can make its inner sanctum more inviolable. Happy is the person who can improve others, not only when present, but even when in their thoughts!”— Seneca

“The character you seem to have been born with is not necessarily who you are; beyond the characteristics you have inherited, your parents, your friends, and your peers have helped to shape your personality. The Promethean task of the powerful is to take control of the process, to stop allowing others that ability to limit and mold them. Remake yourself into a character of power. Working on yourself like clay should be one of your greatest and most pleasurable life tasks. It makes you in essence an artist — an artist creating yourself.”—Robert Greene

Niccolò Machiavelli said,

“A prudent man should always follow in the path trodden by great men and imitate those who are most excellent, so that if he does not attain to their greatness, at any rate he will get some tinge of it.

He should do as those prudent archers do who, aware of the strength of their bow when the target at which they are aiming seems too distant, set their sights much higher than the designated target, not in order to reach such a height with their arrow, but instead to be able, by aiming so high, to strike their target."

Shoot for the stars, aim for the moon—the saying goes.

That passage from Machiavelli was the reason I programmed my mind to make everyone my teacher. I always aim to learn from my friends and enemies, the living and the dead, men and women. I analyze and integrate what works to make them good at what they do, how they conduct themselves to be great & admirable and what ruins them so I can avoid it.

For example, this week I reinforced what greatness means from the greatest quarterback of all time, Tom Brady. He writes,

Greatness can't be context-dependent. It won't come from singular, exceptional achievement. In fact, I would say greatness has to be a way of life in which high achievement is neither singular nor exceptional, but regular and consistent. Greatness has to become a process that involves getting your body and your mind in the right place so you can achieve at the highest level in everything you do, over and over again, on and off the field, every day.

Fundamentally, greatness is about doing the right things, the hard things, consistently and reliably, and doing it not just in the big game, but in every game. The next game. The last game. The game of life.

This doesn't mean you will always win. If anything, it guarantees you will fail fairly often, because to do everything I'm talking about, to put yourself in a position to make greatness possible, means to push the limits. And when you push the limits, the limits push back.


Introduction

Before there was empire, there was a boy with a lion’s gaze, reading Homer by firelight, conversing with the dead. He did not walk, he advanced, as if the earth had been waiting for him to arrive.

They say the gods watched in silence when Alexander crossed the Hellespont—not with reverence, but with fear. He poured libations into the sea and cast a spear into Asia’s soil—not as conqueror, but as a rightful heir come to reclaim what the gods had carelessly scattered.

The winds stilled. The stars watched. History exhaled.

At Granicus, he rode straight into the river, armor flashing like a second sun. At Gaugamela, he broke time itself, three empires tangled in a single hour, undone by a cavalry charge so precise, so final, that even the heavens seemed to stagger.

He named seventy cities like a lover naming children, left monuments in deserts no man returned from, and pursued the ghost of Achilles to the edge of the world. He wasn’t satisfied with glory. He wanted immortality. And when his men begged to turn back beyond the Indus, he wept, not from exhaustion, but from the unbearable truth that no more worlds remained.

Who was this man, raised by Aristotle and trained by war, who held the Iliad beneath his pillow and believed Achilles had merely begun the work? What kind of man dreams beyond empire? What kind of soul believes Olympus itself is not high enough?

That's the theme of today's entry. We'll learn about the Life of Alexander the Great, to integrate his virtues and avoid his vices, as analyzed by the acclaimed moral biographer, Plutarch.


Click on the hypertext to read the others. 1. Lord Chesterfield & Marcus Aurelius on How to Be A Distinguished Man, 2. Machiavelli’s Warning Against Niceness, & 3. Nietzsche’s Consolations for Difficulties.


The Virtues that Made Alexander Great

Plutarch admired many qualities in Alexander. From childhood onward, the young Macedonian displayed traits that set him apart, character that augmented his aura as a conqueror, as a ruler of uncommon soul. It’s easy for a keen mind to discern from his virtues that he was destined to rule and be great, from the outset.


I. Self-Mastery & Discipline

Of all Alexander’s virtues, Plutarch reserves special praise for one: self-control. The ability to master one’s appetites, emotions, and impulses was, in Plutarch’s eyes, the foundation of all leadership and a good life.

“Alexander considered self-mastery a more kingly thing than the conquest of his enemies.”

This discipline was clearest in his attitude toward pleasure. Despite endless opportunities to indulge in the tempting spoils of war, Alexander remained restrained. After the battle of Issus, he refused even to meet the wife of King Darius, the most beautiful woman in Asia. Plutarch tells us that Alexander would not allow anyone to speak lewdly of her in his presence. In a letter to his general Parmenio, Alexander wrote:

“It will be found not only that I have not seen the wife of Darius or desired to see her, but that I have not even allowed people to speak to me of her beauty.”

To Alexander, this was more than good manners. It was a code. When presented with slave boys of rare beauty, meant to please him, he flew into a rage.

“What shameful thing have you ever seen in me,” he thundered at his friend Philoxenus, “that you should make such disgraceful proposals?” The merchant offering the boys was immediately dismissed.

Alexander believed that lust was to be mastered, not indulged. Even the Persian women in his camp, he joked, were “torments to the eyes”—deliberately avoided so he could show off “the beauty of his own sobriety and self-control.” Eventually, he married nobly: one of Darius’s daughters, and later Roxana of Bactria, whom he courted with respect rather than conquest.

This self-discipline extended to other appetites as well. Food and drink were necessities, but Alexander didn’t live to stuff his belly or stay drunk in luxury. Plutarch notes that Alexander’s mother had placed a strict tutor, Leonidas, in charge of his upbringing. He trained Alexander to be hardy and frugal. As a result, even as king, Alexander declined the rich foods and chefs that some hosts offered him. When the queen of Caria kept sending him lavish dishes and desserts, Alexander thanked her but said he already had the best cooks,

“For my breakfast, a night march. For my supper, a light breakfast.”

Hunger and effort, not sauces and sweets, were his preferred seasoning.

He later recalled how Leonidas would sneak into his chambers as a boy to search his chests, “to see that my mother had not smuggled in any softness,” Alexander laughed years later.

His training paid off in war. He endured heat, hunger, and thirst alongside his men. During one desert march, his soldiers scraped together a helmet full of water for him. Alexander accepted it, looked at his parched army, and poured it onto the ground without drinking. If they could not drink, neither would he. Stunned by this gesture of camaraderie, Plutarch tells us the soldiers, “declared that they could not feel tired or thirsty or even like mortal men, so long as they had such a king.” They would follow Alexander anywhere.

Such acts electrified his soldiers. They saw in him not a distant king, but a man of iron discipline, one who asked nothing he would not do himself.

Plutarch also addresses the rumor of Alexander’s heavy drinking. Macedonian kings were infamous for it, and Alexander’s long banquets gave fuel to gossip. But Plutarch insists the truth was different. To the use of wine, he was less addicted than was generally believed. Alexander often talked through the night at these gatherings, more engaged in contests of wit than in cups of wine. When serious matters arose, no pleasure could distract him, not drink, not sleep, not games.

“In the stress of affairs,” Plutarch writes, “he was not to be detained by wine, or sleep, or any sport, or amour.”

This relentless focus and discipline allowed him to achieve more in a short life than most do in decades.

“Though altogether brief,” Plutarch concludes, “he filled [it] to overflowing with the greatest exploits.”

The lesson is clear…


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