Lives of the Stoics: The Art of Living From Zeno to Marcus Aurelius

It cannot be said that Cicero was a Stoic. Nor would he have claimed to be. It’s undeniable, however, that he was a dedicated student of the Stoics. He spent time directly under Posidonius. The blind Stoic Diodotus lived with him for years and even died in Cicero’s home, leaving his estate to the powerful young man he had long tutored. It was the Stoics who, Cicero deemed in his book Tusculan Disputations, “are the only true philosophers.” In fact, it is through Cicero’s writing that much of what we know about Stoicism in the ancient world survives.

But for all this, Cicero could never convince himself to actually live by the principles he would do so much to articulate and preserve. He was a fellow traveler, a man without a party, who for all his success and ambition would turn out to be deficient in the courage and character that his moment in history demanded—that Stoicism demanded he demonstrate.

He was, nonetheless, the great talent of the age.

The first century BC was a time in which the old way of doing things began to break down. There was political conflict and populist uprisings. Demagogues had amassed incredible power. The justice system devolved into a rigged game. The empire frayed at the edges and turned on itself.

This chaos could never slow down a striver like Cicero, but it would define his life.

Cicero was born into a wealthy equestrian family on January 3, 106 BC, in Arpinum, a provincial town about seventy miles southeast of Rome that had only recently received the rights of Roman citizenship. His family name derived from the Latin word for chickpea (cicer), which suggests they had, like Zeno’s family, once been involved in trade.* Unlike the earlier Stoics who had been drawn to politics or public life out of a sense of duty, Cicero was looking for something else—upward social mobility.

How did this upstart country boy find his way into a book of Stoic lives? His inspiration was not the reluctant politics of Diogenes, the ethical bent of Antipater, the behind-the-scenes influence of Panaetius, or even his own Stoic teacher Posidonius. His first inspiration was instead the meteoric rise of Marius, the one whose last breaths had been observed by Posidonius, who had achieved—through raw ambition—immense power and fame even while lacking an illustrious bloodline. Marius too was an upstart from Arpinum. When friends suggested that Cicero change his name to hide his nouveau riche origins, he vowed instead to achieve fame so great that no one would ever say such a thing again. Indeed, he and Marius would both become novi homines, “new men,” the first of their families to rise to senatorial power from outside the patrician ranks of Rome.

Cicero’s life in Rome began in 90 BC, when at the age of sixteen he was sent there by his father to study public speaking and the law. He entered the capital with the benefit of his father’s business connections, and immediately fell in love with what we might now call the life of the “elites.” As biographer Anthony Everitt notes, “It was during these years that Cicero’s ambition to become a famous advocate crystallized. . . . He was swept along by the almost unbearable excitement of the trials in the Forum and the glamour of the lawyer’s job, very much like that of a leading actor.”

While other young men in his position partied and enjoyed their wealth (and lack of parental supervision), Cicero studied like a man with something to prove. He was said to produce—as a deliberate homage to a philosophical hero, no doubt—as many as five hundred lines per night, just as Chrysippus was famed to do. Cicero wrote and read and observed. Did he love philosophy and literature? Of course. But he also saw it as a way to get ahead. It was the vehicle for realizing his potential, just as a natural athlete is drawn to sports and squeezes from the game every advantage they can. Cicero networked too, meeting other young men handpicked for great things, including a boy six years his junior, Gaius Julius Caesar.

Cicero’s early years were almost like a training montage for the cinematic and pivotal events he would face in the prime of his life. And perhaps we see it like that because Cicero—himself the source of so much of what we know about him—was a conspicuous crafter of the narrative of his own rise.

The story goes like this: At eighteen, he attached himself to Philo of Larissa, head of the Platonic Academy who had fled Athens for Rome. He took on his first legal cases during the tumultuous reforms of Sulla, winning several impressive victories against the powers that be. He finished his first book on rhetoric—becoming a respected author at just twenty years old. Then he decamped to Athens for more studying under teachers of every school. Then he hit the road again to study Stoicism with Posidonius in Rhodes, where genius quickly recognized genius.

By the time Cicero returned to Rome at age twenty-nine, he was a man transformed by the crucible of many years of hard work and relentless drive. “And so I came home after two years,” he wrote, “not only more experienced but almost another man; the excessive strain of voice had gone, my style had so to speak simmered down, my lungs were stronger and I was not so thin.”

Notice he lists only attributes, not convictions.

That is the critical question of nearly everything Cicero did, as it is for so many talented, ambitious people: Were the motivations sincere? Or was it all part of some plan? Are they training or résumé building?

It was said that an oracle had warned Cicero early to let his conscience guide his life, not the opinions of the crowd, but for someone as driven as Cicero, such a warning was impossible to heed. Seneca would later write of the importance of choosing oneself “a Cato”—someone to use as a ruler to measure and guide oneself against. Cicero, who lived alongside a real Stoic like Cato, chose, for the most part, to look elsewhere for inspiration. Instead of Cato, Cicero had, in early life, chosen Marius, which is a little like choosing Richard Nixon or Vladimir Putin as one’s lodestar.

It was a strange, revealing choice. As the Stoics were fond of saying, this character trait proved to be destiny.

Having checked all the boxes by the end of his twenties, it was time for Cicero to begin his political ascent, which he had planned for so long. At thirty, a Roman was eligible to stand for the office of quaestor—which translates to “the one who asks questions,” but were simply those who drew up laws and answered to petitioners—and then become a member of the Senate. Cicero’s family leveraged their wealth and contacts to make sure he won his first election handily. He wasn’t just a natural, but a worker. Inspired by craftsmen who knew the names of each of their tools or instruments, Plutarch tells us, Cicero actively cultivated the habit of knowing not only the names of all of his eminent constituents, but the sizes of their estates, their businesses, and their needs.

Not needs in the Stoic sense, as in what was good for the polis, what was good for the state, but needs in the raw political sense. What did they want? What could he do for them? Where did their interests align, quid pro quo. There’s no question that Cicero was an able politician. He was, in fact, the best in a generation. But he operated by a compass quite different from that of Diogenes or Antipater or Posidonius.

By 75 BC, Cicero was ensconced in office, and assigned as a tax collector and manager in Sicily. He took to administration quite easily and ably, but unlike the populists of his time, he remained a lover of high culture and philosophy. While in Sicily he tells the colorful story of tracking down the grave of Archimedes in Syracuse, which by this time was nearly a century and a half old and abandoned and overgrown. In his classic and rather egotistical style, Cicero would praise himself for his work in uncovering it: “So you see, one of the most famous cities of Greece, once indeed a great school of learning as well, would have been ignorant of the tomb of its one most ingenious citizen, had not a man of Arpinum pointed it out.”

If the self-indulgence rings awkward now, imagine what it must have sounded like then.

Sicily had been only a way station for Cicero and served what later biographers would describe as his philodoxia and philotimia—loves of fame and honor, precisely what the oracles had warned him to be wary of. He took the job so he could become a senator, which in and of itself was a dizzyingly high honor for a man whose family just a few generations before was not even afforded the rights of citizenship. By no means sated by this accomplishment, Cicero quickly began planning to leap to higher and higher ones. In 71 BC, he took on as prosecutor the case of extortion brought by Sicilian citizens against Verres, hoping it would aid his next step in his cursus honorum—what the Romans referred to as the “ladder of offices” that the ambitious climbed—to the post of aedile, which regulated and enforced public order, in 70 BC. Cicero conducted a backbreaking fifty-day investigation and returned to Rome with a vast trove of documentary proof against the crimes of Verres.

It was a dramatic case. Verres had stolen forty million sesterces during his three years in Sicily, and Cicero had the proof. As he told the court in his opening statement, “It is this man’s case that will determine whether, with a court composed of Senators, the condemnation of a very guilty and very rich man can possibly occur. And further, the prisoner is such that he is distinguished by nothing except his monstrous offences and immense wealth: If, therefore, he is acquitted, it will be impossible to imagine any explanation but the most shameful; it will not appear that there has been any liking for him, any family bond, any record of other and better actions, no, nor even any moderation in some one vice, that could palliate the number and enormity of his vicious deeds.” Cicero knew the jury had been bribed, and yet he somehow secured a conviction. And now, holding the office of aedile, he was doubly victorious.

It was a great day for that Stoic virtue of justice—of fairness and truth—but was that why he struck it? Does it matter?

The constant theme in Cicero’s life is movement—movement forward, movement upward. Nearly everything he did, including winning important corruption cases like the one against Verres, had a double motive. He often did the right thing, but he did it with more than half an eye on what it could do for him. It wasn’t exactly Stoic . . . but it worked.

Since Cleanthes and Zeno, the Stoics had been, as a rule, indifferent to wealth and status. As much as Cicero respected them, he could not abide by this firmness. He would not abstain from luxury. He would chase it. An accomplished lawyer and politician, he first took Antipater’s advice and married a wonderful and rich woman named Terentia and started a family. Then he used his wealth, both inherited and marital, to acquire property. Ultimately, he would own nine villas, along with other real estate investments—including a seaside resort in Formiae and, the most prized of all his villas, the one in Tusculum that had belonged to Sulla himself. In addition to his family’s money and his wife’s dowry, Cicero amassed a large fortune through what seems like unethical means. Cleanthes, at Zeno’s direction, had rejected bequests offered to him. Marcus Aurelius would do the same for anyone who left him in their will. Cicero, on the other hand, seemed to be almost a professional son—a striver who wormed his way into people’s estates so they might one day leave him money.

Near the end of his life, Cicero gave an astounding tally of this source of income: “Actually my account books show that I have received more than twenty million sesterces in bequests. . . . Nobody ever made me his heir unless he was a friend, so that any benefit there came along with a certain amount of grief.” His Stoic teacher Diodotus could not have been too repulsed by this practice, for he too would leave everything to Cicero when he died in his home in 60 BC. But still, it’s hard to not find the whole thing strange.

“If you have a garden and a library,” Cicero would write in a letter to a friend as they discussed Chrysippus and Diodotus, “you have everything you need.” Clearly there was a part of him that didn’t fully believe that, that could not be content with the simple or the reflective life. Like many people, he seemed to believe that he needed wealth and fame too. Like many of us who crave those same things, he did not quite realize what they would cost him until he got them . . . and by then it was too late.

Still, to his credit, for all his ambitions and expensive tastes, Cicero drew a clear line at corruption. Unlike far too many Roman politicians, he would accept no bribes. An admirable and honest public servant, he refused to take legal fees for his services. Of course, this stand is easier to take when you inherit millions.

Having served as quaestor and then as aedile, the next office to be gained for Cicero was praetor, which he ran for and won at age thirty-nine in 67 BC—serving at the youngest age possible under law at age forty in 66 BC—due in no small part to his support of Pompey. This too was a launching pad for the final and most prized position, particularly as a “new man”: consul. The Senate chairman and commander of the Roman army, the role of consul was almost exclusively reserved for Rome’s most elite families. As the historian Gerard Lavery points out, in the final 150 years of the Roman Republic only ten novi homines were elected consul. Between 93 and 43 BC, Cicero would be the only one.

Cicero’s path to the top would not be uncontested. He faced two rivals for the position, Catiline and Antonius. Playing to his strengths, Cicero began a blistering rhetorical campaign against “the murderous and corrupt” Catiline, warning the Senate and people of a brewing plot to usurp the Republic. It was enough to win Cicero the consulship. But the cost would be high—whether Catiline had been part of a plot before is up for debate, but after being on the wrong end of Cicero’s slander, he was ready to burn the whole system down to exact his revenge.

Cicero took office in 63 BC in the midst of an economic crisis. Eastern trade routes had been closed off by Rome’s enemies. Unemployment was high. Recession affected all walks of life in Rome. Tensions brewed, as they do in such times. Cicero promised concordia ordinum, the concord of the classes—but what he really meant was that he could keep everything from exploding. Actual fairness could not have ranked high on his list of concerns, even if he had been taught its benefits, its virtue, by Posidonius or Diodotus.

Cicero passed a law to increase the penalty for election bribery to ten years of exile—a good law, to be sure. But was it solely for the benefit of the people? Or was it a move against his political enemies? Catiline believed the law had been aimed at him and launched a plan to assassinate Cicero and his allies in the Senate. When a prominent Roman delivered letters purporting to show Catiline’s scheme, Cicero convened the Senate and gave the speech of his life.

“When, O Catiline,” he began, “do you mean to cease abusing our patience? How long is that madness of yours still to mock us? When is there to be an end of that unbridled audacity of yours, swaggering about as it does now?

“Shame on the age and on its principles!” Cicero called as he demanded the execution of his enemy. Catiline, who was in the audience for this harangue, meekly attempted to reply. He was no match for such a brilliant speaker. All he could do was fall back on the tropes of Rome’s elitism. He pointed out that Cicero came from no great family. He questioned the credibility of a self-made man.

It didn’t work.

So he fled—to the army he had in waiting, proving beyond a doubt that Cicero was right. Catiline was a traitor and a rebel. But how serious the threat actually was remains in doubt. Contemporaries and historians alike suspect that Cicero, always looking for power and the spotlight, may have significantly exaggerated the peril of the nation—for personal gain.

The Senate, trusting in Cicero, bestowed on him nearly dictatorial powers to put down the threat. The Republic and Cicero himself, like many empires believing they faced an existential threat to their institutions, warped under the pressure. Cato, the Stoic, urged Cicero to exact the full measure of the law from these criminals. It was only just, he said.

Cicero had absolute power in his hands. He hesitated, but not for moral reasons. He was, as always, thinking of his reputation. His wife, Terentia, proved an unexpected but decisive vote, interpreting a sacrifice that had frightened some others as a sign that her husband must wield the power that had been given to him.

The conspirators were put to death without trial by his order, and thousands more in their supporting armies died. In thanks, the Senate would bestow on him the title of “Father of His Country,” but the extreme measures and the lives touched by so many deaths would hang over him for the rest of his life—and indeed, all of history.

What remained untouched through the ordeal was Cicero’s sense of his own destiny and greatness. Plutarch tells us that within days, Cicero began a campaign to burnish his accomplishments. “One couldn’t attend a Senate or public meeting,” Plutarch wrote, “nor any session of the courts, without having to listen to the endless repetitions. . . . This unpleasing habit of his clung to him like fate.” No amount of credit or praise was enough.

Cicero enshrined what he believed to be his own magnificence in writing as well. He tried to induce Posidonius to cover his consulship in his great fifty-two-volume history. When Posidonius declined, Cicero wrote a letter “the size of a book” to Pompey in 62 BC on the subject of his own achievements. Pompey acknowledged it with no more than a shrug. Cicero was undeterred—he was convinced he had saved the country. History, he thought, was in his debt.

The historian H. J. Haskell captures the contradictions in Cicero’s character well. He was talented, he was brilliant, he was steeped in the wisest philosophy of every school, and yet “he was too sensitive, too vain, too dominated by personal feeling, too open to impression, to become a great leader of men. At times he saw both sides of public questions too vividly to enable him to make up his mind, close it to all doubts, and drive ahead. At other times, when his hatreds became engaged—and he was a fierce hater—he would plunge forward recklessly.”

Cicero knew what the Stoics warned of the passions, but he did little work on reining in his own. And so, time and time again, they would come back to cause exactly the kind of suffering that the Stoics since the days of Zeno had been warning against.

Like the figures in Posidonius’s writings, Cicero would get nearly everything he wanted . . . and come to regret it.

Cicero’s consulship and brief moment of crisis leadership were the high-water mark of his life. It would be a staggered series of downhill declines from there. The country moved on, and as the oracle had predicted, the gratitude of the crowd was not enduring. Caesar, Pompey, and Crassus would form their Triumvirate in 60 BC, creating a front of enemies opposed to Cicero. The next consul, in 58 BC, turned openly against Cicero, passing a proscription against him for having condemned citizens to death without a trial. Cicero had to flee Rome in exile, while his property was destroyed.

It was Seneca who observed how quickly time and fate would afflict on Cicero “everything that a victorious Catiline would have done.” In fact, his banishment was repealed a year later, but still, change—or dissolution—was in the air.

For the most part, Cicero steered clear of the city. He turned, as much as he could, back to writing and philosophy. He pored over the books at the library of Faustus Sulla near his villa in Cumae, which was once the home of the Stoic teacher Blossius. He worked on a book, On Oratory (56 BC), where he compared Cato’s use of rhetoric to that of Rutilius Rufus, showing how Rufus’s decision to maintain his Stoic brevity in the face of his accusers failed him at precisely the moment good rhetoric could have saved him. Worried about the future of Rome, he wrote two works, Republic and Laws, which drew on the Stoics Diogenes of Babylon and Panaetius.

But like many historians, and even readers today, he was missing what was staring him in the face: the lives these figures had lived. He was missing the common thread through those four Stoics. Character. Commitment. Purpose.

In 51 BC, Cicero was awarded the governorship of Cilicia—a position well out of the fray of Roman politics, which helped to reburnish his reputation. Really, though, it was a brief respite from the chaos fate had in store for him and for Rome.

Cicero once wrote that the beginnings of things are small. He would also find in those few short years that the ends of things are surprising and fast. In early 49 BC, Caesar—Cicero’s former friend and peer—would cross the Rubicon. Caesar’s ambition had been slower burning than Cicero’s, less self-aggrandizing, but far more aggressive and unbending—and it was backed by the wealth produced by an unmatched and deeply feared army in Gaul. Civil war ensued. By September 48 BC, Pompey—whom Cicero had praised in his first major political speech, and whom his teacher Posidonius had tried to instruct about virtue—would be dead.

Who could stop Caesar now? One would think that this would be the pivotal moment for such a student of philosophy, and a master orator like Cicero—when fate met the man whose time had come. But Cicero, the ambitious striver, was not prepared to meet it. We have, with the benefit of hindsight, the perspective to see that he had wasted himself on the wrong crisis. Thinking that the Catiline conspiracy was his moment to perform for history, he had moved too soon, too severely. He gained fame from it, but the victory was Pyrrhic.

Now the Republic really was hanging in the balance. Never before had Cicero’s talents—his ability to persuade, to move the crowd, to tell a story that would drive people to the barricades—been more needed, but he could not summon an audience that would listen. He was impotent too, without much power. Spent, he could do nothing.

Or was he a coward? Offered a command of troops in the Republican cause, Cicero inexplicably turned it down.

Only Cato—the Stoic who wrote less but lived the ideas—was willing to fight. But it was not enough. By 46 BC, with Caesar ascendant, Cato committed suicide in Utica, forever a martyr to the Republican cause. Cicero eulogized him, attempting to capture in words the power of this Stoic he both admired and judged, but whose commitment to principles he lacked. He, along with the rest of Rome, was ready to yield to Caesar and “accept the bridle,” as Plutarch puts it.

Cicero’s eulogy of Cato is a case in point—although only fifty words of the tribute survive, we know he censored himself for fear of angering Caesar and Caesar’s supporters. Both Cato and Cicero cared about what was right—but Cicero cared about himself a little bit more. Cato believed in courage. Cicero believed in not getting killed.

The choice earned Cicero a few years of life, but the Stoics would ask—as we should ask of all self-preserving compromises—“At what cost?”

The one upside of Cicero’s capitulation and his fair-weather commitment to philosophy is that by living he was able to continue writing, and to serve as a kind of bridge between Greek and Latin philosophical thought, especially in the area of ethics. And when it came to ethics, he knew of no better source in all of Greek and Latin literature than the Stoics. In the end it wasn’t the accomplishments of public office that made his glory, or how Cicero lived his life, but what he set down in writing—wisdom from the Stoics that would endure to our own time.

In 46 BC, Cicero published the Stoic Paradoxes, dedicated to Marcus Brutus, who himself had strong Stoic leanings. In what was more a rhetorical exercise than a serious philosophical treatment, he explored six of the primary Stoic paradoxes:

that virtue is the only good;

that it is sufficient for happiness;

that all virtues and vices are equal;

that all fools are mad;

that only the sage is truly free;

that the wise person alone is rich.

These were not paradoxes in the logical sense, only in that they flew in the face of common sense. It was actually the counterintuitiveness of these ideas that the Stoics leaned on to catch people’s attention: How can virtue be the only good if we need health and money to live? Is a lie really as bad as killing someone? Plenty of philosophers were visibly poor; how are they rich? The possibilities for discussion, for counterexamples, for gotcha moments, were endless—and Cicero loved noodling with the prompts laid down by Zeno and Cleanthes and Aristo and everyone else.

Ironically, what hurt Cicero in politics—the size of his ambition, his vacillation, his desire to please—suited him supremely well in the self-appointed task of being the first to give an eloquent and detailed account of Greek philosophy in the Latin language. While drawn to the rigor and precision of the Stoics, and to their well-developed ethical thinking, he danced with the Academic/Platonist school most regularly, with its skeptical method and insistence on arguing every side of any issue.

As an Academic, his opportunism made for great writing. So too his ability to talk and entertain ideas he didn’t actually believe. He was a little like Carneades, arguing all sides of the discussion. This habit, infuriating to those around him, undoubtedly preserved all sorts of disparate sources for us that we can continue to enjoy today. It was beautiful writing, with ideas that would shape the world. Saint Jerome would later worry that he loved Cicero’s works more than the Bible. Saint Augustine was converted to philosophy by reading Cicero’s now lost work, the philosophical dialogue Hortensius. Seneca and other Stoics would read his works with great interest. But as a person, as a leader, his foot-in-both-camps mentality was a shameful vice.

Eventually the bill from the latter came due. The last years of Cicero’s life were a mad dash to write and to escape the blows of fate. Indeed, with the exception of a book on rhetoric, De Inventione, composed at the early age of around twenty, his major books were all written in a twelve-year span between 56 BC and 44 BC, and in fact the bulk of them between 46 and 44 BC.

If Cicero had completely retreated into his books, we might admire him. Plutarch tells us that he made it a point to visit Rome and pay his respects to Caesar, and even awarded him honors. When Caesar rebuilt a torn-down statue of his own rival, Pompey, Cicero was there to flatter him, perhaps in the way that he himself had always wished to be flattered. In setting up these statues of Pompey, Cicero slobbered, you have firmly established your own.

Cato, whose martyred body lay fresh in the grave—as did Pompey’s—would have been sick at the scene.

In 45 BC, Cicero’s beloved daughter Tullia died. Here, Stoicism might have served him well, as he would later advise his friend Brutus over his own tragic loss in a few years. Instead, with nothing to fall back on, nothing to reassure himself, only the ideas in his books and his faltering ambitions, he was bereft and broken. His career seemed over. His life was falling apart.

So Cicero continued to write, but not live, philosophically. He continued to write about Stoicism, but declined to take any of it to heart. In a way, this would be a major contribution of his to the philosophy. By falling short of the doctrines he passed along from Zeno, from Chrysipus, and even from Stoic peers he wrote about like Rutilius Rufus and Cato, he was proving why the ideas matter. He was like Diotimus, showing us what not to do.

Cicero would dedicate his book Tusculan Disputations to his friend Brutus, and in 45 BC, Brutus in turn would write a book inspired by Stoicism, On Virtue, which he would dedicate to Cicero.

Unlike Cicero, Brutus wasn’t just dabbling. Like Cato, like a real philosopher, he was prepared to risk everything to save the country he loved: He was going to assassinate Julius Caesar, now the dictator of the republic Cicero and Brutus had loved. When Brutus and Cassius and the other conspirators hatched their plot to kill Caesar, however, they left Cicero out of the loop. They believed he was too nervous, too untrustworthy, too likely to second-guess the plot or undermine it, unintentionally or not. In short, when the moment counted, Cicero couldn’t be counted on. He wasn’t Stoic enough.

Shakespeare renders it this way:

CASSIUS

But what of Cicero? Shall we sound him?

I think he will stand very strong with us. . . .

BRUTUS

O, name him not! Let us not break with him,

For he will never follow anything

That other men begin.

They feared their friend lacked courage and that his ego would hold them back. History would bear this out. Almost immediately after Caesar’s death, Cicero began to take credit for the other men’s deed, claiming that Brutus had shouted his name as he plunged the dagger in.

As Cicero would explain in a speech, “Now why me in particular? Because I knew? Quite possibly the reason [Brutus] called my name was just this: after an achievement similar to my own he called on me rather than another to witness that he was now my rival in glory.”

What’s past is prologue, Shakespeare would say, and so it was with his own life. His need for fame, his tendency to shift with the wind, would dog him to the end. In Caesar’s wake rose young Octavian and Mark Antony. Cicero would again choose the wrong side and, conspicuously, decline to serve in the civil war he helped bring about.

Cicero’s final work, surprisingly, would be on duty. He had never been a man whose career was about duty. Fame. Honor. Proving doubters wrong. That had been his drive. But with his twenty-one-year-old son, Marcus, just completing his first year of philosophical training in Athens, perhaps Cicero wished to instill in his boy a stronger sense of moral purpose than his own ambitious father had in himself. The work premises that Marcus, like Hercules at the crossroads, is being wooed by vice and at risk of forsaking the path of virtue. In response, Cicero took up the Stoic efforts of Diogenes, Antipater, Panaetius (above all), and Posidonius to not only lay down Stoic ethical theory, but give his wayward son the practical precepts he needed to keep him off the road to ruin.

In the work’s dedication, he wrote to Marcus:

Although philosophy offers many problems, both important and useful, that have been fully and carefully discussed by philosophers, those teachings which have been handed down on the subject of moral duties seem to have the widest practical application. For no phase of life, whether public or private, whether in business or in the home, whether one is working on what concerns oneself alone or dealing with another, can be without its moral duty; on the discharge of such duties depends all that is morally right, and on their neglect all that is morally wrong in life.

They are words well written, as was nearly everything Cicero produced. What was missing, it seems, is any personal absorption of them.

In the end, it would be Cicero’s love of rhetoric that would seal his personal fate. He had chided Rutilius Rufus for his brevity in the face of his accusers, saying that rhetoric might have saved him. But walking the plank in 44–43 BC, Cicero delivered fourteen orations against Mark Antony, one of the heirs to Caesar’s power.

It would be one thing if Cicero had, as Cato would have, simply condemned excess and brutality where he saw it. Instead, his Philippics, as the speeches are now known, were a political ploy to play Mark Antony off Octavian, Caesar’s nephew, both with equally authoritarian designs. Cicero was splitting the difference, not standing on principle. And considering his grandiose comparison of his own speeches to those made by Demosthenes more than two hundred years earlier, it’s clear that once again he was motivated more by the limelight than by truth.

The remarks were his undoing. Caesar, though a tyrant, had always shown leniency and good humor—and love for the art of rhetoric. Mark Antony possessed no such gentleness. The Second Triumvirate debated Cicero’s fate for several days, and then, deprived of a trial—as he had deprived his enemies so many years before—the sentence was in: death.

He tried to flee. Then wavered and returned. He contemplated a dramatic suicide like Cato and, shuddering at doing anything so final, struggled on.

Cicero had long talked a big game. He had written about duty; he had admired the great men of history. He had accomplished so much in his life. He had accumulated mansions and honors. He had been to all the right schools. He had held all the right jobs. He had made his name so famous that no one would ever care about his lowly origins again. He was not just a new man, he was, for a period, the man.

But he had compromised much to get there. He had ignored the sterner parts of Stoicism—the parts about self-discipline and moderation (as his chubby visage demonstrates), the duties and the obligations. He had ignored his conscience, in defiance of the oracle, to seek out the cheers of the crowd. If he had followed Posidonius and Zeno better, his life might not have turned out differently, but he would have been steadier. He would have been stronger.

Now, when it counted, there was nothing in him, nothing in his fair-weather personal philosophy that could have helped him stand up in this moment where cruel fate was bearing down on him. He could not rely on the inner citadel that countless Stoics had when they faced death, because he had not built it when he had the chance.

All Cicero could do was hope for mercy.

It did not come. Exhausted, like an animal that’s been chased, he gave up the fight and waited for the killing blow. The assassins caught up with him on a road between Naples and Rome.

He was beheaded, his head, hands, and tongue soon impaled on display at the Forum and Mark Antony’s house.

“Cicero is dead.”

That’s how Shakespeare rendered the sudden fall of this great man. It was abrupt, violent, and final.

One of Caesar’s soldiers, Gaius Asinius Pollio, would write one of the most insightful epitaphs for Cicero:

Would that he had been able to endure prosperity with more self-control, and adversity with more fortitude. . . . He invited enmity with greater spirit than he fought it.

Indeed.