Pope St. Sylvester I is not a guy we know much about.
He was on Pope St. Marcellinus’ staff as a deacon, and rumors swirled around that particular pope. He survived Emperor Diocletian’s persecution for quite a while, and there are different legends about how he did it.
Apparently the true story is that some of the Roman imperial court officials were hiding the pope and his deacons _inside the emperor’s Roman palace_, in their rooms, with the clergy wearing the clothes of normal bureaucrats or servants — although I don’t remember where I read this. But the gossip story was that Pope Marcellinus had sacrificed to idols, and forced his whole staff to do the same. Various heretics brought up this story as justification for their own actions. But Pope St. Marcellinus died in the second year of Diocletian’s persecution, and anciently was considered a saint. (His feast day is April 26.)
Thanks to the persecution, there was no pope from AD 304 to 308. Think about that, when you complain about stuff today. But behind the scenes and despite tons of martyrdoms and imprisonments and apostasies, Christians managed to scramble along: either by fleeing the cities, or by running things through the decentralized management system of deacons and parishes.
In 308, Pope Marcellus was elected. He found a church without places to meet (because properties had been confiscated), and full of dissension between those who had lapsed or fled, and those who had stayed in place and/or suffered. He tried to make peace and imposed grave penances on the lapsed (as had been done after the Decian Persecutions of AD 250).
But there was also a large movement (led by a guy named Heraclius who had apostatized even before the persecution started!), insisting that everybody calling himself Christian should be readmitted to Communion, instantly, without any kind of confession or apology or penance.
Somebody whined to Emperor Maxentius, who banished Marcellus from Rome (officially for causing people to breach the peace). So yup, cafeteria Catholics with a grudge are not just a modern thing.
Pope St. Marcellus died in AD 309, on the way to his place of exile (probably because journeys in winter were not fun), and was immediately acclaimed as a saint. His feast day is January 16.
Pope St. Eusebius was the next lucky contestant, elected pope early in 310. He continued to teach that the lapsed and apostatized could be readmitted to the Church and to Communion (contrary to the Donatists, who wanted things one and done), but that people would have to do lots of penance for quite a while. The Heraclius crowd continued to fight violently and to whine. Heraclius and his crowd declared himself pope (also in 310), thus making him one of the first antipopes.
Emperor Maxentius exiled Eusebius to Sicily for causing breaches of the peace — along with Heraclius (much to his surprise, I bet). Pope St. Eusebius soon died, and his body was brought back to Rome. (We don’t know what happened to Heraclius.) Pope St. Eusebius’ feastday used to be Sept. 26, but now has been moved to Aug. 17.
The next to be elected was Pope St. Miltiades (aka Melchiades), a North African guy who had moved to Rome and ended up (as you recall) in Pope Marcellinus’ chancery. He was elected in July of AD 311. He supposedly ordained the then-deacon Sylvester as a priest.
Emperor Galerius, in a doomed effort to suck up to God, had just issued the Edict of Toleration, ending the official persecution of Christians. Maxentius then proceeded to suck up to the new Pope Miltiades by giving back the confiscated Christian churches, cemeteries, monasteries, and other properties.
But that didn’t save Maxentius from God’s wrath, either, because Emperor Constantine beat him at the Battle of the Milvian Bridge. Constantine proceeded to legalize Christianity more, and build Old St. Peter’s over the grave of St. Peter and make it a big imperial basilica; and he gave the imperial palace of Empress Fausta, the future Lateran Palace, to Pope Miltiades for an official residence/office.
As a gesture of unity, Miltiades began the custom of sending out “fermentum” (blessed, leavened bread that was not for Communion) from his place to all the churches around Rome — this meant particles of a big giant host from the Pope’s Mass, for just the priests to consume, much as bishops had long been sending Host bits to each other as a formal sign of intercommunion (for at least two hundred years before). And eventually this turned into the custom of putting a particle of Host into the cup at every Mass, which has various symbolic meanings (including intercommunion with the Pope). Apparently the “fermentum” was sent around by way of the acolyti, who also brought Communion to the sick.
Miltiades also called the Lateran Council, which ruled that Donatus of the Donatists was wrong about apostates never being able to rejoin the Church. This failed to stop Donatism from spreading in North Africa, or Donatists from whining to the emperor.
Pope Miltiades died in January of 314. His feast day is January 10.
And then came Pope St. Sylvester. The Church was full of super-motivated Donatists with their own churches and bishops, super-unmotivated ex-lapsi, newbie Christian wannabes just trying to get in good with Emperor Constantine, and Constantinople suddenly becoming the new capital of the Empire. Oh, and Arius decided to invent a totally new heresy that said that Jesus wasn’t God, so he had to send papal legates to the first Council of Nicaea.
Obviously Pope St. Sylvester was working hard throughout his reign, until his death in 335. But we know very little about his work, other than the unanimous idea after his death that he was clearly a saint. He built churches, cleared up liturgy questions, got a martyrology list together, and set up a Roman schola for singing. He was buried in a church he built over the Catacombs of Priscilla.
His successor was Pope St. Mark, who reigned for about nine months in AD 336, before dying of natural causes; his feastday is Oct. 7. Mark’s successor was Pope Julius I, a steely-eyed yet diplomatic type who opposed Arianism, helped out St. Athanasius during his exiles, and quietly refused to do what was ordered by Arian Constantinople. He was pope from 337 to 352, and his feastday is April 12.
Ahead of the Church was more Arianism; Pope Liberius who suffered prison in Beirut, exile in Thrace, and apparently had letters faked to make him look Arianized; Emperor Julian the Apostate; and a ton of other troubles. But they still weren’t the worst things to happen ever, and the world didn’t end.
And so, we can see that messiness of history is not just a modern thing. Or division and conflict. Or government meddling in the Church’s business. Or the thankless danger of following Christ, instead of the state or mammon or cheap fellowship.
On St. Sylvester’s Day, it is correct to revel a bit.
In France, they eat champagne and foie gras, or oysters, or mussels. They also kiss under mistletoe only on New Year’s Eve, and there’s often fireworks outside in the yard/garden.
Fish dinners are traditional through most of the Catholic world, because January 1 is a solemn big feast, and the eve of a big feast was traditionally a fast. (Jan. 1 used to be the Feast of the Circumcision, because a bris is done on the seventh day after a boy’s birth. Now it’s the Feast of Mary, Mother of God, following Byzantine and older Western tradition.)
Drinking some kind of wine or beer is also traditional, although moderation is what you’re supposed to observe.
So if it means anything that Pope Emeritus Benedict died on St. Sylvester’s Day, I’d take it as a sign that we are not meant to be sad or worried. St. Sylvester was a good pope, and his feastday is a happy day. He lived in a time of turmoil; but he got through it and so can we.