Baddest of the bad: The worst Popes.

Taking the list from the 1969 book The Bad Popes and adding a few other choices.

Pope Stephen VI (896-897): Mutilated the corpse of his predecessor, Pope Formosus.
Pope Sergius III (904-911): Ordered murders, his papacy has been described as a “pornocracy”.
Pope John XII (955-964): A randy so-and-so who basically turned the Lateran into a brothel.
Pope Benedict IX (1032–1044, 1045, 1047–1048): The dates should tell you everything. Sold the Papacy and called “a disgrace to the chair of Peter”.
Pope Urban II (1088-1099): Responsible for the First Crusade, which started a delightful trend.
Pope Boniface VIII (1294–1303): Earn a place in Hell in Dante’s Divine Comedy.
Pope Urban VI (1378-1389): Had unruly Cardinals tortured.
Pope Pius II (1458-1464): Good buddies with Vlad the Impaler.
Pope Alexander VI (1492-1503): A Borgia famous for nepotism, debauchery and killing Ezio’s family.
Pope Leo X (1513-1521): “a spendthrift member of the Medici family who once spent 1/7 of his predecessors’ reserves on a single ceremony”.
Pope Clement VII (1523-1534): Managed to get Rome sacked, another Medici.
Pope Pius XII (1939-1958): Frequently criticised for not doing enough during the Holocaust.
Pope Benedict XVI (2005- ): Because someone would have mentioned him. Sexual abuse scandals, condoms and AIDS.

For my money, Benedict IX was a pretty obscene piece of work, Segius III is also right up there for his penchant for ordering strangulations.

Edit: Mods, meant to post this in GD - can I request a move?

I don’t know a lot about popes except for Urban II, Pious XII, Julius II, and the unmentioned Sixtus IV. Sixtus was the pope for the Spanish Inquisition (not his doing but still pretty bad) and told the Portuguese to stop enslaving Europeans and go south and enslave the heathens.

All in all, tough call. Some popes may have been personally more morally reprehensible than others while others had a larger “badness impact”

I don’t know a lot about popes except for Urban II, Pious XII, Julius II, and the unmentioned Sixtus IV. Sixtus was the pope for the Spanish Inquisition (not his doing but still pretty bad) and told the Portuguese to stop enslaving Europeans and go south and enslave the heathens.

All in all, tough call. Some popes may have been personally more morally reprehensible than others while others had a larger “badness impact”

I never heard of that book but it’s now on my Amazon wishlist. Also: Pornocracy is my newest favorite word.