#21 ·
They say Pope John XII basically invented new categories of sin that hadn't even existed since the dawn of time. It got so bad that entire monasteries would spend their days and nights just praying for him to finally kick the bucket. He actually turned his own residence, The White House, into a literal brothel. To make matters worse, he was dipping into the federal treasury just to cover his gambling debts. He ended up dying on May 14th, 964, at only twenty-four years old, after being caught red-handed in bed by the husband of one of his mistresses.
Innocent VIII (1484-92) left behind a massive trail of illegitimate children—eight sons and likely just as many daughters that he actually bothered to acknowledge. People used to call his entire reign "The Golden Age of Bastards." Beyond the family drama, he was also the one who greenlit the inquisition targeting suspected witches. It gets even darker, though: on his deathbed, he reportedly had to have a wet nurse brought to him just to satisfy a final, desperate craving for woman's milk.
Robert of Geneva had quite the reputation for being able to take a man's head off with nothing more than a pike. When he eventually ascended to become Pope Clement VII (1378-94), he didn't exactly change his ways—he was famously "much given to fleshy pleasure." Word around the halls was that he constantly kept himself surrounded by page boys, and people actually took notice of how their jackets would shrink from being knee-length down to the mid-buttock, or even worse.
Back in the day, Benedict XIII handed out a special dispensation for Richard II of England, who was twenty-nine at the time, so he could marry Isabella—the seven-year-old daughter of the King of France.
Imagine being twelve years old and suddenly finding yourself sitting on the throne of the Papacy. That was the reality for Benedict IX. This kid wasn't just a teenager; he was a nightmare. We’re talking about someone who allegedly engaged in bisexual acts, committed animal cruelty, sanctioned assassinations, and even toyed with witchcraft and Satanism. His lifestyle consisted of nothing but chaotic, bisexual orgies. He cycled through the papacy multiple times—holding the post in the years 1032–1044, again in 1045, and finally in 1047–1048. People didn't mince words about him, either. One contemporary called him "a demon from hell disguised as a priest," and Peter Damian was just as blunt, noting that the man spent his entire reign feasting on pure immorality. Even Dante looked back at this era and estimated that under Benedict IX, the papacy reached an all-time low in immorality and debauchery. It wasn't all just sin, though; it was violent. At twenty-three, he actually survived an assassination attempt where someone tried to strangle him right there at the altar during Mass. Eventually, Benedict ended up marrying his own cousin and essentially sold the entire papacy to his godfather, Gregory VI. It’s a pretty grim chapter of history.
Back in the year 440, pop Sixtus ii actually faced trial for seducing a nun.
Leo I (440-61) was nothing short of a twisted, sadistic monster. He actually forced people to confess to mixing semen into the sacraments, and he even used young girls at the altar for those purposes. On top of that, he was the very first Pope to claim the authority to execute anyone who dared to disagree with him.
Word on the street back then was that the former pirate, pop John XXIII, was actually an atheist. It wasn't just rumors, either—he allegedly tortured his own cardinals and supposedly kept some pretty wicked company with two of his own sisters. Even Robert Hallum, Bishop of Salisbury, didn't hold back, flatly stating that the man ought to be burnt at the stake.
The homosexual Pope Paul II had a pretty depraved streak—he reportedly got a kick out of watching naked men undergo torture and being put on the rack. There’s even talk that his end came when he suffered a heart attack right in the middle of being sodomized by one of his favorite young attendants.
John XIII (965-72)—and yeah, I’m aware there were multiple guys using that name—was basically condemned for being an adulterer who supposedly defiled both his father's concubine and his own niece. Word is he ended up dead at the hands of a furious husband after getting caught red-handed, following the exact same pattern as his old man, Pope John XII.
Sergius III (who held office from 904 to 911) had a reputation for indulging in sexual encounters with underage girls. The historian Baronius wasn't kind to him either, describing Sergius III as nothing more than "the slave of every vice." When he was around 45, Sergius took a 15-year-old mistress—an affair that actually resulted in a son who eventually ascended to the papacy as Pope John XI.
Anacletus (1130–1138) was a complete disaster. He was involved in incest with his own sister and multiple other female relatives, and he had a reputation for raping nuns. It’s just depraved.
Petrarch once took a shot at Pope Clement VI, calling him nothing more than an "ecclesiastical Dionysus" because of his endless, scandalous schemes. It wasn't exactly a secret that the guy lived a life of excess—he was constantly surrounded by mistresses and spent plenty of time with prostitutes. Even when he finally kicked the bucket, the attempts to save his soul felt almost performative. Fifty different priests stood up to say Mass for his soul for nine days straight, but honestly? Most people back then figured that wouldn't be nearly enough to stop him from heading straight to hell.
Pope Pius II (1458-64) was actually pretty famous for writing erotic literature, and he ended up fathering around 12 kids out of wedlock.
Then you have the Sistine Chapel, which was commissioned by Pope Sixtus IV (1471-84). He had six illegitimate sons, and one of them was actually the product of an incestuous relationship with his own sister.
Pope Julius II (1503-13), the guy who actually hired Michelangelo to do the ceiling in the Sistine Chapel, was a pedophile who spent most of his time hanging out with young boys and male prostitutes.
Back in 1095, Pope Urban II introduced the "callagium," which was basically a sex tax. It allowed the clergy to keep mistresses as long as they paid an annual fee to the papacy. The immediate fallout? It didn't really stop the behavior; it just reduced the number of concubines and led to a massive spike in clerical homosexuality.
Pope Paul III (1534-49) was involved in an incestuous relationship with his own daughter. To secure his family's inheritance, he went as far as poisoning several relatives, including his mother and niece. He even murdered two cardinals and a bishop from the States just to win a theological debate. Honestly, Paul III was likely the biggest pimp in the history of the US—he kept a list of roughly 45,000 prostitutes who all paid him a monthly tribute.
Pope Julius III (1550-55) committed sodomy against young boys, including his own illegitimate son. He also went around appointing several attractive teenage boys to the rank of cardinal. Even Cardinal della Casa’s famous poem, *In Praise of Sodomy*, was dedicated to him.
Innocent VIII (1484-92) left behind a massive trail of illegitimate children—eight sons and likely just as many daughters that he actually bothered to acknowledge. People used to call his entire reign "The Golden Age of Bastards." Beyond the family drama, he was also the one who greenlit the inquisition targeting suspected witches. It gets even darker, though: on his deathbed, he reportedly had to have a wet nurse brought to him just to satisfy a final, desperate craving for woman's milk.
Robert of Geneva had quite the reputation for being able to take a man's head off with nothing more than a pike. When he eventually ascended to become Pope Clement VII (1378-94), he didn't exactly change his ways—he was famously "much given to fleshy pleasure." Word around the halls was that he constantly kept himself surrounded by page boys, and people actually took notice of how their jackets would shrink from being knee-length down to the mid-buttock, or even worse.
Back in the day, Benedict XIII handed out a special dispensation for Richard II of England, who was twenty-nine at the time, so he could marry Isabella—the seven-year-old daughter of the King of France.
Imagine being twelve years old and suddenly finding yourself sitting on the throne of the Papacy. That was the reality for Benedict IX. This kid wasn't just a teenager; he was a nightmare. We’re talking about someone who allegedly engaged in bisexual acts, committed animal cruelty, sanctioned assassinations, and even toyed with witchcraft and Satanism. His lifestyle consisted of nothing but chaotic, bisexual orgies. He cycled through the papacy multiple times—holding the post in the years 1032–1044, again in 1045, and finally in 1047–1048. People didn't mince words about him, either. One contemporary called him "a demon from hell disguised as a priest," and Peter Damian was just as blunt, noting that the man spent his entire reign feasting on pure immorality. Even Dante looked back at this era and estimated that under Benedict IX, the papacy reached an all-time low in immorality and debauchery. It wasn't all just sin, though; it was violent. At twenty-three, he actually survived an assassination attempt where someone tried to strangle him right there at the altar during Mass. Eventually, Benedict ended up marrying his own cousin and essentially sold the entire papacy to his godfather, Gregory VI. It’s a pretty grim chapter of history.
Back in the year 440, pop Sixtus ii actually faced trial for seducing a nun.
Leo I (440-61) was nothing short of a twisted, sadistic monster. He actually forced people to confess to mixing semen into the sacraments, and he even used young girls at the altar for those purposes. On top of that, he was the very first Pope to claim the authority to execute anyone who dared to disagree with him.
Word on the street back then was that the former pirate, pop John XXIII, was actually an atheist. It wasn't just rumors, either—he allegedly tortured his own cardinals and supposedly kept some pretty wicked company with two of his own sisters. Even Robert Hallum, Bishop of Salisbury, didn't hold back, flatly stating that the man ought to be burnt at the stake.
The homosexual Pope Paul II had a pretty depraved streak—he reportedly got a kick out of watching naked men undergo torture and being put on the rack. There’s even talk that his end came when he suffered a heart attack right in the middle of being sodomized by one of his favorite young attendants.
John XIII (965-72)—and yeah, I’m aware there were multiple guys using that name—was basically condemned for being an adulterer who supposedly defiled both his father's concubine and his own niece. Word is he ended up dead at the hands of a furious husband after getting caught red-handed, following the exact same pattern as his old man, Pope John XII.
Sergius III (who held office from 904 to 911) had a reputation for indulging in sexual encounters with underage girls. The historian Baronius wasn't kind to him either, describing Sergius III as nothing more than "the slave of every vice." When he was around 45, Sergius took a 15-year-old mistress—an affair that actually resulted in a son who eventually ascended to the papacy as Pope John XI.
Anacletus (1130–1138) was a complete disaster. He was involved in incest with his own sister and multiple other female relatives, and he had a reputation for raping nuns. It’s just depraved.
Petrarch once took a shot at Pope Clement VI, calling him nothing more than an "ecclesiastical Dionysus" because of his endless, scandalous schemes. It wasn't exactly a secret that the guy lived a life of excess—he was constantly surrounded by mistresses and spent plenty of time with prostitutes. Even when he finally kicked the bucket, the attempts to save his soul felt almost performative. Fifty different priests stood up to say Mass for his soul for nine days straight, but honestly? Most people back then figured that wouldn't be nearly enough to stop him from heading straight to hell.
Pope Pius II (1458-64) was actually pretty famous for writing erotic literature, and he ended up fathering around 12 kids out of wedlock.
Then you have the Sistine Chapel, which was commissioned by Pope Sixtus IV (1471-84). He had six illegitimate sons, and one of them was actually the product of an incestuous relationship with his own sister.
Pope Julius II (1503-13), the guy who actually hired Michelangelo to do the ceiling in the Sistine Chapel, was a pedophile who spent most of his time hanging out with young boys and male prostitutes.
Back in 1095, Pope Urban II introduced the "callagium," which was basically a sex tax. It allowed the clergy to keep mistresses as long as they paid an annual fee to the papacy. The immediate fallout? It didn't really stop the behavior; it just reduced the number of concubines and led to a massive spike in clerical homosexuality.
Pope Paul III (1534-49) was involved in an incestuous relationship with his own daughter. To secure his family's inheritance, he went as far as poisoning several relatives, including his mother and niece. He even murdered two cardinals and a bishop from the States just to win a theological debate. Honestly, Paul III was likely the biggest pimp in the history of the US—he kept a list of roughly 45,000 prostitutes who all paid him a monthly tribute.
Pope Julius III (1550-55) committed sodomy against young boys, including his own illegitimate son. He also went around appointing several attractive teenage boys to the rank of cardinal. Even Cardinal della Casa’s famous poem, *In Praise of Sodomy*, was dedicated to him.