Pope Paul III (1534 - 1549)
Background: Pope Paul III, predecessor to Julius III, reigned during a particularly turbulent time for the Catholic Church and he made some difficult decisions. His edicts against slavery in the New World were the source of a great deal of conflict and he had to grapple with entrenched corruption in the Church, the formation of the Church of England, and the agitation of Martin Luther. He ruthlessly fought Protestantism and was known for having men strangled and then burned.
Why He is Awful: Pope Paul III wasn't just a bad pope, he was a bad person all around. He murdered relatives, including poisoning his mother and niece, to inherit the family fortune. This sort of power was what it took to muscle his way to becoming pope in the disastrous aftermath of Clement VII. The most famous anecdote about Paul III's ruthlessness revolves around a theological dispute between two cardinals and a Polish bishop. When the argument wore on, Paul III had all three men hacked to death with swords.
Paul III was also notoriously corrupt, despite his supposed anti-corruption stance. Any position in the church was for sale and he famously took control of some 45,000 Roman prostitutes and then took a cut of their earnings. That's right, Paul III, the world's first pimp pope. Paul III's most well-known lover was an attractive young lady named Costanza Farnese. She was the pope's daughter.
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Pope Julius II (1550 - 1555)
Background: Julius was one of the rare duly-elected popes of the 16th century, most having come to power through intrigues or even murder. At the time, being pope was to the richest and most powerful families of Italy much like being President of the United States is to the Bushes and the Clintons. Compared to these families, Julius III was like the war hero of cardinals.
Decades before becoming pope, Julius was traded as a hostage by the dumb and cowardly Pope Clement VII to Emperor Charles V during the sacking of Rome. Julius would have been killed, but in a complicated twist Cardinal Pompeo Colonna, enemy of Clement VII and rogue commando cardinal, rescued the hostages including Julius III from the clutches of the Emperor. It was the original special ops mission. Despite such a dramatic history, Julius III would go on to become one of the vilest popes ever to sit on the throne of Saint Peter.
Why He is Awful: Once he was elected pope, Julius III looted the papal coffers to renovate his mansion in Rome. The Villa Giula, as it is known, became the full-time residence of Julius III and the pope oversaw the construction. He hired only the best (including Michelangelo) and had little interest in the affairs of the pope. Following on the heels of meddlesome popes like Clement VII, you might think this was a good thing, but Julius III had some unfortunate uses for all that free time. In addition to the wholesale looting of the Catholic treasury so that he could flip his house, Julius III was known to have a thing for younger men. Alright, he liked to have sex with kids. Okay, he was infamous for having sex with kids.
That mansion of his was decorated with statues and frescoes depicting kids having sex with each other. Julius III didn't just let slip that he molested children, he flaunted it. He decorated his house to flaunt it. He did not need Martin Bashir to ask him about sleeping with some crippled white kid, Julius III was having Michelangelo chisel sculptures of mouth rape. He was bilging with child porn.
Controversial poet and scholar Giovanni Della Casa wrote an poem about Julius III in which Della Casa defended the practice of sodomizing young boys. The poem was known throughout Italy and was written while Julius III was the pope. That's like the 16th century equivalent of having a top 5 song on the Billboard charts name-dropping you as a child rapist.
All of these things combined would easily give Julius a spot on the list, but his masterpiece of shitty popery came when Julius mixed business and pleasure. He had a tendency to appoint hot underage studs to the position of cardinal, but took things to a whole new level when he adopted a beggar. He raised the boy as a sort of foul-mouthed gay slut that hung out in Rome and was bestowed with the title of cardinal-nephew, which sounds and is creepy, but was also an extremely powerful and prestigious position in the church. Julius III and his boy-toy inspired more than a century of anti-papacy sentiment throughout Europe
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Pope John XII (955 - 964)
Background: If the 16th century was the renaissance of shitty popes, the 10th century was the true dark age of the papacy. Popes during this time period were basically Genghis Kahn with a prettier hat. Pope John XII assumed the throne of Saint Peter at the seemingly tender age of 18, but back in the 10th century people lived to be about 25, so that was no excuse for the horrible reign that was to follow.
Why He is Awful: Pope John XII was a notorious sex fiend. He had sex with women and men in the papal palace and when visitors refused his attentions he went ahead and raped them anyway. The same hospitality was extended to his two young sisters. He held massive orgies and took particular pleasure in defiling holy sites, like the tombs of Saint Peter and Saint Paul, with his sinful acts.
A list of crimes John XIII was accused of was included in the Patrologia Latina, which I assume is some ancient text of absolute bastard popes. These crimes are too numerous to mention here, but a few highlights include:Ordaining a 10 year old as bishop, Having sex with his niece, Turning the sacred palace into a brothel, Castrating and then murdering a cardinal, Blinding and then murdering his confessor, Toasting to the devil and invoking pagan gods during dice games, and Refusing to make the sign of the cross, which seems like a job requirement for the pope.
Pope John XII was no stranger to political intrigue. He granted Otto I of Germany the title of emperor in order to protect himself from his political enemies, but Otto I began to take more power than John XII was comfortable with. He conspired against his supposed ally, but Otto I returned to Rome and deposed John XII from the papacy and installed a puppet pope.
John XII fled into exile, but gathered an army of allies and mercenaries. He returned to Rome, ran off the puppet pope, and took back his title. Otto I mustered an army to finish off John XII once and for all, but he was too late. By the time Otto I arrived in Rome Pope John XII was dead. It is rumored that he was killed by a jealous husband when the man caught John XII in bed with his wife. By the way, his son became Pope John XIII and died the exact same way.
Pope John XII was a son of a bitch. There is no getting around it. If he is not the most awful pope of all time, he is certainly in contention as the most evil.
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Pope Benedict IX (1032 - 1048)
Background: The son of an influential family, Benedict IX is said by some sources to be the youngest pope to ever take over the Catholic Church. While official records state he was 18 like John XII, contemporary accounts suggest he might have been as young as 11 or 12. You might think he was unprepared at that age to be the pope, but looking back at the last three popes I would say he fit right in.
Why He is Awful: If you're looking for a pope with a Bartlett's full of nasty quotes from critics, Pope Benedict IX is your man.
St. Peter Damian accused him of "feasting on immortality" and described him as "a demon from hell in the disguise of a priest." Bishop Benno accused him of "many vile adulteries and murders" and Pope Victor III thought he was "so vile, so foul, so execrable" that he shuddered to think of Benedict IX's time as pope.
So what did he do that was so bad? Like John XII he had sex with and raped men, women, boys, and girls. Unlike John XII, Benedict IX extended the papal blessing to animals. He was also a back-stabber (literally) and tended to torture/drown/burn/flay-to-death first and then ask questions later.
Benedict IX's reign was troubled and complicated. See if you can follow:
Benedict IX was deposed, regained the throne with the help of Conrad I, was forced out again, returned with an army to take it back again, sold the papacy to his godfather for a fortune, regretted selling the papacy and came back with another army, found the last guy he deposed and his godfather were both claiming to be pope, went to papal court and failed to show up, the papacy was given to a fourth person, returned with another army and sacked the papal palace, was quickly forced out again by yet another pope, refused to stand trial and was excommunicated, and he finally retired in obscurity.
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Pope Steven VII (896 - 897)
Background: Sometimes referred to as Stephen VI because of confusion over the legitimacy of some of the other Steves, Stephen VII took over as pope during a very turbulent period for the church. Popes were rarely lasting more than a year or two on the throne and intrigues among the powerful ruling families of Rome were at their height. Stephen VII took over for Boniface VI after only 16 days of that ill-fated pope's reign. Some say gout took poor unloved Boniface VI, others claim he was killed to make way for Stephen VII. Whatever the cause of Boniface VI's fate, Stephen VII was in for a bumpy ride as pope.
Why He is Awful: Stephen VII might not be as traditionally evil or disgusting as the other popes on the list, but he is responsible for one of the most bizarre and notorious incidents in papal history.
Before Boniface VI's brief stint as pope, there was the politically controversial Pope Formosus. Formosus did not get along with Pope John VIII and during that pope's reign Formosus acted as a sort of rogue cardinal. He was excommunicated for pissing off John VIII, but following John VIII's death he was reinstated. Two more popes followed and then Formosus became pope and immediately became embroiled in battles, both figurative and literal, between dueling political factions within the church. After five years of contentious rule, Pope Formosus died and was interred in Rome.
Fast forward a couple weeks to Stephen VII. He and his backers really had it in for Formosus and Stephen VII decided that John VIII's original ruling should stand. Rather than just re-excommunicate the deceased pope, Stephen VII undertook what would become known as the Cadaver Synod. A synod is basically an ecclesiastic trial and a cadaver is a dead body. Do you see where this is going?
Stephen VII dug up Formosus, hauled his corpse onto the papal throne, and sought to put it on trial for its crimes. Stephen VII represented the prosecution and Formosus, with the help of a teenage deacon hiding behind the throne, defended himself.
Stephen VII would scream and read out charges, stomping around the throne and playing to the audience. When he would stop screaming the teenage deacon would speak from behind the throne in an imitation of Formosus's voice and deny the charges. Things did not go well for Formosus, proving the old adage that you should never posthumously defend yourself in court and use a teenager as a proxy.
Formosus was found guilty and Stephen VII ordered his fingers cut off, his body stripped of papal vestments and dressed in rags, and reinterred in a pauper's grave. Stephen VII soon after decided this was inadequate and had the corpse dug up again, tied with stones, and thrown into the Tiber river. A monk rescued the corpse.
Stephen VII was considered completely insane by the people of Rome and riots boiled over in the coming months. Stephen VII was stripped of his vestments, imprisoned, and strangled. Incredibly, it took three further synods (sans corpse) to vindicate Formosus and to this day popes will not take his name.
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Pope Alexander VI (1492 - 1509)
Pope Alexander VI (1492 - 1509)
Background: If greed is good, then Alexander VI was the best pope. He literally bought his way into becoming pope, bankrolled by France and Genoa and his own merchant family.
Why He is Awful: Alexander VI became the Halliburton and Dick Cheney of the papacy, swindling his way onto the throne with cash and selling the papacy a piece at a time to warring empires in Europe. While he was raking in the wealth and involving the Holy See in French and Italian political intrigues, he was also amassing women and power for his family.
One of his most infamous stunts was to use his attractive daughter Lucrezia, whom he supposedly had an affair with, as bait for wealthy merchants. When a rich merchant prince would visit Rome Alexander VI would introduce his daughter, have her seduce them, and then marry his daughter off to the merchant for a vast dowry. Unfortunately for the merchant, Alexander VI was the pope and got to decide who was married and who wasn't married. As soon as a wealthier merchant rolled into Rome Lucrezia's marriage would end and she would become available to the next highest bidder.
Alexander VI was also wildly unpopular with devout Catholics because he never made any attempt to be religious. He was a 100% secular pope, ignoring all of the rules and traditions of the church. He married, had children, and sired countless children outside of marriage.
He also held extravagant parties that often tended to become orgies. These parties were so intense that one of them, known as the Banquet of Chestnuts, is actually a part of recorded papal history. 50 prostitutes would bring in baskets of chestnuts and empty them out on the floor. The women's clothes would then be auctioned off and once they were naked they would crawl around on the floor picking up the chestnuts. Then the members of the clergy, including the pope, would have sex with the prostitutes and for prizes.
According to historian William Manchester, "Servants kept score of each man's orgasms, for the pope greatly admired virility and measured a man's machismo by his ejaculative capacity."
When Alexander VI's political intrigues ran him into financial trouble, he instituted a brutal pogrom against the wealthy, confiscating riches under the thin guise of criminal enforcement. If the wealthy resisted they were put to death. These pogroms fueled instability and eventually led to Alexander's involvement in a series of unfortunate military struggles. Assassins, paid by Alexander's many enemies, made repeated attempts on him. In 1503, they finally succeeded with a plate of poisoned food.
John Burchard, a sort of living papal captain's log, recorded Alexander VI's gruesome death. "Alexander VI's stomach became swollen and turned to liquid, while his face became wine-colored and his skin began to peel off. Finally his stomach and bowels bled profusely."
Alexander VI died soon after the poisoning. His last words were, "Wait a minute."