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Seneca had grown and continued to grow quite wealthy under Nero’s regime. In just a few short years, he had amassed, largely through gifts from his boss, a fortune of some three hundred million sesterces. He was certainly the richest Stoic on earth, possibly the richest ever to live. One source notes that Seneca owned some five hundred identical citrus wood tables with ivory legs just for entertaining. It’s an odd picture, thinking of a Stoic philosopher—descended from the frugal school of Cleanthes—throwing Gatsbyesque parties funded by the gifts of his murderous boss.

Although most art renders Seneca as lean and sinewy, in fact the real likeness of him survives only in the form of one statue, dating to the third century, which is actually a double bust of Seneca and Socrates. Seneca loved Socrates, marveling once that “there were thirty tyrants surrounding Socrates, and yet they could not break his spirit.” Both men don the classic philosopher’s toga. Curiously, Socrates’s wraps both shoulders, while Seneca’s right shoulder is bare—perhaps a nod to his line about how a man must realize how little he needs to be happy, it is “the superfluous things that wear our togas threadbare.” But the portrait also reveals Seneca as the older man who had clearly enjoyed his share of sumptuous banquets, and had grown quite fat in Nero’s service.

Much of our knowledge about Seneca’s opulence and fortune comes to us via a man named P. Suillius, a Roman senator who was angry at Seneca, suspecting he was behind the revival of Lex Cincia, a law with a provision that lawyers plead cases without compensation. While Suillius’s motives were quite suspect and he would later be convicted on serious criminal charges and banished from Rome, there was at least some truth to his written attacks on Seneca’s hypocrisy. Even Seneca’s response—in his essay On the Happy Life—seems to set up a standard to which he obviously falls short:

Cease, therefore, forbidding to philosophers the possession of money; no one has condemned wisdom to poverty. The philosopher shall own ample wealth, but it will have been wrested from no man, nor will it be stained with another’s blood—wealth acquired without harm to any man, without base dealing, and the outlay of it will be not less honourable than was its acquisition; it will make no man groan except the spiteful.

Cato was rich. So was Cicero. Neither of them grew rich in the service of someone as odious as Nero, however. Arius and Athenodorus were rewarded handsomely for their service to Augustus . . . but Augustus never murdered his own mother. Cato loaned much of his money to friends without interest, and did not seem interested in growing his fortune for its own sake. “What is the proper limit to wealth?” Seneca would later ask rhetorically. “It is, first, to have what is necessary, and second, to have what is enough.”

Clearly he struggled with that idea of enough. Over several years, he lent out something like forty million sesterces at high rates to Rome’s British colony. It was an aggressive financial play, and when the colony struggled under the debt, a brutal and violent rebellion broke out that eventually needed to be put down by Roman legions.

Seneca had said that a philosopher’s wealth should not be stained in blood, but it’s hard not to see the drops of red on his.

Why couldn’t he stop himself? It’s strange to say that his talent and brilliance were to blame, but it’s true—as it is for so many ambitious people who end up with controversial fame and fortune. He had been groomed since birth for greatness, expected to become a leading man of his time. He had taken every opportunity that life had given him and tried to make the best of it, he had persevered through difficulties that would have sunk anyone who wasn’t a Stoic, and he had enjoyed the good times too. He had not complained, he kept going, kept serving, kept trying to have impact and to do what he had been trained to do. What he had never done was stop and question any of it, never asked where this was leading him and whether it was worth it.

By 62 AD, it was harder to deny the compromises he was forced to make on a daily basis in Nero’s world. Perhaps there was some lost event that broke him out of his stupor. Perhaps the moral conscience he had learned from Attalus finally won out in the battle with his desire to achieve.

Finally, finally, Seneca attempted to withdraw. We know he didn’t confront Nero. That would have been too much. There is no evidence of a principled resignation, as the Stoic-inspired secretary of defense James Mattis would give to President Donald Trump in a disagreement over policy in Syria. Instead, Seneca met with the emperor and futilely attempted to convince Nero that he didn’t need him anymore, that he was old and in bad health and ready to retire. “I cannot any longer bear the burden of my wealth,” he told Nero. “I crave assistance.” He asked Nero to take possession of all his estates and his wealth. He wanted to walk away clean into retirement.

It would not be so easy.

He’d gotten his hand bloody grabbing the money, and there would be blood getting rid of it.

A few days after their meeting, Nero murdered another enemy.

In 64 AD, the Great Fire struck Rome, and, boosted by strong winds, would destroy more than two-thirds of the city. One rumor spread that Nero had started the fire himself, or at least allowed it to burn for six days so that he could rebuild the capital as he liked. His reputation as a dilettante and a psychopath were fertile seeds for these conspiracy theories, and so, moving quickly, Nero found a scapegoat: the Christians. How many he ordered to be rounded up and killed we do not know, but one of them was a brilliant philosopher from Tarsus—the same intellectual ground that spawned Chrysippus, Antipater, and Athenodorus—who had earlier escaped death thanks to Seneca’s brother during Claudius’s reign. Saul of Tarsus, whom we know today as Saint Paul, was added to Nero’s pile of bodies.*

As blood flowed and fires burned, could Seneca feel anything but guilt? Tyrannodidaskalos—tyrant teacher. That’s what they called him. It was true, wasn’t it? Hadn’t that been what he had done? Hadn’t he shaped Nero into the man he had now clearly revealed himself to be? At the very least, it was hard to argue that Seneca hadn’t lent credibility and protection to the Nero regime. Maybe it was despair that Seneca felt in those dark days—what he had tried to hold off for so long was now breaking loose.

“We’ve spent our lives serving the kind of state no decent man ought to serve,” one of the Stoics says in The Blood of the Martyrs, Naomi Mitchison’s haunting 1939 novel about the persecution of the Christians in Nero’s court. “And now we’re old enough to see what we’ve done.”

Centuries before Seneca, in China, Confucius had been a teacher and an advisor to princes. He had danced the same dance as Seneca, trying to be a philosopher within the pragmatic world of power. His balancing principle was as follows: “When the state has the Way, accept a salary; when the state is without the Way, to accept a salary is shameful.” It took Seneca much longer than Confucius to come to this conclusion. It’s inexcusable—the shame was obvious the first time his boss tried to murder his mother . . . at least it should have been to someone trained in virtue.

But that was not how Seneca saw it, not for nearly fifteen years of service with Nero. In time, he would come to echo Confucius, writing that when “the state is so rotten as to be past helping, if evil has entire dominion over it, the wise man will not labor in vain or waste his strength in unprofitable efforts.”

But he had done precisely that for far too long. Withdrawing as best he could, Seneca turned fully to his writing. In a remarkable essay titled On Leisure, published after he retired, he seems to be wrestling with his own complicated experiences. “The duty of a man is to be useful to his fellow-men,” he wrote, “if possible, to be useful to many of them; failing this, to be useful to a few; failing this, to be useful to his neighbors, and, failing them, to himself: for when he helps others, he advances the general interests of mankind.”