Reign: 1032-1044, 1045, 1047-1048
Pope Benedict IX holds the unenviable distinction of being one of the youngest, most corrupt, and most controversial popes in history. He ascended to the papacy at around 20 years old, thanks to his influential family. Benedict's papacy was marked by scandal, including accusations of infidelity, murder, and even witchcraft. He's also the only pope known to have sold the papacy itself. He resigned in exchange for a hefty bribe, only to reclaim the title twice more after his successors proved unpopular. His repeated return to power was a low point for the church in the Middle Ages.
Reign: 1471-1484
Pope Sixtus IV is remembered for both his artistic patronage and his shady political dealings. While he sponsored the construction of the Sistine Chapel, his papacy was rife with nepotism. He appointed six of his nephews as cardinals, granting them vast influence. Sixtus IV also played a key role in the Pazzi Conspiracy, a plot to assassinate Lorenzo and Giuliano d'Medici to secure political power in Florence. The plot failed, but it left a bloody stain on his tenure and exacerbated political instability in Italy.
Reign: 1513-1521
Known for his extravagant spending, Pope Leo X is historically quoted as saying "Since God has given us the papacy, let us enjoy it." This approach to leadership saw him lavish resources on art and architecture, including funding Michelangelo’s work on St. Peter’s Basilica. However, Leo X's most infamous legacy is his role in the sale of indulgences, a controversial practice where people paid to reduce their time in purgatory. This sparked Martin Luther’s Ninety-Five These and the eventual Protestant Reformation. Leo’s excesses may have left a cultural material legacy, but it came at the cost of deep theological divisions in Christianity.
Reign: 1494-1492
Despite his ironic title, Pope Innocent VIII was anything but innocent. His papacy was marked by nepotism, corruption, and the exploitation of church funds. Innocent VIII declared a crusade against heretics and launched brutal witch hunts in Europe, issuing a papal bull that exacerbated the fears of witchcraft and led to widespread persecution. Outside of church policy, Innocent also fathered illegitimate children and used his position to arrange advantageous marriages for them, further tarnishing the papacy's image. He was the pope immediately following Pope Sixtus IV, a string of 3 (or more) in a row of objectively terrible popes!
Reign: 1464-1471
Pope Paul II’s reign is best remembered for his vanity and intolerance. He was criticized for his obsession with extravagant clothing and jewelry, earning him the nickname "Paul the Glistening." However, his cruelty is what solidifies his place on this list. Paul II persecuted intellectuals and philosophers, accusing many of heresy and imprisoning them for their beliefs. His crackdown on burgeoning humanist ideas stifled free thought during an era of burgeoning creativity and progress in Renaissance Italy. But people aren't 100% evil and 100% good. He also introduced printing materials to the Papal States at this time, making books more numerous and more affordable! You win some; you lose some.
Reign: 1724-1730
Not to be confused with the earlier Benedict IX, Pope Benedict XIII’s papacy was marked by incompetence and mismanagement. He was heavily influenced by corrupt advisors, allowing them to seize control of church policies. His reign saw widespread dissatisfaction within the church, as his lack of leadership led to poor governance. While he was personally pious, his failure to control corruption within the Vatican left a negative legacy that overshadowed his intentions.
Reign: 1378-1389
The papacy of Urban VI marked the beginning of the Western Schism, a division that saw multiple rival popes claiming the throne of St. Peter. Pope Urban VI’s divisive leadership plunged the church into decades of chaos and weakened its authority. His temperament was one of his greatest flaws. History knows him for his erratic behavior and violent outbursts, and he alienated supporters while also fueling tensions within the church. His paranoia led him to orchestrate the imprisonment and alleged torture of cardinals he suspected of plotting against him.
Reign: 1492-1503
Few figures embody the corruption of the Renaissance papacy better than Pope Alexander VI, born Rodrigo Borgia. The Borgia family’s name has become synonymous with bribery, nepotism, and immorality. Alexander VI was at the heart of it all. Allegedly securing his election through bribery, Alexander used his position to advance his family’s power. He openly acknowledged his mistresses and illegitimate children, granting them lavish titles and vast wealth. While he was a skilled political operator, his blatant corruption severely damaged the church's reputation during his tenure.
Reign: 955-964
John XII became pope at the tender age of 18, which might explain why his reign mirrored the recklessness of youth. Known more for his hedonistic lifestyle than his spiritual leadership, John XII reportedly turned the papal palace into a den of vice. Chronicles from the era accuse him of gambling, debauchery, and even violence. He was so notorious that the Roman Synod of 963 declared him unfit for the papacy. Pope John XII's reign came to an ignominious end when he allegedly died in bed, either from a stroke or from being attacked by a jealous husband.
Reign: 896–897
If there's one pope who epitomizes bizarre behavior, it's Pope Stephen VI. His papacy is infamous for the "Cadaver Synod," an event so outlandish it sounds like fiction. Stephen VI had the corpse of his predecessor, Pope Formosus, exhumed and placed on trial. Yes, you read that correctly. The rotting corpse was dressed in papal garments and accused of perjury and violating church law. Unsurprisingly, Formosus was "found guilty," stripped of his titles, and his body was thrown into the Tiber River. This ghastly event shocked the church and contributed to political chaos in Rome.
