How to Become the Pope if You’re a Pirate, a Rapist, and Just Really Damn Charming: The Wild Life of Baldassare Cossa (Antipope John XXIII)

Being a pirate in the Middle Ages wasn’t just about treasure and taverns. No no. It was a legit career path. You rob a few churches, melt some golden chalices, flip the loot for cash — and boom, you buy yourself a bishopric. Congratulations, you’re now the Church. You forgive sins. You run the show. Give it a few years and, if your balls are big enough, you might just become the Pope.

Baldassare Cossa’s balls were made of steel. This guy didn’t just dream big — he pillaged his way into papal robes.

When they finally kicked him off the papal throne (as Antipope John XXIII, not to be confused with the later, less spicy John XXIII), the Church hit him with 74 criminal charges. Among them: piracy, raping 300 nuns, sodomy, torturing bishops, poisoning a previous pope, selling church offices, and a charming little family orgy involving mom, dad, kids, and God knows who else.

People joked: “74 charges? Come on, he’s guilty of maybe half!” And the kicker? He lived happily ever after and got a tomb sculpted by frickin’ Donatello. Because let’s face it — everybody loves a charismatic bastard.

A View of the Gulf of Naples from the Island of Procida (1847)

Born to Steal, Blessed to Sin

Baldassare was born in 1370 on the island of Procida, off the coast of Naples. His dad was a count, his brothers were pirates, and his oldest brother had the official title of “Admiral of the Pirate Fleet.” Nice family resume.

At 13, Baldassare joined the family biz — torching towns, stealing cargo, and doing the whole rape-and-pillage thing. But by 20, Mom had enough. “Sweetheart,” she probably said, “stop raiding convents and go get a real education.” And like any good boy, he listened.

He went to the University of Bologna to study theology. Studying God’s word came surprisingly easy to a man who’d spent his teens setting fire to coastal villages. Naturally, he formed a student gang called the “Ten Devils” — because subtlety wasn’t really his thing. They robbed, fought, and ran low-level rackets on campus.

Somewhere in between exams and extortion, he fell for a witch — literally. Her name was Yandra della Scala, officially labeled as such by the Inquisition. She was smart, loud, and way too hot for the 14th century. So of course they burned her at the stake.

Baldassare didn’t take that well. He stabbed two inquisitors and got thrown in prison. His pirate buddies broke him out and together they lit half of Bologna on fire. Dead priests, smashed churches, full-blown riot. Class dismissed.

Back to the Sea, Back to the Sin

Baldassare and his gang hit the sea again — more piracy, more monks on fire, more monasteries robbed blind. They sold nuns into slavery. They burned altars just because they could. God got pissed. One massive storm later, their entire fleet sank.

Floating alone, coughing up seawater, Baldassare looked at the heavens and said, “If I live through this, I’ll become a priest.”

He survived. And immediately got captured by a sadistic psychopath — Pope Urban VI. This guy loved torture and talking about Hell. Strangely enough, they got along.

Urban was weirdly touched by Baldassare’s story and asked, “Wanna be my executioner?” Not exactly the job offer you turn down. So Baldassare started torturing bishops for the glory of God. Eventually he was ordained. Congratulations — the pirate was now a priest. Kinda full circle, right?

From Muscle to Mitre

Urban died (maybe naturally, maybe not), and the next pope, Benedict XIII, kept Baldassare around but kept his distance. The man was terrifying.

To test his loyalty, Benedict sent him to crush a rebellion — in Bologna, of all places. No tears were shed for the alma mater. Baldassare obliterated the revolt so brutally that even seasoned inquisitors got queasy.

Then he pulled a power move — asked for Bologna as a gift. And got it. Streets where he once mugged students were now officially his. He got himself promoted to bishop by, of course, bribing everyone.

And that’s when he got bored. Bishops were cool, sure, but Popes? Now that was sexy.

Welcome to the Great Papal Dumpster Fire

At the time, the Catholic Church was going through what historians politely call “a crisis.” There were already two Popes — one in Rome, one in Avignon — and each claimed the other was a fraud.

So what did Baldassare do? Made himself the third.

He gathered some bishops (friendly reminder: they knew he liked to torture people) and held a council in Pisa. There, they elected a third pope, Alexander V — an old man, perfect puppet. A year later, Alexander conveniently died, and surprise! Baldassare became Pope John XXIII.

Three Popes. One Church. Total chaos.

People didn’t mind. “Sure, he’s a pirate, rapist, possible goat-screwer, but he’s kinda likable,” they said. And crowds poured in.

The Fall of the Charming Devil

But all good heresies must end. In 1415, the Council of Constance gathered all the serious players — emperors, kings, cardinals — and said, “Enough of this circus.”

They deposed all three Popes. Baldassare was hit with 74 charges, including selling relics, denying the afterlife, sex with his own granddaughter, and manipulating currency markets. (That one stings, huh?)

He escaped prison once. Got caught. Thrown back in. Then bailed himself out with 38,000 gold florins. Not a typo. That’s how much it cost to walk free if you’re a VIP heretic.

He had the audacity to ask the new Pope to reinstate him as bishop. And the Pope said… yes. Gave him Bologna back.

He lived quietly for a few years, died of cancer, and got a majestic tomb sculpted by Donatello. Seriously.

The Punchline? The Bank Won.

You’d think that’s the end. But no. There’s a final twist.

One day Baldassare walked into the Medici bank to collect the money he’d deposited back when he was Pope. The banker looked him dead in the eye and said, “Sorry, I took money from Pope John XXIII. That’s not you anymore.”

He got conned. The pirate got pirated.

That, friends, is the moment when power shifted forever — from Popes to bankers. And it’s been that way ever since.