1. The Disgraced Catholic Pope: Pope Benedict IX

Benedictus IX, by Giovanni Battista Cavalieri, 1580, via Trento Municipal Library

Also known as one of the youngest popes in history and the only pope to hold the title three times, Benedict IX (1012-1056) became pontiff at the age of 20. He was appointed due to his family’s connections: his immediate predecessor was his uncle, John XIX, and his wealthy father ensured his successful election through bribery. He was also extremely unpopular.

Described as a demon from hell, Benedict IX supposedly murdered, raped, and sodomized victims wherever he went. He was even accused of bestiality and of hosting orgies. Due to this lifestyle, he was forced out of Rome and a new pope was elected, Sylvester III.

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This is not where his story ends, however. He returned to Rome, and with the help of his supporters he ousted Sylvester and reinstated himself as pope. Then, he had some second thoughts: he decided to resign so that he could marry his cousin. He became the only pope in history to sell the papacy when he agreed to let his godfather, Gregory VI, take over in exchange for reimbursement.

One would think that it would end there, but no, he soon regretted his decision and retook the papacy. Three popes now claimed to be in power, Sylvester, Gregory, and Benedict. This caused such turmoil that the Holy Roman Emperor Henry III was asked to intervene and decided to start from scratch by electing a new pope, Damasus II. Benedict IX refused to appear before the courts on charges of simony, i.e. selling the papacy, and was excommunicated instead. He eventually died in obscurity.

2. Trying the Dead: Pope Stephen VI

Pope Formosus and Stephen VI, by Jean-Paul Laurens, 1870, via Nantes Museum of the Arts

Stephen VI (d. 897) is best known for putting his dead predecessor on trial. This was not at all a symbolic trial; the body was dug up and brought before the court. The deceased Pope Formosus, unable to speak for himself, was instead spoken for by a deacon, and was ultimately found guilty of accepting the papacy while also holding the office of bishop. The corpse was stripped of its vestments, dressed as a pauper, and thrown into a shallow grave, but not before three of his fingers were cut off.

This did not seem like enough of a punishment, so the corpse was dug up again and thrown into the Tiber. The so-called Cadaver Synod of 897 led directly to the demise of Stephen VI. He was stripped of his title and strangled to death a year later.

3. Pope Urban VI: The Church at War

Urbanus VI, by Giovanni Battista Cavalieri, 1580, via Municipal Library of Trento

Described by some historians as the antithesis of what a Christian should be, Urban VI was violent, arrogant, quick to anger, and imprudent. Although he had a knack for business, his ecclesiastical decisions were disastrous and failed to rectify the Great Western Schism. Not only was he battling for control with the French antipope, but his papacy was also marred by war, and he drained church resources in order to fund the War of the Eight Saints.

This was a conflict between Florentine-led provinces and the papal states, and although he was moderately successful, he died of injuries sustained when falling from his mule. Some suspected he had been poisoned as well.

4. Pushing Indulgences: Pope Leo X

Portrait of Leo X, by Raphael, 1518, via Uffizi Gallery, Florence

Born in 1475 to the illustrious Medici family, Pope Leo X was known for being a reckless spender. He led a costly war in order to secure power, and granted indulgences in exchange for money to reconstruct St Peter’s Basilica. An indulgence is when a person’s sin is lessened in exchange for good deeds, donations to charitable organizations, saying specific prayers, and pilgrimage. However, as in the case of Leo X, this practice was often abused by church officials, who lined their pockets with the money donated.

This practice was so controversial that it eventually led to Martin Luther writing his Ninety-five Theses. Leo X failed to see this as a potential threat and was too late in ordering Luther to retract. Lutheranism spread throughout the German and Scandinavian states, which eventually led to many Protestant reformations. He failed to stem the reformation abroad, but locally he managed to capture the coveted provinces of Parma and Piacenza and declare them part of the Papal States.

5. Pope Alexander VI: Corrupt and Salacious

Jacopo Pesaro, Bishop of Paphos, Being Presented by Pope Alexander VI to Saint Peter, by Titian, 1506-1511, via Royal Museum of Fine Arts, Antwerp

Hailing from the noble Borgia family, Alexander VI (1431-1503) was known for having many mistresses and he openly recognized several children as his own. Besides breaking his vows of celibacy, Alexander VI’s name became synonymous with nepotism. He made sure that family members held key positions of power, and he annulled marriages in exchange for alliances. This is how he secured the military support of French king Louis XII. He was fickle, however, and made sure to ally himself with whoever would benefit him the most. During the war between Spain and France, Alexander VI offered papal troops to Spain in exchange for Siena, Pisa, and Bologna, but he also agreed to help France in exchange for Sicily.

Alexander VI, by Giovanni Battista Cavalieri, 1580, via Municipal Library of Trento

Alexander VI was also the subject of many salacious rumors, however, none have been proven to be true. One such rumor was that he hosted the “Banquet of Chestnuts,” a supper purportedly held in the Papal Palace during which clergymen were encouraged to sleep with Rome’s most desirable courtesans.

These courtesans apparently stripped naked and crawled on their hands and feet, picking up chestnuts that attending guests threw on the ground. The only source is from Johann Burchard, who deeply disliked Pope Alexander. Whether or not Alexander VI actually participated in such sinful acts may never be known, but all of his other deeds have earned him the title of most corrupt pope.

6. Pope Sergius III: Nepotism and Murder

Pope Sergius III, via the British Museum

Sergius III (860-911) spent his reign as pope under the influence of the powerful Theophylact of Tusculum. Before becoming pontiff, he actively participated in the Cadaver Synod, and upon assuming power he reportedly had his two predecessors murdered in prison.

During the remainder of his pontificate, he promoted family members and friends to positions of power, allegedly fathered an illegitimate son (who would later become Pope John XI), and participated in acts unbecoming of a pope. Today he is remembered as a ferocious man crippled by his desire to hold power and a malignant blight on the history of the papacy.

7. Pope Sixtus IV: Founder of the Inquisition

Sixtus IV, by Justus van Gent, via The Louvre, Paris

Sixtus IV (1414-1484) is mostly known as a patron of the arts. Under his rule, the Sistine Chapel and the Vatican Library were constructed, and he ordered the creation of Uppsala University in Sweden — the first Scandinavian university.

Although his accomplishments ushered in the Early Renaissance, he also founded the Spanish Inquisition, which led to the torture, execution, and expulsion of thousands of Jews and Muslims if they did not convert to Catholicism. In addition to violent conversion, Sixtus IV was known for nepotism and made sure that positions of power were held by trusted friends and family. He even participated in a plot to depose the powerful Medici family in Florence.

8. Pope Julius II: The Angry Pope

Portrait of Pope Julius II, by Raphael, 1511, via the National Gallery, London

Also known as the Warrior Pope, Julius II (1443-1513) did not choose his papal name in honor of Pope Julius I, but rather to honor Julius Caesar, whom he wanted to emulate. A fiercely efficient pope, he spearheaded the Italian Wars, the creation of the Vatican Museums, and the reconstruction of St Peter’s Basilica. Although he is remembered for his patronage of the arts, he had characteristics that were very un-Christian. He had a violent temper and treated his subordinates and servants very badly. He fathered several children before becoming pope and was accused of sexual misconduct.

Philosopher and Dutch theologian Erasmus even wrote a satire called Julius Excluded from Heaven that focuses on his sexual misconduct. Julius II is described as a drunken pope trying (and failing) to persuade Saint Peter to open the gates of heaven for him. Julius II tries to bribe him with money, and when that does not work, he resorts to threatening him with armies, just as he had done on earth. St Peter is disgusted and ultimately turns him away.

9. Pope Paul IV: Censorship and Anti-Semitism

Pope Paul IV, via LombardiaBeniCultural.org

As with all the other popes on this list Paul IV (1476-1559) was elected due to his powerful connections. Known as the worst pope of the 16th century, he was out of touch with the artistic and intellectual progress of the day, often suggesting that the Sistine Chapel be whitewashed, and introducing harsh censorship that banned certain books that he deemed erroneous. His biggest crime, however, was establishing the Roman Ghetto, a poverty-stricken place to which Jews were confined.

Jews were restricted to low-paying jobs, paid a yearly tax to live in the ghetto, performed humiliating acts for Christians, and were only allowed to bet on low numbers in the lottery. In exchange for the so-called “privilege” of staying in Rome, a Rabbi had to pay homage to the chief of the city councilors by being kicked on the bottom. When traveling outside of the ghetto, Jewish men were forced to wear yellow hats, and Jewish women had to wear yellow veils — a color traditionally worn by prostitutes. The walls of the ghetto were only torn down in 1888.

The Pescheria in the Ghetto, Rome, by Edward Angelo Goodall, 1873, via artuk.org

During his reign, the people of Rome suffered greatly, and they held him accountable. When word spread that he was on his deathbed, mobs gathered and started rioting, tearing down his statues or placing yellow hats on top of them. They tore down his family emblem all around the city and sang songs mocking him. After his death, his family had to rush the rituals and burials for fear that the body and grave would be decimated.

10. A Philandering Catholic Pope: Pope John XII

Ioannes XII, by Giovanni Battista Cavalieri, 1580, via Municipal Library of Trento

Last but not least is John XII (930-964), whose papacy was known for its worldliness and depravity. He was also related to the powerful house of Tusculum, but in spite of his powerful connections, he was unable to control Rome’s nobility. His dual roles as head of the church and secular prince made him unpopular with many nobles. He was characterized as an immoral man who drank, hunted, and had many sexual liaisons. The papal residence was described as a brothel, and legend has it that John XII was defenestrated (thrown out of a window) for sleeping with a married woman. It is clear that his princely inclinations were much stronger than any spiritual office that he held, and modern scholars are in agreement that he was an unfit Pope.