1. Pope Alexander VI (1431 – 1503)

The reward for “Baddest Pope Ever” arguably goes to Rodrigo Borgia, who enjoyed the benefits of having an uncle who just happened to be Pope Calixtus III. Thanks to his convenient social status, Borgia passed through the ranks of bishop, cardinal, and vice-chancellor, gaining enormous wealth along the way. In 1492, he was actually able to buy his way into the papacy, defeating two other opponents by means of bribery.

Alexander was so corrupt that his surname eventually became a byword representing the hellishly low papal standards of the time. He sired at least seven different illegitimate children by his mistresses, and didn’t hesitate to reward them with handsome endowments at the church’s expense. When low on finances, he either established new cardinals in return for payments, or he slammed wealthy people with completely fabricated charges, jailed or murdered them for said false charges, and then stole their money.

Not surprisingly, there is very little about Alexander VI that can be considered godly or even lawful. His goals were selfish and ambitious, and the orderly government he initially administered quickly deteriorated until the city of Rome was in a state of complete disrepair. The words spoken by Giovanni de Medici (the future Pope Leo X) after Borgia’s election are telling:

“Now we are in the power of a wolf, the most rapacious perhaps that this world has ever seen. And if we do not flee, he will inevitably devour us all.”

2. Pope John XII (c. 937 – 964)

Born in Rome, the young Octavianus practically had the papacy handed to him on a silver platter. His father, a patrician of Rome, made the Roman nobles swear an oath that at the next vacancy in the papal seat, Octavianus would be elected. Sure enough, when he was only 18 the reigning pope passed away, and Octavianus was chosen as the successor, taking the name Pope John XII.

Almost everything known about John XII is found in the writings of his enemies, so it’s possible that the accounts we have are factually distorted. Nevertheless, the stories we do have are quite shocking – he was accused of committing many adulteries (even with his own niece), turning the Vatican into a whorehouse, blinding his confessor, castrating and then murdering a subdeacon, invoking demons and foreign gods… the list goes on and on.

Even if some of the reports were falsified, it still appears that John XII made for a pretty bad pope. When we read the account of John’s death that claims he was murdered by a jealous husband whose wife was the object of the pope’s special attention, it’s not too hard to believe it.

3. Pope Benedict IX (c. 1012 – 1065/85)

Benedict IX, born Theophylactus of Tusculum, is known mainly for two things: 1) he held office on three separate occasions, and 2) he is the only pope who ever sold the papacy (to his own godfather, of all people).

Benedict became pontiff at a very young age, thanks to the political prowess of his father, who had managed to get the papacy reserved ahead of time for his son. With little actual training or preparation that qualified him to act as pontiff, Benedict led a highly immoral life, and was accused of various rapes, adulteries, and murders. According to St. Peter Damian, Benedict was “a demon from hell in the disguise of a priest,” and his carousing eventually caused him to be forcefully expelled from Rome.

Benedict managed to regain his throne, but then – surprise, surprise! – he was sidetracked by a prospective marriage (to his cousin) and sold the papal chair for a significant amount of money to his godfather, a priest who named himself Pope Gregory VI. His later repentance and attempt to resume his position created quite a controversy, forcing the German King Henry III to intervene. Benedict was subsequently excommunicated from the church.

“His life as a pope,” wrote Pope Victor III, “was so vile, so foul, so execrable, that I shudder to think of it.”

4. Pope Sergius III (? – 911)

The son of a Roman noble and a member of the ultimately unsuccessful faction which opposed the policies of Pope Formosus, Sergius III must chiefly be understood through the biased writings of his enemies, since almost all sympathetic accounts have been destroyed.

Nevertheless, what we do have on Sergius suggests that he didn’t quite measure up to Christian standards for piety. He was accused of ordering the murders of his predecessor Pope Leo V and Antipope Christopher in prison. It is said that his mistress was the young Marozia (later to become a powerful Roman noblewoman), and it was their son who became Pope John XI in 931.

It gets weirder, though. Pope Stephen VI’s infamous Cadaver Synod had been declared void by succeeding popes, but when Sergius came to power, he voiced his displeasure with Formosus by annulling all of his recently reinstated ordinations. There is even a report that Sergius had the corpse of Formosus exhumed, tried, beheaded, and thrown into the Tiber – all over again!

5. Pope Stephen VI (? – 897)

Little is known about Pope Stephen VI’s personal life and background, although he was a Roman and the son of a priest named John. The reason his name stands out in church history is because of his involvement in what is perhaps the most bizarre ecclesiastical trial of all time – the Cadaver Synod of January 897.

As the name reveals, this grotesque synod was convened to put a corpse on trial. Stephen ordered it for the sole purpose of passing judgment on the freshly-exhumed body of Formosus, who had held the papacy from 891-96. Due to activities in Bulgaria which compromised his duties as bishop of Porto, Formosus had been excommunicated by then-pope John VIII (872-882), but after John VIII’s death he had reassumed his bishopric in Porto and was elected pope in 891.

Political interests regarding rightful claims to the throne of the Holy Roman Emperor resulted in animosities that created a trickle-down effect and impacted later popes. Stephen VI and the Cadaver Synod are the most famous instance of reactions to Pope Formosus.

While it is not perfectly clear who exactly instigated the trial, the fact of the matter is that Stephen ordered Formosus’s body to be disinterred and seated on a throne in the Basilica of St. John Lateran in Rome. A deacon stood next to it to act as its spokesman while Stephen lambasted it with accusations.

The corpse was condemned for transmigrating sees, committing perjury, and acting as bishop after being deposed. As punishment, his body was stripped of its vestments, the three fingers of the right hand used for benedictions were cut off, and all his former ordinations were declared null. The body was then buried, exhumed again, and finally thrown into the Tiber River.

6. Pope Julius III (1487 – 1555)

Born to a famous Roman jurist, Giovanni Maria Ciocchi del Monte was elected pope in 1550 as a compromise candidate, and chose the title Julius III. While his early career in the church shows that he was very capable and successful, his papacy is known for being extremely ineffective and undistinguished. For the most part, Julius withdrew to his palace and spent the majority of his time seeing to his own personal pleasures and keeping out of political affairs.

However, it was his relationship with a boy named Innocenzo that tarnished his name more than anything. Julius discovered Innocenzo as a young beggar in Parma before ascending to the pontificate, and he adopted him as his own nephew. When Julius became pope, he elevated Innocenzo to the status of cardinal-nephew and bestowed many gifts and benefices upon him. In fact, the relationship between Julius and Innocenzo showed signs of being much more intimate than normal family ties, and many reports indicate that Julius actually had an extended sexual affair with the young man.

7. Pope Urban II (ca. 1035 – 1099)

It’s undeniable that Otho de Lagery, who became Pope Urban II in 1088, was a talented diplomat and successful leader, responsible for establishing the modern Roman Curia and supporting reforms of the clergy. What he is most often remembered for, however, is his unfortunate role in launching a bloody holy war against Muslims that has since come to be known as The First Crusade.

In 1095, Byzantine Emperor Alexios I requested Urban’s aid in fighting off the Turks, who had conquered most of Anatolia. Urban responded favorably by using his remarkable rhetorical skills to preach “Just War” – a holy, God-ordained crusade to liberate the eastern churches and the Holy Land from Muslim rule. By appealing to Catholic anger over the rumored (and often unfairly trumped-up) atrocities committed by the invading Turks, and by guaranteeing remission of sins to those who would participate in the fight, Urban was able to organize a large-scale uprising of piously outraged soldiers of Christ.

The religiously-sanctioned First Crusade, while successful in defeating Muslim forces in Anatolia and the Holy Land, was very costly in terms of casualties. Not only was there a huge loss of lives on both sides, but the horrible offenses committed by enraged Christians against Jews, Muslims, and even members of the “schismatic” Eastern church will always be a bloody stain on the pages of church history.