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Sources tell us that Aristo added to this contrarian approach a rather forceful style, and that he spoke much more than he listened, flouting quite deliberately Zeno’s dictum about the natural ratio between ears and mouths. Diogenes reports that Aristo would discourse at great length, and with little grace, overwhelming weaker minds in the process. At times, Zeno had no choice but to interrupt and cut him off. You’re a babbler, he once shouted at him, and I suspect your father was drunk when he sired you.

It wasn’t a Stoic response, but one every frustrated and exhausted teacher can sympathize with. Still, has yelling ever deterred a contrarian? It didn’t stop Aristo’s questioning or contradictions either. Indeed, his antipathy to Stoic orthodoxy extended into writing, where he attacked his fellow Stoics aggressively, even publishing an argumentative book on Zeno’s doctrines and a book titled Against Cleanthes.

These written attacks were answered, Cicero tells us, by Chrysippus, who returned fire with a book against Aristo, and also had a direct personal confrontation with him about the dangers of his commitment to total indifference. “We might ask,” Chrysippus pressed, “how could we live a life if it didn’t matter to us whether we were well or sick, at ease or racked with pain, whether we could keep off cold or hunger or not.”

Indeed, how could we? Life would be chaos.

Aristo was undeterred, answering with confidence and a smile, “You’ll live, splendidly, wonderfully. You will act as seems right to you, you will never sorrow, never desire, never fear.”

It’s as tempting—and empty—a call as any Siren has ever made. And a little beyond the reach of most, however enticing it sounded. Yes, the true sage firmly grounded in the right principles will intuitively know just what to do in every situation and won’t need a rulebook. But what about the rest of us?

Is that even possible—a world where everyone, as Aristo claimed, should simply do “whatever may enter one’s head”? Is that a world anyone would want to live in?

We can imagine these great Stoics pulling their hair out in frustration. We can see their desperation in their tricks and lost tempers. This guy is giving Stoicism a bad name. I thought we were on the same team here. Aristo presents to us the conundrum that John the Baptist presents to Christians and that contrarian figures have always presented to incipient movements. Is this person a rival or a follower? A saint or a heretic? A friend or a foe? Aristo was all these things, then and now.

Shunned by the Stoics, while perhaps still considering himself in their camp, sharing many of the ideas of the Cynics, influenced by the skeptical Academy, locking horns with the Peripatetics, Aristo by his independence earned himself a spot outside the walls of Athens, away from the Stoa Poikilē, in a Cynic gymnasium called, appropriately, the Cynosarges. As with the Sirens for whom he was nicknamed, men flocked to him. Aristo taught there with other radicals like Antisthenes, one of the founders of the Cynics. Aristo earned fame and was soon regarded as the founder of his own school, as Diogenes tells us: the Aristonians, who were known for persuasiveness and decency.

But as a challenger he had his enemies. He would say that “when people build up their reputations little by little, other people attack from all sides,” which is true, though one suspects his contrarianism and challenging demeanor had something to do with the antagonisms he faced more than anything else. Could a more conciliatory and respectful Aristo have accomplished more? Almost certainly, and it would be left to the later Stoics to prove that working within the system was a more effective way of changing minds than challenging everyone and everything.

Aristo taught that beyond following virtue or excellence, when dealing with indifferents, the wise man will simply do whatever pops into his head. He was the first Stoic we know to push the argument that the wise person is like an actor who willingly takes on the roles assigned by fate. We’ll hear this very same argument from Epictetus centuries later, who himself would reprimand his students for asking for rulebooks, as if they could run their whole life by a script. Aristo and Epictetus both felt that when it came to playing our role in life, the script was already written and we shouldn’t be trying to come up with our own. We should work hard at living up to our given roles. But unlike Aristo, that didn’t stop Epictetus from giving lots of good advice.

Diogenes also tells us that Aristo was fond of the idea that he, being a wise man and having true knowledge, would therefore not be misled by mere opinions. This so alarmed the Stoics that they sent Zeno’s scribe to prove him wrong. The prank was simple: He had one twin deposit a sum with Aristo for safekeeping and then the other brother, pretending to be the one who had deposited the money, come and reclaim it. Aristo, who had so arrogantly claimed that he could make a wise decision in any circumstance, stupidly gave the money to the wrong brother.

It was a simple case where a rule—like checking for identification—was vastly superior than relying on your gut. When Aristo discovered that he had given the money to the wrong brother, he was dumbfounded and embarrassed that his wisdom had been so refuted.

Once again, was it Stoic for them to play such a trick? To do so with the intention of humiliating a fellow Stoic over such a minor difference of opinion? The rift was bigger than that, however.

Aristo’s school, in a kind of deliberate hard fork that deviated from Zeno and Cleanthes, had abolished the topics of physics and logic. The former is beyond us and the latter not worthy of concern, was Aristo’s position. Only ethics mattered, only virtue.

With little irony, this master of clever arguments held that the arguments of a logician were like a spider’s web—clearly a product of expertise, but completely useless (though quite useful to spiders!).

Aristo’s questions encouraged other heterodox and renegade thinkers, which must have created the sense inside third-century BC Athens that Stoicism was a school tearing itself apart.

It should humble and shame us a little to see, in retrospect, how insignificant these intensely—and violently—argued debates were. To the early Stoics who fought them, however, the distinctions of “preferred indifferents” were a matter of life and death. Power and influence and ego played a part in this. Only Cleanthes had kept his day job, which meant that these philosophical debates were everything to a Zeno or a Chrysippus or an Aristo. They were like cloistered monks arguing over how many angels could fit on the head of a pin.

It was the narcissism of wanting to be right—to be the one who settled the debate. With the future of the school up for grabs after Zeno and Cleanthes, who could afford to concede? Being remembered by history does very little for you after you’re dead . . . but it’s hard to be indifferent about your legacy.

All understandable, but hardly philosophical, let alone Stoic. It would have been far more impressive if these men could have prevented antagonisms from dominating their relationships with people with whom they mostly agreed. They should have focused on their work, their self-improvement.