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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.