The Italian city of Orvieto, a little over an hour’s journey north of Rome, perches atop a massive, impregnable spur of volcanic rock, but that forbidding first impression dissipates quickly in the friendly, hospitable maze of its medieval streets. The city’s history goes back to Etruscan times, when it was called Velzna and managed an important religious sanctuary (recently rediscovered near the fairgrounds at the foot of what locals call “The Rock”); today Orvieto’s most conspicuous treasures are wine, ceramics, and art—and, of course, this being Italy, the food (a local pasta called umbrichelli, truffles, mushrooms, game). It is hard to imagine that so thoroughly beguiling a place was ever famous for anything but the bounty of its generous earth.

But Orvieto used to be different, as we can see from one of the city’s greatest artistic treasures: a terrifying Renaissance Apocalypse, painted by Luca Signorelli between 1499 and 1504. Here, in a series of frescoes created for a side chapel of Orvieto’s cathedral, blood rains down from the heavens, meteors pelt the earth, hairy blue-green demons torment the damned with astounding inventiveness, angelic trumpets blast the dead clean out of their graves. And in the midst of all the chaos we see the Antichrist, pausing in the middle of a sermon to hear what his demonic advisor instructs him to say next.

Luca Signorelli: Sermon and Deeds of the Antichrist (1499–1504)

The Apocalypse is a rare subject for Italian artists, and this is one of the only known images painted of the Antichrist. It is also one of the most menacing works an Italian painter ever created. But then Orvieto, friendly, beautiful Orvieto, was a completely different city five hundred years ago, a place where a sensitive soul like Luca Signorelli might come to imagine the full depth of human depravity.

In 1499, this Umbrian town was a disease-ridden den of eight thousand souls whose chief claim to notoriety was their enthusiasm for fighting with one another; before 1321, Dante’s Purgatory had ranked the city and its feuding clans, the Monaldeschi and Filippeschi, right up with the Montagues and Capulets of Verona. The Monaldeschi eventually won, wrecked their rivals’ neighborhood—the damage is still visible—and then proceeded to squabble among themselves. When the fifty-five-year-old Signorelli climbed up The Rock to earn the hundred and eighty scudi he was paid for this commission, the streets of Orvieto wound among half-ruined buildings of dark volcanic stone; only the Cathedral’s white-and-gray striped marble facade lifted the general gloom. Plague claimed two or three victims a day. The city’s official governor was none other than Cesare Borgia. It must have been relatively easy in that setting for Signorelli to imagine what the end of the world might look like.

At first glance, the commanding preacher looks remarkably like Jesus delivering the Sermon on the Mount, but swiftly the details give him away as a completely different presence: his audience is rich, and so are the proceeds from his performance—this is no place for “blessed are the meek, for they shall inherit the earth.” The Antichrist’s demonic prompter hovers so close that we can no longer tell whose left arm is wrapped in the overfold of the preacher’s pink toga, his own or the fiend’s. The irises of the Antichrist’s eyes are so uncannily pale as to be almost invisible.

Two kinds of people pay the Antichrist close attention. To his left (our right), a pink-clad dandy echoes the colors of his robe, though the dandy wears Renaissance hose and doublet rather than the Antichrist’s classical toga. This figure is sometimes identified as a member of the perpetually feuding Monaldeschi family (who also endowed the chapel where these paintings appear). He certainly represents the same social class as the Monaldeschi, the feudal aristocracy that could afford to clothe its young people in showy silks like these and train the men in the arts of war.

By 1500, there were too many of these young warriors in central Italy, career soldiers who fought each other in the absence of some more distant enemy like the French or the Turks. Warfare could bring in huge profits, but only if the looting took place far away; local battles only hurt the economy of both victors and vanquished. And the economy is clearly on Signorelli’s mind, because the Antichrist, as we can see, has been engaged in a fund-raising campaign. (A war chest? The pedestal on which he stands shows a warrior on horseback). Piles of gold lie at the Antichrist’s feet as testimony to his success, but now he pauses to hear the demon’s instructions about how to wheedle still more contributions from the audience.

Off to his right, our left, one of his henchmen is working the crowd. Bearded, hook-nosed, dressed in a fur-lined robe with a green hat on his head, an open purse in his hand, the man would have been immediately recognized by sixteenth-century viewers as a Jew, handing out money to the women who gather around him. There were a few dozen Jews living in Signorelli’s Orvieto, mingled in with the local population, many of them professionals, working as doctors, merchants, and moneylenders. Some of them were refugees from Spain, like Moïsé de Blanis, at the time Orvieto’s most prominent physician and manufacturer of wool mattresses, as well as a banker, rabbi, and scholar. Signorelli’s fresco suggests that the Jewish presence in Orvieto, and especially in Orvieto’s economy, is a malevolent one; for example, the blonde woman who takes money from the fur-clad Jew is barefoot, with uncovered head—anything but respectable. The coin he proffers is, in effect, the price of her virtue.

Just behind the Antichrist, a knot of friars argues over an open Bible. They wear the habits of all the major orders: gray-clad Franciscans, black-clad Benedictines and Augustinians, and, in the center of it all, a Dominican in white robe and black mantle who seems to be guiding the discussion. For most of the previous century, preaching friars, Dominicans above all, had thundered relentlessly against Jewish moneylenders, urging Christians to found civic banks that lent money at less onerous rates. The situation for Italy’s Jews was growing steadily more difficult, and Luca Signorelli’s fresco, for all its striking imagery, marks a new spirit of hostility toward the Jews of Orvieto. Moïsé de Blanis did not live to see the worst of it; he was murdered in 1535. But his son, Laudadio, another doctor and rabbi, would see the establishment of ghettos in Rome, Florence and Venice and suffer banishment from Orvieto simply for his religion. Presumably we are meant to see this gathering of stern-faced friars as the antidote to the Antichrist’s malignant sermon, but Signorelli has set up enough visual parallels between the friar and the Tempter that we can never be entirely sure.

There is, however, one thing we can be sure about. The Orvieto we see today, prosperous and friendly, is a hard-won achievement, not a natural fact. Its second Renaissance began in the nineteenth century, when the railroad and a clever water-powered funicular put it definitively on travelers’ maps, and once again its old Etruscan tradition of hospitality took over from feudal isolation. Even so, one of the city’s greatest cultural benefactors of the early twentieth century, the Jewish count Rodolfo Teofilo Cahen (who lived in a former Monaldeschi castle), was forced into exile in 1938 by Mussolini’s infamous “racial laws.”